3721-26-4

Basic information

• Product Name: TRANSAMINE
• Synonyms: (1R)-1β-Amino-2α-phenylcyclopropane;(1R)-2α-Phenylcyclopropane-1β-amine;S-Tranylcypromine;Cyclopropanamine, 2-phenyl-, (1R-trans)- (9ci);Cyclopropylamine, 2-phenyl-, trans-(-)-;L-Tranylcypromine;trans-(-)-2-Phenylcyclopropanamine;(R)-2-Phenyl-cyclopropylaMine
• CAS NO: 3721-26-4
• Molecular Formula: C₉H₁₁N
• Molecular Weight: 133.19034
• Mol File: 3721-26-4.mol

Chemical Properties

• Boiling Point: 218.3°Cat760mmHg
• Flash Point: 90.8°C
• Appearance: /
• Density: 1.065g/cm³
• Storage Temp.: 2-8°C(protect from light)
• PKA: 8.24±0.10(Predicted)
• CAS DataBase Reference: TRANSAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANSAMINE(3721-26-4)
• EPA Substance Registry System: TRANSAMINE(3721-26-4)

Safety Data

• Hazardous Substances Data: 3721-26-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A 2-phenylcyclopropan-1-amine that is the (1S,2R)-enantiomer of tranylcypromine.

Upstream product

• 155-09-9 trans-2-phenylcyclopropylamine 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 93-92-5 1-phenylethyl acetate 
• 141-78-6 ethyl acetate 
• 3471-10-1 (1R,2R)-trans-2-phenyl-1-cyclopropanecarboxylic acid 
• 1036637-32-7 methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate 
• 100-42-5 styrene 
• 874341-82-9 [(1S,2R)-2-nitrocyclopropyl]benzene 
• 874341-58-9 methyl (1R,2S)-1-nitro-2-phenylcyclopropanecarboxylate 
• 185256-47-7 (-)-(1R,2S)-trans (2-phenyl-cyclopropyl)carbaminic acid tert-butyl ester 
• 939-89-9 (1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid 
• 14561-40-1 (+/-)-cis-2-phenyl-cyclopropane-carboxylic acid-⁽¹⁾-hydrazide 
• 5685-38-1 2-phenyl-cyclopropanecarboxylic acid 
• 928054-80-2 (-)-trans-2-phenylcyclopropanecarboxylic acid (2-hydroxy-1-phenylethyl)amide 

Downstream Products

• 103477-53-8 (-)-ethyl 2-(2,4-dichloro-5-fluorobenzoyl)-3-<<(1'R,2'S)-2'-phenylcyclopropyl>amino>acrylate 
• 83586-90-7 C₂₄H₂₆N₄O₅ 
• 50584-02-6 trans-2-Benzamido-1-phenyl-cyclopropan 
• 1521265-14-4 (2S,3S,4S)-4-fluoro-3-methoxy-2-((1R,2S)-2-phenyl-cyclopropylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1401967-20-1 3-(4-((((1R,2S)-2-phenylcyclopropyl)amino)methyl)piperidin-1-yl)propanoic acid 

Relevant articles and documents

CYCLOPROPYLAMINE COMPOUND AS LSD1 INHIBITOR AND USE THEREOF

Provided is a cyclopropylamine compound as lysine-specific demethylase 1 (LSD1) inhibitor, and a use thereof in preparation of drug for treating diseases associated with LSD1. The cyclopropylamine compound is a compound represented by formula (I), an isomer thereof, and a pharmaceutically acceptable salt thereof.

SALT OF LSD1 INHIBITOR AND A POLYMORPH THEREOF

Provided are a compound III serving as an LSD1 inhibitor and a crystal form thereof, as well as use of the compound and the crystal form thereof in preparation of a medicament for treating an LSD1 related disease.

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.

KDM1A INHIBITORS FOR THE TREATMENT OF DISEASE

Disclosed herein are new compounds and compositions and their application as pharmaceuticals for the treatment of diseases. Methods of inhibition of KDMIA, and methods of increasing gamma globin gene expression in a human or animal subject are also provided for the treatment diseases such as sickle cell disease.

COMPLEMENT PATHWAY MODULATORS AND USES THEREOF

The present invention provides a compound of formula I: (I) a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

(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.

(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.

Asymmetric syntheses of pharmaceuticals containing a cyclopropane moiety using catalytic asymmetric Simmons-Smith reactions of allylalcohols: Syntheses of optically active tranylcypromine and milnacipran

Asymmetric synthesis of tranylcypromine was achieved using an enantioselective Simmons-Smith cyclopropanation catalyzed by a simple disulfonamide derived from an -amino acid. The optically active milnacipran was also synthesized by porcine pancreas lipase-catalyzed selective monoacylation of the C4-hydroxy group in (Z)-2-phenylbut-2-ene-1,4-diol and the enantioselective Simmons-Smith cyclopropanation as the key steps.

Catalytic asymmetric synthesis of nitrocyclopropane carboxylates

A Cu(I)-catalyzed asymmetric cyclopropanation of alkenes with an iodonium ylide has been developed. The copper source, hypervalent iodine source, solvent, and additives all have a significant effect on the yields and enantioselectivities. High enantioselectivity (up to 99:1 er) and diastereoselectivity (95:5 dr trans/cis) were achieved for a wide range of alkenes. Conditions were developed to convert the trans products to the cis isomers. In addition, 1-nitrocyclopropyl carboxylates were transformed into the corresponding substituted cyclopropane amino acids and aminocyclopropanes. Moreover, a comparative study between Zn- and In-mediated reduction reactions of the nitro group in these compounds with regards to the er erosion in the process is also documented.

Enantioselective synthesis of tranylcypromine analogues as lysine demethylase (LSD1) inhibitors

Asymmetric cyclopropanation of styrenes by tert-butyl diazoacetate followed by ester hydrolysis and Curtius rearrangement gave a series of tranylcypromine analogues as single enantiomers. The o,- m- and p-bromo analogues were all more active than tranylcypromine in a LSD1 enzyme assay. The m- and p-bromo analogues were micromolar growth inhibitors of the LNCaP prostate cancer cell line as were the corresponding biphenyl analogues prepared from the bromide by Suzuki crosscoupling.