BIOMAT Database Logo BIOMAT Database Logo

One-Pot Synthesis and in Silico Molecular Docking Studies of Arylselanyl Hydrazides as Potential Antituberculosis Agents. 2022

Elton L Borges, and Helen A Goulart, and Gelson Perin, and Paulo H Schneider, and Guilherme S Rieder, and Pablo A Nogara, and João B T da Rocha
Grupo de Pesquisa em Síntese Orgânica da Região Amazônica (LASORA, DAEPA), Fundação Universidade Federal de Rondônia (UNIR), Rua da Paz 4376, 76916-000, Presidente Médici, RO, Brazil.

The present study reports a simple two-step method for the synthesis of arylselanyl hydrazide derivatives using hypophosphorous acid and polyethylene glycol (H3 PO2 /PEG-400) as an alternative reducing system and hydrazine hydrate (NH2 NH2 ⋅xH2 O/50-60 %). This single-vessel procedure was employed with methyl acrylate 2a and methyl bromoacetate 2b using diaryl diselenides to generate the nucleophile species to produce, respectively, 3-(arylselanyl)propane-hydrazides 4a-e and 2-(arylselanyl)acetohydrazides 5a-e with good yields by accelerating the reduction of -Se-Se- bond, when compared to available methods. The synthesized molecules are structurally similar to the isoniazid (INH). Therefore, we perform in silico molecular docking studies, using the lactoperoxidase enzyme, in order to verify whether the INH Se derivatives could interact in a similar way to INH at the active site of the mammalian enzyme. The in silico results indicated a similar type of interaction of the arylselanyl hydrazide derivatives with that of INH. In view of the similar in silico interaction of the selenium derivatives of INH, the arylselanyl hydrazide derivatives reported here should be tested against Mycobacterium tuberculosis in vitro.

UI MeSH Term Description Entries
D007538 Isoniazid Antibacterial agent used primarily as a tuberculostatic. It remains the treatment of choice for tuberculosis. Isonicotinic Acid Hydrazide,Ftivazide,Isonex,Isonicotinic Acid Vanillylidenehydrazide,Phthivazid,Phthivazide,Tubazide,Acid Vanillylidenehydrazide, Isonicotinic,Hydrazide, Isonicotinic Acid,Vanillylidenehydrazide, Isonicotinic Acid
D008322 Mammals Warm-blooded vertebrate animals belonging to the class Mammalia, including all that possess hair and suckle their young. Mammalia,Mammal
D009169 Mycobacterium tuberculosis A species of gram-positive, aerobic bacteria that produces TUBERCULOSIS in humans, other primates, CATTLE; DOGS; and some other animals which have contact with humans. Growth tends to be in serpentine, cordlike masses in which the bacilli show a parallel orientation. Mycobacterium tuberculosis H37Rv
D006834 Hydrazines Substituted derivatives of hydrazine (formula H2N-NH2). Hydrazide
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D000995 Antitubercular Agents Drugs used in the treatment of tuberculosis. They are divided into two main classes: "first-line" agents, those with the greatest efficacy and acceptable degrees of toxicity used successfully in the great majority of cases; and "second-line" drugs used in drug-resistant cases or those in which some other patient-related condition has compromised the effectiveness of primary therapy. Anti-Tuberculosis Agent,Anti-Tuberculosis Agents,Anti-Tuberculosis Drug,Anti-Tuberculosis Drugs,Antitubercular Agent,Antitubercular Drug,Tuberculostatic Agent,Tuberculostatic Agents,Antitubercular Drugs,Agent, Anti-Tuberculosis,Agent, Antitubercular,Agent, Tuberculostatic,Anti Tuberculosis Agent,Anti Tuberculosis Agents,Anti Tuberculosis Drug,Anti Tuberculosis Drugs,Drug, Anti-Tuberculosis,Drug, Antitubercular
D062105 Molecular Docking Simulation A computer simulation technique that is used to model the interaction between two molecules. Typically the docking simulation measures the interactions of a small molecule or ligand with a part of a larger molecule such as a protein. Molecular Docking,Molecular Docking Simulations,Molecular Docking Analysis,Analysis, Molecular Docking,Docking Analysis, Molecular,Docking Simulation, Molecular,Docking, Molecular,Molecular Docking Analyses,Molecular Dockings,Simulation, Molecular Docking

