{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,19]],"date-time":"2026-03-19T22:50:54Z","timestamp":1773960654222,"version":"3.50.1"},"reference-count":99,"publisher":"MDPI AG","issue":"13","license":[{"start":{"date-parts":[[2024,6,25]],"date-time":"2024-06-25T00:00:00Z","timestamp":1719273600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National funds","award":["UIDB\/50026\/2020"],"award-info":[{"award-number":["UIDB\/50026\/2020"]}]},{"name":"National funds","award":["UIDP\/50026\/2020"],"award-info":[{"award-number":["UIDP\/50026\/2020"]}]},{"name":"National funds","award":["NORTE-01-0145-FEDER-000055"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-000055"]}]},{"name":"National funds","award":["UID\/QUI\/00686\/2020"],"award-info":[{"award-number":["UID\/QUI\/00686\/2020"]}]},{"name":"National funds","award":["UID\/QUI\/0686\/2016"],"award-info":[{"award-number":["UID\/QUI\/0686\/2016"]}]},{"name":"National funds","award":["UIDB\/50026\/2020"],"award-info":[{"award-number":["UIDB\/50026\/2020"]}]},{"name":"National funds","award":["UIDP\/50026\/2020"],"award-info":[{"award-number":["UIDP\/50026\/2020"]}]},{"name":"National funds","award":["NORTE-01-0145-FEDER-000055"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-000055"]}]},{"name":"National funds","award":["2020.07919.BD"],"award-info":[{"award-number":["2020.07919.BD"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["UIDB\/50026\/2020"],"award-info":[{"award-number":["UIDB\/50026\/2020"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["UIDP\/50026\/2020"],"award-info":[{"award-number":["UIDP\/50026\/2020"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["NORTE-01-0145-FEDER-000055"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-000055"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["UID\/QUI\/00686\/2020"],"award-info":[{"award-number":["UID\/QUI\/00686\/2020"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["UID\/QUI\/0686\/2016"],"award-info":[{"award-number":["UID\/QUI\/0686\/2016"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["UIDB\/50026\/2020"],"award-info":[{"award-number":["UIDB\/50026\/2020"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["UIDP\/50026\/2020"],"award-info":[{"award-number":["UIDP\/50026\/2020"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["NORTE-01-0145-FEDER-000055"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-000055"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["2020.07919.BD"],"award-info":[{"award-number":["2020.07919.BD"]}]},{"name":"University of Minho, FCT and FEDERCOMPETE","award":["UIDB\/50026\/2020"],"award-info":[{"award-number":["UIDB\/50026\/2020"]}]},{"name":"University of Minho, FCT and FEDERCOMPETE","award":["UIDP\/50026\/2020"],"award-info":[{"award-number":["UIDP\/50026\/2020"]}]},{"name":"University of Minho, FCT and FEDERCOMPETE","award":["NORTE-01-0145-FEDER-000055"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-000055"]}]},{"name":"University of Minho, FCT and FEDERCOMPETE","award":["UID\/QUI\/00686\/2020"],"award-info":[{"award-number":["UID\/QUI\/00686\/2020"]}]},{"name":"University of Minho, FCT and FEDERCOMPETE","award":["UID\/QUI\/0686\/2016"],"award-info":[{"award-number":["UID\/QUI\/0686\/2016"]}]},{"name":"University of Minho, FCT and FEDERCOMPETE","award":["UIDB\/50026\/2020"],"award-info":[{"award-number":["UIDB\/50026\/2020"]}]},{"name":"University of Minho, FCT and FEDERCOMPETE","award":["UIDP\/50026\/2020"],"award-info":[{"award-number":["UIDP\/50026\/2020"]}]},{"name":"University of Minho, FCT and FEDERCOMPETE","award":["NORTE-01-0145-FEDER-000055"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-000055"]}]},{"name":"University of Minho, FCT and FEDERCOMPETE","award":["2020.07919.BD"],"award-info":[{"award-number":["2020.07919.BD"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["UIDB\/50026\/2020"],"award-info":[{"award-number":["UIDB\/50026\/2020"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["UIDP\/50026\/2020"],"award-info":[{"award-number":["UIDP\/50026\/2020"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["NORTE-01-0145-FEDER-000055"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-000055"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["UID\/QUI\/00686\/2020"],"award-info":[{"award-number":["UID\/QUI\/00686\/2020"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["UID\/QUI\/0686\/2016"],"award-info":[{"award-number":["UID\/QUI\/0686\/2016"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["UIDB\/50026\/2020"],"award-info":[{"award-number":["UIDB\/50026\/2020"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["UIDP\/50026\/2020"],"award-info":[{"award-number":["UIDP\/50026\/2020"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["NORTE-01-0145-FEDER-000055"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-000055"]}]},{"name":"Norte Portugal Regional Operational