528587-74-8

Upstream product

• 2947-61-7 (4-methylphenyl)acetonitrile 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 67843-74-7 (S)-epichlorohydrin 
• 1236217-55-2 (-)-(1S,2R)-2-(hydroxymethyl)-1-(4-methylphenyl)-N-(1R)-(phenylethyl)cyclopropanecarboxamide 

Downstream Products

• 528587-82-8 (1S,2R)-1-(4-methylphenyl)-2-(hydroxymethyl)-N,N-diethylcyclopropanecarboxamide 
• 528588-22-9 (1S,4S,5R)-2-oxo-4-ethyl-1-(4-methylphenyl)-3-oxabicyclo[3.1.0]hexane 
• 528587-90-8 (1S,2R)-1-(4-methylphenyl)-2-formyl-N,N-diethylcyclopropanecarboxamide 
• 528587-98-6 (1S,2R)-1-(4-methylphenyl)-2-[(S)-1-hydroxypropyl]-N,N-diethylcyclopropanecarboxamide 
• 528588-06-9 (1S,2R)-1-(4-methylphenyl)-2-[(S)-1-azidopropyl]-N,N-diethylcyclopropanecarboxamide 
• 1236217-61-0 (-)-methyl (1S,2R)-2-(bromomethyl)-1-(4-methylphenyl)cyclopropanecarboxylate 

Relevant academic research and scientific papers

Synthesis and resolution of cis -(±)-methyl (1 R,2 S /1 S,2 R)-2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-1-(4-methylphenyl) cyclopropanecarboxylate [(±)-PPCC)]: New σ receptor ligands with neuroprotective effect

The enantiomers of cis-(±)-methyl (1R,2S/1S,2R)-2-[(4-hydroxy-4- phenylpiperidin-1-yl)methyl]-1-(4-methylphenyl)cyclopropanecarboxylate [1, (±)-PPCC], a selective - ligand, were synthesized. The (+)- and (?)-enantiomers bind predominantly to ?1 receptors and have a reduced ?2 affinity. Both individually restore the astroglial oxidative status modified by glutamate, counteracting also transglutaminase-2 overexpression. They exhibited in vivo anti-opioid effects on - opioid (KOP) receptor-mediated analgesia. Our findings demonstrate that the enantiomers display mainly ?1 agonist activity and that they have neuroprotective effects.

Stereocontrolled synthesis of trisubstituted cyclopropanes: Expedient, atom-economical, asymmetric syntheses of (+)-bicifadine and DOV21947

An expedient, atom-economical, asymmetric synthesis of 1-aryl-3- azabicyclo[3.1.0]hexanes, including (+)-Bicifadine and DOV21947, in a single-stage through process without isolation of any intermediates has been developed. The key of this synthesis is the in-depth mechanistic understanding of the complicated epoxy nitrile coupling at each reaction stage. Therefore, the desired trisubstituted cyclopropane can be prepared in high ee and yield by controlling the reaction pathway through manipulating the nitrile anion aggregation state.

CYCLOPROPYL DERIVATIVES AS NK3 RECEPTOR ANTAGONISTS

The present invention relates to cyclopropyl derivatives of formula (I) and salt thereof. These compounds are NK3 receptor antagonists and may therefore be useful for treatment of diseases where the NK3 receptor is implicated, e.g. psychotic disorders.

Synthesis of derivatives of (1S,2R)-1-phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide (PPDC) modified at the 1-aromatic moiety as novel NMDA receptor antagonists: The aromatic group is essential for the activity

(1S,2R)-1-Phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide (PPDC, 4a), which is a conformationally restricted analogue of antidepressant milnacipran [(±)-1], is a new class of potent noncompetitive NMDA receptor antagonists. A series of PPD