Synthesis, Characterization and Preliminary Antimicrobial Study of Some New Ether and Thioether Derivatives of Sulfadiazine
DOI:
https://doi.org/10.31351/vol34iss1pp176-184Keywords:
Keywords: Antimicrobial Activities, Ether Derivatives, Sulfadiazine, Sulfonamide s, Spectral Studies.Abstract
A new series of ether and thioether derivatives of sulfadiazine (T1-T3 and E1-E3) have been synthesized from reaction of sulfadiazine with chloroacetyl chloride and the resultant compounds treated with different phenols and thiols. The structures of target ether and thioether derivatives were confirmed depending on their analytical and spectral data. The antimicrobial effect of the final derivatives has been tested in vitro with gram-positive and gram-negative bacteria and candida albicans. The antibacterial activity of the target compounds after three days of incubation demonstrated that all the evaluated derivatives exhibited superior antibacterial activity in comparison with amoxicillin and ciprofloxacin against all tested bacteria.
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Kawkab Y. Saour , Ridha I. Al-Bayati and Mohammed K. Hadi Synthesis of New Coumarin and 2-quinolone Derivatives with Expected Biological Activities Iraqi J Pharm Sci, 2012; 21(2): 42-50.
T. Eicher and S. Hauptmann; “The Chemistry of Heterocycles: Structure, Reactions, Synthesis, and Aplications.” Wiley-VCH 2nd ed. 2003; 159-165.
Tanzeela Q., Andleeb A , Praveen Kumar S., Ishtiaq J. and Hitoshi A. A Review on Medicinally Important Heterocyclic Compounds. The Open Medicinal Chemistry Journal. 2022; 16:1-34.
Luiza H. Martins, Jhonatas R. Barbosa, Sabrina B. da Silva, P. Wender. Microbial Degradation of Heterocycles. A Review. Journal of Science & Sustainable Engineering (JSSE) 2023;(1); 1-6
Abduljabbar TT, Hadi MK. Synthesis, Characterization and Antibacterial Evaluation of Some Coumarin Derivatives. Iraqi Journal of Pharmaceutical Sciences, 2021, 30(1):249-257.
Sahib HA, Dakhel ZA, Hadi MK. Synthesis and Preliminary Antimicrobial Activity Evaluation of New Amide Derivatives of 2-aminobenzothiazole. International Journal of Drug Delivery Technology. 2021; 11(4):1258-1261.
Ritu S., Dhara P., and Dhananjay M. Recent developments of heterocyclic chemistry in some drug discovery scaffolds synthesis. Journal of Medicinal and Chemical Sciences 2020; (3): 71-78.
Harshita S., Jaya M., and Anjali G. Indole Derivatives as Potential Anticancer Agents: A Review . J. Chil. Chem. Soc. 2020; 65 (3):
A. Fleming; On the antibacterial action of cultures of a penicillium, with special reference to their use in the isolation of B. influenza.” Br. J. Exp. Pathol. 1929 ; 10(31), 226-36.
C. H. Dash; “Penicillin allergy and the cephalosporins.” J. Antimicrob.Chemother. 1975; 1(3), 107-18.
E. Goldstein; “Norfloxacin, a fluoroquinolone antibacterial agent, Classification, mechanism of action and in vitro activity” Am. J. Med . 1987, 82(6B), 3-17.
R. Lavanya; “Sulphonamides: A Pharmaceutical Review” International Journal of Pharmaceutical Science Invention. 2017, 6(2): 1-3.
Ana T., Vesna N., Ljubiša N., and Ivan S.; Antimicrobial Sulfonamide Drug. Advanced technologies. 2017, 6(1): 58-71.
May M.J.Al-Mudhafar, Maadh Q. Abdulkadir, et.al., Synthesis and microbiological Study of New Sulfonamides, International Journal of Comprehensive Pharmacy, 2012, 3 (6),1-4.
Maadh Q. Abdulkadir, Abdulhafeedh H. Abdulwahab, May M. J. Al-Mudhafar, synthesis and evaluating the antimicrobial activities of various adducts prepared from isatins and proline, International Journal of Drug Delivery Technology, 2022;12(2):682-687.
Neu .H. C, Gootz T. D, in Medical Microbiology, S. Baron Ed., The University of Texas Medical Branch at Galveston, Galveston 1996.
Van Meter K. C., Hubert R. J, Microbiology for the Healthcare Professional, Elsevier, China. 2016; 214- 232.
Gringause A.,Mechanism of drug action., An Introduction to medicinal chemistry: how drugs act and why, Gringause A.(ed), 1st edition, New York wiley-VCH Inc. 1997; 64-7.
Kanda Y., Kawanishi Y., Oda K., Sakata T., Mihara S., Asakura K., KanemasaT., Ninomiya M., Fujimoto M., Kanoike T.: Synthesis and structure-activity relationships of potent and orally active sulfonamide ETB selective antagonists. Bioorg. & Med. Chem. 2001; 9, 897.
