939-89-9

Usage

Uses

Used in Pharmaceutical Industry:
cis-2-Phenylcyclopropanecarboxylic acid is used as a key reagent for the synthesis of tranylcypromine compounds, which are potent and efficacious 5-HT2C receptor agonists. These agonists play a significant role in the treatment of various psychiatric and neurological disorders, such as depression, anxiety, and obsessive-compulsive disorder, by modulating the activity of the serotonin receptor.
Additionally, the unique structural features of cis-2-Phenylcyclopropanecarboxylic acid may also allow it to be used in the development of other pharmaceutical compounds with diverse therapeutic applications. Its ability to form stable intermediates and participate in various chemical reactions makes it a valuable building block in the synthesis of complex organic molecules with potential medicinal properties.

InChI:InChI=1/C10H10O2/c11-10(12)9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6H2,(H,11,12)/t8-,9-/m1/s1

Upstream product

• 63106-93-4 (1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 
• 936-98-1 ((R)-2-Phenyl-cyclopropyl)-methanol 
• 763126-74-5 (1R,2S)-1,2-di(hydroxymethyl)-2-phenylcyclopropane 
• 100-42-5 styrene 
• 623-73-4 diazoacetic acid ethyl ester 
• 766-94-9 vinyl phenyl ether 
• 110-82-7 cyclohexane 
• 84564-98-7 peracide phenyl-2-cyclopropane carboxyloque cis 
• 946-38-3 cis-1-ethoxycarbonyl-2-phenylcyclopropane 
• 5617-74-3 cis-1,2-cyclopropanedicarboxylic acid anhydride 
• 1078-58-6 diphenylzinc 
• 75-47-8 iodoform 
• 140-10-3 cis-cinnamic acid 
• 124-38-9 carbon dioxide 

Downstream Products

• 625389-83-5 (1R,2S)-1-[4-(2,4-dimethylphenyl)piperazyl]carbonyl-2-phenylcyclopropane 
• 307952-37-0 [4-(2,4-Dimethyl-phenyl)-piperazin-1-yl]-((1S,2S)-2-phenyl-cyclopropyl)-methanone 
• 5682-61-1 (1S,2S)-2-phenylcyclopropanecarboxylic acid methyl ester 
• 5682-61-1 (1S,2R)-2-phenylcyclopropanecarboxylic acid methyl ester 
• 105367-36-0 (1R)-menthyl (1S,2S)-(+)-2-phenylcyclopropanecarboxylate 
• 105367-37-1 (1S,2R)-l-menthyl 2-phenylcyclopropane-1-carboxylate 
• 67528-62-5 cis-methyl 2-phenylcyclopropane-1-carboxylate 
• 939-87-7 2-phenyl-1-cyclopropanecarbonyl chloride 
• 4186-30-5 cis-N-Ethyl-2-phenylcyclopropanecarboxamide 
• 3977-92-2 cis-2-phenylcyclopropanecarboxylic acid diethylamide 
• 946-39-4 ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate 
• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 
• 2243-53-0 styrylacetic acid 
• 939-90-2 trans-2-phenylcyclopropane-1-carboxylic acid 

Relevant academic research and scientific papers

Nickel-Catalyzed Reductive Carboxylation of Cyclopropyl Motifs with Carbon Dioxide

A nickel-catalyzed reductive carboxylation technique for the synthesis of cyclopropanecarboxylic acids has been developed. This user-friendly and mild transformation operates at atmospheric pressure of carbon dioxide and utilizes either organic halides or alkene precursors, thus representing the first example of catalytic reductive carboxylation of secondary counterparts lacking adjacent π-components.

(HETERO)ARYL CYCLOPROPYLAMINE COMPOUNDS AS LSD1 INHIBITORS

The invention relates to (hetero)aryl cyclopropylamine compounds, including particularly the compounds of formula (I) as described and defined herein, and their use in therapy, including, e.g., in the treatment or prevention of cancer, a neurological disease or condition, or a viral infection.

Silver-promoted, palladium-catalyzed direct arylation of cyclopropanes: Facile access to spiro 3,3′-cyclopropyl oxindoles

The Pd-catalyzed, Ag(I)-mediated intramolecular direct arylation of cyclopropane C-H bonds is described. Various spiro 3,3′-cyclopropyl oxindoles can be obtained in good to excellent yields from easily accessible 2-bromoanilides. The kinetic isotope effect was determined and epimerization studies were conducted, suggesting that the formation of a putative Pd-enolate is not operative and that the reaction proceeds via a C-H arylation pathway.

