European Journal of Chemistry 2021, 12(1), 37-44 | doi: https://doi.org/10.5155/eurjchem.12.1.37-44.2038 | Get rights and content

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Synthesis, antimicrobial, antioxidant, and ADMET studies of quinoline derivatives


Santhosha Sangapurada Mahantheshappa (1) orcid , Harishkumar Shivanna (2) orcid , Nayak Devappa Satyanarayan (3,*) orcid

(1) Department of Pharmaceutical Chemistry, Kuvempu University, Post Graduate Centre, Kadur-577548, Chikkamagaluru Dt. Karnataka State, India
(2) Department of Pharmaceutical Chemistry, Kuvempu University, Post Graduate Centre, Kadur-577548, Chikkamagaluru Dt. Karnataka State, India
(3) Department of Pharmaceutical Chemistry, Kuvempu University, Post Graduate Centre, Kadur-577548, Chikkamagaluru Dt. Karnataka State, India
(*) Corresponding Author

Received: 31 Aug 2020 | Revised: 10 Jan 2021 | Accepted: 15 Jan 2021 | Published: 31 Mar 2021 | Issue Date: March 2021

Abstract


The synthesis, antimicrobial, and antioxidant activities of new quinoline analogs were carried out with the aim to find possible hits/leads that can be taken up for future drug development. A series of 2-amino-N’-((2-chloroquinolin-3-yl)methylene)acetohydrazide derivatives (6a-h) have been synthesized by reacting 2-chloro-N’-((2-chloroquinolin-3-yl)methylene)acetohydrazide (5a) and N’-((6-bromo-2-chloroquinolin-3-yl)methylene)-2-chloroacetohydrazide (5b) with secondary amines (Morpholine, diethylamine, piperidine and 1-methylpiperazine). The characterization was achieved by FT-IR, 1H NMR, 13C NMR, and mass spectral analysis. The in silico ADMET studies of the synthesized molecules were analyzed for their drug likeliness and toxic properties. The ADMET study indicates that the synthesized compounds were found to be possessing reliable ADME properties and are nontoxic. The antimicrobial properties were tested against bacterial and fungal species with amoxicillin and fluconazole as standard drugs. The compounds 6a, 6c, 6e, and 6g exhibited good antibacterial potency against P. aeruginosa, and the compounds 6a, 6f, and 6h have shown good activity against E. coli with 1000 µg/mL. The compounds 6b, 6c, and 6e have moderate activity against fungal species C. oxysporum and the compounds 6c, 6e, 6f, 6g, and 6h have good activity against P. chrysogenum. Synthesized compounds were also tested for the DPPH· free radical scavenging activity to check the antioxidant potential, and the results revealed that the compounds 6a, 6b, 6c, and 6e have exhibited antioxidant potency than the remaining synthesized derivatives. The possible hits generated from biological activity could be taken for the generation of lead molecules for the drug discovery of antimicrobial and antioxidant entities from quinoline.


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Keywords


DPPH; ADMET; Acetohydrazide; Antioxidant activity; Antimicrobial activity; 2-Chloroquinoline-3-carbaldehyde

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DOI: 10.5155/eurjchem.12.1.37-44.2038

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[1]. José Maurício dos Santos Filho, Marcos Venícius Batista de Souza Castro
Synthesis, structural characterization, and antimicrobial activity of novel ferrocene-N-acyl hydrazones designed by means of molecular simplification strategy Celebrating the 100th anniversary of the birth of Professor Paulo Freire
Journal of Organometallic Chemistry  979, 122488, 2022
DOI: 10.1016/j.jorganchem.2022.122488
/


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How to cite


Mahantheshappa, S.; Shivanna, H.; Satyanarayan, N. Eur. J. Chem. 2021, 12(1), 37-44. doi:10.5155/eurjchem.12.1.37-44.2038
Mahantheshappa, S.; Shivanna, H.; Satyanarayan, N. Synthesis, antimicrobial, antioxidant, and ADMET studies of quinoline derivatives. Eur. J. Chem. 2021, 12(1), 37-44. doi:10.5155/eurjchem.12.1.37-44.2038
Mahantheshappa, S., Shivanna, H., & Satyanarayan, N. (2021). Synthesis, antimicrobial, antioxidant, and ADMET studies of quinoline derivatives. European Journal of Chemistry, 12(1), 37-44. doi:10.5155/eurjchem.12.1.37-44.2038
Mahantheshappa, Santhosha, Harishkumar Shivanna, & Nayak Devappa Satyanarayan. "Synthesis, antimicrobial, antioxidant, and ADMET studies of quinoline derivatives." European Journal of Chemistry [Online], 12.1 (2021): 37-44. Web. 28 Nov. 2022
Mahantheshappa, Santhosha, Shivanna, Harishkumar, AND Satyanarayan, Nayak. "Synthesis, antimicrobial, antioxidant, and ADMET studies of quinoline derivatives" European Journal of Chemistry [Online], Volume 12 Number 1 (31 March 2021)

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