Synthesis of Some New 1-Acylthiosemicarbazides and 1,2,4-Triazol-5-Thiones, and Their Analgesic and Anti-Inflammatory Activities

We synthesized new 1-[3-(2-oxobenzothiazolin-3-yl)propanoyl]-4- substituted-thiosemicarbazides and their corresponding cyclized 3-[2-(2-oxobenzothiazoline-3-yl)ethyl]-4-substituted-1,2,4-triazol-5-thione ana-logs in which position 4 of the triazole ring was substituted by cyclohexyl, methyl, allyl, phenyl, p-methylphenyl, p-methoxyphenyl, p-chlorophenyl, p-nitrophenyl, benzyl, and phenylethyl to screen their analgesic and anti-inflammatory activities as well as gastric ulceration potential in test animals. None of the compounds, except 5a, 5e, and 5h, caused gastric lesions or bleeding. Compound 5g was found to have higher analgesic and anti-inflammatory activity among the synthesized compounds.

Synthesis of Some New 1-Acylthiosemicarbazides and 1,2,4-Triazol-5-Thiones, and Their Analgesic and Anti-Inflammatory Activities

We synthesized new 1-[3-(2-oxobenzothiazolin-3-yl)propanoyl]-4- substituted-thiosemicarbazides and their corresponding cyclized 3-[2-(2-oxobenzothiazoline-3-yl)ethyl]-4-substituted-1,2,4-triazol-5-thione ana-logs in which position 4 of the triazole ring was substituted by cyclohexyl, methyl, allyl, phenyl, p-methylphenyl, p-methoxyphenyl, p-chlorophenyl, p-nitrophenyl, benzyl, and phenylethyl to screen their analgesic and anti-inflammatory activities as well as gastric ulceration potential in test animals. None of the compounds, except 5a, 5e, and 5h, caused gastric lesions or bleeding. Compound 5g was found to have higher analgesic and anti-inflammatory activity among the synthesized compounds.

___

  • J. Meyer-Kirchrath and K. Sch¨or, Curr. Med. Chem. 7, 1121-1129 (2000).
  • M. Osiri and L.W. Moreland, Arthritis Care Res. 12, 351-362 (1999).
  • A.S. Kalgut kar, A.. Marnet t , B.C. Crews, R.P. Rammel and L.J. Marnet t , J. Med. Chem. 43, 2860-2870 (2000).
  • R.S. Bresalier, E.V. Friedewald, R.E. Rakel, W.C. Roberts and G.W. Williams, Am. J. Cardiol. 96, 1589-1604 (2005).
  • J.M. Schwab, H.J. Schluesener and S. Laufer, The Lancet 361, 981-982 (2003).
  • N.M. Davies, R.L. Good, K.A. Roupe and J.A. Yanez, J. Pharm. Pharmaceut. Sci. 7, 217-226 (2004).
  • V.A. Adhikari and V.V. Badiger, Indian J. Chem. 27B, 542 (1988).
  • S¸.G. K¨u¸c¨ukg¨uzel, S. Rollas, H. Erdeniz, M. Kiraz, A.C. Ekinci and A. Vidin, Eur. J. Med. Chem. 35, 771 (2000).
  • N.N. G¨ulerman, H.N. Do˘gan, S. Rollas, C. Johansson and C. C¸ elik, Il Farmaco 56, 953-958 (2001).
  • J.M. Kane, M.W. Dudley, S.M. Sorensen and F.P. Miller, J. Med. Chem. 31, 1253 (1988).
  • S. Bahadur, S.P. Singh and M.K. Shukla, Arch. Pharm. 315, 312 (1982).
  • M.H. Shah, M.Y. Mhasalkar, V.M. Patki, C.V. Deliwala and U.K. Sheth, J. Pharm. Sci. 58, 1398 (1969).
  • M.Y. Mhasalkar, M.H. Shah, P.D. Pilankar, S.T. Nikam, K.G. Anantanarayanan and C.V. Deliwala, J. Med. Chem. 14, 1000 (1971).
  • G. S¸ahin, E. Palaska, P. Kelicen, R. Demirdamar and G. Altinok, Arzneim.-Forsch./Drug Res. 51, 478-484 (2001).
  • E. Palaska, G. S¸ahin, P. Kelicen, N.T. Durlu and G. Altınok, Il Farmaco 57, 101-107 (2002).
  • G. Mazzone, R. Pignatello, S. Mazzone, A. Panico, F. Barbera, T. Catti, S. Chiechio, R. Arrigo-Reina, C. Costorina and A. Russo, Il Farmaco 47, 149 (1992).
  • R.R. Mohan, R. Agarwal and V.S. Misra, Indian J. Chem. 25B, 1234 (1986).
  • A.A. El-Emam and T.M. Ibrahim, Arzneim.-Forsch./Drug Res. 41, 1230-1260 (1991).
  • M.D. Mullican, M.W. Wilson, D.T. Connor, C.R. Kostlan, D.J. Schrier and R.D. Dyer, J. Med. Chem. 36, (1993).
  • D.S. Do˘gruer, S. ¨Unl¨u, E. Ye¸silada and M.F. S¸ahin, Il Farmaco, 52, 745-750 (1997).
  • D.S. Do˘gruer, S. ¨Unl¨u, M.F. S¸ahin and E. Ye¸silada, Il Farmaco, 53, 80-84 (1998).
  • B. C¸ akir, A. Ulu¸cay, D.S. Do˘gruer, A. Isımer and M.F. S¸ahin, Il Farmaco, 54, 846-851 (1999).
  • M. G¨ok¸ce, B. C¸ akir, K. Erol and M.F. S¸ahin, Arch. Pharm. Pharm. Med. Chem. 334, 279-283 (2001).
  • H.T. Fife, J.E.C. Hutchins and M.S. Wang, J. Am. Chem. Soc. 97, 5878-5882 (1975).
  • W. Nimmich, J. Prakt. Chem. 27, 220-224 (1965). C. A., 62, 11798d (1965).
  • R. Okun, S.C. Liddon and L. Lasagnal, J. Pharmacol. Exp. Ther. 139, 107-114 (1963).
  • C. S¸afak, H. Erdo˘gan, E. Palaska, R. Sunal and S. Duru, J. Med. Chem. 35, 1296-1299 (1992).
  • Y. Kasahara, H. Hikino, S. TsuruŞji, M. Watanabe and K. Ohuchi, Planta Med. 51, 325-331 (1985).
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Synthesis of Some New 1-Acylthiosemicarbazides and 1,2,4-Triazol-5-Thiones, and Their Analgesic and Anti-Inflammatory Activities

Yasemin DÜNDAR, Bilge ÇAKIR, Esra KÜPELİ

Mono-, Di- and Trinuclear Copper(II) Complexes of a Schiff Base Ligand, 2-{(E)-[(6-{[(1E)-(2-hydroxyphenyl)methylene]amino}pyridin-2-yl)imino]-methyl}phenol

Nevin KARABÖCEK, Serdar KARABÖCEK and Fatma KORMALI

Convergent Synthesis of Fluorinated Dendrons Using the Mesylate Activation Route

Özgür Altan BOZDEMİR, Meltem DİLEK, Mehmet TUTAŞ

A New Approach to Furan-Containing Macrolactones

Christoph Q. SCHMIDT, Ruth MESSMER, Franz BRACHER, Jürgen KRAUSS

Synthesis, Characterization, and Biocidal Studies of the Newly Synthesized Di- and Triorganotin(IV) Complexes with n-Butylhydrogen Phthalate

Saqib ALI, Saira SHAHZADI

Synthesis and Antimicrobial Activities of Some New 1,2,4-Triazole Derivatives

Nurhan GÜMRÜKÇÜOĞLU, Mevlut SERDAR, Elif ÇELİK

FFT-Adsorptive Voltammetric Technique for Pico-Level Determination of Tetracycline in Capsules at an Au Microelectrode in Flowing Solutions

Parviz NOROUZI, Mohammad Reza GANJALI, Parandis DANESHGAR

Preparation and Properties of Triethoxyvinylsilane-Modified Styrene - Butyl Acrylate Emulsion Copolymers

Hamid Javaherian NAGHASH, Akram KARIMZADEH, Ahmad Reza MOMENI, Ahmad Reza MASSAH, Hamid ALIAN

Mono-, di- and trinuclear copper (II) complexes of a schiff base ligand, 2-{ (E)-[6-{ [(1E)-(2- hydroxyphenyl) methylene] amino} pyridin-2-yl) imino]-methyl} phenol

Nevin KARABÖCEK, Serdar KARABÖCEK, Fatma KORMALI

New Diterpenoids from the Aerial Parts of Salvia pilifera

Ufuk KOLAK