Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives

UĞURLUOĞLU, Reyhan; DEMİRBAŞ, NESLİHAN

Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives

Neslihan DEMİRBAŞ, (Karadeniz Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Reyhan UĞURLUOĞLU (Boş)

Turkish Journal of Chemistry

1 0

Yıl: 2004 Cilt: 28 Sayı: 6 Sayfa Aralığı: 679 - 690 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives

Öz:

A series of 4-(1-naphthylidenamino)-1,2,4-triazol-5-one derivatives (3a-e) were synthesized by condensation of corresponding 3-alkyl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones with 1-naphthaldehyde. Acetylation and alkylation of these compounds gave 4a-e and 5a-e, respectively. Sodium borohydride reduction of 1-naphthylidenamino derivatives afforded naphthylmethylamino derivatives, which were sub-sequently acetylated. Depending on the duration of the acetylation, mono or bis acetamide derivatives were obtained. The in vitro antitumor activities of some selected compounds were screened and compounds 3e, 5c, 6e and 9c were found to be active.

Anahtar Kelime:

Konular: Mühendislik, Kimya

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

1. Ş. Demirayak, K. Benkli and K. Güven, Eur. J. Med. Chem., 35, 1037-40 (2000).
2. A. Demirbaş, C.B. Johansson, N. Duman and A.A. İkizler, Acta Pol. Pharm.-Drug Res., 53, 117-21 (1996).
3. A.A. İkizler, F. Uçar, N. Demirbaş, I. Yasa, A. Demirbaş and T. Genzer, Ind. J. Pharm. Sci., 61, 271-74 (1999).
4. H. Yüksek, A. Demirbaş, A. İkizler, C.B. Johansson, C. Çelik and A.A. İkizler, Arzn.- Forsh. Drug Res.,47, 405-9 (1997).
5. G. Turan-Zitouni, M.F. Sıvacı, S. Kılıç and K. Erol, Eur. J. Med. Chem., 36, 685-89 (2001).
6. A.A. İkizler, E. Uzunali and A. Demirbaş, Indian J. Pharm., 5, 289-92 (2000).
7. N. Demirbaş, R. Ugurluoglu and A. Demirbaş, Bioorg. Med. Chem., 10, 3717-21 (2002).
8. R.N. Feinstein, R. J. Fry and E.F. Staffeld, J. National Cancer Inst., 60, 1113-16 (1978).
9. B.S. Holla, K.N. Poorjary, B.S. Tao and M.K. Shivananda, Eur. J. Med. Chem., 37, 511-17 (2002).
10. B.S. Holla, B.K. Sarojini, B.S. Rao, P.M. Akberali, N.S. Kumari and V. Shatty, Il Farmaco, 56, 565-70 (2001).
11. B.K. Keppler, W. Balzer and V. Seifried, Arzn.-Forsch., 37, 770-71 (1987).
12. N. Demirbaş, S. Alpay Karaoğlu, A. Demirbaş and K. Sancak, Eur. J. Med. Chem., 39, 793-804 (2004).
13. P.E. Goss and K. Strasser-Weippl, Best Pract. Res. Clin. End. Met., 18, 113-30 (2004).
14. J. R. Santen, Steroids, 68, 559-67 (2003).
15. M. Clemons, R.E. Coleman and S. Verma, Cancer Treat. Rew., 30, 325-32 (2004).
16. S.Chen, Y.C. Kao and C. A. Laughton, J. Steroid Biochem., 61, 107-15 (1997).
17. A.A. İkizler and R. Ün, Chem. Acta Turc., 7, 269-90 (1979).
18. B. Kahveci and A.A. İkizler, Turk. J. Chem., 24, 343-51 (2000).
19. J. Daunis, Y. Quindo, R. Jacquer and P. Vialefont, Bull. Soc. Chim. France, 3296-99 (1971).
20. G.D. Gray and E. Wickstrom, Biotechniques, 21, 780-82 (1996).

APA	DEMİRBAŞ N, UĞURLUOĞLU R (2004). Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives. , 679 - 690.
Chicago	DEMİRBAŞ NESLİHAN,UĞURLUOĞLU Reyhan Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives. (2004): 679 - 690.
MLA	DEMİRBAŞ NESLİHAN,UĞURLUOĞLU Reyhan Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives. , 2004, ss.679 - 690.
AMA	DEMİRBAŞ N,UĞURLUOĞLU R Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives. . 2004; 679 - 690.
Vancouver	DEMİRBAŞ N,UĞURLUOĞLU R Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives. . 2004; 679 - 690.
IEEE	DEMİRBAŞ N,UĞURLUOĞLU R "Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives." , ss.679 - 690, 2004.
ISNAD	DEMİRBAŞ, NESLİHAN - UĞURLUOĞLU, Reyhan. "Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives". (2004), 679-690.

APA	DEMİRBAŞ N, UĞURLUOĞLU R (2004). Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives. Turkish Journal of Chemistry, 28(6), 679 - 690.
Chicago	DEMİRBAŞ NESLİHAN,UĞURLUOĞLU Reyhan Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives. Turkish Journal of Chemistry 28, no.6 (2004): 679 - 690.
MLA	DEMİRBAŞ NESLİHAN,UĞURLUOĞLU Reyhan Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives. Turkish Journal of Chemistry, vol.28, no.6, 2004, ss.679 - 690.
AMA	DEMİRBAŞ N,UĞURLUOĞLU R Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives. Turkish Journal of Chemistry. 2004; 28(6): 679 - 690.
Vancouver	DEMİRBAŞ N,UĞURLUOĞLU R Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives. Turkish Journal of Chemistry. 2004; 28(6): 679 - 690.
IEEE	DEMİRBAŞ N,UĞURLUOĞLU R "Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives." Turkish Journal of Chemistry, 28, ss.679 - 690, 2004.
ISNAD	DEMİRBAŞ, NESLİHAN - UĞURLUOĞLU, Reyhan. "Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives". Turkish Journal of Chemistry 28/6 (2004), 679-690.