{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,26]],"date-time":"2026-02-26T23:56:30Z","timestamp":1772150190648,"version":"3.50.1"},"reference-count":18,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2012,10,10]],"date-time":"2012-10-10T00:00:00Z","timestamp":1349827200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemMedChem"],"published-print":{"date-parts":[[2012,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Noscapine is a phthalideisoquinoline alkaloid isolated from the opium poppy <jats:italic>Papaver somniferum<\/jats:italic>. It has long been used as an antitussive agent, but has more recently been found to possess microtubule\u2010modulating properties and anticancer activity. Herein we report the synthesis and pharmacological evaluation of a series of 6\u2032\u2010substituted noscapine derivatives. To underpin this structure\u2013activity study, an efficient synthesis of <jats:italic>N<\/jats:italic>\u2010nornoscapine and its subsequent reduction to the cyclic ether derivative of <jats:italic>N<\/jats:italic>\u2010nornoscapine was developed. Reaction of the latter with a range of alkyl halides, acid chlorides, isocyanates, thioisocyanates, and chloroformate reagents resulted in the formation of the corresponding <jats:italic>N<\/jats:italic>\u2010alkyl, <jats:italic>N<\/jats:italic>\u2010acyl, <jats:italic>N<\/jats:italic>\u2010carbamoyl, <jats:italic>N<\/jats:italic>\u2010thiocarbamoyl, and <jats:italic>N<\/jats:italic>\u2010carbamate derivatives, respectively. The ability of these compounds to inhibit cell proliferation was assessed in cell\u2010cycle cytotoxicity assays using prostate cancer (PC3), breast cancer (MCF\u20107), and colon cancer (Caco\u20102) cell lines. Compounds that showed activity in the cell\u2010cycle assay were further evaluated in cell viability assays using PC3 and MCF\u20107 cells.<\/jats:p>","DOI":"10.1002\/cmdc.201200365","type":"journal-article","created":{"date-parts":[[2012,10,10]],"date-time":"2012-10-10T17:40:40Z","timestamp":1349890840000},"page":"2122-2133","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":45,"title":["Synthesis and Biological Evaluation of <i>N<\/i>\u2010Substituted Noscapine Analogues"],"prefix":"10.1002","volume":"7","author":[{"given":"Aaron J.","family":"DeBono","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jin Han","family":"Xie","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sabatino","family":"Ventura","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Colin W.","family":"Pouton","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ben","family":"Capuano","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Peter J.","family":"Scammells","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2012,10,10]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.2174\/1568011053352569"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.95.4.1601"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1158\/1078-0432.CCR-04-0360"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.2174\/157489109789318532"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M110369200"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmgm.2011.03.004"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.71.7.2627"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1124\/mol.63.4.799"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bcp.2006.05.004"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2006.09.012"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0969-8051(00)90202-6"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0304-3835(02)00722-X"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm0494220"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm050674q"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bcp.2011.03.029"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.canlet.2011.08.015"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo035243z"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/1522-2675(200208)85:8<2458::AID-HLCA2458>3.0.CO;2-L"}],"container-title":["ChemMedChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcmdc.201200365","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cmdc.201200365","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T21:47:53Z","timestamp":1760305673000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cmdc.201200365"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,10,10]]},"references-count":18,"journal-issue":{"issue":"12","published-print":{"date-parts":[[2012,12]]}},"alternative-id":["10.1002\/cmdc.201200365"],"URL":"https:\/\/doi.org\/10.1002\/cmdc.201200365","archive":["Portico"],"relation":{},"ISSN":["1860-7179","1860-7187"],"issn-type":[{"value":"1860-7179","type":"print"},{"value":"1860-7187","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,10,10]]},"assertion":[{"value":"2012-07-31","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2012-10-10","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}