22227-59-4

Usage

Uses

Used in Pharmaceutical Industry:
2-chloro-3-nitro-5-(trifluoromethyl)benzoic acid is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique chemical properties allow for the development of new drugs with improved efficacy and safety profiles. It plays a crucial role in the creation of more complex molecules that can target specific biological pathways, leading to innovative treatments for various diseases.
Used in Agrochemical Industry:
In the agrochemical industry, 2-chloro-3-nitro-5-(trifluoromethyl)benzoic acid is used as a building block for the synthesis of various agrochemicals. Its unique structure and properties enable the development of new pesticides, herbicides, and other agricultural chemicals that can effectively control pests and diseases, thereby increasing crop yields and ensuring food security.
Used in Organic Chemistry Research:
2-chloro-3-nitro-5-(trifluoromethyl)benzoic acid is used as a versatile building block in organic chemistry research. Its unique structure allows chemists to explore new synthetic routes and develop novel compounds with potential applications in various fields. It serves as a valuable tool for understanding the fundamental principles of organic reactions and contributes to the advancement of chemical science.
Used in Medicinal Chemistry and Drug Development:
2-chloro-3-nitro-5-(trifluoromethyl)benzoic acid has been studied for its potential applications in the field of medicinal chemistry and drug development. Its unique chemical properties make it an attractive candidate for the design and synthesis of new drugs with improved pharmacological properties. Researchers are exploring its potential as a precursor for the development of innovative therapeutic agents that can address unmet medical needs and improve patient outcomes.

InChI:InChI=1S/C8H3ClF3NO4/c9-6-4(7(14)15)1-3(8(10,11)12)2-5(6)13(16)17/h1-2H,(H,14,15)

Upstream product

• 657-06-7 2-chloro-5-trifluoromethylbenzoic acid 
• 98-56-6 4-chlorobenzotrifluoride 

Downstream Products

• 87033-30-5 2-chloro-3-nitro-5-(trifluoromethyl)benzoyl chloride 
• 22227-47-0 2-chloro-3-nitro-5-(trifluoromethyl)benzamide 
• 1383531-32-5 TK₄₅₄₇-070E 
• 1161233-85-7 2-[(2S)-2-methyl-1,4-dioxa-8-azaspiro[4.5]dec-8-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one 
• 1377239-83-2 2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one 

Relevant academic research and scientific papers

8-cyanobenzothiazinone analogs with potent antitubercular activity

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. Analysis 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. [Figure not available: see fulltext.].

Benzothiazinone derivative with 6-position substituted with trifluoromethyl as well as preparation method and application thereof

The invention discloses a benzothiazinone derivative with the 6-position substituted with trifluoromethyl as well as a preparation method and application of the benzothiazinone derivative. According to the invention, benzene ring of a benzothiazinone framework is creatively changed, particularly a substituent group is creatively changed, a series of compounds are obtained, and unexpected technical effects are achieved; and specifically, compared with other benzothiazinone derivatives, the benzothiazinone derivative with the 6-position substituted with trifluoromethyl is more stable to liver microsomal enzyme, the metabolic half-life period T1/2 is longer, and the water solubility is better.

Benzoxazinone derivatives and their use as antibacterial agents

The invention discloses benzoxazinone derivatives, a synthesis method and applications thereof. The derivatives can be used as an antibacterial agent for treating infectious diseases caused by bacteria, especially tuberculosis (TB) caused by mycobacterium. Specifically, the invention relates to compounds represented by the formula (I), pharmaceutically acceptable salts thereof, and a pharmaceutical composition comprising the provided compounds; wherein the R1 to R4 are defined in the description. The invention aim to prepare novel compounds capable of inhibiting the mycobacterium activity, the compounds can be used as a potential novel drug for treating infectious diseases caused by bacteria, moreover, the compounds can be used to treat or prevent tuberculosis (TB) caused by mycobacterium, at the same time the problems related with drug resistance can be solved, and the drug metabolism property can be improved on the basis that the mycobacterium tuberculosis resistant activity is not influenced.

BENZOTHIAZINONE DERIVATIVES AS ANTI -TUBERCULOSIS AGENTS

Novel benzothiazinone derivatives of formula (I) or pharmaceutically acceptable salts or solvates thereof have been found to be effective against Mycobacterium tuberculosis strains and may thus be useful in the treatment of tuberculosis: wherein EWG (electron withdrawing group) = NO2, CN, CF3, F, Cl, Br, OCF3, OH, OR, OCHF2, COOR, wherein R is hydrogen or a straight or branched C1-C4 alkyl group, X = a bond or a straight or branched C1-C4 alkylene group which may be substituted with a group selected from F, Cl, Br, I or C1-C4 alkoxy; Y = hydrogen, a straight or branched C1-C4 alkyl group, OH or OR, wherein R is hydrogen or a straight or branched C1-C4 alkyl group; n = 0, 1 or 2; R1, R2 = hydrogen or substituent (s) which may be the same or different from each other and are selected from the group consisting of D, F, Cl, Br, CF3, a straight or branched C1-C4 alkyl group, a phenyl group, OR, SR, NR3R4, wherein R, R3, R4 may be the same or different from each other and are hydrogen or a straight or branched C1-C4 alkyl group or a phenyl group.

Benzothiazinone compounds and their use as anti-tuberculosis agents

Novel benzothiazinone derivatives of formula (I) or a pharmaceutically acceptable salt or solvate thereof have been found to be effective against Mycobacterium tuberculosis strains and may thus be useful in the treatment of tuberculosis

NOVEL ANTI-TUBERCULOSIS AGENTS

Novel benzothiazinone derivatives of formula (I) or a pharmaceutically acceptable salt or solvate thereof have been found to be effective against Mycobacterium tuberculosis strains and may thus be useful in the treatment of tuberculosis (I) wherein, EWG (electron withdrawing group) = N02, CN, CF3, F, CI, Br, OCF3, OH, OR, OCHF2, COOR, wherein R is hydrogen, or a straight or branched C1-C4 alkyl group, X = a bond, or a straight or branched C1-C4 alkylene group; Y = a bond, or a straight or branched C1-C4 alkylene group; wherein either one of X or Y is a bond and the other is a Ci-C4-alkylene group, Z = N or C, n = 1 or 2; R1 = hydrogen, a straight or branched C1-C6 alkyl group, or a C3-C6 cycloalkyl group, which may be substituted with a group selected from F, CI, Br, I or a C1-C4 alkoxy; R2 = a phenyl group, a naphthyl group or a thienyl group, each of which may be unsubstituted or substituted with one or more substituent(s) which may be the same or different from each other, selected from the group consisting of F, CI, Br, I, CN, NO2, or a straight or branched C1-C6 alkyl or phenyl group, which may be substituted with a group selected from F, CI, Br, I, or C1-C4 alkoxy.

TRIFLUOROMETHYLBENZAMIDE DERIVATIVES AND THERAPEUTIC USES THEREOF

Compounds of the formula (I), in which the radicals R1 to R3 and AR are as defined in the description, processes for the preparation thereof, the use thereof in the treatment of cardiovascular diseases, and pharmaceutical compositions comprising them.

Substituted diphenyl ethers

A compound of the formula: STR1 and salts and esters thereof, useful as intermediates for the preparation of compounds of the formula STR2 wherein R1 is an alkyl group optionally substituted by one or more fluorine atoms or by an optionally substituted phenyl group R2 is No2 or Cl and R6 is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms.