8-cyanobenzothiazinone analogs with potent antitubercular activity was written by Zhang, Gang;Sheng, Li;Hegde, Pooja;Li, Yan;Aldrich, Courtney C.. And the article was included in Medicinal Chemistry Research in 2021.Computed Properties of C8H3ClF3NO4 This article mentions the following:
8-Nitrobenzothiazinones (BTZs) exemplified by macozinone are a new class of antitubercular agents with exceptionally potent activity. The aryl nitro group has been considered indispensable for activity since this is bioactivated within mycobacteria by the flavoenzyme DprE1 to a reactive nitroso metabolite that covalently labels Cys387. However, the aryl nitro group is a potential liability with regards to safety, stability, and resistance. In this paper, we introduced a nitrile as a bioisosteric replacement of the nitro group, which we hypothesize can maintain a similar covalent mechanism of inhibition, but mitigate against the aforementioned concerns. 8-cyanobenzothiazinone 1d displayed potent antitubercular activity with an MIC of 130 nM and had an improved volume of distribution in mice that increased the intrinsic half-life by twofold compared to macozinone. Anal. of the C-2 substituent of 1d revealed similar structure-activity relationships as observed for macozinone. Overall, the results confirm the 8-nitro group of benzothiazinones can be successfully replaced with a nitrile to retain useful activity and favorable pharmacokinetic properties. In the experiment, the researchers used many compounds, for example, 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid (cas: 22227-59-4Computed Properties of C8H3ClF3NO4).
2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid (cas: 22227-59-4) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications. The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.Computed Properties of C8H3ClF3NO4
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics