Fleau, Charlotte;Padilla, Angel;Miguel-Siles, Juan;Quesada-Campos, Maria T.;Saiz-Nicolas, Isabel;Cotillo, Ignacio;Cantizani Perez, Juan;Tarleton, Rick L.;Marco, Maria;Courtemanche, Gilles published 《Chagas Disease Drug Discovery: Multiparametric Lead Optimization against Trypanosoma cruzi in Acylaminobenzothiazole Series》. The research results were published in《Journal of Medicinal Chemistry》 in 2019.Product Details of 6285-57-0 The article conveys some information:
Acylaminobenzothiazole hits were identified as potential inhibitors of T. cruzi replication, a parasite responsible for Chagas Disease. We selected compound 1, N-(6-chlorobenzo[d]thiazol-2-yl)cyclopropanecarboxamide, for lead optimization, aiming to improve in parallel its anti-T. cruzi activity (IC50 = 0.630μM) and its human metabolic stability (human clearance = 9.57mL/min/g). A total of 39 analogs of 1 were synthesized and tested in vitro. We established a multiparametric structure activity relationship, allowing optimization of both anti-parasite activity, physicochem. parameters and ADME properties. We identified compound 50, N-(5-Fluoro-6-(trifluoromethyl)benzothiazol-2-yl)cyclopropanecarboxamide, as an advanced lead with an improved anti-T. cruzi activity in vitro (IC50 = 0.079μM), an enhanced metabolic stability (Human Clearance = 0.413mL/min/g) and opportunity for oral route of administration. After tolerability assessment, compound 50 demonstrated a promising in vivo efficacy. And 6-Nitrobenzo[d]thiazol-2-amine (cas: 6285-57-0) was used in the research process.
6-Nitrobenzo[d]thiazol-2-amine(cas:6285-57-0) has been used:
as model analyte for voltammetric determination of electrochemically reducible organic substances;
in the synthesis of 2-methyl-4-nitro-2H-pyrazole-3-carboxylic acid[2-(cyclohexanecarbonylamino)benzothiazol-6-yl]amide derivatives;
in the preparation of push-pull nonlinear optical chromophores containing thiazole and benzothiazole acceptors;
as a base in dye production by diazotation reaction.
Reference:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica