Anti-infective and herbicidal activity of N-substituted 2-aminobenzothiazoles was written by Fajkusova, Dagmar;Pesko, Matus;Keltosova, Stanislava;Guo, Jiahui;Oktabec, Zbynek;Vejsova, Marcela;Kollar, Peter;Coffey, Aidan;Csollei, Jozef;Kralova, Katarina;Jampilek, Josef. And the article was included in Bioorganic & Medicinal Chemistry in 2012.Synthetic Route of C13H10N2S This article mentions the following:
In this study, a series of N-substituted 2-aminobenzothiazoles was prepared according to a recently developed method. Twelve compounds were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the discussed compounds was also performed against fungal, bacterial and mycobacterial species. The biol. activities of some compounds were comparable or higher than the standards phenoxymethylpenicillin or pyrazinamide. The most effective compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. For all compounds, the structure-activity relationships are discussed. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Synthetic Route of C13H10N2S).
N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.Synthetic Route of C13H10N2S
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica