54-97-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenylcyclopropane-1-amine is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
2-Phenylcyclopropane-1-amine is used as a reagent for the preparation of oxadiazole derivatives, which are known for their fungicidal properties. These derivatives can be used in the development of new fungicides to protect crops from fungal infections, thereby increasing agricultural productivity and crop yield.

Upstream product

• 220247-82-5 N,N-dibenzyl-N-(2-phenylcyclopropyl)-amine 
• 102540-15-8 methyl (2E)-3-(2-bromophenyl)-2-propenoate 
• 6630-33-7 ortho-bromobenzaldehyde 
• 102540-15-8 3-(2-bromophenyl)-acrylic acid methyl ester 
• 264144-78-7 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanal 
• 104-55-2 3-phenyl-propenal 
• 155-09-9 trans-2-phenylcyclopropylamine 
• 185256-47-7 (-)-(1R,2S)-trans (2-phenyl-cyclopropyl)carbaminic acid tert-butyl ester 
• 874341-82-9 [(1S,2R)-2-nitrocyclopropyl]benzene 
• 97-71-2 ethyl (S,S)-2-phenylcyclopropane-1-carboxylate 
• 1036637-32-7 methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate 
• 100-42-5 styrene 
• 939-89-9 (1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid 
• 14561-40-1 (+/-)-cis-2-phenyl-cyclopropane-carboxylic acid-⁽¹⁾-hydrazide 

Downstream Products

• 93948-20-0 bis-(3-phenyl-propyl)-amine 
• 1006-66-2 5-phenyl-4,5-dihydroisoxazole 
• 132350-68-6 (2-Nitro-cyclopropyl)-benzene 
• 65-85-0 benzoic acid 
• 847644-86-4 tert-butyl (trans-2-phenylcyclopropyl)carbamate 

Relevant academic research and scientific papers

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.

Synthetic method for arylcyclopropylamine compound

The invention relates to a synthetic method for an arylcyclopropylamine compound. The method comprises the following steps: with a cinnamaldehyde compound as a raw material, reacting the cinnamaldehyde compound with bis(pinacolato)diboron to obtain a boroalkylated product; and then subjecting the boroalkylated product and an aminated compound to a ring-closure reaction so as to obtain the arylcyclopropylamine compound. Compared with the prior art, the invention has the following advantages: the synthetic method of the invention is simple to operate and short in reaction time; reagents used inthe invention are cheap and easily available; the target arylcyclopropylamine compound can be prepared from most substrates at a high overall yield and is mainly in the form of transconfiguration; anda route of the method is obviously improved, more economical, safer and easy for industrial production.

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.

Targeting Cancer with PCPA-Drug Conjugates: LSD1 Inhibition-Triggered Release of 4-Hydroxytamoxifen

Targeting cancer with small molecule prodrugs should help overcome problems associated with conventional cancer-targeting methods. Herein, we focused on lysine-specific demethylase 1 (LSD1) to trigger the controlled release of anticancer drugs in cancer cells, where LSD1 is highly expressed. Conjugates of the LSD1 inhibitor trans-2-phenylcyclopropylamine (PCPA) were used as novel prodrugs to selectively release anticancer drugs by LSD1 inhibition. As PCPA-drug conjugate (PDC) prototypes, we designed PCPA-tamoxifen conjugates 1 a and 1 b, which released 4-hydroxytamoxifen in the presence of LSD1 in vitro. Furthermore, 1 a and 1 b inhibited the growth of breast cancer cells by the simultaneous inhibition of LSD1 and the estrogen receptor without exhibiting cytotoxicity toward normal cells. These results demonstrate that PDCs provide a useful prodrug method that may facilitate the selective release of drugs in cancer cells.

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.