198022-65-0

Basic information

• Product Name: Cyclopentanecarboxylic acid, 2-amino-4-methylene-, (1R,2S)- (9CI)
• Synonyms: Cyclopentanecarboxylic acid, 2-amino-4-methylene-, (1R,2S)- (9CI);Icofungipen
• CAS NO: 198022-65-0
• Molecular Formula: C₇H₁₁NO₂
• Molecular Weight: 141.16774
• Product Categories: AMINOACID
• Mol File: 198022-65-0.mol

Chemical Properties

• Boiling Point: 277.4°C at 760 mmHg
• Flash Point: 121.6°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 0.00123mmHg at 25°C
• Refractive Index: 1.528
• CAS DataBase Reference: Cyclopentanecarboxylic acid, 2-amino-4-methylene-, (1R,2S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentanecarboxylic acid, 2-amino-4-methylene-, (1R,2S)- (9CI)(198022-65-0)
• EPA Substance Registry System: Cyclopentanecarboxylic acid, 2-amino-4-methylene-, (1R,2S)- (9CI)(198022-65-0)

Safety Data

• Hazardous Substances Data: 198022-65-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H11NO2/c1-4-2-5(7(9)10)6(8)3-4/h5-6H,1-3,8H2,(H,9,10)/t5-,6+/m1/s1

Upstream product

• 198022-62-7 (2E)-3-phenyl-2-propenyl (1R,2S)-4-methylene-2-{[(2E)-3-phenyl-2-propenyloxycarbonyl]amino}cyclopentanecarboxylate 
• 4534-68-3 1,2,3,4-butanetetracarboxylic acid 
• 4373-15-3 1,2,3,4-butanetetracarboxylic acid tetraethyl ester 
• 343956-49-0 4-Methylene-cyclopentane-1,2-dicarboxylic acid diethyl ester 
• 914637-96-0 diethyl 4-oxo-1,2-cyclopentanedicarboxylate 
• 1703-61-3 rac-4-oxocyclopentane-1,2-dicarboxylic acid 
• 6261-04-7 2,3,4-tris(ethoxycarbonyl)cyclopentanone 
• 139228-09-4 5-methylenetetrahydrocyclopenta[c]furan-1,3-dione 
• 198022-60-5 (+)-(1S,2R)-4-methylene-2-[(2E)-3-phenyl-2-propenyloxycarbonyl]cyclopentanecarboxylic acid 

Downstream Products

• 777850-76-7 (+)-(1R,2S)-2-amino-4-methyl-cyclopent-3-enecarboxylic acid 
• 156292-40-9 (-)-(1R,5S)-5-amino-3-methyl-cyclopent-2-enecarboxylic acid 

Relevant articles and documents

Efficient asymmetric synthesis of β-amino acid BAY 10-8888/PLD-118, a novel antifungal for the treatment of yeast infections

The β-amino acid BAY 10-8888/PLD-118 is currently being investigated in phase II clinical studies as a novel antifungal for the treatment of yeast infections. An efficient asymmetric synthesis of this compound is described. The key step employed a highly enantioselective, quinine-mediated alcoholysis of a mesoanhydride intermediate.

Novel antifungal β-amino acids: Synthesis and activity against Candida albicans

A series of novel β-amino acids has been synthesized and tested for their in vitro antifungal activity against Candida albicans. A steep SAR was observed. β-Amino acid 21 (BAY 10-8888/PLD-118) revealed the most favourable activity-tolerability profile and was selected for clinical studies as a novel antifungal for the oral treatment of yeast infections.

Efficient and highly enantioselective process for the preparation of enantiomerically pure cyclopentane-β-amino acids

The process according to the invention for the preparation of enantiomerically pure cyclopentane-β-amino acids of the general formula (I) STR1 in which A and D have the meanings given in the description, is characterized in that meso-dicarboxylic acid anhydrides are first converted by asymmetric alcoholysis with allyl alcohols and in the presence of a chiral amine base present in enantiomerically pure form, in inert solvents, via the intermediate enantiomerically pure salt stage, into the enantiomerically pure dicarboxylic acid monoesters, in a further step these dicarboxylic acid monoesters are intermediately converted, in the sense of a Curtius rearrangement by reaction with azides, into the corresponding acid azides, and are subsequently converted into the corresponding rearranged isocyanates and the isocyanates are then reacted with allyl alcohols to give the compounds of the general formula (VII), and finally the cyclopentane-β-amino acids of the general formula (I) are obtained by splitting off the urethane and ester function.

Tolerability of pharmaceutically active β-amino acids

The present invention relates to mixtures of α-amino acids and/or derivatives thereof and cyclopentane-β-amino acids and/or derivatives thereof, dipeptides of the abovementioned α-amino acids and cyclopentane-β-amino acids and mixtures of the abovementioned mixtures and dipeptides which have an improved tolerability in warm-blooded animals compared with the pure cyclopentane-β-amino acids.