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

Journal of Chemical Health Risks

مقاله 8، دوره 10، شماره 3، مهر 2020، صفحه 233-242   

نوع مقاله: Original Article

شناسه دیجیتال (DOI): 10.22034/jchr.2020.1889510.1081

نویسندگان

Oluwaseyi Ovonramwen^{* 1}؛ Bodunde Owolabi¹؛ Amowie Philip Oviawe¹؛ Abiodun Falodun²

¹Department of Chemistry, Faculty of Physical Sciences, University of Benin, Benin City, PMB 1154, Nigeria

²Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Benin, Benin City, PMB 1154, Nigeria

چکیده

A new 5-chloro-1-ethyl-2-methylimidazole-4-sulfonyl-8-quinolinoxide was synthesized starting from diethyloxalate via a four-reaction step. The new compound obtained in a simple and efficient procedure in the solvent and solvent-free with good yield and methanol served as a precipitating agent to isolate compound 2. The purity of 5-chloro-1-ethyl-2-methylimidazole-4-sulfonyl-8-quinolinoxide was tested by thin-layer chromatography (TLC) and characterized by Fourier transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (NMR), Carbon-13 (C13) nuclear magnetic resonance (¹³C-NMR), and DEPT 135 to confirm the presence and nature of CH₂. The solvent-free reaction of compound 1 was better in relation to green chemistry and better yield. The presence of solvent responsible for a color change that differentiates between compound 1 and 2 as they have the same physical data, functional group, and the chemical shift studied. The newly synthesized compound was evaluated and screened in vitro against Gram-positive (methicillin-susceptible Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, and Bacillus subtilis), Gram-negative (Pseudomonas aeruginosa, Escherichia coli, and Klebsiella pneumoniae) bacterial strains, and Candida albicans using the standard microbiological method. 5-Chloro-1-ethyl-2-methylimidazole-4-sulfonyl-8-quinolinoxide exhibited weak activities when compared with the standard drug ciprofloxacin and itraconazole used for many bacterial and fungal infections respectively.

کلیدواژه‌ها

8-hydroxyquinoline؛ Antimicrobial؛ Imidazole؛ N-heterocycle؛ Precipitating agent

مراجع

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).