Probes for narcotic receptor mediated phenomena. 41. Unusual inverse μ-agonists and potent μ-opioid antagonists by modification of the N-substituent in enantiomeric 5-(3-hydroxyphenyl)morphans

Conformational restraint in the N-substituent of enantiomeric 5-(3-hydroxyphenyl)morphans was conferred by the addition of a cyclopropane ring or a double bond. All of the possible enantiomers and isomers of the N-substituted compounds were synthesized. Opioid receptor binding assays indicated that some of them had about 20-fold higher μ-affinity than the compound with an N-phenylpropyl substituent (Ki = 2-450 nM for the examined compounds with various N-substituents). Most of the compounds acted unusually as inverse agonists in the [35S]GTP-γ-S functional binding assay using nondependent cells that stably express the cloned human μ-opioid receptor. Two of the N-substituted compounds with a cyclopropane ring were very potent μ-opioid antagonists ((+)-29, Ke = 0.17 and (-)-30, Ke =0.3) in the [35S]GTP-γ-S functional binding assay. By comparison of the geometry-optimized structures of the newly synthesized compounds, an attempt was made to rationalize their μ-opioid receptor affinity in terms of the spatial position of N-substituents. This article not subject to U.S. Copyright. Published 2011 by the American Chemical Society.

Biochemical, structural, and biological evaluation of tranylcypromine derivatives as inhibitors of histone demethylases LSD1 and LSD2

LSD1 and LSD2 histone demethylases are implicated in a number of physiological and pathological processes, ranging from tumorigenesis to herpes virus infection. A comprehensive structural, biochemical, and cellular study is presented here to probe the potential of these enzymes for epigenetic therapies. This approach employs tranylcypromine as a chemical scaffold for the design of novel demethylase inhibitors. This drug is a clinically validated antidepressant known to target monoamine oxidases A and B. These two flavoenzymes are structurally related to LSD1 and LSD2. Mechanistic and crystallographic studies of tranylcypromine inhibition reveal a lack of selectivity and differing covalent modifications of the FAD cofactor depending on the enantiomeric form. These findings are pharmacologically relevant, since tranylcypromine is currently administered as a racemic mixture. A large set of tranylcypromine analogues were synthesized and screened for inhibitory activities. We found that the common evolutionary origin of LSD and MAO enzymes, despite their unrelated functions and substrate specificities, is reflected in related ligand-binding properties. A few compounds with partial enzyme selectivity were identified. The biological activity of one of these new inhibitors was evaluated with a cellular model of acute promyelocytic leukemia chosen since its pathogenesis includes aberrant activities of several chromatin modifiers. Marked effects on cell differentiation and an unprecedented synergistic activity with antileukemia drugs were observed. These data demonstrate that these LSD1/2 inhibitors are of potential relevance for the treatment of promyelocytic leukemia and, more generally, as tools to alter chromatin state with promise of a block of tumor progression.

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.

The first cyclopropanation reaction of unmasked α,β-unsaturated carboxylic acids: Direct and complete stereospecific synthesis of cyclopropanecarboxylic acids promoted by Sm/CHl3

Equation Presented A samarium-promoted cyclopropanation of unmasked α,β-unsaturated acids is described. This reaction can be carried out on (E)- or (Z)α,β-unsaturated carboxylic acids. In all cases the process is completely stereospecific and stereoselective. A mechanism has been proposed to explain the cyclopropanation reaction.

5-HT2C RECEPTOR AGONISTS AS ANORECTIC AGENTS

This invention relates to compounds which modulate receptors of the 5-HT2 family of receptors, and particularly to compounds which modulate 5-HT2C receptors. Compounds of the invention include agonists and selective agonists for the 5-HT2C receptor. Compounds of the invention include selective agonists for the 5-HT2C receptor which exhibit significantly less or no agonist activity on the 5-HT2A receptor and/or the 5-HT2B receptor. Compounds of this invention are those of Formula I and pharmaceutically acceptable salts, esters and solvates (including hydrates) wherein variables are defined in the specification hereof.

Decarbonylative cross-coupling of cyclic anhydrides: Introducing stereochemistry at an sp3 carbon in the cross-coupling event

Treatment of cyclic anhydrides with stoichiometric amounts of nickel-neocuproine complex generates alkylcarboxylato-nickelalactones upon extrusion of CO. These metalacycles undergo cross-coupling with arylzinc reagents. The generated CO is sequestered in situ by a nickel-dppb complex. The overall sequence effects a secondary sp3(electrophile)-sp2(nucleophile) cross-coupling and allows for control of stereochemistry during the bond-forming event. Copyright

Construction of a cis-Cyclopropane via Reductive Radical Decarboxylation. Enantioselective Synthesis of cis- and trans-1-Arylpiperazyl-2-phenylcyclopropanes Designed as Antidopaminergic Agents

(1S,2S)-, (1S,2R)-, and (1R,2S)-1-(2,4-Dimethylphenyl)piperazyl-2-phenylcyclopropane (2a, 3, and ent-3, respectively), which were designed as conformationally restricted analogues of haloperidol (1), a clinically effective antipsychotic agent, were synthe