1332634-91-9

Basic information

• Product Name: N¹-(4-chlorophenyl)-N²-(5-fluoro-2,4-dinitrophenyl)benzene-1,2-diamine
• Synonyms: N¹-(4-chlorophenyl)-N²-(5-fluoro-2,4-dinitrophenyl)benzene-1,2-diamine
• CAS NO: 1332634-91-9
• Molecular Weight: 402.769
• Mol File: 1332634-91-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: N¹-(4-chlorophenyl)-N²-(5-fluoro-2,4-dinitrophenyl)benzene-1,2-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: N¹-(4-chlorophenyl)-N²-(5-fluoro-2,4-dinitrophenyl)benzene-1,2-diamine(1332634-91-9)
• EPA Substance Registry System: N¹-(4-chlorophenyl)-N²-(5-fluoro-2,4-dinitrophenyl)benzene-1,2-diamine(1332634-91-9)

Safety Data

• Hazardous Substances Data: 1332634-91-9(Hazardous Substances Data)

Upstream product

• 23008-56-2 N-(4-chlorophenyl)-2-nitroaniline 
• 1493-27-2 ortho-nitrofluorobenzene 
• 327-92-4 1,5-difluoro-2,4-dinitrobenzene 
• 68817-71-0 2-(4-chloroanilino)aniline 

Downstream Products

• 1353740-42-7 N¹-(4-chlorophenyl)-N²-[2,4-dinitro-5-(pyridin-3-ylamino)phenyl]benzene-1,2-diamine 
• 1353740-44-9 5-(4-chlorophenyl)-3-imino-N-(pyridin-3-yl)-3,5-dihydrophenazin-2-amine 
• 1353730-91-2 5-(4-chlorophenyl)-3-isopropylimino-2-(3-pyridylamino)-3,5-dihydrophenazine 
• 1353737-67-3 5-(4-chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine 
• 1353737-62-8 5-(4-chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(3-pyridyl)amino-3,5-dihydrophenazine 
• 1401207-31-5 5-(4-chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(5-bromo-3-pyridyl)amino-3,5-dihydrophenazine 
• 1353736-14-7 5-(4-chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(5-bromo-3-pyridyl)amino-3,5-dihydrophenazine 
• 1353737-93-5 5-(4-chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine 
• 1353737-91-3 5-(4-chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine 
• 1353737-77-5 5-(4-chlorophenyl)-3-isopropylimino-2-(6-methyl-3-pyridyl)amino-3,5-dihydrophenazine 
• 1353737-99-1 5-(4-chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine 
• 1353737-97-9 5-(4-chlorophenyl)-3-(4-tetrahydropyranyl)imino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine 
• 1353737-90-2 5-(4-chlorophenyl)-3-isopropylimino-2-(2-methyl-3-pyridyl)amino-3,5-dihydrophenazine 
• 1353737-82-2 5-(4-chlorophenyl)-3-(4-methoxycyclohexyl)imino-2-(2-methoxy-3-pyridyl)amino-3,5-dihydrophenazine 

Relevant articles and documents

Optimization of the clofazimine structure leads to a highly water-soluble C3-aminopyridinyl riminophenazine endowed with improved anti-Wnt and anti-cancer activity in vitro and in vivo

Triple-negative breast cancer (TNBC) is a cancer subtype critically dependent upon excessive activation of Wnt pathway. The anti-mycobacterial drug clofazimine is an efficient inhibitor of canonical Wnt signaling in TNBC, reducing tumor cell proliferation

Systematic evaluation of structure-activity relationships of the riminophenazine class and discovery of a C2 pyridylamino series for the treatment of multidrug-resistant tuberculosis

Clofazimine, a member of the riminophenazine class of drugs, is the cornerstone agent for the treatment of leprosy. This agent is currently being studied in clinical trials for the treatment of multidrug-resistant tuberculosis to address the urgent need for new drugs that can overcome existing and emerging drug resistance. However, the use of clofazimine in tuberculosis treatment is hampered by its high lipophilicity and skin pigmentation side effects. To identify a new generation of riminophenazines that is less lipophilic and skin staining, while maintaining efficacy, we have performed a systematic structure-activity relationship (SAR) investigation by synthesizing a variety of analogs of clofazimine and evaluating their anti-tuberculosis activity. The study reveals that the central tricyclic phenazine system and the pendant aromatic rings are important for anti-tuberculosis activity. However, the phenyl groups attached to the C2 and N5 position of clofazimine can be replaced by a pyridyl group to provide analogs with improved physicochemical properties and pharmacokinetic characteristics. Replacement of the phenyl group attached to the C2 position by a pyridyl group has led to a promising new series of compounds with improved physicochemical properties, improved anti-tuberculosis potency, and reduced pigmentation potential.

RIMINOPHENAZINES WITH 2-(HETEROARYL)AMINO SUBSTITUENTS AND THEIR ANTI-MICROBIAL ACTIVITY

The present invention relates to riminophenazines having heteroaromatic substitutions, including those with 2-heteroaryl-amino substituents, to their preparation, and to their use as drugs for treating Mycobacterium tuberculosis and other microbial infections, either alone or in combination with other anti-infective treatments.