277751-26-5

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 5307-99-3 (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 100-46-9 benzylamine 
• 277751-23-2 (+/-)-cyclopent-2-ene-1,2-dicarboxylic acid 1-methyl ester 
• 277751-22-1 (+/-)-2-formylcyclopent-2-enecarboxylic acid methyl ester 

Downstream Products

• 725265-75-8 cyclopent-2-ene-1,2-dicarboxylic acid 2-benzylamide 1-[2(S)-(acetoxyacetyl)pyrrolidine] amide 
• 725265-70-3 (+/-)-2-benzylcarbamoylcyclopent-2-enecarboxylic acid 

Relevant academic research and scientific papers

A cyclopent-2-enecarbonyl group mimics proline at the P2 position of prolyl oligopeptidase inhibitors

With the aim to replace the natural amino acid proline by a proline mimetic structure, a cyclopent-2-enecarbonyl moiety was studied at the P2 position of prolyl oligopeptidase (POP) inhibitors. The cyclopent-2-enecarbonyl moiety proved to be an excellent proline mimetic at the P2 position of POP inhibitors. The replacement is particularly useful when increased lipophilicity is needed.

COMPOUNDS HAVING PROLYL OLIGOPEPTIDASE INHIBITORY ACTIVITY

The invention provides a compound of formula (I), wherein in the formula X, R1, R2 and R3 are as defined in claim 1, or a pharmaceutically acceptable salt or ester thereof, useful as a prolyl oligopeptidase inhibitor. The compounds of formula (I) can be used for the treatment of diseases or conditions where prolyl oligopeptidase inhibitors are indicated to be effective, for example for the treatment of neurodegenerative diseases, such as Alzheimer's disease and senile dementia

New proline mimetics: Synthesis of thrombin inhibitors incorporating cyclopentane- and cyclopentenedicarboxylic acid templates in the P2 position. Binding conformation investigated by X-ray crystallography

With the aim to prepare nonpeptidic thrombin inhibitors, the amino acids of the thrombin-inhibiting tripeptide chain D-Phe-Pro-Arg were replaced with isosteres. Arg was replaced with the more rigid P1 truncated p- amidinobenzylamine (Pab), Pro with either cyclopentane-1,2-dicarboxylic acid or cyclopentene-1,5-dicarboxylic acid, and D-Phe with a series of readily available lipophilic amines. One of the most potent compounds (25, pIC50 = 6.01) in these series was cocrystallized with thrombin where the X-ray crystal structure provide insight to the structure-activity relationship (SAR).