The asymmetric synthesis and in vitro characterization of succinyl mercaptoalcohol and mercaptoketone inhibitors of matrix metalloproteinases

J I Levin; J F DiJoseph; L M Killar; M A Sharr; J S Skotnicki; D V Patel; X Y Xiao; L Shi; M Navre; D A Campbell

doi:10.1016/s0960-894x(98)00186-3

The asymmetric synthesis and in vitro characterization of succinyl mercaptoalcohol and mercaptoketone inhibitors of matrix metalloproteinases

Bioorg Med Chem Lett. 1998 May 19;8(10):1163-8. doi: 10.1016/s0960-894x(98)00186-3.

Authors

J I Levin¹, J F DiJoseph, L M Killar, M A Sharr, J S Skotnicki, D V Patel, X Y Xiao, L Shi, M Navre, D A Campbell

Affiliation

¹ Wyeth-Ayerst Research, Pearl River, New York 10965, USA.

PMID: 9871728
DOI: 10.1016/s0960-894x(98)00186-3

Abstract

A series of succinyl based mercaptoketones and diastereomeric mercaptoalcohols were prepared and evaluated in vitro as inhibitors of the matrix metalloproteinases collagenase-1 (MMP-1), stromelysin (MMP-3), and gelatinase-B (MMP-9).

MeSH terms

Alcohols / chemical synthesis*
Alcohols / chemistry
Alcohols / pharmacology
Drug Design
Indicators and Reagents
Ketones / chemical synthesis*
Ketones / chemistry
Ketones / pharmacology
Kinetics
Matrix Metalloproteinase 1
Matrix Metalloproteinase 9
Matrix Metalloproteinase Inhibitors
Metalloendopeptidases / antagonists & inhibitors*
Molecular Structure
Protease Inhibitors / chemical synthesis*
Protease Inhibitors / chemistry
Protease Inhibitors / pharmacology
Structure-Activity Relationship
Succinates / chemical synthesis*
Succinates / chemistry
Succinates / pharmacology
Sulfhydryl Compounds / chemical synthesis*
Sulfhydryl Compounds / chemistry
Sulfhydryl Compounds / pharmacology

Substances

Alcohols
Indicators and Reagents
Ketones
Matrix Metalloproteinase Inhibitors
Protease Inhibitors
Succinates
Sulfhydryl Compounds
Metalloendopeptidases
Matrix Metalloproteinase 9
Matrix Metalloproteinase 1