200726-48-3Relevant academic research and scientific papers
Tumor-Activated Benzothiazole Inhibitors of Stearoyl-CoA Desaturase
Williams, Noelle S.,Gonzales, Stephen,Naidoo, Jacinth,Rivera-Cancel, Giomar,Voruganti, Sukesh,Mallipeddi, Prema,Theodoropoulos, Panayotis C.,Geboers, Sophie,Chen, Hong,Ortiz, Francisco,Posner, Bruce,Nijhawan, Deepak,Ready, Joseph M.
, p. 9773 - 9786 (2020/10/19)
A series of N-acyl benzothiazoles shows selective and potent cytotoxicity against cancer cell lines expressing cytochrome P450 4F11. A prodrug form is metabolized by cancer cells into an active inhibitor of stearoyl-CoA desaturase (SCD). Substantial variation on the acyl portion of the inhibitors allowed the identification of (R)-27, which balanced potency, solubility, and lipophilicity to allow proof-of-concept studies in mice. The prodrugs were activated inside the tumor, where they can arrest tumor growth. Together, these observations offer promise that a tumor-activated prodrug strategy might exploit the essentiality of SCD for tumor growth, while avoiding toxicity associated with systemic SCD inhibition.
Synthesis of benzamide-benzothiazole conjugates via palladium-catalysed aminocarbonylation (hydrazinocarbonylation)
Gergely, Máté,Kollár, László
, p. 2027 - 2036 (2019/02/26)
The palladium-catalysed aminocarbonylation of iodoarenes was investigated using 2-amino- and 2-hydrazinobenzothiazole as N-nucleophile. The reaction proved to be highly chemoselective in all cases: carboxamides and the corresponding carbohydrazides, obtained by the acylation at the nitrogen adjacent to the C-2 of the benzothiazole moiety, were obtained exclusively and isolated in moderate to high yields. Systematic investigation of the reaction conditions revealed that the reaction requires relatively high temperature (higher than 70 °C). The effect of the carbon monoxide pressure is different in the synthesis of the two types of products: while the carboxamide formation is favoured, the carbohydrazide formation is lowered by the increasing CO pressure.
METHODS AND COMPOSITIONS FOR SELECTIVE AND TARGETED CANCER THERAPY
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Page/Page column 168, (2015/03/28)
Provided herein are methods and compositions for selective and targeted cancer therapy, in particular certain benzothiophenes, benzothiazoles, oxalamides, N-acyl ureas and chromones, and their use in selectively treating certain adenocarcinomas. In some embodiments, the selective toxicity of the compounds may be mediated through SCD1 and/or CYP450 such as CYP4F11.
