331941-32-3

Upstream product

• 5685-38-1 2-phenyl-cyclopropanecarboxylic acid 
• 4660-02-0 (+/-)-trans-2-phenylcyclopropanecarbonitrile 
• 939-88-8 rac-(1R,2R)-2-phenylcyclopropanecarboxamide 
• 646995-54-2 (+)-(1R,3R)-2,2-dichloro-3-phenylcyclopropanecarboxyamide 
• 646995-49-5 (+)-(1R,3R)-2,2-dibromo-3-phenylcyclopropanecarboxamide 
• 25226-98-6 trans-cinnamaldehyde diethylacetal 
• 1156540-73-6 (1R,2R)-2,5-dioxopyrrolidin-1-yl 2-phenylcyclopropanecarboxylate 
• 621-79-4 cinnamamide 
• 1774-47-6 trimethylsulfoxonium iodide 
• 939-87-7 (1SR,2SR)-2-phenylcyclopropanecarbonyl chloride 
• 646995-44-0 (-)-(1R,3R)-2,2-difluoro-3-phenylcyclopropanecarboxamide 
• 78738-39-3 trans-2-phenyl-1-cyclopropanecarbonyl chloride 
• 939-90-2 trans-2-phenylcyclopropane-1-carboxylic acid 
• 939-89-9 (1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid 

Downstream Products

• 847644-86-4 ((1SR,2RS)-tert-butyl-2-phenylcyclopropyl)carbamate 
• 1199-98-0 4-phenylbutyramide 
• 3360-41-6 4-phenyl-butan-1-ol 
• 1821-12-1 4-Phenylbutyric acid 
• 2046-17-5 methyl 3-(benzyl)propanoate 

Relevant academic research and scientific papers

Rational design of cannabinoid type-1 receptor allosteric modulators: Org27569 and PSNCBAM-1 hybrids

Allosteric modulation offers an alternate approach to target the cannabinoid type-1 receptor (CB1) for therapeutic benefits. Examination of the two widely studied prototypic CB1 negative allosteric modulators (NAMs) Org27569 and PSNCBAM-1 revealed structural resemblance and similar structure–activity relationships (SARs). In silico docking and dynamics simulation studies using the crystal structure of CB1 co-bound with CP55,940 and Org27569 suggested that Org27569 and PSNCBAM-1 occupied the same binding pocket and several common interactions were present in both series with the CB1 receptor. A new scaffold was therefore designed by merging the key structural features from the two series and the hybrids retained these binding features in the in silico docking studies. In addition, one such hybrid displayed similar functions to Org27569 in dynamic simulations by preserving a key R2143.50-D3386.30 salt bridge and maintaining an antagonist-like Helix3-Helix6 interhelical distance. Based on these results, a series of hybrids were synthesized and assessed in calcium mobilization, [35S]GTPγS binding and cAMP assays. Several compounds displayed comparable potencies to Org27569 and PSNCBAM-1 in these assays. This work offers new insight of the SAR requirement at the allosteric site of the CB1 receptor and provides a new scaffold that can be optimized for the development of future CB1 allosteric modulators.

Tranylcypromine-Based LSD1 Inhibitors: Structure-Activity Relationships, Antiproliferative Effects in Leukemia, and Gene Target Modulation

Abstract: LSD1 is a lysine demethylase highly involved in initiation and development of cancer. To design highly effective covalent inhibitors, a strategy is to fill its large catalytic cleft by designing tranylcypromine (TCP) analogs decorated with long,

UREA DERIVATIVES AS CB1 ALLOSTERIC MODULATORS

Heteroaryl and aliphatic analogs of diarylurea-based cannabinoid 1 receptor (CB1 R) allosteric modulators of formula (I) are described. Exemplary analogs can provide improved potencies and pharmacokinetic properties. Methods of using the analogs to treat

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