European Journal of Chemistry 2022, 13(1), 109-116 | doi: https://doi.org/10.5155/eurjchem.13.1.109-116.2216 | Get rights and content

Issue cover




Crossmark

  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Synthesis, antimicrobial, and antitubercular evaluation of new Schiff bases with in silico ADMET and molecular docking studies


Sakshith Raghavendra Prasad (1) orcid , Nayak Devappa Satyanarayan (2,*) orcid , Avarse Satish Kumar Shetty (3) orcid , Basaiah Thippeswamy (4) orcid

(1) Department of Pharmaceutical Chemistry, National College of Pharmacy, Balaraj Urs Road, Shivamogga-577201, Karnataka, India
(2) Department of Pharmaceutical Chemistry, Kuvempu University, Post-Graduate Centre, Kadur-577548, Karnataka, India
(3) Department of Pharmaceutical Chemistry, National College of Pharmacy, Balaraj Urs Road, Shivamogga-577201, Karnataka, India
(4) Department of Post-Graduation Studies and Research in Microbiology, Jnanasahyadri, Kuvempu University, Shankaraghatta-577451, India
(*) Corresponding Author

Received: 18 Nov 2021 | Revised: 31 Dec 2021 | Accepted: 03 Jan 2022 | Published: 31 Mar 2022 | Issue Date: March 2022

Abstract


Schiff bases are a proven moiety in antitubercular drug discovery and the antitubercular drug development. Drug discovery is a never-ending process due to evolving drug resistance by the bacteria, as a result, there is a need of developing new antitubercular drugs. In this continuous process of antitubercular drug discovery, new series of Schiff bases are synthesized using quinoline carbohydrazide upon coupling with different aldehydes in ethanolic media through multistep synthesis. These synthesized compounds were purified and characterized by different spectroscopic techniques. The molecules were in vitro screened for antifungal and antibacterial potential by Agar well diffusion assay, antitubercular activity by using microplate Alamar blue assay, and an attempt has been made to study the in-silico relationship between new Schiff base derivatives 4a-f and the crystal structure of M. tuberculosis (5V3Y) protein by molecular docking studies. Synthesized compounds 4a-f show good interaction with the crystal structure of M. tuberculosis protein (5V3Y) and fulfill ADMET characteristics in silico experiments. Among the compounds tested, compound 4d was found to be active against bacteria and fungi. Compound 4b was found to be sensitive against M. tuberculosis at 50 µg/mL concentration.


Announcements


Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.

1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization between July 1, 2022 and August 15, 2022 (Voucher code: SINGLE2022).

2. Young writers will not be charged for the article processing fee between July 1, 2022 and August 15, 2022 (Voucher code: YOUNG2022).

3. The article processing fee will not be charged from the articles containing a part of the PhD thesis between July 1, 2022 and August 15, 2022 (Voucher code: PhD2022).

Editor-in-Chief

European Journal of Chemistry

Keywords


5V3Y; MABA; In silico; Antifungal activity; Multistep synthesis; Antibacterial activity

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.13.1.109-116.2216

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 251 times | icon graph PDF Article downloaded 72 times

Funding information


Kuvempu University, Shankaraghatta-577451, India.

References


[1]. Alsayed, S. S. R.; Lun, S.; Bailey, A. W.; Suri, A.; Huang, C.-C.; Mocerino, M.; Payne, A.; Sredni, S. T.; Bishai, W. R.; Gunosewoyo, H. Design, synthesis and evaluation of novel indole-2-carboxamides for growth inhibition of Mycobacterium tuberculosis and paediatric brain tumour cells. RSC Adv. 2021, 11, 15497-15511.
https://doi.org/10.1039/D0RA10728J

[2]. Dheda, K.; Gumbo, T.; Maartens, G.; Dooley, K. E.; McNerney, R.; Murray, M.; Furin, J.; Nardell, E. A.; London, L.; Lessem, E.; Theron, G.; van Helden, P.; Niemann, S.; Merker, M.; Dowdy, D.; Van Rie, A.; Siu, G. K. H.; Pasipanodya, J. G.; Rodrigues, C.; Clark, T. G.; Sirgel, F. A.; Esmail, A.; Lin, H.-H.; Atre, S. R.; Schaaf, H. S.; Chang, K. C.; Lange, C.; Nahid, P.; Udwadia, Z. F.; Horsburgh, C. R., Jr; Churchyard, G. J.; Menzies, D.; Hesseling, A. C.; Nuermberger, E.; McIlleron, H.; Fennelly, K. P.; Goemaere, E.; Jaramillo, E.; Low, M.; Jara, C. M.; Padayatchi, N.; Warren, R. M. The epidemiology, pathogenesis, transmission, diagnosis, and management of multidrug-resistant, extensively drug-resistant, and incurable tuberculosis. Lancet Respir. Med. 2017, 5 (4), 291-360.
https://doi.org/10.1016/S2213-2600(17)30079-6

[3]. Schiff, H. Mittheilungen aus dem Universitätslaboratorium in Pisa: Eine neue Reihe organischer Basen. Ann. Chem. Pharm. 1864, 131, 118-119.
https://doi.org/10.1002/jlac.18641310113

[4]. Bharti, S. K.; Nath, G.; Tilak, R.; Singh, S. K. Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2,4-disubstituted thiazole ring. Eur. J. Med. Chem. 2010, 45, 651-660.
https://doi.org/10.1016/j.ejmech.2009.11.008

[5]. Cordeiro, R.; Kachroo, M. Synthesis and biological evaluation of anti-tubercular activity of Schiff bases of 2-Amino thiazoles. Bioorg. Med. Chem. Lett. 2020, 30, 127655.
https://doi.org/10.1016/j.bmcl.2020.127655

[6]. Guo, S.; Song, Y.; Huang, Q.; Yuan, H.; Wan, B.; Wang, Y.; He, R.; Beconi, M. G.; Franzblau, S. G.; Kozikowski, A. P. Identification, synthesis, and pharmacological evaluation of tetrahydroindazole based ligands as novel antituberculosis agents. J. Med. Chem. 2010, 53, 649-659.
https://doi.org/10.1021/jm901235p

[7]. Santoshkumar, S.; Satyanarayana, N. D.; Anantacharya, R.; Sameer, P. Synthesis, antimicrobial, antitubercular and cheminformatic studies of 2-(1-benzofuran-2-yl)-N'-[(3Z)-2-oxo-1, 2-dihydro-3H-indol-3-ylidene] quinoline-4-carbohydrazide and its derivatives. Int. J. Pharm. Pharm. Sci. 2017, 9, 260-267.
https://doi.org/10.22159/ijpps.2017v9i5.17564

[8]. Kumar, S.; Bawa, S.; Gupta, H. Biological activities of quinoline derivatives. Mini Rev. Med. Chem. 2009, 9, 1648-1654.
https://doi.org/10.2174/138955709791012247

[9]. Tseng, C.-H.; Tung, C.-W.; Wu, C.-H.; Tzeng, C.-C.; Chen, Y.-H.; Hwang, T.-L.; Chen, Y.-L. Discovery of indeno[1,2-c]quinoline derivatives as potent dual antituberculosis and anti-inflammatory agents. Molecules 2017, 22, 1001.
https://doi.org/10.3390/molecules22061001

[10]. Gaber, A.; Alsanie, W. F.; Alhomrani, M.; Alamri, A. S.; El-Deen, I. M.; Refat, M. S. Synthesis of 1-[(Aryl)(3-amino-5-oxopyrazolidin-4-ylidene) methyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic Acid Derivatives and Their Breast Anticancer Activity. Crystals (Basel) 2021, 11, 571.
https://doi.org/10.3390/cryst11050571

