Synthesis, Molecular Modeling and In vitro Antimicrobial Evaluation of New Quinolin-4yl-hydrazones

DOI:

https://doi.org/10.37285/ijpsn.2020.13.1.4

Authors

  • Achaiah Garlapati
  • Shivani Pola

Abstract



Antibacterial drugs are the mainstay for the treatment of serious bacterial infections, such as tuberculosis. Twenty new quinolinyl hydrazones were prepared and evaluated for antimicrobial activity against two Gram-positive and two Gram-negative bacteria and antimycobacterial activity against Mycobacterium tuberculosis (H37Rv). In view of the amphiphilic nature of quinalinyl hydrazones, and their ability to penetrate the bacterial cell wall, we sought to synthesize and evaluate them for antimicrobial activity. The new quinolinyl hydrazones with 7-chloro-substitution on quinoline ring and various aryl and heterocyclic substituted hydrazone at 4th position of quinoline ring were prepared and evaluated for antimicrobial activity. Among the series, the two com-pounds 4e, 4k with 3-chromone and 5-methylthiphene heterocyclic systems exhibited significant antitubercular activity with MIC of 0.81 and 0.90 µg/ml respectively and the potency is comparable to that of the standard, isoniazid with MIC of 0.78 µg/ml. In antimicrobial screen-ing, compounds 4h & 4l with 3-pyridyl and 2-furyl rings on hydrazone nitrogen exhibited significant activity against the two Gram+ve and Gram-ve bacterial strains with MIC values in the range of 16-24 µg/ml. Based on these results, the lead compounds appear to possess the potential antibacterial potential against Mycobacerium and other bacteria.   

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Keywords:

Antibacterial;, Antibiotics, Hydrazones;, Tuberculosis, Quinoline, MIC

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Published

2020-01-31

How to Cite

1.
Garlapati A, Pola S. Synthesis, Molecular Modeling and In vitro Antimicrobial Evaluation of New Quinolin-4yl-hydrazones. Scopus Indexed [Internet]. 2020 Jan. 31 [cited 2024 Dec. 11];13(1):4759-65. Available from: https://www.ijpsnonline.com/index.php/ijpsn/article/view/250

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Section

Research Articles

References

Asif M (2016). A Brief Overview on Recent Advances in the Development of Anti-Tubercular compounds containing different heterocyclic ring Systems. Applied Microbiology. 2(4): 1-14.
Auri RD, Pedro HC, Gouvea SD, Geonir MS and Lund R (2011). 7-Chloroquinolin-4-yl arylhydrazone Derivatives: Synthesis and Antifungal Activity. The Scientific World Journal. 11: 1489-1495.
Bingu M, Tan LO, Gardner CR, Sutton SK, Arndt GM, Marshall GM, Cheung B, Kumar N, and Black D (2016). Synthesis, characterization and anti-Cancer activity of hydrazide derivatives incorporating a quinoline moiety. Molecules 21: 915-934.
Coa J, Wilson CG, Wilson M, Carda M, Ospina V, Muñoz JA, Vélez ID and Robledo SM (2017). Synthesis, leishmanicidal, trypanocidal and cytotoxic activities of quinoline-chalcone and quinoline-chromone hybrids. Medicinal Chemistry Research. 26: 1405-1414.
Coa J, Wilson CL, Wilson CG, Carda M, Ospina V, Muñoz JA, Vélez ID and Robledo SM (2015). Synthesis, Leishmanicidal, Trypanocidal and Cytotoxic Activity of quinoline-hydrazone Hybrids. European Journal of Medicinal Chemistry. 104: 1-38.
Coa J, Galeano WC and Restrepo A (2018). Fe3+ chelating quinoline–hydrazone hybrids with proven cytotoxicity, leishmanicidal and trypanocidal activities, Physical Chemistry Chemical Physics. 20 (28): 5385-5394.
Fahm MRG and Kurinawan Y (2019). Heterocyclic hydrazone derivatives as potential antitubercular agents against Mycobacterium tuberculosis. Journal of Experimental and Clinical Microbiology. 2(2):16-21.
Ferreira MDL (2010). Synthesis and antitubercular activity of heteroaromatic isonicotinoyl and 7-chloro-4-quinolinyl hydrazone derivatives. The Scientific World Journal. 10:1347-1355.
Jain R, Patel SR, Gangwal R and Sanghawar AT (2014). Synthesis, biological evaluation and 3D-QSAR study of hydrazide, semicarbazide and thiosemicarbazide derivatives of 4-(adamantan-1-yl) quinoline as anti-tuberculosis agents. European Journal of Medicinal Chemistry. 85: 255-267
Maddela S and Makula A (2016). Design, Synthesis and Docking study of some novel isatin- quinoline hybrids as Potential antitubercular Agents. Anti-Infective Agents. 14:53-62.
Maddela S, Makula A, Gopal MV and Maddela R (2014). Design and synthesis of novel quinoline 3-carbohydrazone derivatives for their antimicrobial and antioxidant activity. International Journal of Pharmceutical Sciences. 6(6): 254-258.
Mandewale MC, Thorat B, Nivid Y, Jadhav R, Nagarsekar A, and Yamgar R (2018). A review on quinoline hydrazone derivatives as a new class of potent antitubercular and anticancer agents, Beni-Suef Journal of Basic and Applied sciences. 1-8.
Metwally KA, Abdel LM, Lashine ESM, Husseiny MI and Badawy RH (2006). Hydrazones of 2-aryl-quinoline-4-carboxylic acid hydrazides. Synthesis and preliminary evaluation as antimicrobial agents. Bioorganic and Medicinal Chemistry. 14: 8675-8682.
Rao AR, Malothu N, Shankar U, Malathi M and Kumar SJ (2015). Synthesis, in vitro anti mycobacterial evaluation and docking studies of some new 5, 6, 7, 8-tetrahydropyrido [4’,3’:4,5] thieno [2,3d] pyrimidin4(3H) one Schiff bases. Bioorganic and Medicinal Chemistry Letters. 22: 4943-4946.
Singh S, Kaur V, Mangla G and Gupta MK (2015). Quinoline and quinolones: promising scaffolds for future antimycobacterial agents. Journal of Enzyme Inhibition and Medicinal Chemistry. 30(3): 492-504.
Upadhyaya RS, Kulkarni GM, Vasireddy NR, Vandavasi JK, Dixit SS, Sharma V and Chattopadhyaya J (2009). Design, synthesis, biological evaluation and molecular modelling studies of novel quinoline derivatives against Mycobacterium tuberculosis. Bioorganic and Medicinal Chemistry. 17: 283.
Venkatesham R, Alla M, Ummani R and Kotipalli SS (2013). Design, diversity-oriented synthesis and structure activity relationship studies of quinolinyl heterocycles as antimycobacterial agents. Euopean Journal of Medicinal Chemistry. 70: 536-547.
Xu H, Yu X, Feng G, and Huang J (2016). Evaluation of some quinoline-based hydrazone derivatives as insecticidal agents. RSC Advances. 6: 30405-30411.