Abstract
Thiazole is a core structural motif presents in a wide range of natural products. Thiazole derivatives also have a wide range of medicinal and biological properties. The reaction of hydrazonoyl halides with 2-(1-(4-(1,3-dioxoisoindolin-2-yl)phenyl)ethylidene)hydrazinecarbothioamidein ethanol and triethylamine yielded 2-(4-(1-(2-(4-(2-Arylhydrazono)-5-s-4,5-dihydrothiazol-2-yl)hydrazono)-ethyl)phenyl)isoindoline-1,3-dione and 2-(4-(1-(2-(5-(2-Arylhydrazono)-4-oxo-4,5-dihydrothiazol-2-yl)hydrazono)ethyl)-phenyl)isoindoline-1,3-dione.The reaction of 2-(4-(1-(2-(4-oxo-4,5-dihydrothiazol-2-yl)hydrazono)ethyl)phenyl)isoindoline-1,3-dione with arylidenemalononitrile also yielded 5-amino-2-(2-(1-(4-(1,3-dioxoisoindolin-2-yl)phenyl)ethylidene)hydrazinyl)-7-substituted-7H-pyrano[2,3-d]thiazole-6-carbonitrile. The structures of the newly synthesized compound were elucidated whenever possible on the basis of elemental analysis, spectral data, and alternative synthetic routes. Three of them were evaluated against a breast cancer cell line for their antitumor activity. Compound (1) has been shown to be useful in the synthesis of a new series of 1,3-thiazole, pyrano[2,3-d]thiazole and 4,5-dihydrothiazolo[4,5-b]pyridine derivatives using hydra...Continue Reading
References
Jul 4, 1990·Journal of the National Cancer Institute·P SkehanM R Boyd
Dec 8, 1995·Journal of Medicinal Chemistry·F W BellR Noréen
Oct 28, 1997·Journal of Medicinal Chemistry·A BadorcJ M Herbert
Aug 8, 1998·Journal of Virology·F C SpectorM G Peterson
Apr 1, 1999·Chemistry & Biology·B E FinkJ A Katzenellenbogen
May 18, 1999·Bioorganic & Medicinal Chemistry Letters·J S CarterB Zweifel
Feb 15, 2001·Journal of Medicinal Chemistry·J RudolphF Geschke
Apr 11, 2001·Bioorganic & Medicinal Chemistry Letters·K J WilsonJ Spurlino
Jul 17, 2001·Bioorganic & Medicinal Chemistry Letters·E W van TilburgA P IJzerman
Mar 14, 2007·European Journal of Medicinal Chemistry·Umadevi Bhoga
Apr 5, 2007·Nature Protocols·Vanicha Vichai, Kanyawim Kirtikara
Jan 8, 2009·Journal of Medicinal Chemistry·Wen-Ting ZhangJian-Guo Chen
Nov 26, 2009·European Journal of Medicinal Chemistry·S K BhartiS K Singh
Jul 16, 2010·Bioorganic & Medicinal Chemistry Letters·Matteo BiagettiLaura Caberlotto
Nov 16, 2010·Journal of Medicinal Chemistry·Bingwei V YangJoel C Barrish
Oct 5, 2011·Journal of Medicinal Chemistry·Diego González CabreraKelly Chibale
Nov 18, 2011·Acta Crystallographica. Section E, Structure Reports Online·Abdullah M AsiriSeik Weng Ng
Sep 27, 2012·Bioorganic & Medicinal Chemistry Letters·Mirjana PopsavinVelimir Popsavin
Feb 18, 2014·European Journal of Medicinal Chemistry·Danylo KaminskyyRoman Lesyk