34649-02-0

Basic information

• Product Name: 2-AMINO-5-CHLORO-4-NITROBENZOIC ACID
• Synonyms: 2-AMINO-5-CHLORO-4-NITROBENZOIC ACID;2-Amino-4-nitro-5-chlorobenzoic acid;5-Chloro-4-nitroanthranilic acid
• CAS NO: 34649-02-0
• Molecular Formula: C₇H₅ClN₂O₄
• Molecular Weight: 216.58
• Mol File: 34649-02-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 268-270℃ (DEC.)
• Appearance: /
• Density: 1.691
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-AMINO-5-CHLORO-4-NITROBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-CHLORO-4-NITROBENZOIC ACID(34649-02-0)
• EPA Substance Registry System: 2-AMINO-5-CHLORO-4-NITROBENZOIC ACID(34649-02-0)

Safety Data

• Hazardous Substances Data: 34649-02-0(Hazardous Substances Data)

Usage

Description

2-Amino-5-chloro-4-nitrobenzoic acid, with the CAS number 34649-02-0, is an organic compound characterized by its unique chemical structure featuring an amino group, a chloro substituent, and a nitro group attached to a benzoic acid backbone. 2-Amino-5-chloro-4-nitrobenzoic acid is known for its potential applications in various fields due to its distinct chemical properties.

Uses

Used in Pharmaceutical Industry:
2-Amino-5-chloro-4-nitrobenzoic acid is used as a reagent for the preparation of N-?guanidino substituted 2,?4-?diamino-?5-?carbonylguanidine molecules. These molecules are related to amiloride, a drug that inhibits the sodium-calcium exchanger in rat insulinoma cells (RINm5F) and human platelets. The application of this compound in the pharmaceutical industry is significant as it contributes to the development of drugs targeting the sodium-calcium exchanger, which plays a crucial role in various physiological processes and disease conditions.

Upstream product

• 34649-00-8 N-(2-methyl-4-chloro-5-nitrophenyl)acetamide 
• 5202-86-8 4-chloro-2-methylacetanilide 
• 95-69-2 4-chloro-2-methylbenzeneamine 
• 3558-19-8 methyl 2-amino-4-nitrobenzoate 
• 530084-00-5 methyl 2-amino-5-chloro-4-nitrobenzoate 
• 34649-01-9 2-acetylamino-5-chloro-4-nitrobenzoic acid 
• 136833-36-8 5-chloro-2,4-dinitrobenzoic acid 

Downstream Products

• 530084-02-7 [(4-chloro-2-formyl-5-nitro-phenylcarbamoyl)-methyl]-phosphonic acid diethyl ester 
• 530084-01-6 (2-amino-5-chloro-4-nitrophenyl)methanol 
• 273401-30-2 2-amino-5-chloro-4-nitrobenzaldehyde 
• 1026651-62-6 N-tert-butyl-3-[(2-amino-5-chloro-4-nitrobenzenecarbonyl)oxy]crotonamide 

Relevant articles and documents

Phenyl [...] compound and its preparation method, pharmaceutical composition, drug use (by machine translation)

The invention provides a phenylurea coupling quinazoline compound or a pharmaceutically acceptable salt thereof represented by formula (I), wherein R1 represents H, represents Br, Cl or F, represents -CH3, -CH2-CH3, -CH2(CH3)2 or -CF3, represents -O-CH3, -O-CH2-CH3 or -O-CH2(CH3)2, or represents -C[triple bond]CH or -C[triple bond]N; n1 is 1, 2, 3, 4 or 5; one of R2 and R3 is a group represented by formula (II); R4 represents H, represents Br, Cl or F, represents -CH3, -CH2-CH3, -CH2(CH3)2 or -CF3, represents -O-CH3, -O-CH2-CH3 or -O-CH2(CH3)2, represents -NH2, or represents -NO2; n2 is 1, 2, 3, 4 or 5; and the other one of R2 and R3 represents H, -O-CH3, -O-CH2-CH3, -O-CH2(CH3)2, or the following groups.

Novel quinolinone-phosphonic acid AMPA antagonists devoid of nephrotoxicity.

We reported previously the synthesis and structure-activity relationships (SAR) in a series of 2-(1H)-oxoquinolines bearing different acidic functions in the 3-position. Exploiting these SAR, we were able to identify 6,7-dichloro-2-(1H)-oxoquinoline-3-phosphonic acid compound 3 (S 17625) as a potent, in vivo active AMPA antagonist. Unfortunately, during the course of the development, nephrotoxicity was manifest at therapeutically effective doses. Considering that some similitude exists between S 17625 and probenecid, a compound known to protect against the nephrotoxicity and/or slow the clearance of different drugs, we decided to synthesise some new analogues of S 17625 incorporating some of the salient features of probenecid. Replacement of the chlorine in position 6 by a sulfonylamine led to very potent AMPA antagonists endowed with good in vivo activity and lacking nephrotoxicity potential. Amongst the compounds evaluated, derivatives 7a and 7s appear to be the most promising and are currently evaluated in therapeutically relevant stroke models.