124276-32-0

Usage

Uses

1-(3-Chlorophenyl)cyclopropanecarbonitrile

InChI:InChI=1/C10H8ClN/c11-9-3-1-2-8(6-9)10(7-12)4-5-10/h1-3,6H,4-5H2

Upstream product

• 1529-41-5 3-chloro-benzeneacetonitrile 
• 107-04-0 1-Bromo-2-chloroethane 
• 106-93-4 ethylene dibromide 
• 96-49-1 [1,3]-dioxolan-2-one 

Downstream Products

• 124276-34-2 1-(3-chlorophenyl)cyclopropane-1-carboxylic acid 
• 98480-33-2 (1-(3-chlorophenyl)cyclopropyl)methanol 
• 115816-31-4 C₁₀H₁₂ClN 

Relevant academic research and scientific papers

Efficient cyclopropanation of active methylene compounds. A serendipitous discovery

Cyclopropanation of active methylene compounds has been achieved in good yields with ethylene carbonate as the cyclopropanating agent in the presence of a simple base.

Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Cyclopropanes

We herein report an Ir-catalyzed enantioselective C(sp3)-H borylation of cyclopropanecarboxamides using a chiral bidentate boryl ligand for the first time. A variety of substrates with α-quaternary carbon centers could be compatible in this reaction to provide β-borylated products with good to excellent enantioselectivities. We have also demonstrated that the borylated products can be used as versatile precursors engaging in stereospecific transformations of C-B bonds, including the synthesis of a bioactive compound Levomilnacipran.

Lewis Basic Sulfide Catalyzed Electrophilic Bromocyclization of Cyclopropylmethyl Amide

A Lewis basic sulfide catalyzed electrophilic bromocyclization of cyclopropylmethyl amide has been developed. The catalytic protocol is applicable to both 1,1- and 1,2-substituted cyclopropylmethyl amides, giving oxazolines and oxazines in good yields and excellent diastereoselectivity.

Discovery of 2-[1-(4-Chlorophenyl)cyclopropyl]-3-hydroxy-8- (trifluoromethyl)quinoline-4-carboxylic acid (PSI-421), a P-selectin inhibitor with improved pharmacokinetic properties and oral efficacy in models of vascular injury

Previously, we reported the discovery of PSI-697 (1a), a C-2 benzyl substituted quinoline salicylic acid-based P-selectin inhibitor. It is active in a variety of animal models of cardiovascular disease. Compound 1a has also been shown to be well tolerated and safe in healthy volunteers at doses of up to 1200 mg in a phase 1 single ascending dose study. However, its oral bioavailability was low. Our goal was to identify a back up compound with equal potency, increased solubility, and increased exposure. We expanded our structure-activity studies in this series by branching at the α position of the C-2 benzyl side chain and through modification of substituents on the carboxylic A-ring of the quinoline. This resulted in discovery of PSI-421 with marked improvement in aqueous solubility and pharmacokinetic properties. This compound has shown oral efficacy in animal models of arterial and venous injury and was selected as a preclinical development compound for potential treatment of such diseases as atherosclerosis and deep vein thrombosis.

Methods and Compositions for Selectin Inhibition

The present teachings relate to novel compounds of formula I: wherein the constituent variables are as defined herein. Compounds of the present teachings can act as antagonists of the mammalian adhesion proteins known as selecting. Methods for treating or preventing selectin-mediated disorders are provided, which include administration of these compounds in a therapeutically effective amount.

Heteroaryl-Pyrazole Derivatives as Cannabinoid CB1 Receptor Antagonists

A heteroaryl-pyrazole compound of formula (I) or a pharmaceutically acceptable salt thereof is effective as a cannabinoid CB1 receptor inverse agonist or antagonist, which is useful for preventing or treating obesity and obesity-related metabolic disorders. The present invention also provides a method for preparing the inventive heteroaryl-pyrasole compounds or a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing same, and a method for preventing or treating obesity and obesity-related metabolic disorders.