Synthesis, biological evaluation and in silico studies with 4-benzylidene-2-phenyl-5(4H)-imidazolone-based benzenesulfonamides as novel selective carbonic anhydrase IX inhibitors endowed with anticancer activity.

Antigens, Neoplasm Antineoplastic Agents / chemical synthesis Apoptosis Carbonic Anhydrase IX / antagonists & inhibitors Carbonic Anhydrase Inhibitors / chemical synthesis Cell Proliferation HCT116 Cells Humans Imidazoles / chemistry MCF-7 Cells Molecular Docking Simulation Molecular Structure Neoplasms / drug therapy Structure-Activity Relationship Sulfonamides / chemical synthesis Benzenesulfonamides
Anticancer activity Benzenesulfonamides Imidazolone Molecular modeling Selective hCA IX inhibitors

Journal

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

Informations de publication

Date de publication:
09 2019
Historique:
received: 02 05 2019
revised: 13 06 2019
accepted: 01 07 2019
pubmed: 13 7 2019
medline: 21 10 2020
entrez: 13 7 2019
Statut: ppublish

Résumé

In the presented work, we report the synthesis of a series of 4-benzylidene-2-phenyl-5(4H)-imidazolone-based benzenesulfonamides 7a-fvia the Erlenmeyer-Plöchl reaction. All the prepared imidazolones 7a-f were evaluated as inhibitors of human (h) carbonic anhydrases (CA, EC 4.2.1.1) cytosolic isoforms hCA I and II, as well as transmembrane tumor-associated isoforms hCA IX and XII. All the tested hCA isoforms were inhibited by the prepared imidazolones 7a-f in variable degrees with the following K

Identifiants

DOI: 10.1016/j.bioorg.2019.103102 PMID: 31299596
pubmed: 31299596
pii: S0045-2068(19)30708-4
doi: 10.1016/j.bioorg.2019.103102
pii:
doi:

Substances chimiques

Antigens, Neoplasm 0
Antineoplastic Agents 0
Carbonic Anhydrase Inhibitors 0
Imidazoles 0
Sulfonamides 0
imidazolone 0
CA9 protein, human EC 4.2.1.1
Carbonic Anhydrase IX EC 4.2.1.1

Types de publication

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

Langues

eng

Sous-ensembles de citation

IM

Pagination

103102

Informations de copyright

Copyright © 2019 Elsevier Inc. All rights reserved.

Auteurs

Wagdy M Eldehna (WM)

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Kafrelsheikh University, Kafrelsheikh, Egypt. Electronic address: wagdy2000@gmail.com.

Mohamed A Abdelrahman (MA)

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Egyptian Russian University, Badr City, Cairo 11829, Egypt.

Alessio Nocentini (A)

Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, University of Florence, Polo Scientifico, Via U. Schiff 6, 50019, Sesto Fiorentino, Firenze, Italy; Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, Laboratory of Molecular Modeling Cheminformatics & QSAR, University of Florence, Polo Scientifico, Via U. Schiff 6, 50019, Sesto Fiorentino, Firenze, Italy.

Silvia Bua (S)

Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, University of Florence, Polo Scientifico, Via U. Schiff 6, 50019, Sesto Fiorentino, Firenze, Italy.

Sara T Al-Rashood (ST)

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

Ghada S Hassan (GS)

Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt.

Alessandro Bonardi (A)

Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, University of Florence, Polo Scientifico, Via U. Schiff 6, 50019, Sesto Fiorentino, Firenze, Italy; Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, Laboratory of Molecular Modeling Cheminformatics & QSAR, University of Florence, Polo Scientifico, Via U. Schiff 6, 50019, Sesto Fiorentino, Firenze, Italy.

Abdulrahman A Almehizia (AA)

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

Hamad M Alkahtani (HM)

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

Amal Alharbi (A)

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

Paola Gratteri (P)

Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, Laboratory of Molecular Modeling Cheminformatics & QSAR, University of Florence, Polo Scientifico, Via U. Schiff 6, 50019, Sesto Fiorentino, Firenze, Italy.

Claudiu T Supuran (CT)

Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, University of Florence, Polo Scientifico, Via U. Schiff 6, 50019, Sesto Fiorentino, Firenze, Italy. Electronic address: claudiu.supuran@unifi.it.

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Classifications MeSH

questionsmedicales.fr › Facteurs biologiques › Antigènes › Antigènes néoplasiques › Synthesis, biological evaluation and in silico...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Utilisations thérapeutiques › Antinéoplasiques › Synthesis, biological evaluation and in silico...
questionsmedicales.fr › Phénomènes physiologiques cellulaires › Mort cellulaire › Mort cellulaire régulée › Apoptose › Synthesis, biological evaluation and in silico...
questionsmedicales.fr › Facteurs biologiques › Antigènes › Antigènes néoplasiques › Carbonic anhydrase IX › Synthesis, biological evaluation and in silico...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Mécanismes moléculaires de l'action pharmacologique › Antienzymes › Inhibiteurs de l'anhydrase carbonique › Synthesis, biological evaluation and in silico...
questionsmedicales.fr › Phénomènes physiologiques › Croissance et développement › Croissance › Processus de croissance cellulaire › Prolifération cellulaire › Synthesis, biological evaluation and in silico...
questionsmedicales.fr › Cellules › Cellules cultivées › Cellules cancéreuses en culture › Lignée cellulaire tumorale › Cellules HCT116 › Synthesis, biological evaluation and in silico...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Primates › Haplorhini › Catarrhini › Hominidae › Humains › Synthesis, biological evaluation and in silico...
questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Azoles › Imidazoles › Synthesis, biological evaluation and in silico...
questionsmedicales.fr › Cellules › Cellules cultivées › Lignée cellulaire › Cellules MCF-7 › Synthesis, biological evaluation and in silico...
questionsmedicales.fr › Sciences de l'information › Méthodologies informatiques › Simulation numérique › Simulation de docking moléculaire › Synthesis, biological evaluation and in silico...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Synthesis, biological evaluation and in silico...
questionsmedicales.fr › Tumeurs › Synthesis, biological evaluation and in silico...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes pharmacologiques › Relation structure-activité › Synthesis, biological evaluation and in silico...
questionsmedicales.fr › Composés chimiques organiques › Composés du soufre › Sulfones › Sulfonamides › Synthesis, biological evaluation and in silico...