82144-38-5

Basic information

• Product Name: Benzeneacetic acid, 3,4-dichloro-a-cyano-, ethyl ester
• Synonyms: Benzeneacetic acid, 3,4-dichloro-a-cyano-, ethyl ester
• CAS NO: 82144-38-5
• Molecular Formula: C₁₁H₉Cl₂NO₂
• Molecular Weight: 258.10066
• Mol File: 82144-38-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzeneacetic acid, 3,4-dichloro-a-cyano-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, 3,4-dichloro-a-cyano-, ethyl ester(82144-38-5)
• EPA Substance Registry System: Benzeneacetic acid, 3,4-dichloro-a-cyano-, ethyl ester(82144-38-5)

Safety Data

• Hazardous Substances Data: 82144-38-5(Hazardous Substances Data)

Upstream product

• 3218-49-3 3,4-dichloro-benzeneacetonitrile 
• 105-58-8 Diethyl carbonate 
• 20555-91-3 3,4-dichloroiodobenzene 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 716327-38-7 ethyl 2-cyano-2-(3,4-dichlorophenyl)-4-(1,3-dioxolan-2-yl)butanoate 
• 135522-12-2 (+/-)-N-methyl-N--1-(3',4'-dichlorophenyl)-cyclopropanecarboxylic amide 
• 342386-78-1 1-(3,4-dichlorophenyl)cyclopropanecarboxylic acid 
• 437650-07-2 1-(3,4-Dichloro-phenyl)-cyclopropanecarbonyl chloride 
• 124276-57-9 1-(3,4-dichlorophenyl)cyclopropanecarbonitrile 
• 130993-46-3 (1',2'-trans)-3-(3,4-dichlorophenyl)-<2'-(N-pyrrolidinyl)cyclohexyl>-2-pyrrolidinone 
• 130993-46-3 (1',2'-trans)-3-(3,4-dichlorophenyl)-<2'-(N-pyrrolidinyl)cyclohexyl>-2-pyrrolidinone 
• 130993-60-1 4-chloro-2-(3,4-dichlorophenyl)-N-<2'-(N-pyrrolidinyl)cyclohexyl>butyramide 

Relevant articles and documents

Discovery of bioavailable 4,4-disubstituted piperidines as potent ligands of the chemokine receptor 5 and inhibitors of the human immunodeficiency virus-1

We describe robust chemical approaches toward putative CCR5 scaffolds designed in our laboratories. Evaluation of analogues in the 125I-[MIP-1β] binding and Ba-L-HOS antiviral assays resulted in the discovery of 64 and 68 in the 4,4-disubstitited piperidine class H, both potent CCR5 ligands (pIC50 = 8.30 and 9.00, respectively) and HIV-1 inhibitors (pIC50 = 7.80 and 7.84, respectively, in Ba-L-HOS assay). In addition, 64 and 68 were bioavailable in rodents, establishing them as lead molecules for further optimization toward CCR5 clinical candidates.

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.