212771-00-1

Basic information

• Product Name: ETHYL 1-(4-METHOXYBENZYL)-4-[(4-METHOXYPHENYL)SULFONYL]-4-PIPERIDINECARBOXYLATE
• Synonyms: ETHYL 1-(4-METHOXYBENZYL)-4-[(4-METHOXYPHENYL)SULFONYL]-4-PIPERIDINECARBOXYLATE;ethyl 4-(4-methoxybenzenesulfonyl)-1-[(4-methoxyphenyl)methyl]piperidine-4-carboxylate
• CAS NO: 212771-00-1
• Molecular Formula: C₂₃H₂₉NO₆S
• Molecular Weight: 447.54
• Mol File: 212771-00-1.mol

Chemical Properties

• Boiling Point: 588.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.230±0.06 g/cm3(Predicted)
• PKA: 6.07±0.10(Predicted)
• CAS DataBase Reference: ETHYL 1-(4-METHOXYBENZYL)-4-[(4-METHOXYPHENYL)SULFONYL]-4-PIPERIDINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 1-(4-METHOXYBENZYL)-4-[(4-METHOXYPHENYL)SULFONYL]-4-PIPERIDINECARBOXYLATE(212771-00-1)
• EPA Substance Registry System: ETHYL 1-(4-METHOXYBENZYL)-4-[(4-METHOXYPHENYL)SULFONYL]-4-PIPERIDINECARBOXYLATE(212771-00-1)

Safety Data

• Hazardous Substances Data: 212771-00-1(Hazardous Substances Data)

Upstream product

• 2850-21-7 2-(4-methoxybenzenesulfonyl)acetic acid ethyl ester 
• 91561-99-8 N,N-bis(2-chloroethyl)-p-methoxybenzylamine 
• 28743-98-8 (4-methoxy-phenylsulfanyl)-acetic acid ethyl ester 
• 696-63-9 4-Methoxybenzenethiol 
• 91562-00-4 2-chloro-N-(2-chloroethyl)-N-(4-methoxybenzyl)ethan-1-amine hydrochloride 

Downstream Products

• 212771-01-2 4-(4-methoxy-benzenesulfonyl)-1-(4-methoxy-benzyl)-piperidine-4-carboxylic acid 

Relevant articles and documents

N-HYDROXY-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- alpha converting enzymes (TACE), a pro-inflammatory cytokine, catalyze the formation of TNF- alpha from membrane-bound TNF- alpha 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- alpha 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. The compounds of this invention are represented by formula (I), where R, R, R and R are described herein.

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-hydroxy-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. The compounds of this invention are represented by the formula where R1, R2, R3and R4are described herein.