Synthesis and comparative carbonic anhydrase inhibition of new Schiff's bases incorporating benzenesulfonamide, methanesulfonamide, and methylsulfonylbenzene scaffolds.

Carbonic Anhydrase Inhibitors / chemical synthesis Carbonic Anhydrases / chemistry Hydrogen Bonding Molecular Docking Simulation Molecular Structure Schiff Bases / chemistry Structure-Activity Relationship Sulfonamides / chemistry Benzenesulfonamides
Acetazolamide Benzenesulfonamide Carbonic anhydrase inhibition Molecular docking Schiff’s base Synthesis

Journal

Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703

Informations de publication

Date de publication:
11 2019
Historique:
received: 26 05 2019
revised: 25 08 2019
accepted: 27 08 2019
pubmed: 8 9 2019
medline: 23 10 2020
entrez: 8 9 2019
Statut: ppublish

Résumé

Herein, we report the synthesis, characterization, and carbonic anhydrase (CA) inhibition of the newly synthesized Schiff's bases 4-18 with benzenesulfonamide, methanesulfonamide, and methylsulfonylbenzene scaffolds. The compound inhibition profiles against human CA (hCA) isoforms I, II, IX, and XII were compared to those of the standard inhibitors, acetazolamide (AAZ) and SLC-0111 (a CA inhibitor in Phase II clinical trials for the treatment of hypoxic tumors). The hCA I was inhibited by compounds 4a-8a with inhibition constants (K

Identifiants

DOI: 10.1016/j.bioorg.2019.103225 PMID: 31493707
pubmed: 31493707
pii: S0045-2068(19)30857-0
doi: 10.1016/j.bioorg.2019.103225
pii:
doi:

Substances chimiques

Carbonic Anhydrase Inhibitors 0
Schiff Bases 0
Sulfonamides 0
methanesulfonamide 3144-09-0
Carbonic Anhydrases EC 4.2.1.1

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

103225

Informations de copyright

Copyright © 2019 Elsevier Inc. All rights reserved.

Auteurs

Adel S El-Azab (AS)

Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia. Electronic address: adelazab@ksu.edu.sa.

Alaa A-M Abdel-Aziz (AA)

Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.

Silvia Bua (S)

Università degli Studi di Firenze, Dipartimento Neurofarba, Sezione di Scienze Farmaceutiche e Nutraceutiche, Via U. Schiff 6, 50019 Sesto Fiorentino, Florence, Italy.

Alessio Nocentini (A)

Università degli Studi di Firenze, Dipartimento Neurofarba, Sezione di Scienze Farmaceutiche e Nutraceutiche, Via U. Schiff 6, 50019 Sesto Fiorentino, Florence, Italy.

Mohammed M Alanazi (MM)

Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.

Nawaf A AlSaif (NA)

Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.

Ibrahim A Al-Suwaidan (IA)

Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.

Mohamed M Hefnawy (MM)

Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.

Claudiu T Supuran (CT)

Università degli Studi di Firenze, Dipartimento Neurofarba, Sezione di Scienze Farmaceutiche e Nutraceutiche, Via U. Schiff 6, 50019 Sesto Fiorentino, Florence, Italy. Electronic address: claudiu.supuran@unifi.it.

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Classifications MeSH

questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Mécanismes moléculaires de l'action pharmacologique › Antienzymes › Inhibiteurs de l'anhydrase carbonique › Synthesis and comparative carbonic anhydrase...
questionsmedicales.fr › Enzymes et coenzymes › Enzymes › Lyases › Carbon-oxygen lyases › Hydro-lyases › Carbonic anhydrases › Synthesis and comparative carbonic anhydrase...
questionsmedicales.fr › Phénomènes chimiques › Liaison hydrogène › Synthesis and comparative carbonic anhydrase...
questionsmedicales.fr › Sciences de l'information › Méthodologies informatiques › Simulation numérique › Simulation de docking moléculaire › Synthesis and comparative carbonic anhydrase...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Synthesis and comparative carbonic anhydrase...
questionsmedicales.fr › Composés chimiques organiques › Imines › Bases de Schiff › Synthesis and comparative carbonic anhydrase...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes pharmacologiques › Relation structure-activité › Synthesis and comparative carbonic anhydrase...
questionsmedicales.fr › Composés chimiques organiques › Composés du soufre › Sulfones › Sulfonamides › Synthesis and comparative carbonic anhydrase...