{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,17]],"date-time":"2026-03-17T10:57:22Z","timestamp":1773745042822,"version":"3.50.1"},"reference-count":69,"publisher":"Wiley","issue":"33","license":[{"start":{"date-parts":[[2020,8,7]],"date-time":"2020-08-07T00:00:00Z","timestamp":1596758400000},"content-version":"am","delay-in-days":366,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#am"},{"start":{"date-parts":[[2019,8,7]],"date-time":"2019-08-07T00:00:00Z","timestamp":1565136000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100006545","name":"National Institute on Minority Health and Health Disparities","doi-asserted-by":"publisher","award":["G12MD007603"],"award-info":[{"award-number":["G12MD007603"]}],"id":[{"id":"10.13039\/100006545","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100006545","name":"National Institute on Minority Health and Health Disparities","doi-asserted-by":"publisher","award":["G12MD007592"],"award-info":[{"award-number":["G12MD007592"]}],"id":[{"id":"10.13039\/100006545","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Org Chem"],"published-print":{"date-parts":[[2019,9,8]]},"abstract":"<jats:p>1,4\u2010Triazolyl combretacoumarins have been prepared by linking the trimethoxyarene unit of combretastatin A4 with coumarins, via a 1,2,3\u2010triazole. For this, 4\u2010azidocoumarins were accessed by a sequential two\u2010step, one\u2010pot reaction of 4\u2010hydroxycoumarins with (benzotriazol\u20101\u2010yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), followed by reaction with NaN<jats:sub>3<\/jats:sub>. In the reaction with BOP, a coumarin\u2010derived phosphonium ion intermediate seems to form, leading to an <jats:italic>O<\/jats:italic><jats:sup>4<\/jats:sup>\u2010(benzotriazolyl)coumarin derivative. For the CuAAC reaction of azidocoumarins with 5\u2010ethynyl\u20101,2,3\u2010trimethoxybenzene, catalytic [(MeCN)<jats:sub>4<\/jats:sub>Cu]PF<jats:sub>6<\/jats:sub> in CH<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub>\/MeOH with 2,6\u2010lutidine, at 50 <jats:sup>o<\/jats:sup>C, was suitable. The 4\u2010azidocoumarins were less reactive as compared to PhN<jats:sub>3<\/jats:sub> and the NBO coefficients of the azido groups were compared by DFT analysis. Compound solubility was a problem in biological assays. On the basis of the biological and solubility data of one 1,4\u2010triazolyl combretacoumarin, four analogs lacking one or two methoxy groups were synthesized. Reactivity differences among the phenylacetylenes were noted and the NBO coefficients of the alkynes were compared by DFT analysis. In cytotoxicity assays, 1\u2010phenyl\u20104\u2010(3,4,5\u2010trimethoxyphenyl)\u20101<jats:italic>H<\/jats:italic>\u20101,2,3\u2010triazole showed activity in CEM and MDA\u2010MB\u2010231 cell lines by apoptosis. The desmethoxy 6\u2010bromo\u20104\u2010(4\u2010(4\u2010methoxyphenyl)\u20101<jats:italic>H<\/jats:italic>\u20101,2,3\u2010triazol\u20101\u2010yl)\u20102<jats:italic>H<\/jats:italic>\u2010chromen\u20102\u2010one also showed cytotoxicity against the two cell lines, but this did not appear to be consistent with apoptosis. The antiviral activity of the compounds was unremarkable.<\/jats:p>","DOI":"10.1002\/ejoc.201900569","type":"journal-article","created":{"date-parts":[[2019,8,7]],"date-time":"2019-08-07T09:21:47Z","timestamp":1565169707000},"page":"5610-5623","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthesis and Evaluations of \u201c1,4\u2010Triazolyl Combretacoumarins\u201d and Desmethoxy Analogs"],"prefix":"10.1002","volume":"2019","author":[{"given":"Tashrique A.","family":"Khandaker","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry The City College of New York  160 Convent Avenue New York NY 10031 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jessica D.","family":"Hess","sequence":"additional","affiliation":[{"name":"Department of Biological Sciences Border Biomedical Research Center The University of Texas at El Paso  El Paso TX 79968 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Renato","family":"Aguilera","sequence":"additional","affiliation":[{"name":"Department of Biological Sciences Border Biomedical Research Center The University of Texas at El Paso  El Paso TX 79968 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Graciela","family":"Andrei","sequence":"additional","affiliation":[{"name":"Department of Microbiology and Immunology Rega Institute of Medical Research  Herestraat 49 \u2013 Box 1043 3000 Leuven Leuven Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Robert","family":"Snoeck","sequence":"additional","affiliation":[{"name":"Department of Microbiology and Immunology Rega Institute of Medical Research  Herestraat 49 \u2013 Box 1043 3000 Leuven Leuven Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dominique","family":"Schols","sequence":"additional","affiliation":[{"name":"Department of Microbiology and Immunology Rega Institute of Medical Research  Herestraat 49 \u2013 Box 1043 3000 Leuven Leuven Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Padmanava","family":"Pradhan","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry The City College of New York  160 Convent Avenue New York NY 10031 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9555-027X","authenticated-orcid":false,"given":"Mahesh K.","family":"Lakshman","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry The City College of New York  160 Convent Avenue New York NY 10031 USA"},{"name":"The Ph.D. Program in Chemistry The Graduate Center of the City University of New York  New York NY 10016 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2019,8,7]]},"reference":[{"key":"e_1_2_6_2_1","volume-title":"Advances in Structure and Activity Relationship of Coumarin Derivatives","author":"Penta S.","year":"2016"},{"key":"e_1_2_6_3_1","volume-title":"Coumarins: Biology, Applications and Mode of Action","author":"O'Kennedy R.","year":"1997"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/0306-3623(95)02112-4"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.2174\/0929867053507315"},{"key":"e_1_2_6_6_1","first-page":"16","volume":"4","author":"Bairagi S. H.","year":"2012","journal-title":"Int. J. Pharm. Res."