Stokes S. S., Albert R., Buurman Ed T., Andrews B., Shapiro A. B., GreenO. M., McKenzie A. R., Otterbein L. R.: Inhibitors of the acetyltransferase domain of N-acetylglucosamine-1-phosphate-uridylyltransferase/glucosamine-1-phosphate acetyl transferase (GlmU). Part 2: Optimization of physicalproperties leading to antibacterial aryl sulfonamides. Bioorg. & Med. Chem.Lett. 2012; 22, 7019.
Chuang Zhao, K.P. Rakesh, L. Ravidar, Wan-Yin Fang, Hua-Li Qin. Pharmaceutical and medicinal significance of sulfur (SVI)-Containing motifs for drug discovery: A critical review.
European Journal of Medicinal Chemistry, 2019: (162); 679-734
Yichao W., Guoqing F., Hongjuan C., Xu D. , Zilong T. Sulfonamide derivatives as potential anti-cancer agents and their SARs elucidation. European Journal of Medicinal Chemistry, 2021: (226): 113837
Fangcheng H., Jing S., Yanju W., Shaobo W., Jixiang C., Xiuhai G., Baoan S., and Deyu H. Synthesis, Antiviral Activity, and Mechanisms of Purine Nucleoside Derivatives Containing a Sulfonamide Moiety. J. Agric. Food Chem. 2019, 67, 31, 8459–8467.
Halah A. Sahib, Mohammed K. Hadi, Maadh Qusay Abdulkadir. Synthesis, and Antimicrobial Evaluation of New hydrazone Derivatives of (2,4-dinitrophenyl) hydrazine. Research Journal of Pharmacy and Technology. 2022; 15(4):1743-8.
Demir Yazıcı, K., Yılmaz, F.N.., Özbek Çelik, B., & Güzel Akdemir, Ö. Evaluation of some o-benzenedisulfonimido–sulfonamide derivatives as potent antimicrobial agents. Istanbul Journal of Pharmacy, 2022:52(3); 297-301.
Skocovska M, Ferencik M, Svoboda M, Svobodova Z (2021): Residues of selected sulfonamides, non-steroidal anti-inflammatory drugs and analgesics-antipyretics in surface water of the Elbe river basin (Czech Republic). Vet Med-Czech, 2021:(66); 208–218.
Arafa, F.M.; Said, H.; Osman, D.; Rezki, N.; Aouad, M.R.; Hagar, M.; Osman, M.; Elwakil, B.H.; Jaremko, M.; Tolba, M.M. Nanoformulation-Based 1,2,3-Triazole Sulfonamides for Anti-Toxoplasma In Vitro Study. Trop. Med. Infect. Dis., 2023, 8, 401.
Haq, F., Siraj, A., Ameer, M., Hamid, T., Rahman, M., Khan, S., Khan, S. and Masud, S. (2021) Comparative Review of Drugs Used in Diabetes Mellitus—New and Old. Journal of Diabetes Mellitus, 2021 :(11);115-131.
Zhuang H., Chuanchao L., Yichuang L., Miao Z., Yitong W., Zhanfang F., Chun G., Bin L., and Yang L. Design, synthesis and biological evaluation of carbohydrate-based sulphonamide derivatives as topical antiglaucoma agents through selective inhibition of carbonic anhydrase II, J Enzyme Inhib Med Chem. 2020; 35(1): 383–390.
Thomas G Medicinal Chemistry, 2nd edition. John Wiley and Sons; 2007.
Mohamed S. A. El-Gabya, Yousry A. Ammarb, Mohamed I.H. El-Qalieia, Ahmed M. Alia , Modather F. Husseina, Faraghally A. Faraghallya. Sulfonamides: Synthesis and The Recent Applications in Medicinal Chemistry. Egyptian Journal of Chemistry. 2020; 63(12): 5289 – 5327.
Mohammed Abdulameer Oleiwi and Munaf H. Zalzala. Synthesis, Molecular Docking Study and Cytotoxicity Evaluation of some Quinazolinone Derivatives as Nonclassical Antifolates and Potential Cytotoxic Agents, Iraqi J Pharm Sci. 2022, 31 ( 2 ),283-296.
Kamms ZD, Hadi MK. Synthesis, Characterization and Preliminary Antimicrobial and Anti-inflammatory Evaluation of New Ibuprofen Hydrazide Derivatives. International Journal of Drug Delivery Technology. 2023; 13(1):376-38.
Abdulraheem SS, Hadi MK. Synthesis and Characterization of New Coumarin Derivatives as Possible Antimicrobial Agents. International Journal of Drug Delivery Technology. 2021; 11(4):1484-1490.
Ohikhena, F. U., Wintola, O. A., & Afolayan, A. J. Evaluation of the antibacterial and antifungal properties of Phragmanthera capitata (Sprengel) Balle (Loranthaceae), a mistletoe growing on rubber tree, using the dilution techniques. The Scientific World Journal, 2017:(2017);1-8
Lewus, C. B., Kaiser, A. L. A. N., & Montville, T. J. Inhibition of food-borne bacterial pathogens by bacteriocins from lactic acid bacteria isolated from meat. Applied and Environmental Microbiology, 1991: 57(6), 1683-1688.
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