174636-71-6

Basic information

• Product Name: 3-methyl-2-phenylquinoline-4-carbonyl chloride
• Synonyms: 3-methyl-2-phenylquinoline-4-carbonyl chloride;4-quinolinecarbonyl chloride, 3-methyl-2-phenyl-;3-methyl-2-phenyl-4-quinolinecarbonyl chloride
• CAS NO: 174636-71-6
• Molecular Formula: C₁₇H₁₂ClNO
• Molecular Weight: 281.73628
• Mol File: 174636-71-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-methyl-2-phenylquinoline-4-carbonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-2-phenylquinoline-4-carbonyl chloride(174636-71-6)
• EPA Substance Registry System: 3-methyl-2-phenylquinoline-4-carbonyl chloride(174636-71-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 174636-71-6(Hazardous Substances Data)

Upstream product

• 43071-45-0 3-methyl-2-phenylquinoline-4-carboxylic acid 
• 433712-63-1 3-Bromomethyl-2-phenyl-quinoline-4-carboxylic Acid Tert-butyl Ester 
• 340962-71-2 [1,4']bipiperidinyl-3-carboxylic acid ethyl ester 

Downstream Products

• 16335-26-5 3-methyl-2-phenylquinoline-4-carboxamide 
• 74960-43-3 3-methyl-2-phenyl-quinoline-4-carboxylic acid methyl ester 
• 402517-03-7 3-methyl-2-phenylquinoline-4-carbohydrazide 
• 5471-16-9 3-methyl-2-phenylquinoline-4-carboxylic acid ethyl ester 
• 174635-69-9 (+/-)-SB 221275 
• 174635-69-9 (-)-(S)-N-(α-ethylbenzyl)-3-methyl-2-phenylquinoline-4-carboxamide 
• 174635-69-9 (+)-SB 222201 
• 540757-68-4 3-methyl-2-phenylquinoline-4-carboxylic acid diisopropylamide 
• 850011-13-1 3-hydroxy-4-phenyl-3H-furo[3,4-c]quinolin-1-one 
• 850011-12-0 3-ethoxy-4-phenyl-3H-furo[3,4-c]quinolin-1-one 
• 850010-56-9 3-bromomethyl-2-phenylquinoline-4-carboxylic acid ethyl ester 
• 850010-68-3 2-phenyl-3-pyrazol-1-ylmethylquinoline-4-carboxylic acid ethyl ester 
• 850011-20-0 3-bromomethyl-2-phenylquinoline-4-carboxylic acid diisopropylamide 
• 850010-66-1 3-morpholin-4-ylmethyl-2-phenylquinoline-4-carboxylic acid ethyl ester 

Relevant articles and documents

Discovery of GSK2193874: An Orally Active, Potent, and Selective Blocker of Transient Receptor Potential Vanilloid 4

Transient Receptor Potential Vanilloid 4 (TRPV4) is a member of the Transient Receptor Potential (TRP) superfamily of cation channels. TRPV4 is expressed in the vascular endothelium in the lung and regulates the integrity of the alveolar septal barrier. Increased pulmonary vascular pressure evokes TRPV4-dependent pulmonary edema, and therefore, inhibition of TRPV4 represents a novel approach for the treatment of pulmonary edema associated with conditions such as congestive heart failure. Herein we report the discovery of an orally active, potent, and selective TRPV4 blocker, 3-(1,4′-bipiperidin-1′-ylmethyl)-7-bromo-N-(1-phenylcyclopropyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxamide (GSK2193874, 28) after addressing an unexpected off-target cardiovascular liability observed from in vivo studies. GSK2193874 is a selective tool for elucidating TRPV4 biology both in vitro and in vivo.

Synthesis of brequinar analogue inhibitors of malaria parasite dihydroorotate dehydrogenase

A series of 2-phenyl quinoline-4-carboxylic acid derivatives related to brequinar, an inhibitor of human dihydroorotate dehydrogenase (DHODH), has been prepared and evaluated as inhibitors of DHODH from the malaria parasite Plasmodium falciparum. Brequinar was essentially inactive against PfDHODH (IC50 880 μM) whereas several members of the series inhibited PfDHODH. Unexpectedly, replacement of the carboxylic acid required for brequinar to inhibit hDHODH was not essential in the diisopropylamides that inhibited PfDHODH.

Stepwise modulation of neurokinin-3 and neurokinin-2 receptor affinity and selectivity in quinoline tachykinin receptor antagonists

A stepwise chemical modification from human neurokinin-3 receptor (hNK-3R)-selective antagonists to potent and combined hNK-3R and hNK-2R antagonists using the same 2-phenylquinoline template is described. Docking studies with 3-D models of the hNK-3 and