Programme (NORTE 2020)","award":["2020.07919.BD"],"award-info":[{"award-number":["2020.07919.BD"]}]},{"name":"FCT","award":["UIDB\/50026\/2020"],"award-info":[{"award-number":["UIDB\/50026\/2020"]}]},{"name":"FCT","award":["UIDP\/50026\/2020"],"award-info":[{"award-number":["UIDP\/50026\/2020"]}]},{"name":"FCT","award":["NORTE-01-0145-FEDER-000055"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-000055"]}]},{"name":"FCT","award":["UID\/QUI\/00686\/2020"],"award-info":[{"award-number":["UID\/QUI\/00686\/2020"]}]},{"name":"FCT","award":["UID\/QUI\/0686\/2016"],"award-info":[{"award-number":["UID\/QUI\/0686\/2016"]}]},{"name":"FCT","award":["UIDB\/50026\/2020"],"award-info":[{"award-number":["UIDB\/50026\/2020"]}]},{"name":"FCT","award":["UIDP\/50026\/2020"],"award-info":[{"award-number":["UIDP\/50026\/2020"]}]},{"name":"FCT","award":["NORTE-01-0145-FEDER-000055"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-000055"]}]},{"name":"FCT","award":["2020.07919.BD"],"award-info":[{"award-number":["2020.07919.BD"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The chromenopyridine scaffold represents an important class of heterocyclic compounds exhibiting a broad spectrum of biological properties. This review describes novel and efficient procedures for the synthesis of this scaffold. Herein, several methods were detailed and grouped according to their starting material (e.g., salicylaldehydes, chromones, chromanones and coumarins) and respective biological activity, when reported. This review highlights the potential of the reported synthetic strategies for preparing chromenopyridine derivatives with promising biological activity, paving the way for further developments in drug discovery.<\/jats:p>","DOI":"10.3390\/molecules29133004","type":"journal-article","created":{"date-parts":[[2024,6,25]],"date-time":"2024-06-25T12:46:56Z","timestamp":1719319616000},"page":"3004","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["The Chromenopyridine Scaffold: A Privileged Platform in Drug Design"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4368-6228","authenticated-orcid":false,"given":"F\u00e1bio","family":"Pedroso de Lima","sequence":"first","affiliation":[{"name":"Chemistry Centre, School of Sciences, University of Minho, Gualtar Campus, 4715-303 Braga, Portugal"},{"name":"Centre for Textile Science and Technology (2C2T), University of Minho, Azur\u00e9m Campus, 4800-058 Guimar\u00e3es, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4287-0659","authenticated-orcid":false,"given":"Marta","family":"Costa","sequence":"additional","affiliation":[{"name":"Life and Health Sciences Research Institute (ICVS), University of Minho, Gualtar Campus, 4710-057 Braga, Portugal"},{"name":"ICVS\/3B\u2019s\u2014PT Government Associate Laboratory, 4710-057 Braga\/Guimar\u00e3es, Portugal"}]},{"given":"Ana","family":"Sousa","sequence":"additional","affiliation":[{"name":"Chemistry Centre, School of Sciences, University of Minho, Gualtar Campus, 4715-303 Braga, Portugal"},{"name":"Life and Health Sciences Research Institute (ICVS), University of Minho, Gualtar Campus, 4710-057 Braga, Portugal"},{"name":"ICVS\/3B\u2019s\u2014PT Government Associate Laboratory, 4710-057 Braga\/Guimar\u00e3es, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5274-1949","authenticated-orcid":false,"given":"Maria Fernanda","family":"Proen\u00e7a","sequence":"additional","affiliation":[{"name":"Chemistry Centre, School of Sciences, University of Minho, Gualtar Campus, 4715-303 Braga, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2024,6,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"347","DOI":"10.1016\/j.cbpa.2010.02.018","article-title":"Privileged scaffolds for library design and Drug Discovery","volume":"14","author":"Welsch","year":"2010","journal-title":"Curr. Opin. Chem. Biol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"7941","DOI":"10.1021\/acs.jmedchem.6b01720","article-title":"Chromone as a Privileged Scaffold in Drug Discovery: Recent Advances","volume":"60","author":"Reis","year":"2017","journal-title":"J. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"340","DOI":"10.1016\/j.ejmech.2014.03.047","article-title":"Chromones as a privileged scaffold in drug discovery: A review","volume":"78","author":"Keri","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"14629","DOI":"10.1021\/ja508343a","article-title":"Privileged Structures: Efficient Chemical \u201cNavigators\u201d toward Unexplored Biologically Relevant Chemical Spaces","volume":"136","author":"Kim","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"869","DOI":"10.2174\/1389557516666160923125801","article-title":"Roles of Pyridine and Pyrimidine Derivatives as Privileged Scaffolds in Anticancer Agents","volume":"17","author":"Prachayasittikul","year":"2017","journal-title":"Mini-Rev. Med. