239797-49-0

Basic information

• Product Name: 4-Piperidinecarboxylic acid, 4-[[4-(4-chlorophenoxy)phenyl]sulfonyl]-1-(phenylmethyl)-
• CAS NO: 239797-49-0
• Molecular Formula: C25H24ClNO5S
• Molecular Weight: 485.988
• Mol File: 239797-49-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-Piperidinecarboxylic acid, 4-[[4-(4-chlorophenoxy)phenyl]sulfonyl]-1-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Piperidinecarboxylic acid, 4-[[4-(4-chlorophenoxy)phenyl]sulfonyl]-1-(phenylmethyl)-(239797-49-0)
• EPA Substance Registry System: 4-Piperidinecarboxylic acid, 4-[[4-(4-chlorophenoxy)phenyl]sulfonyl]-1-(phenylmethyl)-(239797-49-0)

Safety Data

• Hazardous Substances Data: 239797-49-0(Hazardous Substances Data)

Upstream product

• 10429-82-0 N-benzyl-2-chloro-N-(2-chloroethyl)ethanamine hydrochloride 
• 352209-91-7 4-[4-(4-Chlorophenoxy)benzenesulfonyl]-1-benzylpiperidine-4-carboxylic acid methyl ester 
• 352209-77-9 4-(4-chlorophenoxy)phenylsulfonyl fluoride 
• 239796-74-8 [4-(4-chlorophenoxy)benzenesulfonyl]acetic acid ethyl ester 
• 59621-41-9 [4-(4-chlorophenoxy)phenylsulfanyl]acetic acid ethyl ester 
• 30519-00-7 (4-Hydroxy-phenylsulfanyl)-acetic acid ethyl ester 
• 637-89-8 4-sulfanylphenol 
• 239797-48-9 1-benzyl-4-[4-(4-chlorophenoxy)benzenesulfonyl]piperidine-4-carboxylic acid ethyl ester 

Relevant articles and documents

Synthesis and structure - Activity relationship of N-substituted 4-arylsulfonylpiperidine-4-hydroxamic acids as novel, orally active matrix metalloproteinase inhibitors for the treatment of osteoarthritis

The matrix metalloproteinases (MMPs) are a family of zinc-containing endopeptidases that play a key role in both physiological and pathological tissue degradation. In our preceding paper, we have reported on a series of novel and orally active N-hydroxy-α-phenylsulfonylacetamide derivatives. However, these compounds had two drawbacks (moderate selectivity and chirality issues). To circumvent these two problems, a series of novel and orally active N-substituted 4-benzenesulfonylpiperidine-4-carboxylic acid hydroxyamide derivatives have been synthesized. The present paper deals with the synthesis and SAR of these compounds. Among the several compounds synthesized, derivative 55 turned out to be a potent, selective, and an orally active MMP inhibitor in the clinically relevant advanced rabbit osteoarthritis model. Detailed pharmacokinetics and metabolism data are described.

N-hdroxy-2-(alkyl, aryl, or heteroaryl, sulfanyl, sulfinyl or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors

Matrix metalloproteinases (MMPs) are a group of enzymes that have been implicated in the pathological destruction of connective tissue and basement membranes. These zinc containing endopeptidases consist of several subsets of enzymes including collagenases, stromelysins and gelatinases. TNF-α converting enzyme (TACE), a pro-inflammatory cytokine, catalyzes the formation of TNF-α from membrane bound TNF-α precursor protein. It is expected that small molecule inhibitors of MMPs and TACE therefore have the potential for treating a variety of disease states. The present invention provides low molecular weight, non-peptide inhibitors of matrix metalloproteinases (MMPs) and TNF-α converting enzyme (TACE) for the treatment of arthritis, tumor metastasis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, diabetes (insulin resistance) and HIV infection having the formula wherein R2and R3form a heterocyclic ring and A is S, S(O), or S(O)2, and R1and R4are defined herein.