Hexahydrophthalimide-benzothiazole hybrids as a new class of protoporphyrinogen oxidase inhibitors: synthesis, structure-activity relationship, and DFT calculations was written by Wu, Qiong-You;Jiang, Li-Li;Yang, Sheng-Gang;Zuo, Yang;Wang, Zhi-Fang;Xi, Zhen;Yang, Guang-Fu. And the article was included in New Journal of Chemistry in 2014.Name: 6-Fluorobenzo[d]thiazole-2(3H)-thione This article mentions the following:
Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) has attracted continuous interest during the last few decades not only because of its unique biochem. characteristics but also because of its biomedical significance. As a continuation of our research work on the development of new PPO inhibitors, N-(benzothiazol-5-yl)-hexahydro-2H-isoindole-1,3-dithione (1a-j) and N-(benzothiazol-5-yl)-octahydro-3-thioxoisoindol-1-one derivatives (2a-i) were designed and synthesized. These newly prepared compounds were characterized by elemental analyses, 1H NMR and ESI-MS spectroscopy. The in vitro assay indicated that these compounds displayed good inhibition activity against human PPO (hPPO) with Ki values ranging from 0.38 渭M to 6.83 渭M. Notably, most of the monothionated products (1a-j) displayed a higher or comparable PPO-inhibition activity compared with the com. control sulfentrazone. The comparison of the dihedral angles of the representative compound with that of acifluorfen (ACF) complexed with hPPO clearly indicated that the dihedral angle between the thionyl amide or carbonyl amide ring and the benzothiazole ring was closely related to the variation of the PPO inhibition activity of different types of inhibitors. In the experiment, the researchers used many compounds, for example, 6-Fluorobenzo[d]thiazole-2(3H)-thione (cas: 80087-71-4Name: 6-Fluorobenzo[d]thiazole-2(3H)-thione).
6-Fluorobenzo[d]thiazole-2(3H)-thione (cas: 80087-71-4) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Name: 6-Fluorobenzo[d]thiazole-2(3H)-thione
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica