{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,5]],"date-time":"2026-04-05T08:23:08Z","timestamp":1775377388752,"version":"3.50.1"},"reference-count":62,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2020,11,11]],"date-time":"2020-11-11T00:00:00Z","timestamp":1605052800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","award":["CB-2016-28562"],"award-info":[{"award-number":["CB-2016-28562"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A novel strategy via the triple process (multicomponent reactions (MCR)-domino)\/tandem was developed for the synthesis of restricted and constrained bis-1,2,3-triazole-linked pyrrolo[3,4-b]pyridine peptidomimetics dimers in overall yields of 20\u201355%. This strategy allows the construction of six heterocycles in two stages of the reaction.<\/jats:p>","DOI":"10.3390\/molecules25225246","type":"journal-article","created":{"date-parts":[[2020,11,11]],"date-time":"2020-11-11T20:20:33Z","timestamp":1605126033000},"page":"5246","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthesis of Polyheterocyclic Dimers Containing Restricted and Constrained Peptidomimetics via IMCR-Based Domino\/Double CuAAC Click Strategy"],"prefix":"10.3390","volume":"25","author":[{"given":"Shrikant G.","family":"Pharande","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica, Divisi\u00f3n de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S\/N, Col. 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Today"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"278","DOI":"10.1002\/med.20107","article-title":"Click chemistry reactions in medicinal chemistry: Applications of the 1,3-dipolar cycloaddition between azides and alkynes","volume":"28","author":"Tron","year":"2008","journal-title":"Med. Res. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"464","DOI":"10.1016\/j.ejmech.2013.05.016","article-title":"Dimeric and trimeric triazole based molecules as a new class of Hsp90 molecular chaperone inhibitors","volume":"65","author":"Terracciano","year":"2013","journal-title":"Eur. J. Med. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"562","DOI":"10.1016\/j.ejmech.2018.08.010","article-title":"MMB triazole analogs are potent NF-\u03baB inhibitors and anti-cancer agents against both hematological and solid tumor cells","volume":"157","author":"Janganati","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"8578","DOI":"10.1021\/acs.jmedchem.9b00963","article-title":"Triazole Bridged Flavonoid Dimers as Potent, Nontoxic, and Highly Selective Breast Cancer Resistance Protein (BCRP\/ABCG2) Inhibitors","volume":"62","author":"Zhu","year":"2019","journal-title":"J. Med. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"638","DOI":"10.1039\/c1md00071c","article-title":"Triazole-substituted N-hydroxyindol-2-carboxylates as inhibitors of isoform 5 of human lactate dehydrogenase (hLDH5)","volume":"2","author":"Granchi","year":"2011","journal-title":"Med. Chem. Commun."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"230","DOI":"10.2174\/1573406413666171120165226","article-title":"Synthesis, Characterization and Biological Activities of New Symmetric Bis-1,2,3-Triazoles with Click Chemistry","volume":"14","author":"Celik","year":"2018","journal-title":"Med. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"689","DOI":"10.1016\/j.molstruc.2019.06.018","article-title":"Design and microwave-assisted synthesis of dimers of 1,5-benzodiazepine-1,2,3-triazole hybrids bearing alkyl\/aryl spacers and their biological assessment","volume":"1195","author":"Jaafar","year":"2019","journal-title":"J. Mol. Struct."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1977","DOI":"10.1080\/00397911.2015.1056796","article-title":"Synthesis, Characterization, and Antimicrobial Potential of Some 1,4-Disubstituted 1,2,3-Bistriazoles","volume":"45","author":"Kaushik","year":"2015","journal-title":"Synth. Commun."