23020-15-7

Basic information

• Product Name: (1S,2S)-2-Phenylcyclopropane-1-carboxylic acid
• Synonyms: (1S,2S)-2-Phenylcyclopropane-1-carboxylic acid;(1S,2S)-2-Phenylcyclopropanecarboxylic acid;1α-Phenyl-2β-cyclopropanecarboxylic acid;Cyclopropanecarboxylic acid, 2-phenyl-, (1S,2S)-
• CAS NO: 23020-15-7
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• Mol File: 23020-15-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S,2S)-2-Phenylcyclopropane-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-2-Phenylcyclopropane-1-carboxylic acid(23020-15-7)
• EPA Substance Registry System: (1S,2S)-2-Phenylcyclopropane-1-carboxylic acid(23020-15-7)

Safety Data

• Hazardous Substances Data: 23020-15-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1S,2S)-2-Phenylcyclopropane-1-carboxylic acid serves as a key intermediate in organic synthesis, where its unique structure and reactivity contribute to the formation of complex organic molecules. Its cyclopropane ring and carboxylic acid group provide a versatile platform for further chemical modifications and functional group transformations, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Drug Development:
In the pharmaceutical industry, (1S,2S)-2-Phenylcyclopropane-1-carboxylic acid is utilized as a building block for the development of new drugs. Its cyclopropane ring can impart specific biological activities, such as antimicrobial, anti-inflammatory, or analgesic properties, depending on the molecular context. The carboxylic acid group allows for the formation of various derivatives, including esters, amides, and salts, which can enhance the drug's solubility, stability, and bioavailability.
Used in Pharmaceutical Research and Development:
(1S,2S)-2-Phenylcyclopropane-1-carboxylic acid is employed in pharmaceutical research to explore the effects of cyclopropane derivatives on biological systems. Its unique stereochemistry and chemical properties make it an interesting candidate for studying structure-activity relationships and the development of novel therapeutic agents. Researchers can use (1S,2S)-2-Phenylcyclopropane-1-carboxylic acid to investigate its interactions with biological targets, such as enzymes, receptors, or ion channels, and to evaluate its potential as a lead compound for drug discovery.
Used in the Study of Cyclopropane Derivatives' Effects on Biological Systems:
In the field of biological research, (1S,2S)-2-Phenylcyclopropane-1-carboxylic acid is used to understand the impact of cyclopropane derivatives on various biological processes. Its presence in a molecule can influence the compound's ability to modulate cellular signaling pathways, affect gene expression, or interact with specific proteins. This knowledge can be crucial for the development of targeted therapies and the elucidation of the molecular mechanisms underlying various diseases.

Upstream product

• 946-39-4 ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate 
• 124-38-9 carbon dioxide 
• 36617-02-4 1-bromo-2-phenylcyclopropane 
• 946-38-3 ethyl 2-phenylcyclopropylcarboxylate 
• 5685-38-1 2-phenyl-cyclopropanecarboxylic acid 
• 201230-82-2 carbon monoxide 
• 3234-51-3 1,1-dibromo-2-phenylcyclopropane 
• 100-42-5 styrene 
• 75-47-8 iodoform 
• 140-10-3 cis-cinnamic acid 
• 5617-74-3 cis-1,2-cyclopropanedicarboxylic acid anhydride 
• 1078-58-6 diphenylzinc 
• 946-38-3 cis-1-ethoxycarbonyl-2-phenylcyclopropane 
• 110-82-7 cyclohexane 

Downstream Products

• 29667-50-3 (+)-trans-2-Phenylcyclopropylchlorid 
• 23131-56-8 (+)-trans-2-Phenylcyclopropyliodid 
• 110659-58-0 (1S,2S)-trans-1-(hydroxymethyl)-2-phenylcyclopropane 
• 78738-39-3 trans-2-phenyl-1-cyclopropanecarbonyl chloride 
• 1265913-05-0 ((1S,5R)-5-(3-methoxyphenyl)-2-azabicyclo[3.3.1]nonan-2-yl)-((1'S,2'S)-2-phenylcyclopropyl)methanone 
• 1265913-03-8 ((1R,5S)-5-(3-methoxyphenyl)-2-azabicyclo[3.3.1]nonan-2-yl)-((1'S,2'S)-2-phenylcyclopropyl)methanone 
• 1265913-20-9 (1R,5S)-5-(3-methoxyphenyl)-2-(((1'S,2'S)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonane 
• 1265913-22-1 (1S,5R)-5-(3-methoxyphenyl)-2-(((1'S,2'S)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonane 
• 1265968-37-3 3-((1R,5S)-2-(((1'S,2'S)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonan-5-yl)phenol 
• 1265968-38-4 3-((1S,5R)-2-(((1'S,2'S)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonan-5-yl)phenol 
• 1260614-90-1 C₁₄H₁₆O₃ 
• 883894-57-3 2-amino-3-methyl-6-((1S,2S)-2-phenylcyclopropyl)pyrimidin-4(3H)-one 
• 883894-58-4 C₁₃H₁₃N₃O 
• 1416060-81-5 (1S,2R)-1'-methyl-2-phenylspiro[cyclopropane-1,3'-indolin]-2'-one 

