Synthesis and antimycobacterial activity of 3-(Arylaminomethyl)-5-(Pyridin-4-yl)-1,3,4-oxadiazole-(3H)-thi-2-one Derivatives against Mycobacterium tuberculosis H37rv Strain

2020 ◽  
Vol 16 ◽  
Author(s):  
Mohammad Asif ◽  
Mohd Imran
Keyword(s):  
Antimycobacterial Activity ◽  
Mannich Bases ◽  
Tuberculosis H37rv ◽  
Biologically Active ◽  
Mass Spectral ◽  
Mycobacterium Tuberculosis H37rv ◽  
H37rv Strain ◽  
Antimycobacterial Agents ◽  
Oxadiazole Derivatives ◽  
Mic Value

Background: Oxadiazole derivatives are the biologically active hetrocyclic compounds. So we synthesized a series of Mannich bases, 3-(arylaminomethyl)-5-(pyridin-4-yl)- 1,3,4-oxadiazole-(3H)-thi-2-one derivatives (3a-3g) were synthesized from Isoniazid [INH (1)], a first line antimycobacterial drug and these compounds were evaluated as antimycobacterial agents. Methods: The INH was reacted with potassium hydroxide and carbon disulfide to gives 5- (pyridin-4-yl)-1,3,4-oxadiazole-2(3H)-thione (2), followed by reacting of compound 2 with appropriate aromatic amines in the presence of formaldehyde to obtained desired compounds (3a-3g). The structures of these compounds have been established by IR, 1H-NMR and Mass spectral and elemental analysis. These synthesized compounds (3a-3g) were evaluated for their antimycobacterial activity against M. tuberculosis H37Rv strain. Results: All the synthesized compounds (3a-3g) were exhibited antimycobacterial activity and compared to reference drugs Streptomycin (MIC value of 6.25μg/mL), INH (MIC value of 3.125μg/mL) and pyrizinamide (MIC value of 3.125μg/mL). Compounds 3c and 3e were exhibited most promising antimycobacterial activity. Conclusion: All the title compounds were synthesized, characterized and exhibited promising antimycobacterial activity against M. tuberculosis H37Rv strain.

SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME NEW 1,3,4- OXADIAZOLES, 1,2,4-TRIAZOLES AND 1,3,4-THIADIAZOLES

INDIAN DRUGS ◽  
2016 ◽  
Vol 53 (06) ◽  
pp. 18-23
Author(s):  
U. V. Laddi ◽  
◽  
S. R. Desai
Keyword(s):  
Escherichia Coli ◽  
Antimicrobial Activity ◽  
Mycobacterium Tuberculosis ◽  
Antitubercular Activity ◽  
Tuberculosis H37rv ◽  
Research Centre ◽  
Methyl Ethyl ◽  
Rhizoctonia Bataticola ◽  
Mycobacterium Tuberculosis H37rv ◽  
H37rv Strain

Some new 5-[(((α-phenyl/methyl)benzylidene)amino)oxy]methyl/ethyl-2-[4-(substituted aryl)/allyl)] amino-1,3,4-oxadiazoles (4a-p), 3-[(((α-phenyl/methyl)- benzylidene) amino)oxy]methyl/ethyl-4-(4- substitutedaryl)/allyl-5-mercapto-1,2,4-triazoles (5a-p) and 5-[(((α-phenyl/methyl)-benzylidene)amino) oxy]- methyl/ethyl-2-[4-(substituted aryl)/allyl)]amino-1,3,4-thiadiazoles (6a-p) were prepared starting from α/β-[((α-(phenyl/methyl)benzylidene)amino)oxy acetic/propionic acid hydrazides (1a-d). The structures of all the compounds have been established by elemental and spectral (IR, 1HNMR and mass) analysis. All the newly synthesised compounds have been screened for their antimicrobial activity against Escherichia coli, Bacillus cirroflagellosus, Aspergillus niger and Rhizoctonia bataticola. Some of the newly synthesised compounds have been evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv strain by BACTEC radiometric system at Southern Research Institute, Birmingham, AL and Frederick Research Centre, Frederick, MD. Significant antimicrobial activity is observed against Escherichia coli and Rhizoctonia bataticola. A few compounds also exhibited interesting antitubercular activity against Mycobacterium tuberculosis H37Rv strain.

Design, Synthesis and Evaluation of Aryloxybenzylidene Hydrazinyl-Benzoxazoles/Benzothiazoles Analogs as Antimycobacterial Agents

2020 ◽  
Vol 5 (3) ◽  
pp. 185-191
Author(s):  
G. Aruna ◽  
Ravindra Kulkarni ◽  
Baswaraj Machaa ◽  
Malathi Jojula ◽  
Shravan Gunda ◽  
...  
Keyword(s):  
Spectral Data ◽  
Condensation Reaction ◽  
Antitubercular Activity ◽  
Antimycobacterial Activity ◽  
Molecular Hybridization ◽  
Design Synthesis ◽  
Antitubercular Drugs ◽  
Pantothenate Synthetase ◽  
Antimycobacterial Agents ◽  
Mic Value

Substituted 2-(2-(4-aryloxybenzylidene)hydrazinyl)benzothiazole/benzoxazoles series were designed through molecular hybridization and synthesized in condensation reaction of hydrazinylbenzothiazole/ benzoxazole with substituted aryloxy benzaldehydes. All the synthesized compounds were assigned structure based on spectral data and were evaluated for antimycobacterial activity. Among both benzothiazole and benzoxazole derivatives, the compounds 8f and 9e were found to show most potent antitubercular activity with MIC value of 0.89 and 0.92 μM which are on a par with those of standard antitubercular drugs. In order to know the binding interactions of all the compounds were docked within the mycobacterial pantothenate synthetase, which showed interactions with Asp88, Arg200, Ser196, Asn199, Met 195 and Lys 160 of pantothenate synthetase.

scholarly journals Versatility of 7-Substituted Coumarin Molecules as Antimycobacterial Agents, Neuronal Enzyme Inhibitors and Neuroprotective Agents

2017 ◽  
Author(s):  
Erika Kapp ◽  
Hanri Visser ◽  
Samantha L. Sampson ◽  
Sarel F. Malan ◽  
Elizabeth M. Streicher ◽  
...  
Keyword(s):  
Enzyme Inhibitors ◽  
Neuroblastoma Cells ◽  
Antimycobacterial Activity ◽  
Tuberculosis H37rv ◽  
Neuroprotective Agents ◽  
Human Neuroblastoma ◽  
Lead Compounds ◽  
Antimycobacterial Agents ◽  
Insight Into

An in vitro medium-throughput screen using M. tuberculosis H37Rv was employed to screen an in-house library of structurally diverse compounds for antimycobacterial activity.  From this initial screen, eleven 7-substituted coumarin derivatives with confirmed monoamine oxidase-B and cholinesterase inhibitory activities, demonstrated growth inhibition of more than 50% at a 50 µM concentration.  This prompted further exploration of all the 7-substituted coumarins in our library, nineteen in total, as potential antimycobacterial agents. Four derivatives showed promising antimycobacterial activity with MIC99 values of 8.31 – 29.70 µM and 44.15 – 57.17 µM on M. tuberculosis H37Rv in independent assays using Gaste-Fe and 7H9 + OADC media, respectively.   These compounds were found to bind to albumin which may explain the variations in MIC between the two assays.  Preliminary antimycobacterial evaluation of moxifloxacin resistant M. tuberculosis show that these compounds are able to maintain their activity in fluoroquinolone resistant mycobacteria.   Analysis of structure activity relationships for antimycobacterial versus neuronal enzyme inhibitory activity indicate that structural modification on position 4 and/or 7 of the coumarin scaffold may be utilized to improve selectivity towards either inhibition of neuronal enzymes or antimycobacterial effect.  Cytotoxicity evaluations of the compounds indicate moderate cytotoxicity with slight selectivity towards mycobacteria.  Further neuroprotective assays on SH-SY5Y human neuroblastoma cells indicate significant neuroprotection for selected compounds irrespective of their neuronal enzyme inhibitory properties.  These coumarin molecules are thus interesting lead compounds that may provide insight into the design of new antimicrobacterial and/or neuroprotective agents.

scholarly journals Synthesis of Tetrahydro-2H-[1,3,5]thiadiazine-5-(4-pyridylcarboxamido)-2-thione with antitubercular activity

