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Benzothiazole

About: Benzothiazole is a research topic. Over the lifetime, 4740 publications have been published within this topic receiving 65163 citations. The topic is also known as: benzosulfonazole & 1-Thia-3-azaindene.


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Journal ArticleDOI
TL;DR: Corrosion inhibition efficiencies of heterocyclic, unsaturated (aromatic and nonaromatic) compounds (pyrimidines, benzothiazole derivatives, amino acids containing an aromatic part, pyridi...
Abstract: Corrosion inhibition efficiencies of heterocyclic, unsaturated (aromatic and nonaromatic) compounds (pyrimidines, benzothiazole derivatives, amino acids containing an aromatic part, pyridi...

735 citations

Journal ArticleDOI
TL;DR: Mechanistically, this new series of agents contrasts with the previously reported 2-(4-aminophenyl)benzothiazoles; compound 8n is not reliant on induction of CYP1A1 expression for antitumor activity.
Abstract: A series of new 2-phenylbenzothiazoles has been synthesized on the basis of the discovery of the potent and selective in vitro antitumor properties of 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (8n; GW 610, NSC 721648). Synthesis of analogues substituted in the benzothiazole ring was achieved via the reaction of o-aminothiophenol disulfides with substituted benzaldehydes under reducing conditions. Compounds were evaluated in vitro in four human cancer cell lines, and compound 8n was found to possess exquisitely potent antiproliferative activity (GI(50) < 0.1 nM for MCF-7 and MDA 468). Potent and selective activity was also observed in the NCI 60 human cancer cell line panel. Structure-activity relationships established that the compound 8n stands on a pinnacle of potent activity, with most structural variations having a deactivating in vitro effect. Mechanistically, this new series of agents contrasts with the previously reported 2-(4-aminophenyl)benzothiazoles; compound 8n is not reliant on induction of CYP1A1 expression for antitumor activity.

412 citations

Journal ArticleDOI
TL;DR: A series of water-soluble L-lysyl- and L-alanyl-amide prodrugs of the lipophilic antitumor 2-(4-aminophenyl)benzothiazoles has been synthesized to address formulation and bioavailability issues related to the desired parenteral administration of the chosen clinical candidate.
Abstract: A series of water-soluble L-lysyl- and L-alanyl-amide prodrugs of the lipophilic antitumor 2-(4-aminophenyl)benzothiazoles has been synthesized to address formulation and bioavailability issues related to the desired parenteral administration of the chosen clinical candidate. The prodrugs exhibit the required pharmaceutical properties of good water solubility (in weak acid) and stability at ambient temperature and degradation to free base in vivo. The lysyl-amide of 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (NSC 710305, 6d) has been selected for phase 1 clinical evaluation.

390 citations

Journal ArticleDOI
TL;DR: Four compounds have been evaluated in vivo against human mammary carcinoma models in nude mice and compound 9a showed the most potent growth inhibition against the ER+ (MCF-7 and BO) and ER- (MT-1 and MT-3) tumors.
Abstract: 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...

370 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
2023194
2022390
2021187
2020197
2019219
2018245