Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties

Alpay Karaoğlu, Şengül; DEMİRBAŞ, NESLİHAN; DEMİRBAŞ, Ahmet; BEKTAŞ, Hakan; BAYRAK, Hacer

Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties

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

Ahmet DEMİRBAŞ, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Giresun, Türkiye)

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

Hacer BAYRAK, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Giresun, Türkiye)

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

Turkish Journal of Chemistry

2 0

Yıl: 2010 Cilt: 34 Sayı: 4 Sayfa Aralığı: 517 - 527 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties

Öz:

2-(4-Amino-3-(4-chlorophenyl)-5-oxo-4,5–dihydro-1H -1,2,4-triazol-1-yl)-N' -[(2,6-dihalogenophenyl)- methylene]acetohydrazides (3a,b) was obtained via the formation of 2-(4-amino-3-(4-chlorophenyl)-5-oxo- 4,5-dihydro-1H -1,2,4-triazol-1-yl)acetohydrazide (2), which was obtained starting from 4-amino-5-(4-chlorophenyl)- 2,4-dihydro-3H -1,2,4-triazol-3-one (1) in 2 steps. 2-{[4-amino-3-(4-chlorophenyl)-5-oxo-4,5–dihydro- 1H-1,2,4-triazol-1-yl]acetyl}-N-phenylhydra-zine carbothioamide (4), which was prepared starting from 2, was converted to the corresponding 1,3,4-thiadiazole derivative (5) in acidic media. Moreover, the basic treatment of 4 resulted in the formation of 4-amino-5-(4-chlorophenyl)-2-[(4-phenyl-5-thioxo-4,5-dihydro- 1H-1,2,4-triazol-3-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (7). The reactions of compounds 5 and 7 with methyl iodide in the presence of sodium ethoxide afforded the corresponding N-methyl (6) and Smethyl (8) derivatives, respectively. The synthesis of Mannich bases (10a and 10b) was performed from the reaction of 7 with morpholine or piperazine in the presence of formaldehyde. All the newly synthesized compounds were screened for their antimicrobial activity. The antimicrobial activity study revealed that compounds 3a, 3b, and 5 showed good antimicrobial activities against the test microorganisms as compared with ampicillin.

Anahtar Kelime:

Konular: Mühendislik, Kimya

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

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APA	BEKTAŞ H, DEMİRBAŞ A, DEMİRBAŞ N, BAYRAK H, Alpay Karaoğlu Ş (2010). Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties. , 517 - 527.
Chicago	BEKTAŞ Hakan,DEMİRBAŞ Ahmet,DEMİRBAŞ NESLİHAN,BAYRAK Hacer,Alpay Karaoğlu Şengül Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties. (2010): 517 - 527.
MLA	BEKTAŞ Hakan,DEMİRBAŞ Ahmet,DEMİRBAŞ NESLİHAN,BAYRAK Hacer,Alpay Karaoğlu Şengül Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties. , 2010, ss.517 - 527.
AMA	BEKTAŞ H,DEMİRBAŞ A,DEMİRBAŞ N,BAYRAK H,Alpay Karaoğlu Ş Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties. . 2010; 517 - 527.
Vancouver	BEKTAŞ H,DEMİRBAŞ A,DEMİRBAŞ N,BAYRAK H,Alpay Karaoğlu Ş Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties. . 2010; 517 - 527.
IEEE	BEKTAŞ H,DEMİRBAŞ A,DEMİRBAŞ N,BAYRAK H,Alpay Karaoğlu Ş "Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties." , ss.517 - 527, 2010.
ISNAD	BEKTAŞ, Hakan vd. "Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties". (2010), 517-527.

APA	BEKTAŞ H, DEMİRBAŞ A, DEMİRBAŞ N, BAYRAK H, Alpay Karaoğlu Ş (2010). Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties. Turkish Journal of Chemistry, 34(4), 517 - 527.
Chicago	BEKTAŞ Hakan,DEMİRBAŞ Ahmet,DEMİRBAŞ NESLİHAN,BAYRAK Hacer,Alpay Karaoğlu Şengül Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties. Turkish Journal of Chemistry 34, no.4 (2010): 517 - 527.
MLA	BEKTAŞ Hakan,DEMİRBAŞ Ahmet,DEMİRBAŞ NESLİHAN,BAYRAK Hacer,Alpay Karaoğlu Şengül Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties. Turkish Journal of Chemistry, vol.34, no.4, 2010, ss.517 - 527.
AMA	BEKTAŞ H,DEMİRBAŞ A,DEMİRBAŞ N,BAYRAK H,Alpay Karaoğlu Ş Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties. Turkish Journal of Chemistry. 2010; 34(4): 517 - 527.
Vancouver	BEKTAŞ H,DEMİRBAŞ A,DEMİRBAŞ N,BAYRAK H,Alpay Karaoğlu Ş Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties. Turkish Journal of Chemistry. 2010; 34(4): 517 - 527.
IEEE	BEKTAŞ H,DEMİRBAŞ A,DEMİRBAŞ N,BAYRAK H,Alpay Karaoğlu Ş "Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties." Turkish Journal of Chemistry, 34, ss.517 - 527, 2010.
ISNAD	BEKTAŞ, Hakan vd. "Synthesis and antimicrobial activities of some new biheterocyclic compounds containing 1,2,4-triazol-3-one and 1,3,4-thiadiazole moieties". Turkish Journal of Chemistry 34/4 (2010), 517-527.