178804-13-2Relevant academic research and scientific papers
Design and synthesis of three series of novel antitumor–azo derivatives
Lamie, Phoebe F.,Philoppes, John N.
, p. 1228 - 1240 (2017)
Three new series of thiazoles, quinolones, and thiazolidinones merged with benzimidazole, benzoxazole, and benzothiazole nuclei were synthesized. The compounds were subjected to Infrared, 1H nuclear magnetic resonance, 13C nuclear ma
Antitumour benzothiazoles. Part 20: 3′-cyano and 3′-alkynyl-substituted 2-(4′-aminophenyl)benzothiazoles as new potent and selective analogues
Hutchinson, Ian,Bradshaw, Tracey D.,Matthews, Charles S.,Stevens, Malcolm F. G.,Westwell, Andrew D.
, p. 471 - 474 (2003)
The synthesis of a new series of antitumour 2-(4-aminophenyl)benzothiazole analogues, substituted in the 3′-position by cyano or alkynyl groups, is described. Several of the analogues, notably the 5-fluorinated compounds 7c and 9c, were found to possess potent in vitro activity against MCF-7 and MDA 468 human cancer cell lines. More comprehensive in vitro analysis (NCI 60-cell line) established compound 7c as a particularly potent and selective 2-(4-aminophenyl)benzothiazole analogue.
Design and synthesis of new benzoxazole/benzothiazole-phthalimide hybrids as antitumor-apoptotic agents
Philoppes, John N.,Lamie, Phoebe F.
, (2019/05/29)
Herein, we synthesized a series of twelve benzoxazole and benzothiazole derivatives incorporated with phthalimide core as anticancer agents. The most active compounds were 5a and 5g against HepG2 and MCF7 cell lines with IC50 = 0.011 and 0.006 μM, respectively. They evaluated against EGFR and HER2 enzymes. From cell cycle analysis, it was observed that test compounds exerted pre G1 apoptosis and cell cycle arrest at G2/M phase. The achieved results suggested that apoptosis was due to activation of caspase-7 and caspase-9. EGFR was chosen as a biological target for carrying molecular modeling study for the newly synthesized compounds.
Antitumor benzothiazoles. 3. Synthesis of 2-(4- aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo
Shi, Dong-Fang,Bradshaw, Tracey D.,Wrigley, Samantha,McCall, Carol J.,Lelieveld, Peter,Fichtner, Iduna,Stevens, Malcolm F. G.
, p. 3375 - 3384 (2007/10/03)
A new series of 2-(4-aminophenyl)benzothiazoles substituted in the phenyl ring and benzothiazole moiety has been synthesized by simple, high- yielding routes. The parent molecule 5a shows potent inhibitory activity in vitro in the nanomolar range against a panel of human breast cancer cell lines, but is inactive (IC50 > 30 μM) against other cell types: activity against the sensitive breast lines MCF-7 and MDA 468 is characterized by a biphasic dose-response relationship. Structure-activity relationships derived using these cell types has revealed that activity follows the heterocyclic sequence benzothiazole > benzoxazole >> benzimidazole and that 2-(4-aminophenyl)benzothiazoles bearing a 3'-methyl- 9a, 3'-bromo- 9c, 3'- iodo- 9f, and 3'-chloro-substituent 9i are especially potent and their activity extends to ovarian, lung, and renal cell lines. Four compounds have been evaluated in vivo against human mammary carcinoma models in nude mice. Compound 9a showed the most potent growth inhibition against the ER+ (MCF- 7 and BO) and ER- (MT-1 and MT-3) tumors. Our efforts to identify a pharmacological mechanism of action for these intriguing compounds have not, as yet, been successful.
