437650-07-2

Upstream product

• 342386-78-1 1-(3,4-dichlorophenyl)cyclopropanecarboxylic acid 
• 124276-57-9 1-(3,4-dichlorophenyl)cyclopropanecarbonitrile 
• 3218-49-3 3,4-dichloro-benzeneacetonitrile 
• 82144-38-5 ethyl cyano(3,4-dichlorophenyl)acetate 

Downstream Products

• 135522-12-2 (+/-)-N-methyl-N--1-(3',4'-dichlorophenyl)-cyclopropanecarboxylic amide 
• 1252638-13-3 (4R)-4-[(2-chlorophenyl)sulfonyl]-N-(1-cyanocyclopropyl)-1-{[1-(3,4-dichlorophenyl)cyclopropyl]carbonyl}-L-prolinamide 

Relevant academic research and scientific papers

Systematic investigation of halogen bonding in protein-ligand interactions

Halogen bonding triggers activity: Increasing binding affinity was observed for a series of covalent human Cathepsin L inhibitors by exchanging an aryl ring H atom with Cl, Br, and I, which undergo halogen bonding with the C=O group of Gly61 in the S3 pocket of the enzyme. Fluorine, in contrast, strongly avoids halogen bonding (see scheme). The strong distance and angle dependence of halogen bonding was confirmed for biological systems. Copyright

N-Methyl-N--1-phenylcyclopropanecarboxylic amides - analogs of U50488 with much reduced opiate affinity and loss of κ-selectivity

(+/-)-N-methyl-N--1-phenylcyclopropanecarboxylic amide (1) and its dichloro analog (2) were synthesized.Compounds 1 and 2 are related to the κ-selective opiate U-50488 in that the benzylic methylene moiety in U-50488 has been replaced by a cyclopropane ring.As compared to U-50488, a 600-fold reduction in kappa-affinity was observed with these 2 compounds; while the reduction in μ-affinity was less than 2-fold.Unlike U-50488, 1 and 2 also show measurable δ-binding.To explain the observed anomaly, the steric interaction between the N-methyl group and the cyclopropane ring and the tendency of the cyclopropane ring to conjugate with the neighboring phenyl group, both affecting the accessible conformations of the amide side chains of 1 and 2, are cosidered important factors.