The Lossen rearrangement in biological systems. Inactivation of leukocyte elastase and alpha-chymotrypsin by (dl)-3-benzyl-N-(methanesulfonyloxy) succinimide.

doi:10.1016/S0006-291X(86)80235-2

Paper

DOI: 10.1016/S0006-291X(86)80235-2

The Lossen rearrangement in biological systems. Inactivation of leukocyte elastase and alpha-chymotrypsin by (dl)-3-benzyl-N-(methanesulfonyloxy) succinimide.

Published Dec 15, 1986 · W. Groutas, P. Giri, James Crowley

Biochemical and biophysical research communications

Q1 SJR score

Citations

Influential Citations

Full textSemantic Scholar

Abstract

Abstract hidden due to publisher request; this does not indicate any issues with the research. Click the full text link above to read the abstract and view the original source.

Study Snapshot

(dl)-3-benzyl-N-(methanesulfonyloxy) succinimide 5 efficiently and irreversibly inactivates human leukocyte elastase and alpha-chymotrypsin, potentially acting as a mechanism-based inhibitor of serine

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Full text analysis coming soon...

References

DOI: 10.1021/JM00157A034

Inactivation of leukocyte elastase by aryl azolides and sulfonate salts. Structure-activity relationship studies.

Aryl azolides and sulfonate salts show potent inhibitory activity against human leukocyte elastase, with compounds 23 and 26 being the most active, influenced by the nature of the leaving group.

1986·13citations·W. Groutas et al.·Journal of medicinal chemistry

Journal of medicinal chemistry

DOI: 10.1021/JM00146A023

Substituted 2-pyrones, 2-pyridones, and other congeners of elasnin as potential agents for the treatment of chronic obstructive lung diseases.

C-3 alkyl substituted 2-pyrones 11 and 12 show potential as effective treatments for chronic obstructive lung diseases by inhibiting human leukocyte elastase.

1985·38citations·W. Groutas et al.·Journal of medicinal chemistry

Journal of medicinal chemistry

DOI: 10.1016/0006-291X(85)91648-1

Sulfonate salts of amino acids: novel inhibitors of the serine proteinases.

Sulfonate salts of amino acids effectively and selectively inhibit human leukocyte elastase, demonstrating their potential as novel inhibitors for serine proteinases.

1985·14citations·W. Groutas et al.·Biochemical and biophysical research communications

Biochemical and biophysical research communications

DOI: 10.1021/BI00329A006

Inhibition of human leukocyte elastase, cathepsin G, chymotrypsin A alpha, and porcine pancreatic elastase with substituted isobenzofuranones and benzopyrandiones.

Substituted isobenzofuranones and benzopyran-1,4-diones effectively inhibit human leukocyte elastase and chymotrypsin A alpha, but not porcine pancreatic elastase or cathepsin G

1985·17citations·K. Hemmi et al.·Biochemistry

Biochemistry

DOI: 10.1021/JM00380A010

Amino acid derived latent isocyanates: irreversible inactivation of porcine pancreatic elastase and human leukocyte elastase.

Latent isocyanates derived from appropriate amino acids can serve as selective inhibitors of serine proteases and have potential pharmacological value.

1985·15citations·W. Groutas et al.·Journal of medicinal chemistry

Journal of medicinal chemistry

Citations

DOI: 10.3389/fchem.2021.662533

Lossen Rearrangement of p-Toluenesulfonates of N-Oxyimides in Basic Condition, Theoretical Study, and Molecular Docking

The basicity of the amine used in the reaction plays a crucial role in the reaction mechanism, and molecular docking suggests potential as serine protease inhibitors.

2021·24citations·M. Kijewska et al.·Frontiers in Chemistry

Frontiers in Chemistry

DOI: 10.1080/14728222.2018.1541235

HDAC6 as a potential therapeutic target for peripheral nerve disorders

HDAC6 inhibitors show potential as a preventative and therapeutic strategy for inherited and acquired peripheral neuropathies.

2018·32citations·Robert Prior et al.·Expert Opinion on Therapeutic Targets

Expert Opinion on Therapeutic Targets

DOI: 10.1039/c8md00107c

Assessment of the trifluoromethyl ketone functionality as an alternative zinc-binding group for selective HDAC6 inhibition.

Replacing hydroxamic acid with trifluoromethyl ketone in HDAC6 inhibitors showed reduced potency and should not be considered a standard strategy in inhibitor development.

2018·3citations·Yves Depetter et al.·MedChemComm

MedChemComm

DOI: 10.1002/cmdc.201600190

Covalent Inhibition of HIV‐1 Integrase by N‐Succinimidyl Peptides

This study presents a promising new strategy for designing lead compounds by covalently inhibiting HIV-1 integrase with LEDGF/p75-derived peptides and N-succinimidyl peptides.

2016·4citations·K. Chandra et al.·ChemMedChem

ChemMedChem

DOI: 10.1016/j.bmcl.2012.08.104

Novel histone deacetylase 8 ligands without a zinc chelating group: exploring an 'upside-down' binding pose.

Novel HDAC8 inhibitors without a zinc-chelating group bind in an 'upside-down' fashion in a secondary binding site proximal to the main catalytic site, with the most potent ligand showing an IC 50 of 28 M.

2012·18citations·A. Vaidya et al.·Bioorganic & medicinal chemistry letters

Bioorganic & medicinal chemistry letters

DOI: 10.1039/B513741A

Crystal-state studies on p-toluenesulfonates of N-oxyimides—a possible structural basis of serine proteases inhibition

P-toluenesulfonates of N-oxyimides show a flattened pyramidal geometry, potentially responsible for their inhibitory properties against serine proteases.

2006·10citations·P. Stefanowicz et al.·New Journal of Chemistry

New Journal of Chemistry

DOI: 10.1016/J.ABB.2004.05.018

Mechanism-based inactivation of human leukocyte elastase via an enzyme-induced sulfonamide fragmentation process.

This novel class of inhibitors inactivates human leukocyte elastase via an enzyme-induced sulfonamide fragmentation cascade, offering a potential general class of mechanism-based inhibitors of (chymo)trypsin-like serine proteases.

2004·6citations·Liuqing Wei et al.·Archives of biochemistry and biophysics

Archives of biochemistry and biophysics

DOI: 10.1007/PL00000884

Strategies for the inhibition of serine proteases

Peptide- and heterocyclic-based compounds are effective inhibitors of serine proteases, exploiting their substrate specificity characteristics for diverse biological roles.

2001·87citations·Brian Walker et al.·Cellular and Molecular Life Sciences CMLS

Cellular and Molecular Life Sciences CMLS

DOI: 10.1016/S0968-0896(00)00281-9

6-Acylamino-2-1[(ethylsulfonyl)oxy]-1H-isoindole-1,3-diones mechanism-based inhibitors of human leukocyte elastase and cathepsin G: effect of chirality in the 6-acylamino substituent on inhibitory potency and selectivity.

The best inhibitor of human leukocyte elastase is 6-((1′S)-camphanyl)amino-2-[(ethylsulfonyl)oxy)-1H-isoindole-1,3-dione 5b, which shows preference

2001·8citations·L. M. Vagnoni et al.·Bioorganic & medicinal chemistry

Bioorganic & medicinal chemistry