Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives

BEKTAŞ, Hakan; DEMİRBAŞ, NESLİHAN; DEMİRBAŞ, Ahmet; Alpay Karaoğlu, Şengül; ŞAHİN, DENİZ

Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives

Ahmet DEMİRBAŞ, (Karadeniz Teknik Üniversitesi, Trabzon, Türkiye)

Deniz ŞAHİN, (Karadeniz Teknik Üniversitesi, Trabzon, Türkiye)

Neslihan DEMİRBAŞ, (Karadeniz Teknik Üniversitesi, Trabzon, Türkiye)

ŞENGÜL ALPAY KARAOĞLU, (Karadeniz Teknik Üniversitesi, Trabzon, Türkiye)

Hakan BEKTAŞ (Giresun Üniversitesi, Kimya Bölümü, Giresun, Türkiye)

Turkish Journal of Chemistry

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Yıl: 2010 Cilt: 34 Sayı: 3 Sayfa Aralığı: 347 - 358 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives

Öz:

The synthesis of 4-amino-2-[(5-mercapto-1,3,4-oxadiazol-2-yl)methyl]-5-(4-methylphenyl)-2,4-dihydro-3H - 1,2,4-triazol-3-one (2) and 4-amino-2-[(4-amino-5-mercapto-4H -1,2,4-triazol-3-yl)methyl]-5-(4-methylphenyl)- 2,4-dihydro-3H -1,2,4-triazol-3-one (5) was performed starting from 2-[4-amino-3-(4-methylphenyl)-5-oxo- 4,5-dihydro-1H -1,2,4-triazol-1-yl]acetohydrazide (1). The treatment of 2 and 5 with 4-fluorobenzaldehyde (for 8) or salicylaldehyde (for 6) afforded the corresponding Schiff bases (6 and 8). The condensation of 5 with phenacyl bromide produced 4-amino-5-(4-methylphenyl)-2-[(6-phenyl-7H-[1,2,4]triazolo[3,4- b][1,3,4]thiadiazin-3-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (7). The alkylation of 2 and 8 was carried out by using methyl iodide in basic media. Compounds 3 and 10a,b were prepared by aminoalkylation of 2 and 8 with 4-fluorophenyl piperazine, morpholine, or 4-methyl piperazine in the presence of formaldehyde. The synthesized compounds were screened for their antimicrobial activities and, with the exception of 2, 4, 7, and 9, were found to possess good or moderate activities against the screened bacterial strains except Candida tropicalis and Candida albicans.

Anahtar Kelime:

Konular: Mühendislik, Kimya

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

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APA	DEMİRBAŞ A, ŞAHİN D, DEMİRBAŞ N, Alpay Karaoğlu Ş, BEKTAŞ H (2010). Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives. , 347 - 358.
Chicago	DEMİRBAŞ Ahmet,ŞAHİN DENİZ,DEMİRBAŞ NESLİHAN,Alpay Karaoğlu Şengül,BEKTAŞ Hakan Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives. (2010): 347 - 358.
MLA	DEMİRBAŞ Ahmet,ŞAHİN DENİZ,DEMİRBAŞ NESLİHAN,Alpay Karaoğlu Şengül,BEKTAŞ Hakan Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives. , 2010, ss.347 - 358.
AMA	DEMİRBAŞ A,ŞAHİN D,DEMİRBAŞ N,Alpay Karaoğlu Ş,BEKTAŞ H Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives. . 2010; 347 - 358.
Vancouver	DEMİRBAŞ A,ŞAHİN D,DEMİRBAŞ N,Alpay Karaoğlu Ş,BEKTAŞ H Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives. . 2010; 347 - 358.
IEEE	DEMİRBAŞ A,ŞAHİN D,DEMİRBAŞ N,Alpay Karaoğlu Ş,BEKTAŞ H "Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives." , ss.347 - 358, 2010.
ISNAD	DEMİRBAŞ, Ahmet vd. "Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives". (2010), 347-358.

APA	DEMİRBAŞ A, ŞAHİN D, DEMİRBAŞ N, Alpay Karaoğlu Ş, BEKTAŞ H (2010). Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives. Turkish Journal of Chemistry, 34(3), 347 - 358.
Chicago	DEMİRBAŞ Ahmet,ŞAHİN DENİZ,DEMİRBAŞ NESLİHAN,Alpay Karaoğlu Şengül,BEKTAŞ Hakan Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives. Turkish Journal of Chemistry 34, no.3 (2010): 347 - 358.
MLA	DEMİRBAŞ Ahmet,ŞAHİN DENİZ,DEMİRBAŞ NESLİHAN,Alpay Karaoğlu Şengül,BEKTAŞ Hakan Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives. Turkish Journal of Chemistry, vol.34, no.3, 2010, ss.347 - 358.
AMA	DEMİRBAŞ A,ŞAHİN D,DEMİRBAŞ N,Alpay Karaoğlu Ş,BEKTAŞ H Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives. Turkish Journal of Chemistry. 2010; 34(3): 347 - 358.
Vancouver	DEMİRBAŞ A,ŞAHİN D,DEMİRBAŞ N,Alpay Karaoğlu Ş,BEKTAŞ H Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives. Turkish Journal of Chemistry. 2010; 34(3): 347 - 358.
IEEE	DEMİRBAŞ A,ŞAHİN D,DEMİRBAŞ N,Alpay Karaoğlu Ş,BEKTAŞ H "Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives." Turkish Journal of Chemistry, 34, ss.347 - 358, 2010.
ISNAD	DEMİRBAŞ, Ahmet vd. "Synthesis and antimicrobial activities of 2-(5-mercapto)- 1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives". Turkish Journal of Chemistry 34/3 (2010), 347-358.