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1016\/j.ejmech.2019.04.007","article-title":"Novel symmetric bis-benzimidazoles: Synthesis, DNA\/RNA binding and antitrypanosomal activity","volume":"173","author":"Popov","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_13","first-page":"13","article-title":"Bivalent Dopamine D2 Receptor Ligands: Synthesis and Binding Properties","volume":"54","author":"Gmeiner","year":"2011","journal-title":"J. Med. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1007\/7081_2011_67","article-title":"\u201cClick-Triazole\u201d Coordination Chemistry: Exploiting 1,4-Disubstituted-1,2,3-Triazoles as Ligands","volume":"Volume 28","year":"2012","journal-title":"Click Triazoles. Topics in Heterocyclic Chemistry"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2522","DOI":"10.1039\/c3cs60386e","article-title":"Beyond click chemistry\u2014supramolecular interactions of 1,2,3-triazoles","volume":"43","author":"Schulzeab","year":"2014","journal-title":"Chem. Soc. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"7343","DOI":"10.1021\/jm4008906","article-title":"Optimization of activity, selectivity, and liability profiles in 5-oxopyrrolopyridine DPP4 inhibitors leading to clinical candidate (Sa)-2-(3-(aminomethyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)-N,N-dimethylacetamide (BMS-767778)","volume":"56","author":"Devasthale","year":"2013","journal-title":"J. Med. Chem."},{"key":"ref_17","unstructured":"Unverferth, K., Arnold, T., Lankau, H., Rostock, A., Tober, C., Dost, R., Rundfeldt, C., and Gasparic, A. (2020, October 29). 6,7-Dihydro-Pirrolo[3,4-b]Pyridin-5-One With an Anticonvulsive Action and Methods for the Same World Intellectual WO 02\/18381 A1, Geneva, Switzerland. Available online: https:\/\/worldwide.espacenet.com\/patent\/search\/family\/007653968\/publication\/WO0218381A1?q=WO0218381."},{"key":"ref_18","unstructured":"Chang, H.-F., Chapdelaine, M., Dembofsky, B.T., Herzog, K.J., Horschler, C., and Schmiesing, R.J. (2020, October 29). Compounds and Uses Thereof\u2212848. Patent Cooperation Treaty (PCT). WO2008\/155572 A1, 2008. Geneva: World Intellectual Property Organization. Property Organization. A: Geneva, Switzerland. Available online: https:\/\/worldwide.espacenet.com\/patent\/search\/family\/040084145\/publication\/WO2008155572A2?q=WO2008155572A2."},{"key":"ref_19","unstructured":"Pajouhesh, H., Hollan, R., Zhou, Y., Zhu, Y., Grimwood, M.E., and Chahal, N. (2012). Bisaylsufone and Dialkylarylsulfone Compounds as Calcium Channel Blockers. (WO2012\/061926 A1), Patent Cooperation Treaty (PCT), Available online: https:\/\/worldwide.espacenet.com\/patent\/search\/family\/046050268\/publication\/WO2012061926A1?q=WO2012061926A1."},{"key":"ref_20","unstructured":"Lindsley, C.W., Conn, P.J., Wood, M.R., Hopkins, C.R., Melancon, B.J., Poslusney, M.S., and Engers, D.W. (2013). Substituted 2-(4-heterocyclylbenzyl)Isoindolin-1-One Analogs as Positive Allosteric Modulators of Muscarinic Acethylcholine ReceptorM1. (WO2013\/063549 A1), Patent Cooperation Treaty (PCT), Available online: https:\/\/worldwide.espacenet.com\/patent\/search\/family\/048168630\/publication\/WO2013063549A1?q=pn%3DWO2013063549A1."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1995","DOI":"10.1021\/acschemneuro.7b00155","article-title":"Identification and Profiling of a Selective and Brain Penetrant Radioligand for in Vivo Target Occupancy Measurement of Casein Kinase 1 (CK1) Inhibitors","volume":"8","author":"Wager","year":"2017","journal-title":"ACS Chem. Neurosci."},{"key":"ref_22","first-page":"54","article-title":"Neuropharmacological activity of newly synthesized derivatives of valin","volume":"38","author":"Tantcheva","year":"2006","journal-title":"Bulg. Chem. Comm."},{"key":"ref_23","first-page":"133","article-title":"Structure-activity relationships of new L-Valine derivatives with neuropharmacological effects","volume":"41","author":"Tsekova","year":"2009","journal-title":"Bulg. Chem. Comm."