BIOMAT Database Logo BIOMAT Database Logo

Synthesis, biological evaluation and molecular docking study of some novel indole and pyridine based 1,3,4-oxadiazole derivatives as potential antitubercular agents. 2016

N C Desai, and Hardik Somani, and Amit Trivedi, and Kandarp Bhatt, and Laxman Nawale, and Vijay M Khedkar, and Prakash C Jha, and Dhiman Sarkar
Division of Medicinal Chemistry, Department of Chemistry (DST-FIST Sponsored), Mahatma Gandhi Campus, Maharaja Krishnakumarsinhji Bhavnagar University, Bhavnagar 364 002, Gujarat, India. Electronic address: dnisheeth@rediffmail.com.

A series of indole and pyridine based 1,3,4-oxadiazole derivatives 5a-t were synthesized and evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Ra (MTB) and Mycobacterium bovis BCG both in active and dormant state. Compounds 5b, 5e, 5g and 5q exhibited very good antitubercular activity. All the newly synthesized compounds 5a-t were further evaluated for anti-proliferative activity against HeLa, A549 and PANC-1 cell lines using modified MTT assay and found to be noncytotoxic. On the basis of cytotoxicity and MIC values against Mycobacterium bovis BCG, selectivity index (SI) of most active compounds 5b, 5e, 5g and 5q was calculated (SI=GI50/MIC) in active and dormant state. Compounds 5b, 5e and 5g demonstrated SI values ⩾10 against all three cell lines and were found to safe for advance screening. Compounds 5a-t were further screened for their antibacterial activity against four bacteria strains to assess their selectivity towards MTB. In addition, the molecular docking studies revealed the binding modes of these compounds in active site of enoyl reductase (InhA), which in turn helped to establish a structural basis of inhibition of mycobacteria. The potency, low cytotoxicity and selectivity of these compounds make them valid lead compounds for further optimization.

UI MeSH Term Description Entries
D007211 Indoles Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
D008826 Microbial Sensitivity Tests Any tests that demonstrate the relative efficacy of different chemotherapeutic agents against specific microorganisms (i.e., bacteria, fungi, viruses). Bacterial Sensitivity Tests,Drug Sensitivity Assay, Microbial,Minimum Inhibitory Concentration,Antibacterial Susceptibility Breakpoint Determination,Antibiogram,Antimicrobial Susceptibility Breakpoint Determination,Bacterial Sensitivity Test,Breakpoint Determination, Antibacterial Susceptibility,Breakpoint Determination, Antimicrobial Susceptibility,Fungal Drug Sensitivity Tests,Fungus Drug Sensitivity Tests,Sensitivity Test, Bacterial,Sensitivity Tests, Bacterial,Test, Bacterial Sensitivity,Tests, Bacterial Sensitivity,Viral Drug Sensitivity Tests,Virus Drug Sensitivity Tests,Antibiograms,Concentration, Minimum Inhibitory,Concentrations, Minimum Inhibitory,Inhibitory Concentration, Minimum,Inhibitory Concentrations, Minimum,Microbial Sensitivity Test,Minimum Inhibitory Concentrations,Sensitivity Test, Microbial,Sensitivity Tests, Microbial,Test, Microbial Sensitivity,Tests, Microbial Sensitivity
D009163 Mycobacterium bovis The bovine variety of the tubercle bacillus. It is called also Mycobacterium tuberculosis var. bovis. BCG,Calmette-Guerin Bacillus
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
D010069 Oxadiazoles Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms. Oxadiazole
D011725 Pyridines Compounds with a six membered aromatic ring containing NITROGEN. The saturated version is PIPERIDINES.
D002460 Cell Line Established cell cultures that have the potential to propagate indefinitely. Cell Lines,Line, Cell,Lines, Cell
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
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

Related Publications

N C Desai, and Hardik Somani, and Amit Trivedi, and Kandarp Bhatt, and Laxman Nawale, and Vijay M Khedkar, and Prakash C Jha, and Dhiman Sarkar
Synthesis, molecular docking and biological evaluation of 1,3,4-oxadiazole derivatives as potential immunosuppressive agents.
February 2012, Bioorganic & medicinal chemistry,
N C Desai, and Hardik Somani, and Amit Trivedi, and Kandarp Bhatt, and Laxman Nawale, and Vijay M Khedkar, and Prakash C Jha, and Dhiman Sarkar
Synthesis, biological evaluation and molecular docking studies of 1,3,4-oxadiazole derivatives as potential immunosuppressive agents.
May 2012, Bioorganic & medicinal chemistry,
N C Desai, and Hardik Somani, and Amit Trivedi, and Kandarp Bhatt, and Laxman Nawale, and Vijay M Khedkar, and Prakash C Jha, and Dhiman Sarkar
Synthesis, biological evaluation, and molecular docking studies of 1,3,4-oxadiazole derivatives possessing 1,4-benzodioxan moiety as potential anticancer agents.
November 2011, Bioorganic & medicinal chemistry,
N C Desai, and Hardik Somani, and Amit Trivedi, and Kandarp Bhatt, and Laxman Nawale, and Vijay M Khedkar, and Prakash C Jha, and Dhiman Sarkar
Synthesis, biological evaluation, and molecular docking studies of 2-chloropyridine derivatives possessing 1,3,4-oxadiazole moiety as potential antitumor agents.
November 2010, Bioorganic & medicinal chemistry,
N C Desai, and Hardik Somani, and Amit Trivedi, and Kandarp Bhatt, and Laxman Nawale, and Vijay M Khedkar, and Prakash C Jha, and Dhiman Sarkar
Synthesis, Molecular Docking, and Biological Evaluation of Some Novel 2- (5-Substituted 1,3,4-oxadiazole-2-yl)-1,3-benzothiazole Derivatives as Anticonvulsant Agents.
January 2021, Central nervous system agents in medicinal chemistry,
N C Desai, and Hardik Somani, and Amit Trivedi, and Kandarp Bhatt, and Laxman Nawale, and Vijay M Khedkar, and Prakash C Jha, and Dhiman Sarkar
1,3,4-oxadiazole derivatives as potential biological agents.
October 2013, Mini reviews in medicinal chemistry,
N C Desai, and Hardik Somani, and Amit Trivedi, and Kandarp Bhatt, and Laxman Nawale, and Vijay M Khedkar, and Prakash C Jha, and Dhiman Sarkar
Design, synthesis, biological evaluation and molecular modeling of novel 1,3,4-oxadiazole derivatives based on Vanillic acid as potential immunosuppressive agents.
July 2012, Bioorganic & medicinal chemistry,
N C Desai, and Hardik Somani, and Amit Trivedi, and Kandarp Bhatt, and Laxman Nawale, and Vijay M Khedkar, and Prakash C Jha, and Dhiman Sarkar
Synthesis, Biological Evaluation and Computational Studies of New Hydrazide Derivatives Containing 1,3,4-Oxadiazole as Antitubercular Agents.
December 2022, International journal of molecular sciences,
N C Desai, and Hardik Somani, and Amit Trivedi, and Kandarp Bhatt, and Laxman Nawale, and Vijay M Khedkar, and Prakash C Jha, and Dhiman Sarkar
Synthesis, molecular docking study and anticancer activity of novel 1,3,4-oxadiazole derivatives as potential tubulin inhibitors.
February 2023, Heliyon,
N C Desai, and Hardik Somani, and Amit Trivedi, and Kandarp Bhatt, and Laxman Nawale, and Vijay M Khedkar, and Prakash C Jha, and Dhiman Sarkar
Synthesis of novel 1,3,4-oxadiazole derivatives as potential antimicrobial agents.
January 2010, Acta poloniae pharmaceutica,
Copied contents to your clipboard!