Relevant articles and documents

Nitrile and Amide Biotransformations for Efficient Synthesis of Enantiopure gem-Dihalocyclopropane Derivatives

Catalyzed by Rhodococcus sp. AJ270 microbial cells, trans-2,2-dihalo-3- phenylcyclopropanecarbonitriles and -amides underwent enantioselective hydrolysis under very mild conditions. Both the efficiency and enantioselectivity of the nitrile hydratase and a

Discovery of a Novel Inhibitor of Histone Lysine-Specific Demethylase 1A (KDM1A/LSD1) as Orally Active Antitumor Agent

We report the stereoselective synthesis and biological activity of a novel series of tranylcypromine (TCPA) derivatives (14a-k, 15, 16), potent inhibitors of KDM1A. The new compounds strongly inhibit the clonogenic potential of acute leukemia cell lines. In particular three molecules (14d, 14e, and 14g) showing selectivity versus MAO A and remarkably inhibiting colony formation in THP-1 human leukemia cells, were assessed in mouse for their preliminary pharmacokinetic. 14d and 14e were further tested in vivo in a murine acute promyelocytic leukemia model, resulting 14d the most effective. Its two enantiomers were synthesized: the (1S,2R) enantiomer 15 showed higher activity than its (1R,2S) analogue 16, in both biochemical and cellular assays. Compound 15 exhibited in vivo efficacy after oral administration, determining a 62% increased survival in mouse leukemia model with evidence of KDM1A inhibition. The biological profile of compound 15 supports its further investigation as a cancer therapeutic.

Gram-Scale Synthesis of Chiral Cyclopropane-Containing Drugs and Drug Precursors with Engineered Myoglobin Catalysts Featuring Complementary Stereoselectivity

Engineered hemoproteins have recently emerged as promising systems for promoting asymmetric cyclopropanations, but variants featuring predictable, complementary stereoselectivity in these reactions have remained elusive. In this study, a rationally driven strategy was implemented and applied to engineer myoglobin variants capable of providing access to 1-carboxy-2-aryl-cyclopropanes with high trans-(1R,2R) selectivity and catalytic activity. The stereoselectivity of these cyclopropanation biocatalysts complements that of trans-(1S,2S)-selective variants developed here and previously. In combination with whole-cell biotransformations, these stereocomplementary biocatalysts enabled the multigram synthesis of the chiral cyclopropane core of four drugs (Tranylcypromine, Tasimelteon, Ticagrelor, and a TRPV1 inhibitor) in high yield and with excellent diastereo- and enantioselectivity (98–99.9% de; 96–99.9% ee). These biocatalytic strategies outperform currently available methods to produce these drugs.

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.

Discovery of New Potential Anti-Infective Compounds Based on Carbonic Anhydrase Inhibitors by Rational Target-Focused Repurposing Approaches

In academia, compound recycling represents an alternative drug discovery strategy to identify new pharmaceutical targets from a library of chemical compounds available in house. Herein we report the application of a rational target-based drug-repurposing approach to find diverse applications for our in-house collection of compounds. The carbonic anhydrase (CA, EC 4.2.1.1) metalloenzyme superfamily was identified as a potential target of our compounds. The combination of a thoroughly validated docking screening protocol, together with in vitro assays against various CA families and isoforms, allowed us to identify two unprecedented chemotypes as CA inhibitors. The identified compounds have the capacity to preferentially bind pathogenic (bacterial/protozoan) CAs over human isoforms and represent excellent hits for further optimization in hit-to-lead campaigns.

ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds of Formula (IVA), or a salt thereof, and pharmaceutical formulations (pharmaceutical compositions) comprising those compounds, or a salt thereof: Formula (IVA), wherein "RIa", "RIb", "RIc", "RId", "RIe", are defined herein above, which compounds are believed suitable for use in positive modulation of the alpha 7 nicotinic acetylcholine receptor (α7 nAChR) receptors, for example, those found in the cerebral cortex and the hippocampus. Such compounds and pharmaceutical formulations are believed to be useful in treatment or management of neurodegenerative diseases, for example, Alzheimer's disease (AD), schizophrenia, and Parkinson's disease (PD), or movement disorders arising from use of certain medications used in the treatment or management of Parkinson's disease.

α7 NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS AND USES THEREOF-I

The present invention relates to chemical compounds of formula (I), with the substituents as described in the specification, useful in the positive modulation of the alpha 7 nicotinic acetylcholine receptor (α7 nAChR). The invention also relates to the use of these compounds in the treatment or prevention of a broad range of diseases in which the positive modulation of α7 nAChR is advantageous, including neurodegenerative and neuropsychiatric diseases and also neuropathic pain and inflammatory diseases.

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.

(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.

New Positive allosteric modulators of nicotinic acetylcholine receptor

The present invention relates to compounds useful in therapy, to compositions comprising said compounds, and to methods of treating diseases comprising administration of said compounds. The compounds referred to are positive allosteric modulators (PAMs) of the nicotinic acetylcholine α7 receptor.