Synthesis and cytotoxicity of new thiazolo[4,5-b]pyridine-2(3H)-one derivatives based on α,β-unsaturated ketones and α-ketoacids

Synthesis and cytotoxicity of new thiazolo[4,5-b]pyridine-2(3H)-one derivatives based on... derivatives were obtained via [3 ? 3]-cyclization of 4-amino-5H-thiazol-2-one and a,b-unsaturated ketones or a-ketoacids. The structures of newly synthesized com- pounds were established by spectral data and a single- crystal X-ray diffraction analysis. Target compounds were screened for their anticancer activity according to US NCI protocols and moderate inhibitory activity against the tes- ted cell line was confirmed. 5-Phenyl-7-(pyridin-3-yl)-3H- Keywords 4-Amino-5H-thiazol-2-one  Thiazolo[4,5- thiazolo[4,5-b]pyridin-2-one (3) and 2-oxo-7-thiophen-2- b]pyridin-2(3H)-one  X-ray study  Cell lines  HepG2 yl-2,3-dihydrothiazolo[4,5-b]pyridine-5-carboxylic acid Balb/c 3T3 (12) were screened for their cytotoxicity effects on HepG2 and Balb/c 3T3 cells which revealed promising results using MTT, NRU and TPC assays. Introduction Among condensed pyridine derivatives, it has been drawn a considerable attention and interest to thiazolo[4,5- b]pyridines due to their diverse biological activity and clinical applications. Thus, thiazolopyridine derivatives have shown a broad range of interesting biological activi- ties, such as analgesic, antioxidant, antiinflammatory, anticancer, antifungal, and herbicidal properties (Chaban Electronic supplementary material The online version of this article (doi:10.1007/s11696-017-0318-1) contains supplementary et al. 2013, 2016; Hegde and Mahoney 1993; El-Gaby et al. material, which is available to authorized users. 2006). Moreover, thiazolo[4,5-b]pyridines are well-known as ErbB family of tyrosine kinase (EGFR) inhibitors (Lin & Roman http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemical Papers Springer Journals

Synthesis and cytotoxicity of new thiazolo[4,5-b]pyridine-2(3H)-one derivatives based on α,β-unsaturated ketones and α-ketoacids

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Publisher
Springer International Publishing
Copyright
Copyright © 2017 by Institute of Chemistry, Slovak Academy of Sciences
Subject
Chemistry; Chemistry/Food Science, general; Industrial Chemistry/Chemical Engineering; Biochemistry, general; Medicinal Chemistry; Materials Science, general; Biotechnology
ISSN
0366-6352
eISSN
1336-9075
D.O.I.
10.1007/s11696-017-0318-1
Publisher site
See Article on Publisher Site

Abstract

derivatives were obtained via [3 ? 3]-cyclization of 4-amino-5H-thiazol-2-one and a,b-unsaturated ketones or a-ketoacids. The structures of newly synthesized com- pounds were established by spectral data and a single- crystal X-ray diffraction analysis. Target compounds were screened for their anticancer activity according to US NCI protocols and moderate inhibitory activity against the tes- ted cell line was confirmed. 5-Phenyl-7-(pyridin-3-yl)-3H- Keywords 4-Amino-5H-thiazol-2-one  Thiazolo[4,5- thiazolo[4,5-b]pyridin-2-one (3) and 2-oxo-7-thiophen-2- b]pyridin-2(3H)-one  X-ray study  Cell lines  HepG2 yl-2,3-dihydrothiazolo[4,5-b]pyridine-5-carboxylic acid Balb/c 3T3 (12) were screened for their cytotoxicity effects on HepG2 and Balb/c 3T3 cells which revealed promising results using MTT, NRU and TPC assays. Introduction Among condensed pyridine derivatives, it has been drawn a considerable attention and interest to thiazolo[4,5- b]pyridines due to their diverse biological activity and clinical applications. Thus, thiazolopyridine derivatives have shown a broad range of interesting biological activi- ties, such as analgesic, antioxidant, antiinflammatory, anticancer, antifungal, and herbicidal properties (Chaban Electronic supplementary material The online version of this article (doi:10.1007/s11696-017-0318-1) contains supplementary et al. 2013, 2016; Hegde and Mahoney 1993; El-Gaby et al. material, which is available to authorized users. 2006). Moreover, thiazolo[4,5-b]pyridines are well-known as ErbB family of tyrosine kinase (EGFR) inhibitors (Lin & Roman

Journal

Chemical PapersSpringer Journals

Published: Oct 16, 2017

References

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