203940-18-5

Upstream product

• 184763-69-7 2-((S)-3-Acetoxy-1-bromo-3-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-propyl)-benzoic acid methyl ester 
• 4965-33-7 2-methyl-7-chloroquinoline 
• 52178-50-4 Methyl 3-formylbenzoate 
• 181139-72-0 methyl-[(E)]-2-[3(S)-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl] benzoate 
• 184763-59-5 2-((S)-3-Acetoxy-3-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-propyl)-benzoic acid methyl ester 

Downstream Products

• 203940-19-6 ethyl 5-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}oxazol-4-carboxylate 
• 1021946-05-3 (E)-3-[7-chloro-(2-quinolinylethenyl)]benzoyl chloride 
• 203940-21-0 (+/-)-2-amino-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethanol 
• 904916-30-9 (+/-)-methyl 3-[(2-{4-chlorophenylsulfonylamino}-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]propanoate 
• 904916-35-4 (+/-)-methyl 4-{[(2-{phenylsulfonylamino}-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]methyl}benzoate 
• 904916-31-0 (+/-)-methyl 4-[(2-{4-chlorophenylsulfonylamino}-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]-3,3-dimethylbutyrate 
• 904916-36-5 (+/-)-methyl 4-{[(2-{4-bromophenylsulfonylamino}-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]methyl}benzoate 
• 203940-25-4 (+/-)-methyl 4-{[(2-{4-chlorophenylsulfonylamino}-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]methyl}benzoate 
• 203940-24-3 (+/-)-methyl 4-{[(1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}-2-phthalimidoethyl)thio]methyl}benzoate 
• 904916-38-7 (+/-)-methyl 4-{[(2-{4-fluorophenylsulfonylamino}-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]methyl}benzoate 

Relevant academic research and scientific papers

A novel dual antagonist of thromboxane A2 and leukotriene D 4 receptors: Synthesis and structure-activity relationships of chloroquinolylvinyl derivatives

To discover an orally active thromboxane A2 (TXA2) and leukotriene D4 (LTD4) dual antagonist, we designed and synthesized chloroquinolylvinyl derivatives based on the structures of the TXA2 antagonist daltroban and the LTD4 antagonist montelukast. Among these derivatives, 4-{[(2-(4-chlorophenylsulfonylamino)-1-{3- [(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethyl)thio]methyl}benzoic acid (18d) showed potent inhibitory activity against U46619-induced aggregation of guinea pig platelets and LTD4-induced contraction in the guinea pig ileum, with IC50 values of 340 nm and 0.40 nm, respectively. Oral administration of 18 d also inhibited both the LTD4-induced acceleration of plasma leakage to skin in guinea pig and the U46619-induced increase in airway resistance in guinea pig with ED50 values of 0.47 mg/kg and 3.3 mg/kg, respectively.

Synthesis of Montelukast (MK-0476) metabolic oxidation products

We report the chemical synthesis of six oxidized derivatives of MK-0476 (Montelukast, L-706631), which have been key tools in the identification of its metabolites. We have prepared three diastereoisomeric pairs of potential oxidative metabolites of MK-0476, starting from the (S)-hydroxy ester 7 in 10 and five steps, and starting from MK-0476 itself in one step. The key benzylic hydroxyl of 1 and 2 was introduced by a bromination and saponification reaction sequence. In the case of the hydroxyl of 3 and 4, the key step was the addition of a hydroxymethyl carbanion equivalent on ketone 20. The two sulfoxide 5 and 6 were prepared by a direct oxidation of MK-0476 with m-chloroperbenzoic acid.