Molecular modelling design, synthesis and cytotoxic evaluation of certain substituted 2-(3,4,5-triacetoxybenzoylamino)benzo[d]thiazole and 2-(galloylamino)benzo[d]thiazole derivatives having potential topoisomerase-I inhibitory activity was written by Ismail, Mohamed A. H.;Tratrat, Christophe;Haroun, Michelyne G.. And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2013.Name: 5,6-Dimethoxybenzo[d]thiazol-2-amine This article mentions the following:
New 2-(3,4,5-triacetoxybenzoylamino)benzothiazoles (4a∼5f) and 2-(galloylamino)benzothiazoles (6a∼7f), were designed as topoisomerase-I inhibitors. Compare/fit studies between these mols. and the generated topoisomerase-I inhibitors hypothesis revealed that 4a∼5f have higher fitting values than (6a∼7f). Also, docking of 4a∼7f with the topoisomerase-I enzyme prioritized the higher activity of (4a∼5f) than (6a∼7f). These mols. were synthesized and biol. evaluated for their in vitro cytotoxic activity against Hela and MCF7 human cancer cell lines in comparison to Camptothecin (topo-I inhibitor) and doxorubicin (topo-II inhibitors) as reference drugs. Such screening revealed that compounds 4d, 4e, 4h, 5b, 5c and 5e have comparable higher cytotoxic activity in both cultures than these reference drugs. The highest active mol. was 5f that gave 1.5 folds higher cytotoxic activity against Hela cell cultures and 1.9 folds higher activity against MCF7 cell lines than doxorubicin and 1.6 folds and 2.2 folds higher activity towards the two resp. cultures than Camptothecin. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Name: 5,6-Dimethoxybenzo[d]thiazol-2-amine).
5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Name: 5,6-Dimethoxybenzo[d]thiazol-2-amine
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica