Synthesis and Antimicrobial Activity of 5-chloro-1-ethyl-2-methylimidazole-4-sulfonyl-8-Quinolinoxide

Subject Areas : Journal of Chemical Health Risks

Oluwaseyi  Ovonramwen ¹ (Department of Chemistry, Faculty of Physical Sciences, University of Benin, Benin City, PMB 1154, Nigeria)
Bodunde  Owolabi ² (Department of Chemistry, Faculty of Physical Sciences, University of Benin, Benin City, PMB 1154, Nigeria)
Amowie  Philip Oviawe ³ (Department of Chemistry, Faculty of Physical Sciences, University of Benin, Benin City, PMB 1154, Nigeria)
Abiodun  Falodun ⁴ (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Benin, Benin City, PMB 1154, Nigeria)

Received: 2019-12-30 Accepted : 2020-07-11 Published : 2020-07-15

Keywords:

References:

1. El Faydy M., Djassinra T., Haida S., Rbaa M., Ounine K., Kribii A., Lakhrissi B., 2017. Synthesis and investigation of antibacterial and antioxidants properties of some new 5-substituted-8-hydroxyquinoline derivatives. J. M. E. S. 8(11), 3855-3863.

2. Srisung S., Suksrichavalit T., Prachayasittikul S., Ruchirawat S., Prachayasittikul V., 2013. Antimicrobial Activity of 8-Hydroxyquinoline and Transition Metal Complexes. International Journal of Pharmacology. 9, 170-175.

3. Cherdtrakulkiat R., Boonpangrak S., Sinthupoom N., Prachayasittikul S., Ruchirawatd S., Prachayasittikul V., 2016. Derivatives (halogen, nitro, and amino) of 8-hydroxyquinoline with highly potent antimicrobial and antioxidant activities. Biochemistry and Biophysics Reports. 6, 135-141. https :// doi. Org /10. 1016/j.bbrep. 2016.03.014.

4. Shah P., Abadi L.F., Gaikwad S., Chaudhari D., Kushwah V., Jain S., Bhutani K.K., Kulkarni S., Singh Inder P., 2018. Synthesis and Biological Evaluation of 8‐Hydroxyquinoline‐hydrazones for Anti‐HIV‐1 and Anticancer Potential. Chemistry select 3. 38, 10727-10731. https://doi.org/10.1002/slct.201802283.

5. Krawczyk M., Pastuch-Gawolek G., Mrozek-Wilczkiewicz A., Kuczak M., Skonieczna M., Musiol R., 2019. Synthesis of 8-hydroxyquinoline glycoconjugates and preliminary assay of their β1,4-GalT inhibitory and anti-cancer properties. Bioorg Chem. 84, 326-338. https://doi.org/10.1016/j.bioorg.2018.11.047.

6. Krawczyk M., Pastuch-Gawolek G., Pluta A., Erfurt K., Domiński A., Kurcok P., 2019. 8-Hydroxyquinoline Glycoconjugates: Modifications in the Linker Structure and Their Effect on the Cytotoxicity of the Obtained Compounds. Molecules. 24(22), 4181-4220. https://doi.org/10.3390/molecules24224181.

7. Gümüş A., Okumuş V., Gümüş S., 2018. Synthesis of 2-substituted 8-propargyloxyquinoline derivatives and determination of their antioxidant, antibacterial, and DNA binding activities. Turk  J Chem.42, 1358 – 1369© TÜBİTAK doi:10.3906/kim-1805-77.

8. Scalese G., Machado I., Correia I., Pessoa J.C., Bilbao L., Pérez-Diaz L., Gambino D., 2019. Exploring oxidovanadium (iv) homoleptic complexes with 8-hydroxyquinoline derivatives as prospective antitrypanosomal agents. New J Chem. 43, 17756-17773. DOI: 10.1039/C9NJ02589H.

9. Velthuisen E.J., Johns B.A., Temelkoff D.P., Brown K.W., Danehower S.C., 2016. The design of 8-hydroxyquinoline tetracyclic lactams as HIV-1 integrase strand transfer inhibitors. Eur J Med Chem. 117, 99-112. doi: 10.1016/j.ejmech.2016.03.038.

10. Yin X.D., Sun Y., Lawoe R.K., Yang G.Z., Liu Y.Q., Shang X.F., Liu H., Yang Y.D., Zhu J.K., Huang X.L., 2019.  Synthesis and anti-phytopathogenic activity of 8-hydroxyquinoline derivatives. R S C Adv. 9, 30087-30099.

11. Aleksandrova E.V., Kravchenko A.N., Kochergin P.M., 2011. Methods for the synthesis of Haloimidazoles (Review). Chemistry of Heterocyclic Compounds. 46(11), 1295-1317.

12. World Health Organization., 2017. WHO Model List of Essential Medicines (20^th List). 13, 18, 49.

13. Trout G.E., 1966. Imidazoles and imidazole metabolism. Thesis submitted to the University of the Witwatersrand, Johannesburg, South Africa. pp. 60-64.

14. Ovonramwen O.B., Owolabi B.J., Oviawe A.P., 2019. Synthesis of (2Z)-4,6-Diphenyl-N-((2-(Piperidin-1yl)Ethyl]-2H-1,3-Thiazin-2-Imino Hydrochloride  and its Antimicrobial Activities. Asian Journal of Physical and Chemical Sciences. 7(3), 1-9.

15. Babaiwa U.F., Erharuyi O., Falodun A., Akerele J.O., 2017. Antimicrobial activity of ethyl acetate extract of Citrullus lanatus seeds, Tropical Journal of Pharmaceutical Research. 16(7), 1631-1636.

16. Pretsch E., B¨uhlmann P., Badertscher M., 2009. Structure Determination of Organic Compounds. Springer-Verlag Berlin Heidelberg Fourth Ed. pp. 269-324. ISBN 978-3-540-93809-5.

17. Sigma-Aldrich (330248 Aldrich). (Accessed December 2019). 5-Chloro-1-ethyl-2-methylimidazole. Specification Sheet FTNMR (PDF).