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New thiopyridine complexes: design, electrochemical preparation and biological assessment

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Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Novel complexes of Ru (III), Cu (II) and Au (III) (2–4) were prepared using 6-phenyl-2-thioxo-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile (HL, 1) adopting either electrochemical or traditional chemical methods. The electrochemical method is preferred in the synthesis of the complexes than the chemical one because it affords pure products with higher yields in shorter reaction time. The novel thiopyridine complexes were characterized by elemental analyses, IR, 1H, 19F-NMR, TGA and DTA measurements. The antimicrobial activity evaluation revealed that the complex bearing copper metal 3 has nearly the same activity as the reference drug ciprofloxacin. Anti-inflammatory activity evaluation showed that complex 4 containing gold displayed anti-inflammatory activity higher than the reference drug celecoxib upon using carrageenan rat hind paw edema method.
Rocznik
Strony
20--25
Opis fizyczny
Bibliogr. 19 poz., rys., tab.
Twórcy
  • Department of Pharmaceutical Chemistry, College of Pharmacy, Taif University, P.O. Box: 888 Al-Haweiah, Zip Code 21974, Taif, Saudi Arabia
  • Department of Pharmaceutical Chemistry, College of Pharmacy, Taif University, P.O. Box: 888 Al-Haweiah, Zip Code 21974, Taif, Saudi Arabia
  • Department of Pharmaceutical Chemistry, College of Pharmacy, Taif University, P.O. Box: 888 Al-Haweiah, Zip Code 21974, Taif, Saudi Arabia
Bibliografia
  • 1. Qadri, F., Svennerholm, A.M., Faruque, A.S.G. & Sack, R.B. (2005). Enterotoxigenic Escherichia coli in developing countries: epidemiology, microbiology, clinical features, treatment, and prevention. Clin Microbiol Rev 18, 465–483.
  • 2. Dreyse, P.A., Isaacs, M.A., Iturriaga, P.E. , Villagra, D.A., Aguirre, M.J., Kubiak, C.P., Glover, S.D. & Goeltz, J.C. (2010). Electrochemical preparation of conductive fi lms of tetrapyridylporphyrins coordinated to four [Ru(5-NO2-phen)2Cl]+ groups. J. Electroanal. Chem. 648 98–104.
  • 3. Nevase, M.C., Pawar, R.D., Munjal, P.S., Dongare, A.E. & Satkar, R.S. (2018). review on various molecule activity, biological activity and chemical activity of pyridine. Europ. J. Pharmac. Med. Res., 5(11), 184–192.
  • 4. Jai, D., Nisha, B. & Suman, K. (2011). Synthesis and characterization of novel Organosilicon (IV) complexes with pyridine dicarboxylic acid and Mercapto pyridine carboxylic acid; Int. J. Res. Chem. Environ. 1, 50–56.
  • 5. Prachayasittikul, S., Treeratanapiboon, L., Ruchirawat, S. & Prachayasittikul, V. (2009). novel activities of 1-adamantylthiopyridines as antibacterials, antimalarials and anticancers. EXCLI Journal, 8, 121–129.
  • 6. Rodrigues, M.V.N., Corrêa, R.S., Vanzolini, K.L., Santos, D.S., Batista, A.A. & Cass, Q.B. (2015). Characterization and screening of tight binding inhibitors of xanthine oxidase: an on-flow assay. RSC Adv.,5, 37533–37538.
  • 7. Schmid, W.F., Zorbas-Seifried, S., John, R.O., Arion, V.B., Jakupec, M.A., Roller, A., Galanski, M., Chiorescu, I., Zorbas, H. & Keppler, B.K. (2007). The first ruthenium--based paullones: syntheses, X-ray diffraction structures, and spectroscopic and antiproliferative properties in vitro. Inorg. Chem., 46, 3645–3656.
