34649-02-0

Usage

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 2-Amino-5-chloro-4-nitrobenzoic acid 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

• 34649-01-9 2-acetylamino-5-chloro-4-nitrobenzoic acid 
• 530084-00-5 methyl 2-amino-5-chloro-4-nitrobenzoate 
• 3558-19-8 methyl 2-amino-4-nitrobenzoate 
• 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 
• 136833-36-8 5-chloro-2,4-dinitrobenzoic acid 

Downstream Products

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

Relevant academic research and scientific papers

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.

RHO KINASE INHIBITORS

Disclosed are novel substituted 2H-isoquinolin-1-one and 3H-quinazolin-4-one derivatives useful as inhibitors of Rho kinase and for treating a variety of diseases and disorders that are mediated or sustained through the activity of Rho kinase, including c

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.

Novel inhibitors of the sodium-calcium exchanger: Benzene ring analogues of N-guanidino substituted amiloride derivatives

A series of N-guanidino substituted 2,4-diamino-5-carbonylguanidine molecules related to amiloride were synthesised and evaluated for their ability to inhibit the sodium-calcium exchanger in rat insulinoma cells (RINm5F) and human platelets. Specific chemical pathways were used to prepare the benzene derivatives designed as bioisosteric analogues of the pyrazine derivatives of amiloride. Several so-called 'simplified analogues', where some substituents of amiloride were omitted or replaced, were also prepared and included in the biological evaluation. The inhibitory potency of the sodium-calcium exchanger was screened on both cell types by measuring their effect on 45Ca2+ uptake. Among the most active compounds, N-(2-amino-5-chloro-4-nitrobenzoyl)-N′-(1-naphtylmethyl)guanidine (IC50 = 3.4 μM) was found more active than amiloride (IC50 = 690 μM) and 3,4-dichlorobenzamil (IC50 = 15.2 μM), the reference inhibitor.