185256-47-7

Usage

Uses

Used in Agricultural Applications:
Tert-Butyl (2-phenylcyclopropyl)carbamate is used as a pesticide for controlling various pests in crops. It is effective due to its ability to target the acetylcholinesterase enzyme in insects, disrupting their nervous system and leading to their death.
Used in Household Applications:
In household settings, Tert-Butyl (2-phenylcyclopropyl)carbamate is used as an insecticide to eliminate pests such as cockroaches and ants. Its mode of action is the same as in agricultural applications, targeting the acetylcholinesterase enzyme in insects to cause paralysis and death, thereby protecting homes from infestations.
Used in Public Health Applications:
Tert-Butyl (2-phenylcyclopropyl)carbamate is also utilized in public health initiatives to control disease-carrying insects like mosquitoes and flies. By inhibiting the acetylcholinesterase enzyme, it helps to reduce the populations of these vectors, thereby limiting the spread of diseases such as malaria, dengue, and other vector-borne illnesses.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 95-62-5 (1R,2S)-1-amino-2-phenylcyclopropane 
• 5685-38-1 2-phenyl-cyclopropanecarboxylic acid 
• 928054-80-2 (-)-trans-2-phenylcyclopropanecarboxylic acid (2-hydroxy-1-phenylethyl)amide 
• 4192-77-2 ethyl cinnamate 
• 946-38-3 ethyl 2-phenylcyclopropylcarboxylate 
• 110659-58-0 (1R,2R)-1-hydroxymethyl-2-phenylcyclopropane 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 3471-10-1 (1R,2R)-trans-2-phenyl-1-cyclopropanecarboxylic acid 
• 75-65-0 tert-butyl alcohol 
• 847644-86-4 ((1SR,2RS)-tert-butyl-2-phenylcyclopropyl)carbamate 
• 946-39-4 ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate 
• 97-71-2 (1R,2R)-2-phenyl-cyclopropanecarboxylic acid ethyl ester 
• 97-71-2 ethyl (S,S)-2-phenylcyclopropane-1-carboxylate 

Downstream Products

• 95-62-5 (1R,2S)-1-amino-2-phenylcyclopropane 
• 3721-28-6 (1S,2R)-tranylcypromine 
• 1986-47-6 tranylcypromine hydrochloride 

Relevant academic research and scientific papers

A catalytic enantioselective synthesis of antidepressant tranylcypromine

An efficient catalytic enantioselective synthesis of the antidepressant tranylcypromine is described.

Discovery of new tranylcypromine derivatives as highly potent LSD1 inhibitors

Tranylcypromine (TCP)-based structural modifications lead to the discovery of new LSD1 inhibitors, of which compounds 26b and 29b effectively inhibit LSD1 with the IC50 values of 17 and 11 nM, respectively and also show good selectivity over MAO-B. Mechanistic studies showed that compound 29b concentration-dependently induced H3K4me1/2 accumulation in LSD1 overexpressed MGC-803 cells and also inhibited metastasis of MGC-803 cells. Collectively, both compounds could be promising lead compounds for further investigation.

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.

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.

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.

Synthesis of the enantiomer of the antidepressant tranylcypromine

Both enantiomers of the antidepressant tranylcypromine, trans 2-phenyl-cyclopropylamine 1, were prepared in enantiomerically pure form by a chemoenzymatic approach starting from racemic (±)-(1RS, 2RS)-trans ethyl 2-phenyl-cyclopropane carboxylate (±)-3.