[11]. Salve, P. S.; Alegaon, S. G.; Sriram, D. Three-component, one-pot synthesis of anthranilamide Schiff bases bearing 4-aminoquinoline moiety as Mycobacterium tuberculosis gyrase inhibitors. Bioorg. Med. Chem. Lett. 2017, 27, 1859-1866.
https://doi.org/10.1016/j.bmcl.2017.02.031

[12]. Hunter, A. D. ACD/ChemSketch 1.0 (freeware); ACD/ChemSketch 2.0 and its Tautomers, Dictionary, and 3D Plug-ins; ACD/HNMR 2.0; ACD/CNMR 2.0. J. Chem. Educ. 1997, 74, 905.
https://doi.org/10.1021/ed074p905

[13]. Pettersen, E. F.; Goddard, T. D.; Huang, C. C.; Couch, G. S.; Greenblatt, D. M.; Meng, E. C.; Ferrin, T. E. UCSF Chimera--a visualization system for exploratory research and analysis. J. Comput. Chem. 2004, 25, 1605-1612.
https://doi.org/10.1002/jcc.20084

[14]. Dallakyan, S.; Olson, A. J. Small-molecule library screening by docking with PyRx. Methods Mol. Biol. 2015, 1263, 243-250.
https://doi.org/10.1007/978-1-4939-2269-7_19

[15]. Kemmish, H.; Fasnacht, M.; Yan, L. Fully automated antibody structure prediction using BIOVIA tools: Validation study. PLoS One 2017, 12, e0177923.
https://doi.org/10.1371/journal.pone.0177923

[16]. Harishkumar, S.; Satyanarayan, N. D.; Santhosha, S. M. Antiproliferative and in silico admet study of new 4-(piperidin-1-ylmethyl)-2- (thiophen-2-yl) quinoline analogues. Asian J. Pharm. Clin. Res. 2018, 11, 306-313.
https://doi.org/10.22159/ajpcr.2018.v11i4.24147

[17]. Aggarwal, A.; Parai, M. K.; Shetty, N.; Wallis, D.; Woolhiser, L.; Hastings, C.; Dutta, N. K.; Galaviz, S.; Dhakal, R. C.; Shrestha, R.; Wakabayashi, S.; Walpole, C.; Matthews, D.; Floyd, D.; Scullion, P.; Riley, J.; Epemolu, O.; Norval, S.; Snavely, T.; Robertson, G. T.; Rubin, E. J.; Ioerger, T. R.; Sirgel, F. A.; van der Merwe, R.; van Helden, P. D.; Keller, P.; Böttger, E. C.; Karakousis, P. C.; Lenaerts, A. J.; Sacchettini, J. C. Development of a Novel Lead that Targets M. tuberculosis Polyketide Synthase 13. Cell 2017, 170, 249-259.e25.
https://doi.org/10.1016/j.cell.2017.06.025

[18]. PyMOL. The PyMOL Molecular Graphics System, Version 2.0 Schrödinger, LLC. http://www.pymol.org/pymol (accessed January 2, 2022).

[19]. Gaillard, T. Evaluation of AutoDock and AutoDock Vina on the CASF-2013 benchmark. J. Chem. Inf. Model. 2018, 58, 1697-1706.
https://doi.org/10.1021/acs.jcim.8b00312

[20]. Cheng, F.; Li, W.; Zhou, Y.; Shen, J.; Wu, Z.; Liu, G.; Lee, P. W.; Tang, Y. admetSAR: a comprehensive source and free tool for assessment of chemical ADMET properties. J. Chem. Inf. Model. 2012, 52, 3099-3105.
https://doi.org/10.1021/ci300367a

[21]. Lin, J. H.; Yamazaki, M. Role of P-glycoprotein in pharmacokinetics: clinical implications: Clinical implications. Clin. Pharmacokinet. 2003, 42, 59-98.
https://doi.org/10.2165/00003088-200342010-00003

