Synthesis of novel thiazole, pyranothiazole, thiazolo[4,5- b]pyridines and thiazolo[5',4':5,6]pyrano[2,3- d]pyrimidine derivatives and incorporating isoindoline-1,3-dione group

Mona A Hosny; Yasser H Zaki; Wafaa A Mokbel; Abdou O Abdelhamid

doi:10.1186/s13065-019-0559-x

Synthesis of novel thiazole, pyranothiazole, thiazolo[4,5- b]pyridines and thiazolo[5',4':5,6]pyrano[2,3- d]pyrimidine derivatives and incorporating isoindoline-1,3-dione group

BMC Chem. 2019 Mar 26;13(1):37. doi: 10.1186/s13065-019-0559-x. eCollection 2019 Dec.

Authors

Mona A Hosny¹, Yasser H Zaki², Wafaa A Mokbel¹, Abdou O Abdelhamid³

Affiliations

¹ 1Department of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams University, Heliopolis, Cairo 11757 Egypt.
² 2Department of Chemistry, Faculty of Science, Beni-Suef University, Beni‑Suef, 62514 Egypt.
³ 3Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613 Egypt.

Abstract

Background: 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.

Results: 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.

Conclusions: 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 hydrazonoyl halides as precursors. The anticancer efficacy of compounds (9b), (9e), and (9f) against MCF-7, a breast cancer cell line, was also compared to the standard anticancer drug doxorubicin.

Keywords: 3-dione; 5-b]pyridine; Aminoacetophenone; Hydrazonoyl halide; Isobenzofuran-1; Thiazole; Thiazolo[4.