  • 8. Lima, B.A.V., Corrêa, R.S., Graminha, A.E. , Kuznetsov, A., Ellena, J., Pavan, F.R., Leite, C.Q.F. & Batista, A.A. (2016). “Anti-Mycobacterium tuberculosis and Cytotoxicity Activities of Ruthenium(II)/ Bipyridine/Diphosphine/Pyrimidine-2-thiolate Complexes: The Role of the Non- Coordinated N-Atom” J. Braz. Chem. Soc., 27(1), 30–40,; http://dx.doi.org/10.5935/0103-5053.20150237.
  • 9. Kulkarni, A.D., Patil, S.A. & Badami, P.S. (2009). Electrochemical Properties of some Transition Metal Complexes: Synthesis, Characterization and In-vitro antimicrobial studies of Co (II), Ni(II), Cu(II), Mn(II) and Fe (III) Complexes. Int. J. Electrochem. Sci., 4, 717–729.
  • 10. Medici, S., Peana, M., Nurchi, V.M., Lachowicz, J.I., Crisponi, G. & Zoroddu, M.A. (2015). Noble metals in medicine: Latest advances. Coord. Chem. Rev., 284, 329–350.
  • 11. Scheffler, H., You, Y. & Ott, I. (2010). Comparative studies on the cytotoxicity, cellular and nuclear uptake of a series of chloro gold(I) phosphine complexes. Polyhedron, 29, 66–69.
  • 12. Yeo, C.I., Ooi, K.K. & Tiekink, E.R.T. (2018). Gold-Based Medicine: A Paradigm Shift in Anti-Cancer Therapy? Molecules, 23, 1410; DOI: 10.3390/molecules23061410.
  • 13. Jumaa, T., Chasib, M., Hamid, M.K. & Al-Haddad, R. (2014). Effect of the Electric Field on the Antibacterial Activity of Au Nanoparticles on Some Gram-positive and Gram-negative Bacteria. Nanosci. Nanotech. Res., 2(1),1–7; DOI: 10.12691 /nnr-2-1-1.
  • 14. Amin, R.R. (2010). Chemical and Electrochemical Preparation for Co(II) Complexes of Some Novel Pyridine-2-(1H)--Thione Ring Fused Cycloalkane Derivatives; Phosphorus, Sulfur, and Silicon and the Related Elements 185(3), 537–543.
  • 15. Amin, R.R. & Elgemeie, G.E.H. (2001). The direct electrochemical synthesis of Co(II), Ni(II), AND Cu(II) complexes of some pyridinethione derivatives; Synth. React. Inorg. Met.-Org. Chem., 31(3), 431–440.
  • 16. Reiss, A., Florea, S. & Rudorf, W.D. (2000). Transition metal complexes of heterocyclic ligands. Part III. Complexes of 6-aryl-3- cyano-4-trifl uormethyl-pyridine-2(1H)-thione with Co(II), Ni(II), Cu(II) and Zn(II). Polish J. Chem. 74, 589–594.
  • 17. Rodinovskaya, L.A, Sharanin, Yu.A., Litvinov, V.P., Shestopalov, A.M., Promonenkov, V.K., Zolotarev, V.K., Mortikov, V.Yu., (1985). Nitrile cyclization reactions. 8. Synthesis and transformation of 6-aryl-4-trifl uoromethyl-3-cyano-2 (1H)-pyridinethiones. Zh. Org. Khim., 21 2439.
  • 18. Reeves, D.S. & White, L.O. (1983) Principles of methods of Assaying Antibiotics in Pharmaceutical Microbiology, 3rd ed., Blackwell Scientifi c Publication, p. 140–162.
  • 19. Winter, C.A., Risley, E.A., Nuss, G.W. (1962). Carrageenin-Induced Edema in Hind Paw of the Rat as an Assay for Antiinfl ammatory Drugs. Proc. Soc. Exp. Biol. Med. 111, 544–547. https://doi.org/10.3181/00379727-111-27849.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-e41f5852-da8f-4f40-a6de-bb256aa5261b
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