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2235","DOI":"10.1021\/jm00120a002","article-title":"Methods for drug discovery: Development of potent, selective, orally effective cholecystokinin antagoniststs","volume":"31","author":"Evans","year":"1988","journal-title":"J. Med. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Hu, Z., Wang, C., Sitkoff, D., Cheadle, N.L., Xu, S., Muckelbauer, J.K., Adam, L.P., Wexler, R.R., and Quan, M.L. (2020). Identification of 5H-chromeno [3,4-c]pyridine and 6H-isochromeno[3,4-c]pyridine derivatives as potent and selective dual ROCK inhibitors. Bioorg. Med. Chem. Lett., 30.","DOI":"10.1016\/j.bmcl.2020.127474"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"7121","DOI":"10.1021\/cr900166w","article-title":"Targeting the histamine H4 receptor","volume":"111","author":"Marson","year":"2011","journal-title":"Chem. Rev."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"238","DOI":"10.1021\/cr0682195","article-title":"Adenosine receptor antagonists: Translating medicinal chemistry and pharmacology into clinical utility","volume":"108","author":"Baraldi","year":"2008","journal-title":"Chem. Rev."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Martinez-Gualda, B., Pu, S.Y., Froeyen, M., Herdewijn, P., Einav, S., and De Jonghe, S. (2020). Structure-activity relationship study of the pyridine moiety of isothiazolo[4,3-b]pyridines as antiviral agents Targeting cyclin G-associated kinase. Bioorg. Med. Chem., 28.","DOI":"10.1016\/j.bmc.2019.115188"},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Barreiro, E.J. (2016). Chapter 1: Privileged Scaffolds in Medicinal Chemistry: An Introduction. Privileged Scaffolds in Medicinal Chemistry: Design, Synthesis, Evaluation, The Royal Society of Chemistry.","DOI":"10.1039\/9781782622246-00001"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"3443","DOI":"10.1021\/jo070114u","article-title":"One-Step Synthesis of Heterocyclic Privileged Medicinal Scaffolds by a Multicomponent Reaction of Malononitrile with Aldehydes and Thiols","volume":"72","author":"Evdokimov","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"6043","DOI":"10.1016\/j.tet.2004.04.043","article-title":"De Novo Synthesis of Substituted Pyridines","volume":"60","author":"Henry","year":"2004","journal-title":"Tetrahedron"},{"key":"ref_14","unstructured":"Edwards, J.P., Kindrachuk, D.E., and Venable, J.D. (2009). Benzo-Imidazolyl Pyridines as Modulators of the Histamine H4 Receptor. Hong. (HK1124767A1), Kong Patent."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Radwan, M.A.A., Alshubramy, M.A., Abdel-Motaal, M., Hemdan, B.A., and El-Kady, D.S. (2020). Synthesis, molecular docking and antimicrobial activity of new fused pyrimidine and pyridine derivatives. Bioorg. Chem., 96.","DOI":"10.1016\/j.bioorg.2019.103516"},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Jian, X.E., Yang, F., Jiang, C.S., You, W.W., and Zhao, P.L. (2020). Synthesis and biological evaluation of novel pyrazolo[3,4-b]pyridines as cis-restricted combretastatin A-4 analogues. Bioorg. Med. Chem. Lett., 30.","DOI":"10.1016\/j.bmcl.2020.127025"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"487","DOI":"10.1016\/j.ejmech.2016.07.057","article-title":"Biological importance of structurally diversified chromenes","volume":"123","author":"Costa","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1016\/j.ejmech.2018.07.058","article-title":"Exploitation of new chalcones and 4H-chromenes as agents for cancer treatment","volume":"157","author":"Pontes","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"669","DOI":"10.1080\/00397911.2019.1710850","article-title":"Design, synthesis, anti-proliferative activity, and molecular docking studies of novel benzo[f]chromene, chromeno[2,3-d]pyrimidines and chromenotriazolo[1,5-c]pyrimidines","volume":"50","author":"Elgubbi","year":"2020","journal-title":"Synth. Commun."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"560","DOI":"10.1016\/j.bioorg.2019.03.059","article-title":"Antiproliferative effect, cell cycle arrest and Aaoptosis generation of novel synthesized anticancer heterocyclic derivatives based 4H-benzo[h]chromene","volume":"87","author":"Alblewi","year":"2019","journal-title":"Bioorg. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"2624","DOI":"10.1007\/s00044-017-1961-3","article-title":"Anticancer activities, molecular docking and structure\u2013activity relationship of novel synthesized 4H-chromene, and 5H-chromeno[2,3-d]pyrimidine candidates","volume":"26","author":"Halawa","year":"2017","journal-title":"Med. Chem. Res."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"476","DOI":"10.1016\/j.ejmech.2015.07.010","article-title":"Coumarins as anticancer agents: A review on synthetic strategies, mechanism of action and SAR studies","volume":"101","author":"Thakur","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"702","DOI":"10.1016\/j.molstruc.2019.05.081","article-title":"Efficient and easy synthesis of new Benzo[h]chromene and Benzo[h]quinoline derivatives as a new class of cytotoxic agents","volume":"1195","author":"Haiba","year":"2019","journal-title":"J. Mol. Struct."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1016\/j.bioorg.2019.03.016","article-title":"Synthesis and antiproliferative activity of new 2-glyco-3-nitro-2H-chromenes","volume":"87","author":"Light","year":"2019","journal-title":"Bioorg. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Okasha, R.M., Alsehli, M., Ihmaid, S., Althagfan, S.S., El-Gaby, M.S.A., Ahmed, H.E.A., and Afifi, T.H. (2019). First example of Azo-Sulfa conjugated chromene moieties: Synthesis, characterization, antimicrobial assessment, docking simulation as potent class I histone deacetylase inhibitors and antitumor agents. Bioorg. Chem., 92.","DOI":"10.1016\/j.bioorg.2019.103262"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"765","DOI":"10.1016\/j.ejmech.2010.12.015","article-title":"Synthesis of 4H-Chromene, Coumarin, 12H-Chromeno[2,3-d]Pyrimidine Derivatives and Some of Their Antimicrobial and Cytotoxicity Activities","volume":"46","author":"Sabry","year":"2011","journal-title":"Eur. J. Med. Chem."},{"key":"ref_27","first-page":"11","article-title":"Pharmacological Activities of Chromene Derivatives: An Overview","volume":"6","author":"Thomas","year":"2013","journal-title":"Asian J. Pharm. Clin. Res."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"3511","DOI":"10.1016\/j.tetlet.2018.07.046","article-title":"Asymmetric synthesis and biological evaluation of 3-nitro-2H-chromenes as potential antibacterial agents","volume":"59","author":"Li","year":"2018","journal-title":"Tetrahedron Lett."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"454","DOI":"10.1016\/j.ejmech.2019.01.060","article-title":"Efficient click chemistry towards novel 1H-1,2,3-triazole-tethered 4H-chromene\u2212D-glucose conjugates: Design, synthesis and evaluation of in vitro antibacterial, MRSA and antifungal activities","volume":"167","author":"Thanh","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"841","DOI":"10.1007\/s11030-017-9758-3","article-title":"Synthesis of substituted 2H-chromenes by a three-component reaction as potential antioxidants","volume":"21","author":"Subbareddy","year":"2017","journal-title":"Mol. Divers."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"436","DOI":"10.1016\/j.bioorg.2018.01.036","article-title":"3-(E)-Styryl-2H-chromene derivatives as potent and selective monoamine oxidase B inhibitors","volume":"77","author":"Takao","year":"2018","journal-title":"Bioorg. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"377","DOI":"10.1021\/jm00308a049","article-title":"Steroidal Analog of a Tetrahydrocannabinol","volume":"11","author":"Razdan","year":"1968","journal-title":"J. Med. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"3664","DOI":"10.1021\/ja00967a047","article-title":"Physiologically Active Nitrogen Analogs of Tetrahydrocannabinols. Tetrahydrobenzopyrano[3,4-d]Pyridines","volume":"88","author":"Pars","year":"1966","journal-title":"J. Am. Chem. Soc."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"445","DOI":"10.1021\/jm00226a001","article-title":"Drugs derived from cannabinoids. 1. Nitrogen analogs, benzopyranopyridines and benzopyranopyrroles","volume":"19","author":"Pars","year":"1976","journal-title":"J. Med. Chem."},{"key":"ref_35","unstructured":"Meyer, M.D., Altenbach, R.J., Basha, F.Z., Carroll, W.A., Drizin, I., Kerwin, J.F., Wendt, M.D., Haight, A.R., and Zhang, W. (1998). Benzopyranopyrrole and Benzopyranopyridine Alpha-1 Adrenergic Compounds. (WO9824791A1), WO Patent."},{"key":"ref_36","unstructured":"Brown, R.E., Puchalski, C., and Shavel, J. (1976). Novel Substituted Benzopyranopyridine. (3,962,266), U.S. Patent."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1561","DOI":"10.1002\/jhet.5570210564","article-title":"Synthesis of 1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-c]pyridin-5-ones. II. Substitution at the 3-position with 2-aminoethyl and 2-aminopropyl side chains","volume":"21","author":"Connor","year":"1984","journal-title":"J. Heterocycl. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1557","DOI":"10.1002\/jhet.5570210563","article-title":"Synthesis of 1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-c]pyridin-5-ones. I. 3-unsubstituted compounds","volume":"21","author":"Connor","year":"1984","journal-title":"J. Heterocycl. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1477","DOI":"10.1007\/s00706-006-0537-6","article-title":"New 3,4-Annelated Coumarin Derivatives: Synthesis, Antimicrobial Activity, Antioxidant Capacity, and Molecular Modeling","volume":"137","author":"Radulovic","year":"2006","journal-title":"Monatshefte Chem.\/Chem. Mon."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"237","DOI":"10.1002\/jhet.234","article-title":"An efficient one-pot synthesis of some new 2,4-diaryl pyrido[3,2-c]coumarins as potent antimicrobial agents","volume":"47","author":"Dawane","year":"2010","journal-title":"J. Heterocycl. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"4761","DOI":"10.2174\/092986711797535272","article-title":"Chromenopyridines: Promising Scaffolds for Medicinal and Biological Chemistry","volume":"18","author":"Squella","year":"2011","journal-title":"Curr. Med. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"10996","DOI":"10.1021\/acs.jmedchem.8b00876","article-title":"From Oxiranes to Oligomers: Architectures of U.S. FDA Approved Pharmaceuticals Containing Oxygen Heterocycles","volume":"61","author":"Delost","year":"2018","journal-title":"J. Med. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"2229","DOI":"10.1080\/00397911.2011.555284","article-title":"K2CO3-Mediated, One-Pot, Multicomponent Synthesis of Medicinally Potent Pyridine and Chromeno[2,3-b]Pyridine Scaffolds","volume":"42","author":"Mishra","year":"2012","journal-title":"Synth. Commun."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"9309","DOI":"10.1016\/j.tetlet.2006.10.110","article-title":"Convenient one-step synthesis of a medicinally relevant benzopyranopyridine system","volume":"47","author":"Evdokimov","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"17152","DOI":"10.3390\/molecules200917152","article-title":"Design, Synthesis and Biological Evaluation of Novel 5H-Chromenopyridines as Potential Anti-Cancer Agents","volume":"20","author":"Banerjee","year":"2015","journal-title":"Molecules"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"8669","DOI":"10.1002\/slct.201801867","article-title":"Borax Catalysed Domino Synthesis of Highly Functionalised Spirooxindole and Chromenopyridine Derivatives: X-Ray Structure, Hirshfeld Surface Analysis and Molecular Docking Studies","volume":"3","author":"Molla","year":"2018","journal-title":"ChemistrySelect"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"424","DOI":"10.1016\/j.mencom.2015.11.008","article-title":"Pot, atom and step economic (PASE) synthesis of 5-isoxazolyl-5H-chromeno[2,3-b]pyridine scaffold","volume":"25","author":"Vereshchagin","year":"2015","journal-title":"Mendeleev Commun."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"4593","DOI":"10.1002\/slct.201700606","article-title":"PASE Pseudo-Four-Component Synthesis and Docking Studies of New 5-C-Substituted 2,4-Diamino-5H-Chromeno[2,3-b]Pyridine-3-Carbonitriles","volume":"2","author":"Vereshchagin","year":"2017","journal-title":"ChemistrySelect"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"766","DOI":"10.1016\/j.molstruc.2017.06.044","article-title":"Synthesis, structural, spectroscopic and docking studies of new 5C-substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitriles","volume":"1146","author":"Vereshchagin","year":"2017","journal-title":"J. Mol. Struct."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"372","DOI":"10.1016\/j.mencom.2018.07.010","article-title":"PASE facile and efficient multicomponent approach to the new type of 5-C-substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine scaffold","volume":"28","author":"Elinson","year":"2018","journal-title":"Mendeleev Commun."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1695","DOI":"10.1007\/s11172-018-2278-1","article-title":"Multicomponent transformation of salicylaldehydes, 2-aminoprop-1-ene-1,1,3-tricarbonitrile, and pyrazolin-5-ones into substituted 2,4-diamino-5-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitriles","volume":"67","author":"Elinson","year":"2018","journal-title":"Russ. Chem. Bull."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1073","DOI":"10.1007\/s00706-019-02388-5","article-title":"Selective multicomponent \u2018one-pot\u2019 approach to the new 5-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)chromeno[2,3-b]pyridine scaffold in pyridine\u2013ethanol catalyst\/solvent system","volume":"150","author":"Elinson","year":"2019","journal-title":"Monatshefte Chem.\/Chem. Mon."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"4171","DOI":"10.1002\/ejoc.201900240","article-title":"Pot-, Atom- and Step-Economic (PASE) Multicomponent Approach to the 5-(Dialkylphosphonate)-Substituted 2,4-Diamino-5H-Chromeno[2,3-b]Pyridine Scaffold","volume":"2019","author":"Elinson","year":"2019","journal-title":"Eur. J. Org. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"617","DOI":"10.1007\/s11030-019-09968-x","article-title":"Pot, atom and step economic (PASE) assembly of salicylaldehydes, malononitrile dimer and 4-hydroxypyridine-2(1H)-ones into medicinally relevant 5H-chromeno[2,3-b]pyridine scaffold","volume":"24","author":"Elinson","year":"2019","journal-title":"Mol. Divers."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"384","DOI":"10.1016\/j.mencom.2018.07.014","article-title":"Pseudo six-component stereoselective synthesis of 2,4,6-triaryl-3,3,5,5-tetracyanopiperidines","volume":"28","author":"Vereshchagin","year":"2018","journal-title":"Mendeleev Commun."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/j.jfluchem.2018.06.008","article-title":"A facile and efficient multicomponent approach to 5-[5-hydroxy-3-(trifluoromethyl)-1H-pyrazol-4-yl]-5H-chromeno[2,3-b]pyridines","volume":"213","author":"Elinson","year":"2018","journal-title":"J. Fluor. Chem."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1002\/open.201800207","article-title":"Homophtalonitrile for Multicomponent Reactions: Syntheses and Optical Properties of o-Cyanophenyl- or Indol-3-Yl-SubstitutedChromeno[2,3-c]Isoquinolin-5-Amines","volume":"8","author":"Festa","year":"2019","journal-title":"ChemistryOpen"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"451","DOI":"10.1016\/j.mencom.2017.09.006","article-title":"Sequential three-component reaction of homophthalonitrile, salicylaldehydes and nitromethane","volume":"27","author":"Festa","year":"2017","journal-title":"Mendeleev Commun."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"179","DOI":"10.1007\/s11030-009-9152-x","article-title":"A new one-pot three-component synthesis of 2,4-diamino-5H-chromeno[2,3-b] pyridine-3-carbonitrile derivatives","volume":"14","author":"Shaabani","year":"2010","journal-title":"Mol. Divers."},{"key":"ref_60","doi-asserted-by":"crossref","unstructured":"Lopes, D., Oliveira-Pinto, S., Pontes, O., Sampaio-Marques, B., Costa, M.D., Carvalho, L., Gon\u00e7alves, C.S., Costa, B.M., Maciel, P., and Ludovico, P. (2020). Unravelling the anticancer potential of functionalized chromeno[2,3-b]pyridines for breast cancer treatment. Bioorg. Chem., 100.","DOI":"10.1016\/j.bioorg.2020.103942"},{"key":"ref_61","first-page":"258","article-title":"Multicomponent Synthesis of Novel Penta-Heterocyclic Ring Systems Incorporating a Benzopyranopyridine Scaffold","volume":"46","author":"Gomha","year":"2014","journal-title":"Synthesis"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"413","DOI":"10.1590\/S0103-50532010000300003","article-title":"On the one pot syntheses of chromeno[4,3-b]pyridine-3-carboxylate and chromeno[3,4-c]pyridine-3-carboxylate and dihydropyridines","volume":"21","author":"Salazar","year":"2010","journal-title":"J. Braz. Chem. Soc."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"1878","DOI":"10.1007\/BF00843814","article-title":"Reaction of benzylideneaniline with some unsaturated compounds","volume":"12","author":"Povarov","year":"1963","journal-title":"Russ. Chem. Bull."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"14174","DOI":"10.1021\/acs.joc.0c01699","article-title":"Intramolecular Povarov Reactions for the Synthesis of Chromenopyridine Fused 2-Pyridone Polyheterocycles Binding to \u03b1-Synuclein and Amyloid-\u03b2 Fibrils","volume":"85","author":"Adolfsson","year":"2020","journal-title":"J. Org. Chem."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"372","DOI":"10.3998\/ark.5550190.p008.754","article-title":"Ultrasound promoted synthesis of chromeno[2,3-b]pyridines and their evaluation as lipid peroxidation inhibitors","volume":"2014","author":"Dimitriadou","year":"2014","journal-title":"Arkivoc"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"1624","DOI":"10.1007\/s10593-014-1632-y","article-title":"Synthesis of Some Novel Heteroannelated Chromones by Basic Rearrangement of 6-Methylchromone-3-Carbonitrile","volume":"50","author":"Ibrahim","year":"2015","journal-title":"Chem. Heterocycl. Compd."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"859","DOI":"10.1002\/jhet.2355","article-title":"Studies on the Chemical Transformations of 6-Methylchromone-3-Carbonitrile under Nucleophilic Conditions","volume":"53","author":"Ibrahim","year":"2016","journal-title":"J. Heterocycl. Chem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"186","DOI":"10.1002\/ejoc.201601138","article-title":"Reactions of 3-Acylchromones with Heterocyclic Ketene Aminals: One-Pot Synthesis and Phosphatase Inhibitory Activity of Fused Pyridine Derivatives","volume":"2017","author":"Savych","year":"2017","journal-title":"Eur. J. Org. Chem."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"818","DOI":"10.2478\/s11696-010-0072-0","article-title":"Novel benzopyranopyridine derivatives of 2-amino-3-formylchromone","volume":"64","author":"Siddiqui","year":"2010","journal-title":"Chem. Pap."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1016\/j.optmat.2015.11.022","article-title":"Synthesis, optical and photoelectrical characterizations of the novel 10-chloro-6H,8H-dichromeno[2,3-b:3\u2032,4\u2032-e]pyridine-6,8-dione (CDPD) and its photodiode application","volume":"51","author":"Ibrahim","year":"2016","journal-title":"Opt. Mater."