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

Synthesis of Some Novel 3,5-Diaryl-1,2,4-Triazole Derivatives and Investigation of Their Antimicrobial Activities

Sayfa
315–326
Yayın Tarihi
2007-03-01
DOI
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⚡ TL;DR(1 Cümlede Hızlı Çıkarım)

Compounds 5c and 6d showed marginal antimicrobial activities against Staphylococcus aureus, while compound 6b displayed moderate antifungal activity towards Candida tropicalis.

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Amaç & Hipotez:A series of acylhydrazones (2a-d) was synthesized from the reactions of iminoester hydrochlorides (1a-e) with acyl hydrazines. 2,5-Dialkyl 1,3,4-oxadiazoles (3a-d) were obtained in the same reaction media.
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Temel Bulgular & Veri:The treatment of acylhydrazones with hydrazine hydrate afforded 4-amino-3,5-dialkyl-1,2,4-triazoles (4a-c).
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Sonuç & Katkı:Compounds 5c and 6d showed marginal antimicrobial activities against Staphylococcus aureus, while compound 6b displayed moderate antifungal activity towards Candida tropicalis.
🔬Tür:Araştırma Makalesi
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:Acyl hydrazone · 4-triazole · 4-oxadiazole

Özet

A series of acylhydrazones (2a-d) was synthesized from the reactions of iminoester hydrochlorides (1a-e) with acyl hydrazines. 2,5-Dialkyl 1,3,4-oxadiazoles (3a-d) 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-(4-hydroxyphenyl)-5-phenyl-4H-1,2,4-triazole (4a) produced 4-amino-5-(4-acetoxyphenyl)-3-phenyl-4H-1,2,4-triazole (9), while the acetylation of 4-amino-3-(4-tolyl)-5-phenyl-4H-1,2,4-triazole (4b) gave 4-acetylamino-3-phenyl-5-(4-tolyl)-4H-1,2,4-triazole (10). The treatment of compound 4b with various aromatic aldehydes or acetophenone and 4-nitroacetophenone resulted in the formation of 4-arylidenamino-3,5-dialkyl-4H-1,2,4-triazoles (5a-e and 7a,b). Sodium borohydride reduction of 4-arylidenamino derivatives of 1,2,4-triazoles afforded 4-alkylamino-3,5-dialkyl-4H-1,2,4-triazoles (6a-e and 8a,b). All newly synthesized compounds were screened for their antimicrobial and antifungal activities using agar-well diffusion. Compounds 5c and 6d showed marginal antimicrobial activities against Staphylococcus aureus, while compound 6b displayed moderate antifungal activity towards Candida tropicalis.

Abstract

A series of acylhydrazones (2a-d) was synthesized from the reactions of iminoester hydrochlorides (1a-e) with acyl hydrazines. 2,5-Dialkyl 1,3,4-oxadiazoles (3a-d) 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-(4-hydroxyphenyl)-5-phenyl-4H-1,2,4-triazole (4a) produced 4-amino-5-(4-acetoxyphenyl)-3-phenyl-4H-1,2,4-triazole (9), while the acetylation of 4-amino-3-(4-tolyl)-5-phenyl-4H-1,2,4-triazole (4b) gave 4-acetylamino-3-phenyl-5-(4-tolyl)-4H-1,2,4-triazole (10). The treatment of compound 4b with various aromatic aldehydes or acetophenone and 4-nitroacetophenone resulted in the formation of 4-arylidenamino-3,5-dialkyl-4H-1,2,4-triazoles (5a-e and 7a,b). Sodium borohydride reduction of 4-arylidenamino derivatives of 1,2,4-triazoles afforded 4-alkylamino-3,5-dialkyl-4H-1,2,4-triazoles (6a-e and 8a,b). All newly synthesized compounds were screened for their antimicrobial and antifungal activities using agar-well diffusion. Compounds 5c and 6d showed marginal antimicrobial activities against Staphylococcus aureus, while compound 6b displayed moderate antifungal activity towards Candida tropicalis.

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Bu Makaleye Atıf Yap

SERDAR, M., GÜMRÜKÇÜOĞLU, N., KARAOĞLU, Ş. A. (2007). Synthesis of Some Novel 3,5-Diaryl-1,2,4-Triazole Derivatives and Investigation of Their Antimicrobial Activities. Turkish Journal of Chemistry, Cilt: 31 - Sayı: 3, 315–326. https://ajindex.com/articles/185017

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