2004 ◽  
Vol 72 (1) ◽  
pp. 35-41 ◽  
Author(s):  
D. Sriram ◽  
K. Jyothi Mallika ◽  
P. Yogeeswari
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Antitubercular Activity ◽  
Antimycobacterial Activity ◽  
Therapeutic Use ◽  
Tuberculosis H37rv ◽  
Mycobacterium Tuberculosis H37rv ◽  
Radiometric System ◽  
Elemental Analyses ◽  
Derivatives Of

3-Substituted-5-(4-pyridylcarboxamide)tetrahydro-2H-[1,3,5]thiadizine-2-thione derivatives (1-9) were synthesized as derivatives of isoniazid (INH) to overcome the resistance developed with its therapeutic use. The structures were confirmed by their spectral and elemental analyses data. These derivatives revealed higher lipophilicity compared with INH. The antimycobacterial activity of the synthesized compounds and INH was evaluated in vitro against Mycobacterium tuberculosis H37Rv at 6.25 µg/ml in BACTEC 12B medium using the BACTEC 460 radiometric system. The derivatives exhibited antitubercular activity.

scholarly journals Design and characterisation of piperazine-benzofuran integrated dinitrobenzenesulfonamide as Mycobacterium tuberculosis H37Rv strain inhibitors

2021 ◽  
Vol 36 (1) ◽  
pp. 1751-1759
Author(s):  
Vallabhaneni S. Murthy ◽  
Yasinalli Tamboli ◽  
Vagolu Siva Krishna ◽  
Dharmarajan Sriram ◽  
Siddique Akber Ansari ◽  
...  
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Tuberculosis H37rv ◽  
Mycobacterium Tuberculosis H37rv ◽  
H37rv Strain

scholarly journals ANTITUBERCULAR ACTIVITY OF SOME NEWER 6-PYRIDAZINONE DERIVATIVES

2011 ◽  
Vol 19 (19) ◽  
pp. 17-23
Author(s):  
Asif HUSAIN ◽  
Aftab AHMAD ◽  
Anil BHANDARI ◽  
Veerma RAM
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Antitubercular Activity ◽  
Tuberculosis H37rv ◽  
Mycobacterium Tuberculosis H37rv ◽  
H37rv Strain ◽  
Pyridazinone Derivatives

Two series of 6-pyridazinone derivatives (17-30) were synthesized and evaluated for antitubercular activities against the Mycobacterium tuberculosis H37Rv strain. The results indicated that among the synthesized compounds, 5-( 4-hydroxy-3-methoxybenzyl}-3-phenyl-1,6-dihydro-6-pyridazinone (23) showed good antitubercular activity. Three more compounds, (18, 25 & 27) were significant in their antitubercular action. The present study reveals the antitubercular potential of 6-pyridazinones.

Antimycobacterial assessment and Microwave-assisted synthesis of 2-aryl-3-(4-methylphenylamino)thiazolidin-4-one derivatives

2021 ◽  
Vol 18 ◽  
Author(s):  
Saad Alghamdi ◽  
Mehnaz Kamal ◽  
Mohammad Asif
Keyword(s):  
Inhibitory Concentration ◽  
Aromatic Aldehydes ◽  
Microwave Assisted Synthesis ◽  
Alamar Blue ◽  
Mycobacterium Tuberculosis H37rv ◽  
Lead Compounds ◽  
Microwave Assisted ◽  
H37rv Strain ◽  
Antimycobacterial Agents

: This article reports the microwave-assisted synthesis, characterization, and evaluation of some -4-one derivatives (2a-2h) for their in-vitro antimycobacterial activities against Mycobacterium tuberculosis H37Rv strain by microplate Alamar blue assay (MABA) method. All these final compounds (2a-2h) were synthesized from Schiff’s bases, 1-arylidene-2-(4-methylphenyl)hydrazines (1a-1h), and thioglycolic acid by using zinc chloride as a catalyst. Compounds (1a-1h) were synthesized from the reaction of 4-methylhydrazine and appropriate aromatic aldehydes by Schiff’s reaction. Among the target compounds, 2-(4-ethoxyphenyl)-3-(4-methylarylamino)thiazolidin-4-one (2f) and 2-(4-ethylphenyl)-3-(4-methylarylamino)thiazolidin-4-one (2g) were promising with a minimum inhibitory concentration (MIC) of 12.5 μg/mL against M. tuberculosisH37Rv. Based on the preliminary results, compounds 2f and 2g were considered as lead compounds for the advanced design and development of antimycobacterial agents.

Sign in / Sign up

Export Citation Format

Share Document