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"7766","DOI":"10.1002\/slct.201801089","article-title":"Water-PEG-400 Mediated an Efficient One-Pot Eco-Friendly Synthesis of Functionalized Isoxazole Substituted Chromeno[2,3-b]pyridine-3-carboxylate Derivatives","volume":"3","author":"Ponduri","year":"2018","journal-title":"ChemistrySelect"},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"1960","DOI":"10.1016\/j.tetlet.2013.01.122","article-title":"A Three-Component Synthesis of Benzochromenodiazocines and Chromenopyridines","volume":"54","author":"Dolatkhah","year":"2013","journal-title":"Tetrahedron Lett."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"4981","DOI":"10.1021\/acs.joc.8b00099","article-title":"Three-Component Site-Selective Synthesis of Highly Substituted 5H-Chromeno-[4,3-b]Pyridines","volume":"83","author":"Zhang","year":"2018","journal-title":"J. Org. Chem."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"96","DOI":"10.1007\/s10593-018-2238-6","article-title":"An alternative approach to the synthesis of 5H-chromeno[4,3-b]pyridin-5-one system using the cleavage of 5H,9H-pyrano[2\u2032,3\u2032:5,6]chromeno[4,3-b]pyridine-5,9-diones with binucleophiles","volume":"54","author":"Lozinski","year":"2018","journal-title":"Chem. Heterocycl. Comp."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"1838","DOI":"10.1002\/jhet.3912","article-title":"Microwave-assisted synthesis and heterocyclic functionalization of chromenopyridines on calixarene scaffold","volume":"57","author":"Ali","year":"2020","journal-title":"J. Heterocycl. Chem."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"3201","DOI":"10.1016\/j.ejmech.2011.04.029","article-title":"Synthesis of 2,4-diaryl chromenopyridines and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship","volume":"46","author":"Thapa","year":"2011","journal-title":"Eur. J. Med. Chem."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"1769","DOI":"10.5012\/bkcs.2012.33.5.1769","article-title":"2,4-Diaryl-5,6-Dihydro-1,10-Phenanthrolines with Furyl or Thienyl Moiety at 4-Position: Synthesis, Topoisomerase I and II Inhibitory Activity, and Cytotoxicity","volume":"33","author":"Thapa","year":"2012","journal-title":"Bull. Korean Chem. Soc."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"6454","DOI":"10.1016\/j.bmc.2015.08.018","article-title":"Design and synthesis of conformationally constrained hydroxylated 4-phenyl-2-aryl chromenopyridines as novel and selective topoisomerase II-targeted antiproliferative agents","volume":"23","author":"Thapa","year":"2015","journal-title":"Bioorg. Med. Chem."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"1100","DOI":"10.1021\/jm501023q","article-title":"A Series of Novel Terpyridine-Skeleton Molecule Derivants Inhibit Tumor Growth and Metastasis by Targeting Topoisomerases","volume":"58","author":"Kwon","year":"2015","journal-title":"J. Med. Chem."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"1909","DOI":"10.1016\/j.bmc.2018.02.035","article-title":"Synthesis and SAR study of new hydroxy and chloro-substituted 2,4-diphenyl 5H-chromeno[4,3-b]pyridines as selective topoisomerase II\u03b1-targeting anticancer agents","volume":"26","author":"Magar","year":"2018","journal-title":"Bioorg. Med. Chem."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"34065","DOI":"10.1021\/acsomega.1c05347","article-title":"Green Protocol for the Novel Synthesis of Thiochromeno[4,3-b]Pyridine and Chromeno[4,3-b]Pyridine Derivatives Utilizing a High-Pressure System","volume":"6","author":"Behbehani","year":"2021","journal-title":"ACS Omega"},{"key":"ref_82","first-page":"191","article-title":"Synthesis of New Chromeno[4,3-b]pyrazolo[4,3-e]pyridines Derivatives with Antimicrobial Evaluation","volume":"51","year":"2013","journal-title":"J. Heterocycl. Chem."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"1027","DOI":"10.1080\/00397910802463878","article-title":"Efficient one-pot synthesis of 4-aryl-3-cyano-2,5-dihydro-1H-indeno[1,2-b]pyridin-2-one and 4-aryl-3-cyano-1,2,5,6-tetrahydrobenzo[h] quinolin-2-one derivatives under solvent-free conditions","volume":"39","author":"Rong","year":"2009","journal-title":"Synth. Commun."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"999","DOI":"10.1016\/j.bmc.2017.12.032","article-title":"Discovery of chromenes as inhibitors of macrophage migration inhibitory factor","volume":"26","author":"Kok","year":"2018","journal-title":"Bioorg. Med. Chem."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"4381","DOI":"10.1007\/s00044-012-9978-0","article-title":"Synthesis, characterization and biological evaluation of some pyridine and quinoline fused chromenone derivatives","volume":"21","author":"Patel","year":"2012","journal-title":"Med. Chem. Res."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"15705","DOI":"10.1039\/c3ra41569d","article-title":"Molecular iodine catalyzed one-pot multicomponent reactions for the synthesis of dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-ones","volume":"3","author":"Pal","year":"2013","journal-title":"RSC Adv."