[22]. Arthington-Skaggs, B. A.; Motley, M.; Warnock, D. W.; Morrison, C. J. Comparative evaluation of PASCO and national committee for clinical laboratory standards M27-A broth microdilution methods for antifungal drug susceptibility testing of yeasts. J. Clin. Microbiol. 2000, 38, 2254-2260.
https://doi.org/10.1128/JCM.38.6.2254-2260.2000

[23]. Rocha, L.; Marston, A.; Potterat, O.; Kaplan, M. A.; Stoeckli-Evans, H.; Hostettmann, K. Antibacterial phloroglucinols and flavonoids from Hypericum brasiliense. Phytochemistry 1995, 40, 1447-1452.
https://doi.org/10.1016/0031-9422(95)00507-4

[24]. MacLowry, J. D.; Jaqua, M. J.; Selepak, S. T. Detailed methodology and implementation of a semiautomated serial dilution microtechnique for antimicrobial susceptibility testing. Appl. Microbiol. 1970, 20, 46-53.
https://doi.org/10.1128/am.20.1.46-53.1970

[25]. Portillo, A.; Vila, R.; Freixa, B.; Adzet, T.; Cañigueral, S. Antifungal activity of Paraguayan plants used in traditional medicine. J. Ethnopharmacol. 2001, 76, 93-98.
https://doi.org/10.1016/S0378-8741(01)00214-8

[26]. Maria, C. S. L.; Marcus, V. N.; de Souza. Alessandra, C. P.; Marcelle de, L. F.; Raoni S. B. G.; Thais Cristina, M. N.; Monica, A. P. Evaluation of anti-tubercular activity of nicotinic and isoniazid analogues. ARKIVOC 2007, 2007, 181-191.
https://doi.org/10.3998/ark.5550190.0008.f18

[27]. Lipinski, C. A. Lead- and drug-like compounds: the rule-of-five revolution. Drug Discov. Today Technol. 2004, 1, 337-341.
https://doi.org/10.1016/j.ddtec.2004.11.007


How to cite


Prasad, S.; Satyanarayan, N.; Shetty, A.; Thippeswamy, B. Eur. J. Chem. 2022, 13(1), 109-116. doi:10.5155/eurjchem.13.1.109-116.2216
Prasad, S.; Satyanarayan, N.; Shetty, A.; Thippeswamy, B. Synthesis, antimicrobial, and antitubercular evaluation of new Schiff bases with in silico ADMET and molecular docking studies. Eur. J. Chem. 2022, 13(1), 109-116. doi:10.5155/eurjchem.13.1.109-116.2216
Prasad, S., Satyanarayan, N., Shetty, A., & Thippeswamy, B. (2022). Synthesis, antimicrobial, and antitubercular evaluation of new Schiff bases with in silico ADMET and molecular docking studies. European Journal of Chemistry, 13(1), 109-116. doi:10.5155/eurjchem.13.1.109-116.2216
Prasad, Sakshith, Nayak Devappa Satyanarayan, Avarse Satish Kumar Shetty, & Basaiah Thippeswamy. "Synthesis, antimicrobial, and antitubercular evaluation of new Schiff bases with in silico ADMET and molecular docking studies." European Journal of Chemistry [Online], 13.1 (2022): 109-116. Web. 12 Aug. 2022
Prasad, Sakshith, Satyanarayan, Nayak, Shetty, Avarse, AND Thippeswamy, Basaiah. "Synthesis, antimicrobial, and antitubercular evaluation of new Schiff bases with in silico ADMET and molecular docking studies" European Journal of Chemistry [Online], Volume 13 Number 1 (31 March 2022)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.13.1.109-116.2216

CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | scibey | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2022, 13(1), 109-116 | doi: https://doi.org/10.5155/eurjchem.13.1.109-116.2216 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c) 2022 Authors

Creative Commons License
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).



© Copyright 2010 - 2022  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2022 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.