},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1111\/cbdd.12629"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.15584\/ejcem.2017.2.12"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.2174\/1567201812666150702102800"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2015.07.010"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2015.08.033"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.2174\/1871520615666150101125503"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm960228q"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm9802158"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm970522y"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm801240d"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm101337v"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.7b00665"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2016.07.056"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.2174\/138955707782795647"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF01954881"},{"key":"e_1_2_6_22_1","doi-asserted-by":"crossref","first-page":"200","DOI":"10.1016\/S0026-895X(25)09364-2","volume":"34","author":"Lin C. M.","year":"1988","journal-title":"Mol. Pharmacol."},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi00443a031"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.drup.2006.04.003"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd3253"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1038\/srep28139"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2016.12.005"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2006.06.007"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2013.12.095"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7NJ01469D"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201100325"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm100245q"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.6b01128"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2010.07.032"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol0499203"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja054114s"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570310426"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF00810876"},{"key":"e_1_2_6_37_3","doi-asserted-by":"publisher","DOI":"10.1007\/BF00810043"},{"key":"e_1_2_6_37_4","doi-asserted-by":"publisher","DOI":"10.3987\/R-1987-01-0035"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm401002r"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1039\/a805574b"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja064682n"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo7021795"},{"key":"e_1_2_6_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo702558n"},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.1002\/0471142700.nc0122s36"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1039\/b905298d"},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo902342z"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules201018437"},{"key":"e_1_2_6_46_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB01170E"},{"key":"e_1_2_6_47_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB02334G"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1002\/cpnc.73"},{"key":"e_1_2_6_49_1","unstructured":"A. Nesturi Synthesis of 4\u2010Azidocoumarins and Their Use in Copper\u2010Catalyzed Azide\u2010Alkyne Cycloaddition Reactions MS Thesis. The City College of New York 2013.https:\/\/academicworks.cuny.edu\/cgi\/viewcontent.cgi?article=1519&context=cc_etds_theses."},{"key":"e_1_2_6_50_1","doi-asserted-by":"publisher","DOI":"10.1080\/00397918908050700"},{"key":"e_1_2_6_51_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2003-44346"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1996-5474"},{"key":"e_1_2_6_52_1","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.11.31"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1999-3570"},{"key":"e_1_2_6_53_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b02398"},{"key":"e_1_2_6_54_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)94157-7"},{"key":"e_1_2_6_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo011148j"},{"key":"e_1_2_6_56_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020715)114:14<2708::AID-ANGE2708>3.0.CO;2-0"},{"key":"e_1_2_6_57_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol047955x"},{"key":"e_1_2_6_58_1","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201600002"},{"key":"e_1_2_6_59_1","first-page":"1","volume":"1","author":"Lema C.","year":"2011","journal-title":"Curr. Cell Biochem."},{"key":"e_1_2_6_60_1","doi-asserted-by":"publisher","DOI":"10.1517\/13543784.13.9.1171"},{"key":"e_1_2_6_61_1","doi-asserted-by":"publisher","DOI":"10.1016\/0022-1759(95)00072-I"},{"key":"e_1_2_6_62_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2007.03.107"},{"key":"e_1_2_6_63_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b10069"}],"container-title":["European Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fejoc.201900569","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ejoc.201900569","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/ejoc.201900569","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/am-pdf\/10.1002\/ejoc.201900569","content-type":"application\/pdf","content-version":"am","intended-application":"syndication"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ejoc.201900569","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T11:27:39Z","timestamp":1760527659000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/ejoc.201900569"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,8,7]]},"references-count":69,"journal-issue":{"issue":"33","published-print":{"date-parts":[[2019,9,8]]}},"alternative-id":["10.1002\/ejoc.201900569"],"URL":"https:\/\/doi.org\/10.1002\/ejoc.201900569","archive":["Portico"],"relation":{},"ISSN":["1434-193X","1099-0690"],"issn-type":[{"value":"1434-193X","type":"print"},{"value":"1099-0690","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,8,7]]},"assertion":[{"value":"2019-04-14","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-08-07","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}