Synthesis and biological evaluation of new naphthoquinone-containing pyrrolo-thiazoles as anticancer agents

✍ Scribed by Susana M. M. Lopes; Mafalda Laranjo; Arménio C. Serra; Ana Margarida Abrantes; António M. d'A. Rocha Gonsalves; Maria Filomena Botelho; Ana Matos Beja; Manuela Ramos Silva; Teresa M. V. D. Pinho e Melo

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2010
• Tongue: English
• Weight: 479 KB
• Volume: 47
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.396

✦ Synopsis

Abstract

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Naphthoquinones undergo 1,3‐dipolar cycloaddition with bicyclic münchnones generated from thiazolidines affording new pyrrolo‐thiazoles with a fused quinone nucleus. The products were obtained as single enantiomers in good yields. These benzo[f]thiazolo[4,3‐a]isoindole‐6,11(1__H__,3__H__)‐diones are comprised of four fused rings and present a very planar structure. The evaluation of their anticancer activity against melanoma A375 and colorectal adenocarcinoma WiDr human cell lines showed only moderate activity but gave insight into the modeling of new structures. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.] J. Heterocyclic Chem., (2010).