Synthesis of novel isatin-thiazoline and isatin-benzimidazole conjugates as anti-breast cancer agents

Abstract

A series of new isatin-thiazoline 3a-h and isatin-benzimidazole 4a-h derivatives were synthesized via condensation of isatin Mannich bases 2a-h with either 2-aminothiazoline or 2-aminobenzimidazole. The structures of the newly synthesized compounds were characterized by spectral data. The anti-breast cancer activity of some of the synthesized compounds was assessed in the MCF-7 human breast cancer cell line. The results showed that compounds 4b, 4d and 4g possess significant antiproliferative activity against MCF-7 cells.

Design, synthesis and QSAR study of certain isatin-pyridine hybrids as potential anti-proliferative agents

“…Compound IV (Figure 1), elicited excellent activity with IC 50 values of 14.99, 5.26 and 4.23 µM against MDA-MB231, MDA-MB468 and MCF7 cancer cells, respectively [27,28]. Also, A. T. Taher et al [29] explored the anti-breast cancer activity of isatin-thiazoline and isatin-benzimidazole conjugates against breast cancer cell line MCF7. Besides, the cytotoxic activities of isatin-arylsulfoanilide [30], isatin-4-piperazinylquinoline [31], isatin-benzoxazole [32], isatin-quinazoline-4(3H)-one [33] and isatinpyrazoline [34] hybrids were reported.…”

Synthesis of Novel Class of <i>N</i>-Alkyl-isatin-3-iminobenzoic Acid Derivatives and Their Biological Activity in Zebrafish Embryos and Human Cancer Cell Lines

“…The zebrafish embryos that were exposed after 48 hpf did not respond to the treatment and the blood cells formed normally ( Figure 2D). whereas the embryos which were exposed to compound 3f from shield stage until 48hpf did not stain with O-dianisidine, C) A weaker staining was observed in those embryos which were exposed compound 3f from 24-48hpf not before, D) The embryos which were exposed after 48hpf to compound 3f did not respond at all to the treatment and the blood cells formed normally similar like control normally shown by positive erythrocyte staining (white arrow) Semaxanib (SU5416), which is an isatin derivative molecule 8) was used as positive control in this study. SU5416 is a VEGF receptor tyrosine kinase inhibitor 9) and antiangiogenic activity of this compound has been reported previously [9][10][11] , however, the hematopoietic activity of SU5614 in zebrafish embryos is largely unknown.…”

Recent Highlights in the Development of Isatin-Based Anticancer Agents

“…further contributed to this work in the search for new anti-breast cancer agents through the synthesis of novel isatin-thiazoline and isatin-benzimidazole derivatives (compounds of type 73 and 74, Fig. (22)) via condensation of isatin Mannich bases with either 2-aminothiazoline or 2-aminobenzimidazole, respectively [159]. Benzimidazole-based compounds have been reported to demonstrate cytotoxic activity against hormone-dependant breast cancer cells such as MCF-7 [160], while thiazoline derivatives possess both cytotoxic and cytostatic activity against a broad spectrum of cancer cell lines [161].…”

“…methyl}indol-2(3H)-one, derived from the benzimidazole series 74, showed potent activity with an IC 50 of 22.59 nM against MCF-7 breast cancer cells [159].…”