58641-87-5

Upstream product

• 939-88-8 rac-(1R,2R)-2-phenylcyclopropanecarboxamide 
• 1156540-73-6 (1R,2R)-2,5-dioxopyrrolidin-1-yl 2-phenylcyclopropanecarboxylate 
• 5685-38-1 2-phenyl-cyclopropanecarboxylic acid 
• 621-79-4 cinnamamide 
• 1774-47-6 trimethylsulfoxonium iodide 
• 4660-02-0 (+/-)-trans-2-phenylcyclopropanecarbonitrile 
• 939-90-2 trans-2-phenylcyclopropane-1-carboxylic acid 
• 939-87-7 (1SR,2SR)-2-phenylcyclopropanecarbonyl chloride 
• 939-89-9 (1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid 
• 3471-10-1 (1R,2R)-trans-2-phenyl-1-cyclopropanecarboxylic acid 
• 37107-48-5 (1R,2R)-trans-2-phenylcyclopropane-1-carboxyl chloride 

Downstream Products

• 301861-27-8 (-)-(1R,2R)-trans-1-aminomethyl-2-phenylcyclopropane 
• 936-95-8 cis-(2-phenylcyclopropyl)methylamine 
• 4660-02-0 (+/-)-trans-2-phenylcyclopropanecarbonitrile 
• 936-95-8 trans-(2-phenylcyclopropyl)methylamine 
• 847644-86-4 ((1SR,2RS)-tert-butyl-2-phenylcyclopropyl)carbamate 
• 23020-15-7 (1S,2S)-2-phenylcyclopropane-1-carboxylic acid 
• 928054-81-3 (1S,2S)-2-phenylcyclopropanecarboxamide 
• 58641-87-5 (1R,2R)-trans-2-phenylcyclopropane-1-carboxamide 
• 3471-10-1 (1R,2R)-trans-2-phenyl-1-cyclopropanecarboxylic acid 
• 1199-98-0 4-phenylbutyramide 
• 3360-41-6 4-phenyl-butan-1-ol 
• 2046-17-5 methyl 3-(benzyl)propanoate 
• 1821-12-1 4-Phenylbutyric acid 
• 5861-31-4 methyl trans-2-phenylcyclopropanecarboxylate 

Relevant academic research and scientific papers

Compounds advantageous in the treatment of central nervous system diseases and disorders

A series of novel compounds showing anticonvulsant activity is described. Such pharmaceutically active compounds may also show utility in the treatment of other central nervous system (“CNS”) diseases and disorders, such as anxiety, depression, insomnia,

ASYMMETRIC CYCLOPROPANATION WITH SUCCINIMIDYL DIAZOACETATE

Cobalt(ll) complexes of the D2-symmetric chiral porphyrins are effective catalysts for asymmetric cyclopropanation reactions with succinimidyl diazoacetate. The Co-catalyzed reaction is suitable for various olefins, providing the corresponding cyclopropane succinimidyl esters in high yields and excellent diastereo- and enantio-selectivity. The resulting enantioenriched cyclopropane succinimidyl esters can serve as convenient synthons for the general synthesis of optically active cyclopropyl carboxamides through mild reactions with a wide range of amine derivatives, including unprotected peptides and amino sugars

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.

Asymmetric Co(II)-catalyzed cyclopropanation with succinimidyl diazoacetate: General synthesis of chiral cyclopropyl carboxamides

[Co(P1)] is an effective catalyst for asymmetric cyclopropanation with succinimidyl diazoacetate. The Co(II)-catalyzed reaction is suitable for various olefins, providing the desired cyclopropane succinimidyl esters in high yields and excellent diastereo-

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.

Synthesis of high enantiomeric purity gem-dihalocyclopropane derivatives from biotransformations of nitriles and amides

Enantioselective biotransformations of geminally dihalogenated cyclopropanecarbonitriles and amides are described. Both the reaction rate and enantioselectivity of the nitrile hydratase and amidase involved in Rhodococcus sp. AJ270 microbial cells are strongly governed by the nature of gem-disubstituents on the cyclopropane ring; the amidase generally exhibits steric dependence on the substituents while both the steric and electronic factors of the substituents may affect the action of the nitrile hydratase. The match of steric bulkiness of the substituents at 2- with that at 3-positions on the cyclopropane ring benefits the efficient and highly enantioselective reaction. Coupled with facile chemical transformations, biocatalytic transformations of nitrile and amide supply an effective synthesis of optically active 2,2-disubstitued-3-phenylcyclopropanecarboxylic acid and amide in both enantiomeric forms.

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

A novel approach to enantiopure cyclopropane compounds from biotransformation of nitriles

Rhodococcus sp. AJ270, a powerful and versatile nitrile hydratase/amidase containing microbial whole-cell system, catalyzed the enantioselective hydrolysis of both racemic trans- and cis-2-arylcyclopropanecarbonitriles to afford the corresponding amides and acids with enantiomeric excesses as high as >99%. The reaction rate and enantioselectivity observed for both nitrile hydratase and amidase were also strongly dependent upon the nature of the substituent and substitution pattern on the benzene ring of the substrates. The application of and the advantages of biotransformation of nitriles were demonstrated by preparing (1S,2R)-2-phenylcyclopropylamine and (1R,2R)-2-phenylcyclopropylmethylamine through facile and straightforward chemical manipulations of (1S,2S)-2-phenylcyclopropanecarboxylic acid and (1R,2R)-2-phenylcyclopropanecarboxamide, respectively.

Enantioselective synthesis of chiral cyclopropane compounds through microbial transformations of trans-2-arylcyclopropanecarbonitriles

Enantioselective biotransformations of racemic trans-2-arylcyclopropanecarbonitriles catalyzed by Rhodococcus sp. AJ270 cells proceeded efficiently to give good to excellent optical yields of (-)-(1R,2R)-2-arylcyclopropanecarboxamides and (+)-(1S,2S)-2-arylcyclopropanecarboxylic acids, which were converted into optically active cyclopropylmethylamine and cyclopropylamine derivatives upon reduction and the Curtius rearrangement. (C) 2000 Elsevier Science Ltd.