},{"key":"ref_24","first-page":"262","article-title":"New L- valine peptide mimetics as potential neuropharmacological agents","volume":"44","author":"Tancheva","year":"2012","journal-title":"Bulg. Chem. Comm."},{"key":"ref_25","first-page":"637","article-title":"The influence of solvents on the molecular structure and biological activity Of N,N\/-Bis(N-nicotinoyl-l-valyl)-diaminohexane","volume":"48","author":"Tsekova","year":"2013","journal-title":"J. Chem. Technol. Metall."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"2260","DOI":"10.1107\/S0108270196005045","article-title":"Anticancer and Antifertility Agents. II. N,N\u2019-Hexamethylenebis(3-pyridinecarboxamide)","volume":"52","author":"Liu","year":"1996","journal-title":"Acta Crystallogr. Sect. C: Cryst. Struct. Commun."},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Lubell, W.D. (2017). Topics in Heterocyclic Chemistry: Peptidomimetics I, Springer.","DOI":"10.1007\/978-3-319-49124-0"},{"key":"ref_28","first-page":"199","article-title":"Cyclic Peptidomimetics and Pseudopeptides from Multicomponent Reactions","volume":"Volume 23","author":"Orru","year":"2010","journal-title":"Synthesis of Heterocycles via Multicomponent Reactions I. Topics in Heterocyclic Chemistry"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"6234","DOI":"10.1002\/anie.201006515","article-title":"Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity","volume":"50","author":"Ruijter","year":"2011","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Tietze, L.F. (2013). Multicomponent Domino Process: Rational Design and Serendipity. Domino Reactions: Concepts for Efficient Organic Synthesis, Wiley-VCH Verlag GmbH & Co. KGaA, Boschstr.","DOI":"10.1002\/9783527671304"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"877","DOI":"10.1021\/ol007055q","article-title":"A Novel Multicomponent Synthesis of Polysubstituted 5-Aminooxazole and Its New Scaffold-Generating Reaction to Pyrrolo[3,4-b]pyridine","volume":"3","author":"Sun","year":"2001","journal-title":"Org. Lett."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"546","DOI":"10.3389\/fchem.2019.00546","article-title":"Synthesis of Tris-Heterocycles via a Cascade IMCR\/Aza Diels-Alder + CuAAC Strategy","volume":"7","author":"Pharande","year":"2019","journal-title":"Front. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"5245","DOI":"10.1016\/j.tetlet.2011.07.134","article-title":"A short microwave-assisted synthesis of tetrahydroisoquinolin-pyrrolopyridinones by a triple process: Ugi-3CR\u2013aza Diels\u2013Alder\/S-oxidation\/Pummerer","volume":"52","year":"2011","journal-title":"Tetrahedron Lett."},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Islas-J\u00e1come, A., C\u00e1rdenas-Galindo, L.E., Jerezano, A.V., Tamariz, J., Gonz\u00e1lez-Zamora, E., and G\u00e1mez-Monta\u00f1o, R. (2012). Synthesis of Nuevamine Aza-Analogues by a Sequence: I-MCR\u2013Aza-Diels\u2013Alder\u2013Pictet\u2013Spengler. Synlett, 2951\u20132956.","DOI":"10.1055\/s-0032-1317622"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"6470","DOI":"10.1039\/c3ob41349g","article-title":"Synthesis of 3-tetrazolylmethyl-azepino[4,5-b]indol-4-ones in two reaction steps: (Ugi-azide\/N-acylation\/SN2)\/free radical cyclization and docking studies to a 5-Ht6 model","volume":"11","author":"Robles","year":"2013","journal-title":"Org. Biomol. Chem."},{"key":"ref_36","first-page":"49","article-title":"aper Synthesis of 2-Tetrazolylmethyl-2,3,4,9-tetrahydro-1H-\u03b2-carbolines by a One-Pot Ugi-Azide\/Pictet\u2013Spengler Process","volume":"46","year":"2014","journal-title":"Synthesis"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2333","DOI":"10.1016\/j.bmcl.2016.03.036","article-title":"Synthesis of azepino[4,5-b]indol-4-ones via MCR\/free radical cyclization and in vitro\u2013in silico studies as 5-Ht6R ligands","volume":"26","author":"Robles","year":"2016","journal-title":"Bioorg. Med. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"943","DOI":"10.1021\/acsomega.6b00281","article-title":"G\u00e1mez-Monta\u00f1o, R. Synthesis of 2-Tetrazolylmethyl-isoindolin-1-ones via a One-Pot Ugi-Azide\/(N-Acylation\/exo-Diels\u2013Alder)\/Dehydration Process","volume":"1","year":"2016","journal-title":"ACS Omega"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1600","DOI":"10.1039\/C7NJ03829A","article-title":"Synthesis of 1\u2032-tetrazolylmethyl-spiro[pyrrolidine-3,3\u2032-oxindoles] via two coupled one-pot processes Ugi-azide\/Pictet\u2013Spengler and oxidative spiro-rearrangement","volume":"42","author":"Unnamatla","year":"2018","journal-title":"New J. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"5177","DOI":"10.1021\/acsomega.8b00170","article-title":"Solvent- and Catalyst-Free One-Pot Green Bound-Type Fused Bis-Heterocycles Synthesis via Groebke\u2013Blackburn\u2013Bienaym\u00e9 Reaction\/SNAr\/Ring-Chain Azido-Tautomerization Strategy","volume":"3","author":"Pharande","year":"2018","journal-title":"ACS Omega"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"10576","DOI":"10.1021\/acs.joc.6b01576","article-title":"Multicomponent One-Pot Synthesis of 3-Tetrazolyl and 3-Imidazo[1,2-a]pyridin Tetrazolo[1,5-a]quinolines","volume":"81","author":"Unnamatla","year":"2016","journal-title":"J. Org. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"4355","DOI":"10.1016\/j.tetlet.2018.10.062","article-title":"Ultrasound-assisted green one-pot synthesis of linked bis-heterocycle peptidomimetics via IMCR\/post-transformation\/tandem strategy","volume":"59","author":"Kaveti","year":"2018","journal-title":"Tetrahedron Lett."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"176","DOI":"10.1021\/co4001259","article-title":"One-Pot Synthesis of Coumarin-3-carboxamides Containing a Triazole Ring via an Isocyanide-Based Six-Component Reaction","volume":"16","author":"Shaabani","year":"2014","journal-title":"ACS Comb. Sci."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2167","DOI":"10.1016\/j.tetlet.2018.04.050","article-title":"One-pot synthesis of 3-triazolyl-quinolin-2-(1H)-ones via sequential Ugi-\u201cclick\u201d-Knoevenagel condensations","volume":"59","author":"Qian","year":"2018","journal-title":"Tetrahedron Lett."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"8360","DOI":"10.1016\/j.tet.2011.08.061","article-title":"A novel one-pot pseudo-four-component isocyanide-based reaction: An unexpected approach for the synthesis of tetrahydrodiisoindoloquinoxalines and tetrahydrobenzodiisoindoloquinoxalines","volume":"67","author":"Shaabani","year":"2011","journal-title":"Tetrahedron"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"25924","DOI":"10.1039\/c3ra44496a","article-title":"Efficient one-pot synthesis of mono and bis-N-cyclohexyl-3-alkyl(aryl)-quinoxaline-2-amines using N-halo catalysts","volume":"3","author":"Amiri","year":"2013","journal-title":"RSC Advances"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1519","DOI":"10.3390\/molecules20011519","article-title":"Synthesis of Novel bis-1,5-Disubstituted-1H-Tetrazoles by an Efficient Catalyst-Free Ugi-Azide Repetitive Process","volume":"20","year":"2015","journal-title":"Molecules"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1396","DOI":"10.1002\/jhet.2720","article-title":"Expedient Access to Novel Bis-tetrazolopiperazines via Ugi-azide Reactions","volume":"54","author":"Ghandi","year":"2016","journal-title":"J. Heterocycl. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"483","DOI":"10.1021\/acs.orglett.9b04239","article-title":"Organocatalytic Double Ugi Reaction with Statistical Amplification of Product Enantiopurity: A Linker Cleavage Approach To Access Highly Enantiopure Ugi Products","volume":"22","author":"Feng","year":"2020","journal-title":"Org. Lett."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"958","DOI":"10.1021\/cc050099b","article-title":"A Concise and Diversity-Oriented Strategy for the Synthesis of Benzofurans and Indoles via Ugi and Diels\u2212Alder Reactions","volume":"7","author":"Lu","year":"2005","journal-title":"J. Comb. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"4905","DOI":"10.1039\/c4ob00444b","article-title":"Experimental and theoretical studies on the effect of the oxo group in 1,4-benzodiazepines","volume":"12","author":"Pertejo","year":"2014","journal-title":"Org. Biomol. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"627","DOI":"10.1016\/j.tetlet.2014.12.018","article-title":"Synthesis of cyclic analogues of hexamethylenebis(3-pyridine)amide (HMBPA) in a one-pot process","volume":"56","year":"2015","journal-title":"Tetrahedron Lett."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"3496","DOI":"10.1016\/j.tetlet.2016.06.099","article-title":"Jim\u00e9nez-Halla, J.O.C. G\u00e1mez-Monta\u00f1o, R. Selective reaction route in the construction of the pyrrolo[3,4-b]pyridin-5-one core from a variety of 5-aminooxazoles and maleic anhydride. A DFT study","volume":"57","year":"2016","journal-title":"Tetrahedron Lett."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"2560","DOI":"10.1021\/ja017563a","article-title":"Ammonium Chloride-Promoted Four-Component Synthesis of Pyrrolo[3,4-b]pyridin-5-one","volume":"124","author":"Janvier","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"2227","DOI":"10.1021\/cr010289i","article-title":"Kobayashi S. Scandium triflate in organic synthesis","volume":"102","author":"Kobayashi","year":"2002","journal-title":"Chem. Rev."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"2596","DOI":"10.1002\/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4","article-title":"A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective \u201cLigation\u201d of Azides and Terminal Alkynes","volume":"41","author":"Rostovtsev","year":"2002","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"3057","DOI":"10.1021\/jo011148j","article-title":"Peptidotriazoles on Solid Phase:\u2009[1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides","volume":"67","author":"Christensen","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref_58","doi-asserted-by":"crossref","unstructured":"Bock, V.D., Hiemstra, H., and van Maarseveen, J.H. (2006). CuI -Catalyzed Alkyne\u2013Azide \u201cClick\u201d Cycloadditions from a Mechanistic and Synthetic Perspective. Eur. J. Org. Chem., 51\u201368.","DOI":"10.1002\/ejoc.200500483"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1302","DOI":"10.1039\/b904091a","article-title":"Copper-catalyzed azide\u2013alkynecycloaddition (CuAAC) and beyond: New reactivity of copper(i) acetylides","volume":"39","author":"Hein","year":"2010","journal-title":"Chem. Soc. Rev."},{"key":"ref_60","doi-asserted-by":"crossref","unstructured":"Lauria, A., Delisi, R., Mingoia, F., Terenzi, A., Martorana, A., Barone, G., and Almerico, A.M. (2014). 1,2,3-Triazole in Heterocyclic Compounds, Endowed with Biological Activity, through 1,3-Dipolar Cycloadditions. Eur. J. Org. Chem., 3289\u20133306.","DOI":"10.1002\/ejoc.201301695"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"15998","DOI":"10.1021\/ja054114s","article-title":"Ruthenium-Catalyzed Cycloaddition of Alkynes and Organic Azides","volume":"127","author":"Zhang","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"14726","DOI":"10.1021\/acs.chemrev.6b00466","article-title":"Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications","volume":"116","author":"Johansson","year":"2016","journal-title":"Chem. Rev."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/22\/5246\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T10:31:53Z","timestamp":1760178713000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/22\/5246"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,11,11]]},"references-count":62,"journal-issue":{"issue":"22","published-online":{"date-parts":[[2020,11]]}},"alternative-id":["molecules25225246"],"URL":"https:\/\/doi.org\/10.3390\/molecules25225246","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,11,11]]}}}