Related Publications

Elton L Borges, and Helen A Goulart, and Gelson Perin, and Paulo H Schneider, and Guilherme S Rieder, and Pablo A Nogara, and João B T da Rocha
Design, Synthesis, and Molecular Docking Studies of a Conjugated Thiadiazole-Thiourea Scaffold as Antituberculosis Agents.
January 2016, Biological & pharmaceutical bulletin,
Elton L Borges, and Helen A Goulart, and Gelson Perin, and Paulo H Schneider, and Guilherme S Rieder, and Pablo A Nogara, and João B T da Rocha
Efficient one-pot synthesis, molecular docking and in silico ADME prediction of bis-(4-hydroxycoumarin-3-yl) methane derivatives as antileishmanial agents.
January 2015, EXCLI journal,
Elton L Borges, and Helen A Goulart, and Gelson Perin, and Paulo H Schneider, and Guilherme S Rieder, and Pablo A Nogara, and João B T da Rocha
Synthesis, In silico and In vitro Analysis of Hydrazones as Potential Antituberculosis Agents.
January 2021, Current computer-aided drug design,
Elton L Borges, and Helen A Goulart, and Gelson Perin, and Paulo H Schneider, and Guilherme S Rieder, and Pablo A Nogara, and João B T da Rocha
One-pot synthesis, spectral characterization, biological evaluation, molecular docking studies and in silico ADME/Tox profiling of new 2,4,5 triaryl imidazole derivatives as anti tubercular agents.
October 2023, The Indian journal of tuberculosis,
Elton L Borges, and Helen A Goulart, and Gelson Perin, and Paulo H Schneider, and Guilherme S Rieder, and Pablo A Nogara, and João B T da Rocha
One-Pot Synthesis of Triazolo-Heterolignans: Biological Evaluation and Molecular Docking Studies as Tubulin Inhibitors.
January 2018, Anti-cancer agents in medicinal chemistry,
Elton L Borges, and Helen A Goulart, and Gelson Perin, and Paulo H Schneider, and Guilherme S Rieder, and Pablo A Nogara, and João B T da Rocha
Design, One Pot Synthesis and Molecular Docking Studies of Substituted-1H-Pyrido[2,1-b] Quinazolines as Apoptosis-Inducing Anticancer Agents.
February 2020, Asian Pacific journal of cancer prevention : APJCP,
Elton L Borges, and Helen A Goulart, and Gelson Perin, and Paulo H Schneider, and Guilherme S Rieder, and Pablo A Nogara, and João B T da Rocha
Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles.
January 2018, Beilstein journal of organic chemistry,
Elton L Borges, and Helen A Goulart, and Gelson Perin, and Paulo H Schneider, and Guilherme S Rieder, and Pablo A Nogara, and João B T da Rocha
In silico molecular docking studies of oxadiazole and pyrimidine bearing heterocyclic compounds as potential antimicrobial agents.
October 2021, Archiv der Pharmazie,
Elton L Borges, and Helen A Goulart, and Gelson Perin, and Paulo H Schneider, and Guilherme S Rieder, and Pablo A Nogara, and João B T da Rocha
Synthesis and molecular docking studies of novel pyrimidine derivatives as potential antibacterial agents.
November 2020, Molecular diversity,
Elton L Borges, and Helen A Goulart, and Gelson Perin, and Paulo H Schneider, and Guilherme S Rieder, and Pablo A Nogara, and João B T da Rocha
Dexibuprofen amide derivatives as potential anticancer agents: synthesis, in silico docking, bioevaluation, and molecular dynamic simulation.
January 2019, Drug design, development and therapy,
Copied contents to your clipboard!