Discovery of hydrazone containing thiadiazoles as Mycobacterium tuberculosis growth and enoyl acyl carrier protein reductase (InhA) inhibitors.

Animals Antitubercular Agents / chemical synthesis Bacterial Proteins / antagonists & inhibitors Cell Survival / drug effects Crystallography, X-Ray Dose-Response Relationship, Drug Drug Discovery Enzyme Inhibitors / chemical synthesis Hydrazones / chemistry Mice Microbial Sensitivity Tests Molecular Docking Simulation Molecular Structure Mycobacterium tuberculosis / drug effects Oxidoreductases / antagonists & inhibitors RAW 264.7 Cells Structure-Activity Relationship Thiadiazoles / chemical synthesis
Hydrazone InhA Molecular modeling Synthesis Thiadiazole Tuberculosis

Journal

European journal of medicinal chemistry
ISSN: 1768-3254
Titre abrégé: Eur J Med Chem
Pays: France
ID NLM: 0420510

Informations de publication

Date de publication:
15 Feb 2020
Historique:
received: 02 12 2019
revised: 03 01 2020
accepted: 03 01 2020
pubmed: 18 1 2020
medline: 24 10 2020
entrez: 18 1 2020
Statut: ppublish

Résumé

Tuberculosis, caused by Mycobacterium tuberculosis, is a serious infectious disease and remains a global health problem. There is an increasing need for the discovery of novel therapeutic agents for its treatment due to the emerging multi-drug resistance. Herein, we present the rational design and the synthesis of eighteen new thiadiazolylhidrazones (TDHs) which were synthesized by intramolecular oxidative N-S bond formation reaction of 2-benzylidene-N-(phenylcarbamothioyl)hydrazine-1-carboximidamide derivatives by phenyliodine(III) bis(trifluoroacetate) (PIFA) under mild conditions. The compounds were characterized by various spectral techniques including FTIR,

Identifiants

DOI: 10.1016/j.ejmech.2020.112035 PMID: 31951850
pubmed: 31951850
pii: S0223-5234(20)30002-7
doi: 10.1016/j.ejmech.2020.112035
pii:
doi:

Substances chimiques

Antitubercular Agents 0
Bacterial Proteins 0
Enzyme Inhibitors 0
Hydrazones 0
Thiadiazoles 0
Oxidoreductases EC 1.-
InhA protein, Mycobacterium EC 1.3.1.9

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

112035

Informations de copyright

Copyright © 2020 Elsevier Masson SAS. All rights reserved.

Déclaration de conflit d'intérêts

Declaration of competing interest The authors declared no potential conflicts of interest.

Auteurs

Hilal Doğan (H)

Department of Chemistry, Faculty of Science, Erciyes University, 38039, Kayseri, Turkey; Department of Basic Sciences, Faculty of Pharmacy, Erciyes University, 38039, Kayseri, Turkey.

Şengül Dilem Doğan (ŞD)

Department of Basic Sciences, Faculty of Pharmacy, Erciyes University, 38039, Kayseri, Turkey. Electronic address: dogandilem@gmail.com.

Miyase Gözde Gündüz (MG)

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Hacettepe University, Sıhhiye, 06100, Ankara, Turkey.

Vagolu Siva Krishna (VS)

Department of Pharmacy, Birla Institute of Technology and Science-Pilani, 500078, Hyderabad, India.

Christian Lherbet (C)

LSPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118, route de Narbonne, 236 Cours Eugène Cosserat, 31062, Toulouse Cedex, France.

Dharmarajan Sriram (D)

Department of Pharmacy, Birla Institute of Technology and Science-Pilani, 500078, Hyderabad, India.

Onur Şahin (O)

Scientific and Technological Research Application and Research Center, Sinop University, 57000 Sinop, Turkey.

Emin Sarıpınar (E)

Department of Chemistry, Faculty of Science, Erciyes University, 38039, Kayseri, Turkey.

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Classifications MeSH

questionsmedicales.fr › Eucaryotes › Animaux › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Utilisations thérapeutiques › Anti-infectieux › Antibactériens › Antituberculeux › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Acides aminés, peptides et protéines › Protéines › Protéines bactériennes › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Phénomènes physiologiques cellulaires › Survie cellulaire › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Techniques d'investigation › Techniques de chimie analytique › Cristallographie aux rayons X › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes toxicologiques › Relation dose-effet des médicaments › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Techniques d'investigation › Développement de médicament › Découverte de médicament › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Mécanismes moléculaires de l'action pharmacologique › Antienzymes › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Composés chimiques organiques › Hydrazines › Hydrazones › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Rodentia › Muridae › Murinae › Souris › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Techniques d'investigation › Évaluation préclinique de médicament › Tests de sensibilité microbienne › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Sciences de l'information › Méthodologies informatiques › Simulation numérique › Simulation de docking moléculaire › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Bactéries › Bactéries à Gram positif › Bâtonnets à Gram positif › Bâtonnets asporogènes à Gram positif › Bâtonnets asporogènes réguliers à Gram positif › Mycobacteriaceae › Mycobacterium › Mycobacterium tuberculosis › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Enzymes et coenzymes › Enzymes › Oxidoreductases › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Cellules › Cellules RAW 264.7 › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes pharmacologiques › Relation structure-activité › Discovery of hydrazone containing thiadiazoles...
questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Azoles › Thiazoles › Thiadiazoles › Discovery of hydrazone containing thiadiazoles...