32082-99-8

Basic information

• Product Name: methyl 4-chloro-2-(4-methoxyphenyl)aminobenzoate
• Synonyms: methyl 4-chloro-2-(4-methoxyphenyl)aminobenzoate
• CAS NO: 32082-99-8
• Molecular Weight: 291.734
• Mol File: 32082-99-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl 4-chloro-2-(4-methoxyphenyl)aminobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-chloro-2-(4-methoxyphenyl)aminobenzoate(32082-99-8)
• EPA Substance Registry System: methyl 4-chloro-2-(4-methoxyphenyl)aminobenzoate(32082-99-8)

Safety Data

• Hazardous Substances Data: 32082-99-8(Hazardous Substances Data)

Upstream product

• 104-94-9 4-methoxy-aniline 
• 50-84-0 2,4 dichlorobenzoic acid 
• 91-38-3 4-chloro-2-(4-methoxyphenylamino)benzoic acid 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 212892-02-9 methyl 4-chloro-2-(((trifluoromethyl)sulfonyl)oxy)benzoate 

Downstream Products

• 23857-08-1 7-chloro-2-methoxy-1-(4-methoxy-phenyl)-2-thioxo-1,2-dihydro-2λ⁵-benzo[d][1,3,2]thiazaphosphinin-4-one 
• 86-38-4 6,9-dichloro-2-methoxyacridine 
• 91-38-3 4-chloro-2-(4-methoxyphenylamino)benzoic acid 
• 23857-43-4 6-chloro-1-(4-methoxy-phenyl)-1H-benzo[c]isothiazole-3-thione 
• 23857-38-7 7-chloro-2-methoxy-1-(4-methoxy-phenyl)-2-thioxo-1,2-dihydro-2λ⁵-benzo[d][1,3,2]thiazaphosphinine-4-thione 

Relevant articles and documents

N-aryl-6-methoxy-1,2,3,4-tetrahydroquinolines: A novel class of antitumor agents targeting the colchicine site on tubulin

Structural optimizations of the prior lead 1a led to the discovery of a series of N-aryl-6-methoxy-1,2,3,4-tetrahydroquinoline derivatives as a novel class of tubulin polymerization inhibitors targeted at the colchicine binding site. The most active compound 6d showed extremely high cytotoxicity against a human tumor cell line panel (A549, KB, KBvin, and DU145) with GI50 values ranging from 1.5 to 1.7 nM, significantly more potent than paclitaxel, especially against the drug-resistant KBvin cell line, in the same assays. Analogs 5f, 6b, 6c, and 6e were also quite potent, with a GI50 range of 0.011-0.19 μM. In further studies, active compounds 6b-e and 5f significantly inhibited tubulin assembly, with IC 50 values of 0.92 -1.0 μM and strongly inhibited colchicine binding to tubulin, with inhibition rates of 75-99% (at 5 μM), comparable with or more potent than combretastatin A-4 (IC50 0.96 μM). Current studies included design, synthesis, and biological evaluations of 24 new compounds (series 3-6). Related SAR analysis, molecular modeling, and evaluation of essential drug-like properties, i.e. water solubility, log P, and in vitro metabolic stability, were also performed.