80789-69-1

Usage

Chemical Properties

cream to grey crystalline powder or crystals

Biochem/physiol Actions

1-(4-Chlorophenyl)-1-cyclopentanecarboxylic acid reacts with diorganotin(IV) oxide or dichloride to yield organotin(IV) complexes having antitumor activities against various human cancer cell lines.

InChI:InChI=1/C12H13ClO2/c13-10-5-3-9(4-6-10)12(11(14)15)7-1-2-8-12/h3-6H,1-2,7-8H2,(H,14,15)/p-1

Upstream product

• 64399-26-4 1-(4-chlorophenyl)cyclopentanecarboxylic acid 
• 140-53-4 p-chlorobenzyl cyanide 
• 914106-85-7 1-(4-chlorophenyl)-1-cyclopentanecarboxylic acid methyl ester 
• 52449-43-1 (4-chloro-phenyl)-acetic acid methyl ester 

Downstream Products

• 71501-44-5 1-(4-chlorophenyl)cyclopentane-1-carboxylic acid chloride 
• 269070-14-6 1-(3-{[5-(2-Adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carbonyl]-amino}-phenyl)-cyclopentanecarboxylic Acid 
• 764691-72-7 C₁₅H₁₅ClN₂OS 
• 143407-69-6 Sodium; (2S,5R,6R)-6-{[1-(4-chloro-phenyl)-cyclopentanecarbonyl]-amino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 
• 143407-73-2 Sodium; (6R,7R)-7-{[1-(4-chloro-phenyl)-cyclopentanecarbonyl]-amino}-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 1620085-08-6 (S)-methyl 2-(1-(4’-(2-((R)-2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)cyclopentanecarboxamido)propanoate 
• 1620085-07-5 (R)-methyl 2-(1-(4’-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)cyclopentanecarboxamido)acetate 
• 1620085-05-3 (R)-methyl1-(4’-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)cyclopentanecarboxylate 
• 1620085-03-1 (R)-tert-butyl 4-(1-(4’-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)cyclopentanecarboxamido)butanoate 
• 1620085-02-0 (R)-tert-butyl 3-(1-(4’-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)cyclopentanecarboxamido)propanoate 
• 1620085-01-9 (R)-methyl 3-(1-(4’-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)cyclopentanecarboxamido)propanoate 
• 1620085-00-8 (1R,2S)-ethyl 2-(1-(4’-(2-((R)-2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)cyclopentanecarboxamido)cyclohexanecarboxylate 
• 1620084-96-9 (R)-methyl 4-(1-(4’-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)cyclopentanecarboxamido)butanoate 
• 1620084-95-8 (R)-ethyl 3-(1-(4’-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)cyclopentanecarboxamido)propanoate 

Relevant academic research and scientific papers

Achiral Derivatives of Hydroxamate AR-42 Potently Inhibit Class i HDAC Enzymes and Cancer Cell Proliferation

AR-42 is an orally active inhibitor of histone deacetylases (HDACs) in clinical trials for multiple myeloma, leukemia, and lymphoma. It has few hydrogen bond donors and acceptors but is a chiral 2-arylbutyrate and potentially prone to racemization. We report achiral AR-42 analogues incorporating a cycloalkyl group linked via a quaternary carbon atom, with up to 40-fold increased potency against human class I HDACs (e.g., JT86, IC50 0.7 nM, HDAC1), 25-fold increased cytotoxicity against five human cancer cell lines, and up to 70-fold less toxicity in normal human cells. JT86 was ninefold more potent than racAR-42 in promoting accumulation of acetylated histone H4 in MM96L melanoma cells. Molecular modeling and structure-activity relationships support binding to HDAC1 with tetrahydropyran acting as a hydrophobic shield from water at the enzyme surface. Such potent inhibitors of class I HDACs may show benefits in diseases (cancers, parasitic infections, inflammatory conditions) where AR-42 is active.

Synthesis and Biological Activity of Arylcyclopentane-1-carboxylic Acids Aminoesters

1-Arylcyclopentane-1-carboxylic acids were synthesized by alkaline hydrolysis of the corresponding nitriles. Reactions of the acid chlorides with N,N-dialkylaminoalkyl-and hetarylalkylalkanols provided new aminoester derivatives of 1-arylcyclopentane-1-carboxylic acids. Sympatholytic and adrenolytic activity of the obtained amino esters hydrochlorides was studied.

HISTONE DEACETYLASE INHIBITORS AND COMPOSITIONS AND METHODS OF USE THEREOF

Provided are certain histone deacetylase (HDAC) inhibitors of Formula I, compositions thereof, and methods of their use.