KaydedilenlerDerginizi ekleyin

Dergiler / Turkish Journal of Chemistry / 2007 / Cilt: 31 - Sayı: 3

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

Nurhan GÜMRÜKÇÜOĞLU
Mevlut SERDAR
Elif ÇELİK
Sayfa
335–348
Yayın Tarihi
2007-03-01
DOI
—
🏛️Bu makalenin bibliyografik verileri ve tam metin bağlantısı DergiPark üzerinden sağlanmıştır.
DergiPark Kaydı ↗
✨

Yapay Zeka Hızlı Bakış & Çıkarımlar

AI Insight
⚡ TL;DR(1 Cümlede Hızlı Çıkarım)

Compounds 4b, 4c, 7, 8d, and 11c showed good antifungal activity only against yeast-like fungi, while compounds 3e, 6, 8e, and 9e showed antimicrobial activity against bacteria and yeast-like fungi.

📌 3 Maddede Bu Makale

🎯
Amaç & Hipotez:A series of acylhydrazones (2a-f) were synthesized by the condensation of iminoester hydrochlorides (1a-f) with acyl hydrazines. 2,5-Dialkyl 1,3,4-oxadiazoles (3a,c,e) were obtained in the same reaction media.
📊
Temel Bulgular & Veri:The treatment of acylhydrazones with hydrazine hydrate afforded 4-amino-3,5-dialkyl-1,2,4-triazoles (4a-c).
💡
Sonuç & Katkı:Compounds 4b, 4c, 7, 8d, and 11c showed good antifungal activity only against yeast-like fungi, while compounds 3e, 6, 8e, and 9e showed antimicrobial activity against bacteria and yeast-like fungi.
🔬Tür:Araştırma Makalesi
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:Acyl hydrazone · 4-triazole · 4-oxadiazole

Özet

A series of acylhydrazones (2a-f) were synthesized by the condensation of iminoester hydrochlorides (1a-f) with acyl hydrazines. 2,5-Dialkyl 1,3,4-oxadiazoles (3a,c,e) were obtained in the same reaction media. The treatment of acylhydrazones with hydrazine hydrate afforded 4-amino-3,5-dialkyl-1,2,4-triazoles (4a-c). The acetylation of 4-amino-3,5-dialkyl-1,2,4-triazoles produced N-[3,5-dialkyl-4H-1,2,4-triazol-4-yl] acetamides (5-7). The treatment of compounds 4a and 4c with various aromatic aldehydes resulted in the formation of 4-arylidenamino-3,5-dialkyl-1,2,4-triazoles (8a,d, e, and 10a-e). Sodium borohydride reduction of 4-arylidenamino derivatives afforded 4-alkylamino-3,5-dialkyl-1,2,4-triazoles (9a,d, e, and 11a-e). Compounds 4b, 4c, 7, 8d, and 11c showed good antifungal activity only against yeast-like fungi, while compounds 3e, 6, 8e, and 9e showed antimicrobial activity against bacteria and yeast-like fungi.

Abstract

A series of acylhydrazones (2a-f) were synthesized by the condensation of iminoester hydrochlorides (1a-f) with acyl hydrazines. 2,5-Dialkyl 1,3,4-oxadiazoles (3a,c,e) were obtained in the same reaction media. The treatment of acylhydrazones with hydrazine hydrate afforded 4-amino-3,5-dialkyl-1,2,4-triazoles (4a-c). The acetylation of 4-amino-3,5-dialkyl-1,2,4-triazoles produced N-[3,5-dialkyl-4H-1,2,4-triazol-4-yl] acetamides (5-7). The treatment of compounds 4a and 4c with various aromatic aldehydes resulted in the formation of 4-arylidenamino-3,5-dialkyl-1,2,4-triazoles (8a,d, e, and 10a-e). Sodium borohydride reduction of 4-arylidenamino derivatives afforded 4-alkylamino-3,5-dialkyl-1,2,4-triazoles (9a,d, e, and 11a-e). Compounds 4b, 4c, 7, 8d, and 11c showed good antifungal activity only against yeast-like fungi, while compounds 3e, 6, 8e, and 9e showed antimicrobial activity against bacteria and yeast-like fungi.

🔖

Bu Makaleye Atıf Yap

GÜMRÜKÇÜOĞLU, N., SERDAR, M., ÇELİK, E. (2007). Synthesis and Antimicrobial Activities of Some New 1,2,4-Triazole Derivatives. Turkish Journal of Chemistry, Cilt: 31 - Sayı: 3, 335–348. https://ajindex.com/articles/184967

📄 Tam Metin PDF Okuyucu

📄

PDF görüntüleyici hazırlanıyor...

Kaynakça (17)

  1. V. Klimeˇsova, L. Zahajka, K. Waisser, J. Kaustova and U. M¨ollmann, Il Farmaco 59, 279-288 (2004).
  2. F. Zani, P. Vicini and M. Incerti, Eur. J. Med. Chem. 39, 135-40 (2004).
  3. S. Tehranchian, T. Akbarzadeh, M. R. Fazeli, H. Jamalifar and A. ShaŞee, Bioorg. Med. Chem. Lett. 15, 25 (2005).
  4. L.F. Awad and S.H. El Ashry, Carbohydrate Res. 312, 9-22 (1998).
  5. M. Amir and K. Shikha, Eur. J. Med. Chem. 39, 535-45 (2004).
  6. E. Palaska, G. Sahin, P. Kelicen, N.T. Durlu and G. Altınok, Il Farmaco 57, 101-07 (2002).
  7. B.S. Holla, K.N. Poorjary, B.S. Rao and M.K. Shivananda, Eur. J. Med. Chem. 37, 511-17 (2002).
  8. J.P. Henichart, R. Houssin and J.L. Berier, J. Het. Chem. 23, 1531-33 (1986).
  9. N. Demirbas, S. Alpay Karaoglu, A. Demirbas and K. Sancak, Eur. J. Med. Chem. 39, 793-804 (2004). N. Demirba¸s, A. Demirba¸s, S¸. Alpay-Karao˘glu and E. C¸ eli k, ARKIVOC (i), 75-91 (2005).
  10. N. Demirbas, A. Demirbas and S¸.A. Karao˘glu, Russian J. Bioorg. Chem. 31, 387-97 (2005).
  11. A. Demirbas, N. Demirbas and A.A. Ikizler, Indian J. Het. Chem. 9, 87-94 (1999). A. ˙Iki zler, N. Demi rbas and A.A. ˙Ikizler, J. Het. Chem. 33, 1765-69 (1996). A. ˙Iki zler, N. Demi rba¸s and A.A. ˙Ikizler, Polish J. Chem. 70, 1114-20 (1996). N. Demirba¸s, A. Demirba¸s and K. Sancak, Turk. J. Chem. 26, 801-806 (2002).
  12. H. Weidinger and J. Kranz, Chem. Ber. 96, 1064-70 (1963). E. Ay¸ca, A.A. ˙Ikizler and R. Aslan, Chim. Acta Turc. 12, 305-314 (1984). A.A. ˙Ikizler, A. ˙Ikizler, H. Y¨uksek, S¸. Bah¸ceciand K. Sancak, Turk. J. Chem. 18, 51-56 (1994). R. ¨Un and A. ˙Ikizler, Chim. Acta Turk. 3, 113-132 (1975). A.A. ˙Iki zler, E. Uzunali and A. Demi rbas, Ind. J. Pharm. Sci. 5, 289-92 (2000).
  13. R.N. Feinstein, R.J. Fry, and E.F. Staffeld, J. National Cancer Inst. 60, 1113-16 (1978). N. Demirba¸s and R. U˘gurluo˘glu, Turk. J. Chem. 28, 679-90 (2004). N. Demirba¸s and R. U˘gurluo˘glu, Turk. J. Chem. 28, 559-71 (2004). A. Demirba¸s, Turk. J. Chem., 28, 311-23 (2004).
  14. R.A. Todeshini, A.N. Miranda, K.C.M. Silva, S.C. Parrini and E. Barreiro, Eur. J. Med. Chem. 33, 189-99 (1998).
  15. M. Mamolo, V. Falagiani, D. Zampieri, L. Vio and E. BanŞ, Il Farmaco 56, 587-92 (2001).
  16. E. Wyrzykiewicz and D. Prukah, J. Het. Chem. 35, 381-87 (1998).
  17. N. Galic, B. Peric, B. Kojic-Prodic and Z. Cimerman, J. Mol. Struc. 559, 187-94 (2001). N. Yıldırım, “Bazı Ester Formilhidrazon’ların Sentezi ve Reaksiyonlarının Incelenmesi” PhD Thesis, Karadeniz Technical University, Institute of Sciences, Trabzon, 1996. R. ¨Un and A. ˙Ikizler, Chim. Acta Turk. 3, 113-132