Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives

Alpay Karaoğlu, Şengül; DÜĞDÜ, Esra; SANCAK, KEMAL; ER, MUSTAFA; ÜNVER, YASEMİN

Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives

Yasemin ÜNVER, (Karadeniz Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Esra DÜĞDÜ, (Karadeniz Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Kemal SANCAK, (Karadeniz Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Mustafa ER, (Karadeniz Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

ŞENGÜL ALPAY KARAOĞLU (Rize Üniversitesi, Fen Edebiyat Fakültesi, Biyoloji Bölümü, Rize, Türkiye)

Turkish Journal of Chemistry

5 0

Yıl: 2008 Cilt: 32 Sayı: 4 Sayfa Aralığı: 441 - 455 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives

Öz:

A series of novel di-[3(thiophen-2-yl-methyl)-4,5-dihydro-1H-[1,2,4]triazole-5-one-4yl]n-alkanes (2a-h) were obtained by the reaction of N’-1-ethoxy-2-thiophen-2-yl-ethylydene hydrazino carboxylic acid ethyl ester (1) and diamines. Compound 3 was reacted with aldehydes and 4-(arylidene-amino)- 3-thiophen-2-yl-methyl-4,5-dihydro-1H-[1,2,4] triazole-5-ones (4, 5, and 8) with Schiff base character were synthesized. (4-(arylidene-amino)-5-oxo-3-thiophen-2-yl-methyl-4,5-dihydro-1H-[1,2,4]triazole- 1-yl)-acetic acid ethyl esters (6, 7, and 9) were obtained by the reaction of 4-(arylidene-amino)-3- thiophen-2-yl-methyl-4,5-dihydro-1H-[1,2,4]triazole-5-ones (4, 5, and 8) and ethyl bromoacetate. The structures of the new compounds were inferred through IR, $^1H/^{13}C$ NMR, elemental analyses, and mass spectral data. Compound 8i was characterized by IR, $^1H/^{13}C$ NMR, elemental analyses, mass, and X-ray spectral techniques. Geometry optimization of compounds 2a, 2c, 2f, 4, and 5 was achieved by computer using the AM1 method. Compounds 2f, 4, 5, 6, 7, 8i, and 9k showed good antifungal activity only against yeast fungi, while compound 2d showed antimicrobial activity against the bacteria Pseudomonas aeruginosa ATCC10145, Enterococcus faecalis ATCC29212 and the yeast fungi Candida albicans ATCC 60193 and Candida tropicalis ATCC 13803.

Anahtar Kelime:

Konular: Mühendislik, Kimya

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

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APA	ÜNVER Y, DÜĞDÜ E, SANCAK K, ER M, Alpay Karaoğlu Ş (2008). Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives. , 441 - 455.
Chicago	ÜNVER YASEMİN,DÜĞDÜ Esra,SANCAK KEMAL,ER MUSTAFA,Alpay Karaoğlu Şengül Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives. (2008): 441 - 455.
MLA	ÜNVER YASEMİN,DÜĞDÜ Esra,SANCAK KEMAL,ER MUSTAFA,Alpay Karaoğlu Şengül Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives. , 2008, ss.441 - 455.
AMA	ÜNVER Y,DÜĞDÜ E,SANCAK K,ER M,Alpay Karaoğlu Ş Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives. . 2008; 441 - 455.
Vancouver	ÜNVER Y,DÜĞDÜ E,SANCAK K,ER M,Alpay Karaoğlu Ş Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives. . 2008; 441 - 455.
IEEE	ÜNVER Y,DÜĞDÜ E,SANCAK K,ER M,Alpay Karaoğlu Ş "Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives." , ss.441 - 455, 2008.
ISNAD	ÜNVER, YASEMİN vd. "Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives". (2008), 441-455.

APA	ÜNVER Y, DÜĞDÜ E, SANCAK K, ER M, Alpay Karaoğlu Ş (2008). Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives. Turkish Journal of Chemistry, 32(4), 441 - 455.
Chicago	ÜNVER YASEMİN,DÜĞDÜ Esra,SANCAK KEMAL,ER MUSTAFA,Alpay Karaoğlu Şengül Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives. Turkish Journal of Chemistry 32, no.4 (2008): 441 - 455.
MLA	ÜNVER YASEMİN,DÜĞDÜ Esra,SANCAK KEMAL,ER MUSTAFA,Alpay Karaoğlu Şengül Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives. Turkish Journal of Chemistry, vol.32, no.4, 2008, ss.441 - 455.
AMA	ÜNVER Y,DÜĞDÜ E,SANCAK K,ER M,Alpay Karaoğlu Ş Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives. Turkish Journal of Chemistry. 2008; 32(4): 441 - 455.
Vancouver	ÜNVER Y,DÜĞDÜ E,SANCAK K,ER M,Alpay Karaoğlu Ş Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives. Turkish Journal of Chemistry. 2008; 32(4): 441 - 455.
IEEE	ÜNVER Y,DÜĞDÜ E,SANCAK K,ER M,Alpay Karaoğlu Ş "Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives." Turkish Journal of Chemistry, 32, ss.441 - 455, 2008.
ISNAD	ÜNVER, YASEMİN vd. "Synthesis and antimicrobial evaluation of novel di-triazoles and 4-arylidene amino 4,5 dihydro-1H-[1,2,4] triazole-5-one derivatives". Turkish Journal of Chemistry 32/4 (2008), 441-455.