Category: 22227-59-4

Design, synthesis and biological activity of N-(amino)piperazine-containing benzothiazinones against Mycobacterium tuberculosis was written by Wang, Apeng;Xu, Shijie;Chai, Yun;Xia, Guimin;Wang, Bin;Lv, Kai;Ma, Chao;Wang, Dan;Wang, Aoyu;Qin, Xiaoyu;Liu, Mingliang;Lu, Yu. And the article was included in European Journal of Medicinal Chemistry in 2021.SDS of cas: 22227-59-4 This article mentions the following:

A series of novel benzothiazinone derivatives containing a N-(amino)piperazine moiety I (R₁ = H, Me, iso-Bu, etc.; R₂ = cyclohexyl, 4-(methoxyimino)cyclohexyl, 4-F₃CC₆H₄, etc.), II (R = cyclohexylmethyl, 4-trifluoromethoxybenzyl, cyclohexanecarbonyl, pyridin-4-ylmethyl) based on the structure of WAP-1902 discovered, were designed and synthesized as new anti-TB agents. Many of the compounds exhibited excellent in vitro activity against both drug-sensitive MTB strain H37Rv and multidrug-resistant clin. isolates (MIC: < 0.016渭g/mL), and good safety index (CC₅₀: >64渭g/mL). Especially compound I (R₁ = Me; R₂ = 4-(methoxyimino)cyclohexyl) displayed low hERG cardiac toxicity and acceptable oral pharmacokinetic profiles, indicating its promising potential to be a lead compound for future antitubercular drug discovery. In the experiment, the researchers used many compounds, for example, 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid (cas: 22227-59-4SDS of cas: 22227-59-4).

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. Alkyl chlorides readily react with amines to give substituted amines. Alkyl chlorides are substituted by softer halides such as the iodide in the Finkelstein reaction.SDS of cas: 22227-59-4

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Structure-Based Design of Potent and Ligand-Efficient Inhibitors of CTX-M Class A β-Lactamase was written by Nichols, Derek A.;Jaishankar, Priyadarshini;Larson, Wayne;Smith, Emmanuel;Liu, Guoqing;Beyrouthy, Racha;Bonnet, Richard;Renslo, Adam R.;Chen, Yu. And the article was included in Journal of Medicinal Chemistry in 2012.Quality Control of 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid This article mentions the following:

The emergence of CTX-M class A extended-spectrum β-lactamases poses a serious health threat to the public. We have applied structure-based design to improve the potency of a novel noncovalent tetrazole-containing CTX-M inhibitor (K_i = 21 μM) more than 200-fold via structural modifications targeting two binding hot spots, a hydrophobic shelf formed by Pro167 and a polar site anchored by Asp240. Functional groups contacting each binding hot spot independently in initial designs were later combined to produce analogs with submicromolar potencies, including 6-trifluoromethyl-3H-benzoimidazole-4-carboxylic acid [3-(1H-tetrazol-5-yl)-phenyl]-amide, which had a K_i value of 89 nM and reduced the MIC of cefotaxime by 64-fold in CTX-M-9 expressing Escherichia coli. The in vitro potency gains were accompanied by improvements in ligand efficiency (from 0.30 to 0.39) and LipE (from 1.37 to 3.86). These new analogs represent the first nM-affinity noncovalent inhibitors of a class A β-lactamase. Their complex crystal structures provide valuable information about ligand binding for future inhibitor design. In the experiment, the researchers used many compounds, for example, 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid (cas: 22227-59-4Quality Control of 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid).

2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid (cas: 22227-59-4) belongs to organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. While alkyl bromides and iodides are more reactive, alkyl chlorides tend to be less expensive and more readily available. Alkyl chlorides readily undergo attack by nucleophiles.Quality Control of 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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

Molecular Insight into the Discrepancy of Antitubercular Activity between 8-Nitro and 8-Cyano Benzothiazinones was written by Zhang, Gang;Chen, Daoxing;Wang, Sufang;Chen, Hualong;Wei, Ning;Chen, Guirong. And the article was included in ChemistrySelect in 2020.Recommanded Product: 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid This article mentions the following:

Benzothiazinones with 8-NO₂ group was a novel class of compounds with potent antitubercular activity, especially BTZ043 I and PBTZ169 II, which covalently inhibit DprE1. 8-CN benzothiazinones III [R = H, Me; R¹ = H, Me; R² = cyclopropyl, cyclopentyl, oxetan-3-yl, etc.] was reported as another type of benzothiazinones with potent antitubercular activity. Taking this as the starting point, a series of 8-CN benzothiazinones III were synthesized and evaluated for their antitubercular activity. To better understand the antitubercular activity of this series of benzothiazinones III, the difference between the mol. structures of CN01 and PBTZ169 in crystal were analyzed. CN01 III [R = H; R¹ = H; R² = cyclohexyl] and PBTZ169 II showed completely different conformations of the piperazine ring. D. functional theory anal. (DFT) and mol. dynamics (MD) simulation were performed to provide more details to explain the different antitubercular activity. All the anal. based on crystallog., quantum chem., and mol. modeling lay a foundation for the subsequent structural optimization of 8-CN benzothiazinones III. In the experiment, the researchers used many compounds, for example, 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid (cas: 22227-59-4Recommanded Product: 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid).

2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid (cas: 22227-59-4) belongs to organic chlorides. Organic chlorides can be used in production of: PVC, pesticides, chloromethane, teflon, insulators. Alkyl chlorides readily react with amines to give substituted amines. Alkyl chlorides are substituted by softer halides such as the iodide in the Finkelstein reaction.Recommanded Product: 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics