Yıl: 2005 Cilt: 29 Sayı: 3 Sayfa Aralığı: 247 - 254 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity

Öz:
Two regioisomer series, 2-(3-ethyl-4(3H)-quinazolinone-2- ylmercaptoacetylhydrazono)-3-alkyl/3-aryl-5-methyl-4-thiazolidinones (12-21) and 2-arylimino-3-(3-ethyl-4(3H)-quinazolinone-2-ylmercaptoacetylamino)- 5-methyl-4-thiazolidinones (22-26), were synthesized by the cyclization of 1-(3-ethyl-4(3H)-quinazolinone-2-ylmercaptoacetyl)-4-alkyl/aryl thiosemicarbazides (1-11) with ethyl 2-bromopropionate in the presence of anhydrous sodium acetate in anhydrous ethanolic medium. The structures of 12-26 were confirmed by analytical and spectral data (IR, $^1H-NMR$ and EIMS). Selected members of the thiosemicarbazides and thiazolidinones were subjected to anticonvulsant activity tests by the National Institute of Neurological Disorders and Stroke MD, USA.
Anahtar Kelime:

Konular: Mühendislik, Kimya
Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • 1.R. Lakhan and B. J. Rai, J. Chem. Eng. Data 32, 384 (1987).
  • 2.M.J. Hour, L.J. Huang, S.C. Kuo, Y. Xia, K. Bastow, Y. Nakanishi, E. Hamel and K.H. Lee, J. Med. Chem.43, 4479 (2000).
  • 3.E. Hamel, CM. Lin, J. Plowman, H.K. Wang, K.H. Lee and K.D. Paul, Biochem. Pharmacol. 51, 53 (1996).
  • 4.J.W. Corbett, S.S. Ko, J.D. Rodgers, L.A. Gearhart, N.A. Magnus, L.T. Bacheler, S. Diamond, S. Jeffrey,R.M. Klabe, B.C. Cordova, S. Garber, K. Logue, G.L. Trainor, P.S. Anderson and S.K. Erickson-Viitanen, J. Med. Chem. 43, 2019 (2000).
  • 5.C.O. Usifoh and G.K. Scriba, Arch. Pharm. (Weinheim) 333, 261 (2000).
  • 6.A. Gürsoy and N. Karalı, II Farmaco 50, 857 (1995).
  • 7.P. Kumar, K.N. Dhawan, S. Vrat, K.P. Bhargava and K. Kishore, Arch. Pharm. (Weinheim) 316, 759(1983).
  • 8.J. Bartroli, E. Turmo, M. Alguero, E. Boncompte, M.L. Vericat, L. Conte, J. Ramis, M. Merlos, J. Garcia-Rafanell and J. Forn, J. Med. Chem. 41, 1869 (1998).
  • 9.A.A. Shalaby, A.M. El-Khamry, S.A. Shiba, A.A. Ahmet and A.A. Hanafi, Arch. Pharm. (Weinheim) 333,365 (2000).
  • 10.I.R. Ager, D.R. Harrison, P.D. Kennewell and J.B. Taylor, J. Med. Chem., 20, 379 (1977).
  • 11.P. Daenens and M. Van Boven, Arzneim.-Forsch./Drug Res. 24, 195 (1974).
  • 12.C. Ferrando, J.M. Foy, C.N.F.W. Pratt and J.R. Purvis, J. Pharm. Pharmacol. 33, 219 (1981).
  • 13.E. Cohen, Arzneim.-Forsch./Drug Res. 13, 660 (1963).
  • 14.S. Grasso, A. Chimirri, P. Monforte, G. Fenech, M. Zappala and A.M. Monforte, II Farmaco 43, 851 (1988).
  • 15.M.L. Barreca, A. Chimirri, L. De Luca, A.M. Monforte, P. Monforte, A. Rao, M. Zappala, J. Balzarini, E. De Clercq, C. Pannecougue and M. Witvrouw, Biorg. & Med. Chem. Lett. 11, 1793 (2001).
  • 16.S.A.H. El-Feky and Z.K. Abd El-Samii, Arch. Pharm. (Weinheim) 324, 381 (1991).
  • 17.S.A. El-Feky, Pharmazie 48, 894 (1993).
  • 18.M.M. Dutta, B.N. Goswami and J.C.S. Kataky, Indian Chem. Soc. 67, 332 (1990).
  • 19.A. Gürsoy and N. Ilhan, II Farmaco 50, 559 (1995).
  • 20.N. Terzioğlu, "Synthesis and Identification of 4-Thiazolidinone Derivatives Bearing Quinazolinone Ring", PhD Thesis, Istanbul University, Istanbul, Turkey, 1999.
  • 21.D.R. St. Laurent, Q. Gao, D. Wu and M.H. Serrano-Wu, Tetrahedron Lett. 45, 1907 (2004).
  • 22.K.D. Klika, L. Janovec, J. Imrich, G. Suchâr, P. Kristian, R. Sillanpââ and K. Pihlaja, Eur. J. Org. Chem.1248 (2002).
  • 23.S.K.P. Sinha and M.P. Thakur, J. Indian Chem. Soc. 51, 457 (1974).
  • 24.N. Karalı and A. Gürsoy, II Farmaco 49, 819 (1994).
  • 25.Sadtler, Research Laboratories, Inc., Philadelphia, 1972, 13248M.
  • 26.N. Karalı, A. Gürsoy, N. Terzioğlu, S. Özkırımlı, H. Özer and A.C. Ekinci, Arch. Pharm.-Pharm. Med.Chem. 331, 254 (1998).
  • 27.W. Czuba, D. Prelicz, D.S. Hibner, K. Utko and L. Wyzgowska, Pr. Chem., 27, 7 (1982).
  • 28.M.S. Reddy and C.S. Ratnam, Org. Mass Spectrom. 20, 698 (1985).
  • 29.F.A. Ashour, N.S. Habib, R. Soliman and M. El-Taibbi, Bull. Fac. Pharm. Cairo Univ. 31, 381 (1993).
  • 30.R.J. Porter, J.J. Cereghino, G.D. Gladding, B.J. Hessie, H.J. Kupferberg, B. Scoville and E.P. White, Cleve.Clin. Q. 51, 293 (1984).
APA GÜRSOY A, TERZİOĞLU N (2005). Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity. , 247 - 254.
Chicago GÜRSOY Aysel,TERZİOĞLU Nalan Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity. (2005): 247 - 254.
MLA GÜRSOY Aysel,TERZİOĞLU Nalan Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity. , 2005, ss.247 - 254.
AMA GÜRSOY A,TERZİOĞLU N Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity. . 2005; 247 - 254.
Vancouver GÜRSOY A,TERZİOĞLU N Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity. . 2005; 247 - 254.
IEEE GÜRSOY A,TERZİOĞLU N "Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity." , ss.247 - 254, 2005.
ISNAD GÜRSOY, Aysel - TERZİOĞLU, Nalan. "Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity". (2005), 247-254.
APA GÜRSOY A, TERZİOĞLU N (2005). Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity. Turkish Journal of Chemistry, 29(3), 247 - 254.
Chicago GÜRSOY Aysel,TERZİOĞLU Nalan Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity. Turkish Journal of Chemistry 29, no.3 (2005): 247 - 254.
MLA GÜRSOY Aysel,TERZİOĞLU Nalan Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity. Turkish Journal of Chemistry, vol.29, no.3, 2005, ss.247 - 254.
AMA GÜRSOY A,TERZİOĞLU N Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity. Turkish Journal of Chemistry. 2005; 29(3): 247 - 254.
Vancouver GÜRSOY A,TERZİOĞLU N Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity. Turkish Journal of Chemistry. 2005; 29(3): 247 - 254.
IEEE GÜRSOY A,TERZİOĞLU N "Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity." Turkish Journal of Chemistry, 29, ss.247 - 254, 2005.
ISNAD GÜRSOY, Aysel - TERZİOĞLU, Nalan. "Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity". Turkish Journal of Chemistry 29/3 (2005), 247-254.