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Novel Furan Coupled Quinoline Diamide Hybrid Scaffolds as Potent Antitubercular Agents: Design, Synthesis and Molecular Modelling

Author(s):

Anantacharya Rajpurohit, Satyanarayan Nayak Devappa*, Lokesh Pathak, Siva Ayyanar, Chidambaram Ramaswamy Rishinaradamangalam and Praveen Shoorapani   Pages 1 - 10 ( 10 )

Abstract:


Background: A novel series of 2-[(2-{[2-(furan-2-yl) quinolin-4-yl] carbonyl} hydrazinyl) carbonyl] benzoic acid, -4-oxobut-2-enoic acid and -4-oxobutanoic acids were synthesized and screened for in vitro antitubercular activity.

Objectives: In the present investigation, we describe the synthesis and biological screening of furan C-2 quinoline coupled diamides for antitubercular activity.

Methods: The mycobacterium tuberculai testing was carried out by MABA method and molecular docking studies were done by open source molecular docking program, Autovina, using Pyrx 0.8 interface.

Results: The results revealed that the compounds inhibited the growth of H37Rv strain at concentrations as low as 1.6 to 12 µg/ml. Molecular binding of furan, quinoline and diamide (FQD) derivatives on five targets were good and these compounds fit very well within the binding domain of the target protein.

Conclusion: The synthesized FQD derivatives exhibited moderate to good inhibition activity especially compounds 5f, 5b and 8a exhibited very good inhibition activity due to the presence of three different scaffolds, such as INH, phenyl ketobutyric acid and fluoroquinolines. Hybridized molecules might have multiple mode of action / inhibit more than one tubercular target and could pave way for novel drug discovery in the field of tuberculosis.

Keywords:

Furan, Quinoline-4-carboxylic acid, carbonyl benzoic acid, antitubercular and MABA method

Affiliation:

Department of Pharmaceutical Chemistry, Kuvempu University, Post Graduate Centre, Kadur-577548, Chikkamagalur Dist., Karnataka, Department of Pharmaceutical Chemistry, Kuvempu University, Post Graduate Centre, Kadur-577548, Chikkamagalur Dist., Karnataka, Department of Pharmaceutical Chemistry, Al-Ameen College of Pharmacy, Bengaluru-560027, Karnataka, Department of Inorganic Chemistry, School of Chemistry, Madurai Kamaraj University, Palkalai Nagar, Madurai-625 021, Tamilnadu St, Department of Inorganic Chemistry, School of Chemistry, Madurai Kamaraj University, Palkalai Nagar, Madurai-625 021, Tamilnadu St, Department of Pharmaceutical Chemistry, Kuvempu University, Post Graduate Centre, Kadur-577548, Chikkamagalur Dist., Karnataka



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