143816-56-2

Basic information

• Product Name: 5-(3-(2-(7-CHLOROQUINOLIN-2-YL)ETHENYL)PHENYL)-8-CARBAMYL-4,6-DITHIAOCTANOIC ACID
• CAS NO: 143816-56-2
• Molecular Weight: 487.043
• Mol File: 143816-56-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5-(3-(2-(7-CHLOROQUINOLIN-2-YL)ETHENYL)PHENYL)-8-CARBAMYL-4,6-DITHIAOCTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3-(2-(7-CHLOROQUINOLIN-2-YL)ETHENYL)PHENYL)-8-CARBAMYL-4,6-DITHIAOCTANOIC ACID(143816-56-2)
• EPA Substance Registry System: 5-(3-(2-(7-CHLOROQUINOLIN-2-YL)ETHENYL)PHENYL)-8-CARBAMYL-4,6-DITHIAOCTANOIC ACID(143816-56-2)

Safety Data

• Hazardous Substances Data: 143816-56-2(Hazardous Substances Data)

Upstream product

• 115104-22-8 dimethyl 5-(3-formylphenyl)-4,6-dithianonanedioate 
• 1028266-50-3 3-((2-Carbamoyl-ethylsulfanyl)-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-methylsulfanyl)-propionic acid methyl ester 
• 115125-09-2 ((7-chloroquinolin-2-yl)methyl)triphenylphosphonium bromide 
• 120385-96-8 dimethyl 5-<3-<2-(7-chloro-2-quinolinyl)-(E)-ethenyl>phenyl>-4,6-dithianonanedioate 
• 4965-33-7 2-methyl-7-chloroquinoline 
• 115104-25-1 2-(Bromomethyl)-7-chloroquinoline 
• 626-19-7 Isophthalaldehyde 

Relevant articles and documents

Development of a novel series of styrylquinoline compounds as high- affinity leukotriene D4 receptor antagonists: Synthetic and structure- activity studies leading to the discovery of (±)-3-[[[3-[2-(7-chloro-2- quinolinyl)-(E)-ethenyl]phenyl][[3-(dimethylamino)-3- oxopropyl]thio]methyl]thio]propionic acid

Based on LTD4 receptor antagonist activity of 3-(2-quinolinyl-(E)- ethenyl)pyridine (2) found in broad screening, structure-activity studies were carried out which led to the identification of 3-[[[3-[2-(7-chloro-2- quinolinyl)-(E)-ethenyl]phenyl][[3-(dimethylamino)-3- oxopropyl]thio]methyl]thio]propionic acid (1, MK-571) as a potent and orally active LTD4 receptor antagonist. These studies demonstrated that a phenyl ring could replace the pyridine in 2 without loss of activity, that 7-halogen substitution in the quinoline group was optimal for binding, that the (E)- ethenyl linkage was optimal, that binding was enhanced by incorporation of a polar acidic group or groups in the 3-position of the aryl ring, and that two acidic groups could be incorporated via a dithioacetal formed from thiopropionic acid and the corresponding styrylquinoline 3-aldehyde to yield compounds such as 20 (IC50 = 3 nM vs [3H]LTD4 binding to the guinea pig lung membrane). It was found that one of the acidic groups could be transformed into a variety of the amides without loss of potency and that the dimethylamide 1 embodied the optimal properties of intrinsic potency (IC50 = 0.8 nM on guinea pig lung LTD4 receptor) and oral in vivo potency in the guinea pig, hyperreactive rat, and squirrel monkey. The evolution of 2 to 1 involves the increase of >6000-fold in competition for [3H]LTD4 binding to guinea pig lung membrane and a >40-fold increase in oral activity as measured by inhibition of antigen-induced dyspnea in hyperreactive rats.

2-Substituted quinoline dioic acids

Compounds having the formula: are antagonists of leukotrienes and inhibitors of their biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents.