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Synthesis, admetSAR Predictions, DPPH Radical Scavenging Activity, and Potent Anti-mycobacterial Studies of Hydrazones of Substituted 4-(anilino methyl) benzohydrazides (Part 2)

[ Vol. 17 , Issue. 4 ]

Author(s):

Vijay J. Desale, Suraj N. Mali, Bapu R. Thorat* and Ramesh S. Yamgar   Pages 493 - 503 ( 11 )

Abstract:


Background: For the past several decades, the presence of tuberculosis (TB) is being remarked as the most common infectious disease leading to mortality.

Objective: Hydrazone containing azometine group (-NHN=CH-) compounds have been reported for a broad range of bioactivities such as antiplatelet, analgesic, anti-inflammatory, anticonvulsant, antidepressant, antimalarial, vasodilator, antiviral, and antimicrobial, etc.

Methods: For the synthesis of compounds (4a-4d) and (6a-6e), aromatic amines were treated with methyl terephthalaldehydate in methanol, giving Schiff’s bases, followed by reductive amination and further treatment with hydrazine hydrate gave acid hydrazides (4a-4d). These acid hydrazides were then treated with different aromatic aldehydes to yield hydrazones (6a-6d). All the synthesized compounds were subjected to FT-IR, NMR, and UV spectroscopic characterization.

Results: Compounds (4a-4d) and (6a-6e) were found to have highly potent activity against Mycobacteria tuberculosis (Vaccine strain, H37 RV strains): ATCC No- 27294 (MIC:1.6-6.25 μg/mL) than standard anti-TB drugs. The compounds exhibited good radical scavenging potentials(0- 69.2%), as checked from DPPH protocol. All compounds also demonstrated good in-silico ADMET results.

Conclusion: The current study revealed promising in vitro anti-tuberculosis and anti-oxidant profiles of hydrazide-hydrazone analogues.

Keywords:

Hydrazide-hydrazones, anti-oxidant activity, anti-tuberculosis activity, in silico analysis, tuberculosis, synthesis.

Affiliation:

Department of Chemistry, Government of Maharashtra’s Ismail Yusuf College, Jogeshwari, Mumbai-400060, Government College of Pharmacy, Karad, Maharashtra, Department of Chemistry, Government of Maharashtra’s Ismail Yusuf College, Jogeshwari, Mumbai-400060, Department of Chemistry, Patkar-Varde College of Arts, Science and Commerce, Goregaon (W), Mumbai 400 062

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