32082-99-8

Upstream product

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

Downstream Products

• 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 
• 23857-43-4 6-chloro-1-(4-methoxy-phenyl)-1H-benzo[c]isothiazole-3-thione 
• 91-38-3 4-chloro-2-(4-methoxyphenylamino)benzoic acid 
• 86-38-4 6,9-dichloro-2-methoxyacridine 
• 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 

Relevant academic research and scientific papers

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.

A convenient procedure for parallel ester hydrolysis

The treatment of alkyl esters with barium hydroxide octahydrate in methanol followed by protonation with anhydrous hydrogen chloride affords carboxylic acids. The procedure does not require aqueous workup and is particularly suitable for parallel synthesis applications.