71830-07-4

Usage

Uses

Used in Pharmaceutical Industry:
(1S,3R)-3-Aminocyclopentanecarboxylic acid is used as a key synthetic intermediate for the development of pharmaceuticals. Its unique structure allows for the creation of chiral molecules with specific biological activities, making it an essential component in the synthesis of drugs targeting various therapeutic areas.
Used in Drug Synthesis:
(1S,3R)-3-Aminocyclopentanecarboxylic acid is utilized in the synthesis of chiral drugs, which are essential for achieving desired pharmacological effects and minimizing side effects. Its specific stereochemistry ensures that the final drug product has the correct configuration for optimal biological activity and selectivity.
Used in Chiral Compound Development:
(1S,3R)-3-Aminocyclopentanecarboxylic acid is employed in the development of chiral compounds for research purposes. Its unique structure provides a foundation for the study of stereochemistry and its impact on biological systems, contributing to a better understanding of the role of chirality in drug action and development.

InChI:InChI=1/C6H11NO2/c7-5-2-1-4(3-5)6(8)9/h4-5H,1-3,7H2,(H,8,9)/t4-,5+/m0/s1

Upstream product

• 134003-04-6 (1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid 
• 134003-03-5 (+)-2-Azabicyclo<2.2.1>heptan-3-one 
• 140386-94-3 (1S,3R)-3-Carbamoyl-cyclopentanecarboxylic acid 
• 19042-33-2 (+/-)-cis-3-(aminocarbonyl)cyclopentanecarboxylic acid 
• 876-05-1 cis-1,3-cyclopentanedicarboxylic acid 
• 24647-29-8 2-Azabicyclo[2.2.1]heptan-3-one 
• 714195-06-9 methyl 3-aminocyclopentane-1-carboxylate 
• 49805-27-8 3-tosyl-2-azabicyclo [2.2.1]hepta-2,5-diene 
• 3047-38-9 cyclopent-1-enecarbonitrile 
• 96443-42-4 (+)-cis-(1S,3R)-3-carbomethoxycyclopentane carboxylic acid 
• 74201-94-8 methyl 3-(N-benzyloxycarbonylamino)cyclopent-1-ene-1-carboxylate 
• 74201-88-0 3-aminocyclopent-1-ene-1-carboxylic acid 
• 74201-92-6 3-bromocyclopent-1-ene-1-carbonitrile 
• 102579-71-5 cis-4-amino-cyclopent-2-ene-1-carboxylic acid 

Downstream Products

• 919116-63-5 (1S,3R)-3-(2-{4-[methyl-(1-methyl-piperidin-4-yl)-carbamoyl]-phenylamino}-5-trifluoromethyl-pyrimidin-4-ylamino)-cyclopentanecarboxylic acid 
• 625108-11-4 C₇H₁₃NO₂ 
• 1263371-66-9 (1S,3R)-3-(5'-chloro-6-(3-fluorobenzylamino)-2,4'-bipyridin-2'-yl-amino)cyclopentanecarboxylic acid 
• 347185-68-6 tert-butyl ((1R,3S)-3-(hydroxymethyl)cyclopentyl)carbamate 
• 624734-28-7 C₂₀H₂₁NO₂ 
• 1418200-19-7 toluene-4-sulfonic acid (1S,3R)-3-(6-benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6H-1,3,5,6-tetraaza-as-indacen-1-yl)-cyclopentylmethyl ester 
• 1418200-18-6 ((1S,3R)-3-(6-benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6H-1,3,5,6-tetraaza-as-indacen-1-yl)-cyclopentyl)-methanol 
• 1418200-17-5 (1S,3R)-3-(6-benzenesulfonyl-2-(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl-6H-1,3,5,6-tetraaza-as-indacen-1-yl)-cyclopentanecarboxylic acid methyl ester 
• 1418200-16-4 (1S,3R)-3-[6-benzenesulfonyl-2-((R)-1-hydroxyethyl)-6H-1,3,5,6-tetraaza-as-indacen-1-yl]-cyclopentanecarboxylic acid methyl ester 
• 1418200-15-3 (1S,3R)-3-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentanecarboxylic acid methyl ester 
• 1418200-14-2 (1S,3R)-3-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentanecarboxylic acid methyl ester 
• 1418200-50-6 3-((1R,3R)-3-[6-benzenesulfonyl-2-((R)-1-hydroxyethyl)-6H-1,3,5,6-tetraaza-as-indacen-1-yl]-cyclopentyl)-propionitrile 
• 1418200-04-0 3-((1R,3R)-3-(6-benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6H-1,3,5,6-tetraaza-as-indacen-1-yl)-cyclopentyl)-propionitrile 
• 1418200-03-9 3-((1S,3R)-3-(6-benzenesulfonyl-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6H-1,3,5,6-tetraaza-as-indacen-1-yl)-cyclopentyl)-acrylonitrile 