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"4745","DOI":"10.1007\/s00044-013-0489-4","article-title":"Synthesis of a new series of 2-(2-oxo-2H-chromen-3-yl)-5H-chromeno[4,3-b]pyridin-5-ones by two facile methods and evaluation of their antimicrobial activity","volume":"22","author":"Patel","year":"2013","journal-title":"Med. Chem. Res."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"2345","DOI":"10.1016\/j.tetlet.2012.02.114","article-title":"Michael Initiated Ring Closure (MIRC) reaction on in situ generated benzylidenecyclohexane-1,3-diones for the construction of chromeno[3,4-b]quinoline derivatives","volume":"53","author":"Khan","year":"2012","journal-title":"Tetrahedron Lett."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"6418","DOI":"10.1016\/j.tetlet.2012.09.051","article-title":"A simple and expedient synthesis of functionalized pyrido[2,3-c] coumarin derivatives using molecular iodine catalyzed three-component reaction","volume":"53","author":"Khan","year":"2012","journal-title":"Tetrahedron Lett."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"327","DOI":"10.3184\/174751913X13667064139394","article-title":"An Efficient Protocol for Multicomponent Synthesis of 1H-Chromeno[4,3-b]Pyridin-5(4H)-Ones Derivatives","volume":"37","author":"Chen","year":"2013","journal-title":"J. Chem. Res."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"2795","DOI":"10.1002\/jhet.3988","article-title":"A facile one-step synthesis of chromeno[4,3-b]pyridine derivatives promoted by niobium pentachloride","volume":"57","author":"Oshiro","year":"2020","journal-title":"J. Heterocycl. Chem."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"2206","DOI":"10.1016\/j.tetlet.2012.02.077","article-title":"An efficient green protocol for the synthesis of coumarin fused highly decorated indenodihydropyridyl and dihydropyridyl derivatives","volume":"53","author":"Paul","year":"2012","journal-title":"Tetrahedron Lett."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"1839","DOI":"10.1007\/s10593-013-1217-1","article-title":"Solvent-free synthesis of novel 5-oxo-5H-chromeno [4,3-b]pyridine derivatives","volume":"48","author":"Motamedi","year":"2013","journal-title":"Chem. Heterocyc. Compd."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"6517","DOI":"10.1016\/j.tetlet.2013.09.089","article-title":"Synthesis of methyl substituted [5,6]- and [7,8]-fused pyridocoumarins via the iodine-catalyzed reaction of aminocoumarins with n-butyl vinyl ether","volume":"54","author":"Symeonidis","year":"2013","journal-title":"Tetrahedron Lett."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"1564","DOI":"10.1016\/j.tetlet.2014.01.078","article-title":"One-pot access to pyridocoumarins via Povarov-hydrogen transfer cascade under auto-tandem catalysis of iodine in aqueous micelles","volume":"55","author":"Ganguly","year":"2014","journal-title":"Tetrahedron Lett."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"9796","DOI":"10.1021\/jm501266w","article-title":"Lead Optimization and Modulation of HERG Activity in a Series of Aminooxazoline Xanthene \u03b2-Site Amyloid Precursor Protein Cleaving Enzyme (BACE1) Inhibitors","volume":"57","author":"Epstein","year":"2014","journal-title":"J. Med. Chem."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"210","DOI":"10.1021\/ml500458t","article-title":"An Orally Available BACE1 Inhibitor That Affords Robust CNS A\u03b2 Reduction without Cardiovascular Liabilities","volume":"6","author":"Cheng","year":"2015","journal-title":"ACS Med. Chem. Lett."},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"9156","DOI":"10.1021\/jm300598e","article-title":"Structure- and Property-Based Design of Aminooxazoline Xanthenes as Selective, Orally Efficacious, and Cns Penetrable BACE Inhibitors for the Treatment of Alzheimers Disease","volume":"55","author":"Huang","year":"2012","journal-title":"J. Med. Chem."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"9811","DOI":"10.1021\/jm5012676","article-title":"Inhibitors of \u03b2-Site Amyloid Precursor Protein Cleaving Enzyme (BACE1): Identification of (S)-7-(2-Fluoropyridin-3-yl)-3-((3-methyloxetan-3-yl)ethynyl)-5\u2032H-Spiro[Chromeno[2,3-b]pyridine-5,4\u2032-oxazol]-2\u2032-amine (AMG-8718)","volume":"57","author":"Dineen","year":"2014","journal-title":"J. Med. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/13\/3004\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T15:03:53Z","timestamp":1760108633000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/13\/3004"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,6,25]]},"references-count":99,"journal-issue":{"issue":"13","published-online":{"date-parts":[[2024,7]]}},"alternative-id":["molecules29133004"],"URL":"https:\/\/doi.org\/10.3390\/molecules29133004","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,6,25]]}}}