16633-45-7

Basic information

• Product Name: Cyclopropanecarboxylic acid, 2-(3-chlorophenyl)-, (1R,2R)-rel-
• CAS NO: 16633-45-7
• Molecular Formula: C10H9ClO2
• Molecular Weight: 196.633
• Mol File: 16633-45-7.mol

Chemical Properties

• CAS DataBase Reference: Cyclopropanecarboxylic acid, 2-(3-chlorophenyl)-, (1R,2R)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarboxylic acid, 2-(3-chlorophenyl)-, (1R,2R)-rel-(16633-45-7)
• EPA Substance Registry System: Cyclopropanecarboxylic acid, 2-(3-chlorophenyl)-, (1R,2R)-rel-(16633-45-7)

Safety Data

• Hazardous Substances Data: 16633-45-7(Hazardous Substances Data)

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 2039-85-2 3-Chlorostyrene 
• 92576-45-9 2-(3-Chlor-phenyl)-cyclopropan-carbonsaeure-⁽¹⁾-ethylester 
• 586-39-0 1-nitro-3-vinyl-benzene 
• 42175-03-1 methyl (E)-3-(3-chlorophenyl)prop-2-enoate 
• 1866-38-2 m-Chlorocinnamic acid 
• 84953-64-0 trans-2-(m-nitrophenyl)cyclopropanecarboxylic acid 

Downstream Products

• 131844-46-7 trans-2-(3-chlorophenyl)cyclopropan-1-amine hydrochloride 
• 515179-15-4 (+)-(1S,2S)-2-(3-chlorophenyl)cyclopropanecarboxylic acid 
• 1237495-02-1 (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-((1S,2R/1R,2S)-2-(3-chlorophenyl)cyclopropylamino)ethoxy)pyrrolidine-1-carboxylate 

Relevant articles and documents

CARBOXYLIC ACID AROMATIC 1,2-CYCLOPROPYLAMIDES

The present invention relates to carboxylic acid aromatic 1,2-cyclopropylamides of general formula (I) as described and defined herein, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of neurogenic disorder, as a sole agent or in combination with other active ingredients.

Cyclopropyl- and methyl-containing inhibitors of neuronal nitric oxide synthase

Inhibitors of neuronal nitric oxide synthase have been proposed as therapeutics for the treatment of different types of neurological disorders. On the basis of a cis-3,4-pyrrolidine scaffold, a series of trans-cyclopropyl- and methyl-containing nNOS inhib

POTENT AND SELECTIVE NEURONAL NITRIC OXIDE SYNTHASE INHIBITORS WITH IMPROVED MEMBRANE PERMEABILITY

Compounds and related compositions and methods as can be used to inhibit neuronal nitric oxide synthase and as can be employed in the treatment of various neurodegenerative diseases.

Novel trans-2-aryl-cyclopropylamine analogues as potent and selective dipeptidyl peptidase IV inhibitors

A series of trans-2-aryl-cyclopropylamine derived compounds were synthesized and evaluated their biological activities against DPP-IV. The structure-activity relationships (SAR) led to the discovery of novel series of DPP-IV inhibitors, having IC50 values of 100 nM with excellent selectivity over the closely related enzymes, DPP8, DPP-II and FAP. The studies identified a potent and selective DPP-IV inhibitor 24b, which exhibited the ability to both significantly inhibit plasma DPP-IV activity in rats and improve glucose tolerance in lean mice and diet induced obese mice.

Selective 5-hydroxytryptamine 2c receptor agonists derived from the lead compound tranylcypromine: Identification of drugs with antidepressant-like action

We report here the design, synthesis, and pharmacological properties of a series of compounds related to tranylcypromine (9), which itself was discovered as a lead compound in a high-throughput screening campaign. Starting from 9, which shows modest activity as a 5-HT2C agonist, a series of 1-aminomethyl-2- phenylcyclopropanes was investigated as 5-HT2C agonists through iterative structural modifications. Key pharmacophore feature of this new class of ligands is a 2-aminomethyl-trans-cyclopropyl side chain attached to a substituted be zene ring. Among the tested compounds, several were potent and efficacious 5-HT2C receptor agonists with selectivity over both 5-HT2A and 5-HT2B receptors in functional assays. The most promising compound is 37, with 120- and 14-fold selectivity over 5-HT 2A and 5-HT2B, respectively (EC50) 585, 65, and 4.8 nM at the 2A, 2B, and 2C subtypes, respectively). In animal studies, compound 37 (10-60 mg/kg) decreased immobility time in the mouse forced swim test.

Exploring distal regions of the A3 adenosine receptor binding site: Sterically constrained N6-(2-phenylethyl)adenosine derivatives as potent ligands

We synthesized phenyl ring-substituted analogues of N6-(1S,2R)- (2-phenyl-1-cyclopropyl)adenosine, which is highly potent in binding to the human A3AR with a Ki value of 0.63nM. The effects of these structural changes on affinity at human and rat adenosine receptors and on intrinsic efficacy at the hA3AR were measured. A 3-nitrophenyl analogue was resolved chromatographically into pure diastereomers, which displayed 10-fold stereoselectivity in A3AR binding in favor of the 1S,2R isomer. A molecular model defined a hydrophobic region (Phe168) in the putative A3AR binding site around the phenyl moiety. A heteroaromatic group (3-thienyl) could substitute for the phenyl moiety with retention of high affinity of A3AR binding. Other related N6-substituted adenosine derivatives were included for comparison. Although the N 6-(2-phenyl-1-cyclopropyl) derivatives were full A3AR agonists, several other derivatives had greatly reduced efficacy. N 6-Cyclopropyladenosine was an A3AR antagonist, and adding either one or two phenyl rings at the 2-position of the cyclopropyl moiety restored efficacy. N6-(2,2-Diphenylethyl)adenosine was an A 3AR antagonist, and either adding a bond between the two phenyl rings (N6-9-fluorenylmethyl) or shortening the ethyl moiety (N 6-diphenylmethyl) restored efficacy. A QSAR study of the N 6 region provided a model that was complementary to the putative A3AR binding site in a rhodopsin-based homology model. Thus, a new series of high-affinity A3AR agonists and related nucleoside antagonists was explored through both empirical and theoretical approaches.

A novel approach to enantiopure cyclopropane compounds from biotransformation of nitriles

Rhodococcus sp. AJ270, a powerful and versatile nitrile hydratase/amidase containing microbial whole-cell system, catalyzed the enantioselective hydrolysis of both racemic trans- and cis-2-arylcyclopropanecarbonitriles to afford the corresponding amides and acids with enantiomeric excesses as high as >99%. The reaction rate and enantioselectivity observed for both nitrile hydratase and amidase were also strongly dependent upon the nature of the substituent and substitution pattern on the benzene ring of the substrates. The application of and the advantages of biotransformation of nitriles were demonstrated by preparing (1S,2R)-2-phenylcyclopropylamine and (1R,2R)-2-phenylcyclopropylmethylamine through facile and straightforward chemical manipulations of (1S,2S)-2-phenylcyclopropanecarboxylic acid and (1R,2R)-2-phenylcyclopropanecarboxamide, respectively.