Relevant academic research and scientific papers

Design, synthesis, and evaluation of transition-state analogs as inhibitors of the bacterial quorum sensing autoinducer synthase CepI

Quorum sensing is a bacterial signaling system that involves the synthesis, secretion and detection of signal molecules called autoinducers. The main autoinducer in Gram-negative bacteria are acylated homoserine lactones, produced by the LuxI family of autoinducer synthases and detected by the LuxR family of autoinducer receptors. Quorum sensing allows for changes in gene expression and bacterial behaviors in a coordinated, cell density dependent manner. Quorum sensing controls the expression of virulence factors in some human pathogens, making quorum sensing an antibacterial drug target. Here we describe the design and synthesis of transition-state analogs of the autoinducer synthase enzymatic reaction and the evaluation of these compounds as inhibitors of the synthase CepI. One such compound potently inhibits CepI and constitutes a new type of inhibitor against this underdeveloped antibacterial target.

Identification and application of enantiocomplementary lactamases for Vince lactam derivatives

Four enzymes showing hydrolytic activity on derivatives of 2-azabicyclo[2.2.1]hept-5-en-3-one (Vince lactam) were successfully identified through analysis of protein crystal structure and amino acid sequence alignments. Enantiocomplementary activities were observed on Vince lactam and its saturated analog 2-azabicyclo[2.2.1]heptan-3-one with non-heme chloroperoxidase (CPO-T) from Streptomyces aureofaciens, cyclic imide hydrolase (CIH) from Pseudomonas putida, polyamidase (NfpolyA) from Nocardia farcinica, and amidase (AMI) from Rhodococcus globerulus, and perfect kinetic resolution was achieved (E>200). Computational analysis of amide bond resonance stabilization in lactams correlated well with the overall reactivity pattern of the lactams as a function of ring size and strain. The biocatalysts cloned and investigated in this study could be of interest for the synthesis of enantiopure carbocyclic nucleoside analogues.

AMINOCYCLOPENTYL PYRIDOPYRAZINONE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

Compounds of Formula I and Formula II (wherein A, E, j, k, m, n, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R15, R16, R17, R18, R19, R24, R25, R26, R27, R28, R29, R30, R31, R32, R33, R34, X, Y and Z are as defined herein) which are modulators of chemokine receptor activity and are useful in the prevention or treatment of certain inflammatory and immunoregulatory disorders and diseases, allergic diseases, atopic conditions including allergic rhinitis, dermatitis, conjunctivitis, and asthma, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which chemokine receptors are involved.

ALKYLAMINO, ARYLAMINO, AND SULFONAMIDO CYCLOPENTYL AMIDE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

Compounds of the formula (I) which are modulators of chemokine receptor activity useful in the prevention or treatment of certain inflammatory and immunoregulatory disorders and diseases, allergic diseases, atopic conditions including allergic rhinitis, dermatitis, conjunctivitis, and asthma, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis, and pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which chemokine receptors are involved.

3,3-DISUBSTITUTED TETRAHYDROPYRANYL CYCLOPENTYL AMIDE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

Compounds of Formula I (wherein n, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R15, R16, R17, R18, Y and Z are as defined herein) which are modulators of chemokine receptor activity and are useful in the prevention or treatment of certain inflammatory and im

TETRAHYDROPYRANYL CYCLOPENTYL TETRAHY-DROPYRIDOPYRIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

Compounds of Formula I (wherein n, R1, R3, R4, R5, R6, R7, R8, R9, R10, R15, R16, Y and Z are as defined herein) which are modulators of chemokine receptor activity and are useful in the prevention or treatment of certain inflammatory and immunoregulatory

Synthesis of optically active monothioimides with chirality due to sulphur substitution

Two optically active bicyclic monothioimides were prepared via chiral derivatives of cis-1,2-cyclopropanedicarboxylic and cis-1,3-cyclopentanedicarboxylic acids and their absolute configurations were assigned.

Enantioselective synthesis of (+) and (-)-cis-3-aminocyclopentanecarboxylic acids by enzymatic asymmetrization

Both enantiomers of cis-3-aminocyclopentanecarboxylic acid (GABA analogs, inhibitory neurotransmitter) have been prepared via enzymatic asymmetrization of cis -1,3-cyclopentanedicarboxylic acid.

Synthesis of Either Enantiomer of cis-3-Aminocyclopentanecarboxylic Acid from Both Enantiomers of Racemic 2-Azabicyclohept-5-en-3-one

(-)-2-Azabicyclohept-5-en-3-one (-)-1 was converted into (-)-cis-3-aminocyclopentanecarboxylic acid (-)-2 in two steps and into the enantiomeric amino-acid (+)-2 in three steps.