European Journal of Chemistry 2017, 8(4), 422-429 | doi: https://doi.org/10.5155/eurjchem.8.4.422-429.1651 | Get rights and content

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Synthesis, single crystal X-ray diffraction, Hirshfeld surface and biological activity of quinolone derivatives


Huma Bano (1) , Sarah Shafi (2) , Hina Siddiqui (3) , Muhammad Iqbal Choudhary (4) , Sammer Yousuf (5,*)

(1) H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan
(2) H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan
(3) H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan
(4) Department of Biochemistry, Faculty of Science, King Abdulaziz Universisty, Jeddah-21412, Kingdom of Saudi Arabia
(5) H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan
(*) Corresponding Author

Received: 11 Sep 2017 | Revised: 19 Oct 2017 | Accepted: 20 Oct 2017 | Published: 31 Dec 2017 | Issue Date: December 2017

Abstract


Two new quinolone derivatives, 5-nitroquinolin-8-yl-3-bromobenzoate (1) and 5-nitroquinolin-8-yl-3-chlorobenzoate (2), were synthesized and their structures were elucidated using X-ray diffraction techniques. Both compounds crystallized in P21/n (monoclinic) space group having four independent molecules in asymmetric unit. The dihedral angle between benzene and planner quinoline rings in compounds 1 and 2 were found to be 117.7(2) and 117.4(2)ᵒ, respectively. No intermolecular hydrogen bonding was observed in compound 1. However, C-H···O intermolecular interaction was found to connect the molecules in crystal lattice of compound 2. Hirshfeld surfaces analysis was performed to evaluate the directions, and strength of interactions of molecules of compounds and 1 and 2 with neighbouring molecules, and the major contribution in the crystal packing was due to O-H (1, 24.6% and 2, 25.1%) interactions. The synthesized quinoline derivatives were found as potent anti-bacterial agents against E. coli reference (ATCC25922 and ATCC 35218) and multi-drug resistant strains (M2 and M3) with 91.42 to 94.72% inhibition. Both compounds 1 and 2 showed weak antileishmanial activity against L. Major promastigotes in vitro with IC50 values 73.2±3.1 and 72.2±2.3 mg/mL, respectively, and also found as cytotoxic in nature against 3T3 fibroblast cell line.


Keywords


Multi-drug resistance; Quinoline derivatives; Anti-bacterial activity; X-ray crystallography; Antileishmanial activity; Hirshfeld surface analysis

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DOI: 10.5155/eurjchem.8.4.422-429.1651

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Funding information


The Higher Education Commission of Pakistan for the financial support through research fundings 20-2830/R&D/HEC and 20-2216/R&D/ HEC.

References


[1]. Solomon, R.; Lee, H. Curr. Med. Chem. 2011, 18(10), 1488-1508.
https://doi.org/10.2174/092986711795328382

[2]. LaMontagne, M. P.; Markovac, A. M. S.; Sami, K. M. J. Med. Chem. 1982, 25, 964-968.
https://doi.org/10.1021/jm00350a016

[3]. Denny, W. A.; Wilson, W. R.; Ware, D. C.; Atwell, G. J.; Milbank, J. B.; Stevenson, R. J. US Patent 7064117B2, 2006.

[4]. Muruganantham, N.; Sivakumar, R.; Anbalagan, N.; Gunasekaran, V.; Leonard; J. T. Biol. Pharm. Bull. 2004, 27, 1683-1687.
https://doi.org/10.1248/bpb.27.1683

[5]. Keri, R. S.; Patil, S. A. Biomed. Pharmacother. 2014, 68(8), 1161-1175.
https://doi.org/10.1016/j.biopha.2014.10.007

[6]. Leatham, P. A.; Bird, H. A.; Wright, V.; Seymour, D.; Gordon A. Eur. J. Rheumatol. Inflamm. 1983, 6, 209-211.

[7]. Wilson, W. D.; Zhao, M.; Patterson, S. E.; Wydra, R. L.; Janda, L.; Strekowski, L. Med. Chem. Res. 1992, 2, 102-110.

[8]. Strekowski, L.; Mokrosz, J. L.; Honkan, V. A.; Czarny, A.; Cegla, M. T.; Patterson, S. E. J. Med. Chem. 1991, 34, 1739-1746.
https://doi.org/10.1021/jm00109a031

[9]. Bruker (2009). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

[10]. Sheldrick, G. M. Acta Cryst. A 2008, 64, 112-122.
https://doi.org/10.1107/S0108767307043930

[11]. Spek, A. L. Acta Cryst. D 2009, 65, 148-155.
https://doi.org/10.1107/S090744490804362X

[12]. Spek, A. L. J. Appl. Cryst. 2003, 36, 7-13.
https://doi.org/10.1107/S0021889802022112

[13]. Wolff, S.; Grimwood, D.; McKinnon, J.; Turner, M.; Jayatilaka, D.; Spackman, M., Crystal Explorer, The University of Western Australia Perth, Australia, 2012.

[14]. Oxford Diffraction, CrysAlis PRO and CrysAlis RED, Oxford Diffraction Ltd., Abingdon, Oxfordshire, England, 2010.

[15]. Moreno-Fuquen, R.; Castillo, J. C.; Abonia, R.; Portilla, J.; Henao, J. A. Molbank 2017, 1, m934-m934.
https://doi.org/10.3390/M934

[16]. Choudhary, M. I.; Yousuf, S.; Ahmed, S.; Samreen; Yasmeen, K.; Atta-ur-Rahman, Chem. Biodivers. 2005, 2(9), 1164-1173.
https://doi.org/10.1002/cbdv.200590086

[17]. Siddiqui, H.; Tasneem, S.; Farooq, S.; Sami, A. Atta-Ur-Rahman; Choudhary, M. I., Med. Chem. 2017, 13(5), 465-476.

[18]. Oladimeji, A. O; Oladosu, I. A.; Ali, M. S.; Khan, S. A.; Yousuf, S. J. Biol. Activ. Prod. Nat. (TBAP) 2016, 6(5,6), 365-372.


Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Bano, H.; Shafi, S.; Siddiqui, H.; Choudhary, M.; Yousuf, S. Eur. J. Chem. 2017, 8(4), 422-429. doi:10.5155/eurjchem.8.4.422-429.1651
Bano, H.; Shafi, S.; Siddiqui, H.; Choudhary, M.; Yousuf, S. Synthesis, single crystal X-ray diffraction, Hirshfeld surface and biological activity of quinolone derivatives. Eur. J. Chem. 2017, 8(4), 422-429. doi:10.5155/eurjchem.8.4.422-429.1651
Bano, H., Shafi, S., Siddiqui, H., Choudhary, M., & Yousuf, S. (2017). Synthesis, single crystal X-ray diffraction, Hirshfeld surface and biological activity of quinolone derivatives. European Journal of Chemistry, 8(4), 422-429. doi:10.5155/eurjchem.8.4.422-429.1651
Bano, Huma, Sarah Shafi, Hina Siddiqui, Muhammad Iqbal Choudhary, & Sammer Yousuf. "Synthesis, single crystal X-ray diffraction, Hirshfeld surface and biological activity of quinolone derivatives." European Journal of Chemistry [Online], 8.4 (2017): 422-429. Web. 27 Oct. 2021
Bano, Huma, Shafi, Sarah, Siddiqui, Hina, Choudhary, Muhammad, AND Yousuf, Sammer. "Synthesis, single crystal X-ray diffraction, Hirshfeld surface and biological activity of quinolone derivatives" European Journal of Chemistry [Online], Volume 8 Number 4 (31 December 2017)

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