Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus

DEMİRCİ, Serpil; DEMİRBAŞ, NESLİHAN; DEMİRBAŞ, Ahmet; Alpay Karaoğlu, Şengül; ÖZYANIK, Muhammet; BEKTAŞ, Hakan

Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus

Muhammet ÖZYANIK, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Serpil DEMİRCİ, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

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

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

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

ŞENGÜL ALPAY KARAOĞLU (Rize Üniversitesi, Kimya Bölümü, Rize, Türkiye)

Turkish Journal of Chemistry

1 0

Yıl: 2012 Cilt: 36 Sayı: 2 Sayfa Aralığı: 233 - 246 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus

Öz:

Quinoline-2-carbohydrazide (2) obtained from quinaldic acid (1) was converted to the corresponding carbothioamide 3 and carboxamide 6 by treatment with benzyliso(thio)cyanate. The basic treatment of 3 and 6 yielded the corresponding 1,2,4-triazole derivatives 4 and 7. The synthesis of 5-(quinolin-2-yl)-1,3,4- oxadiazol-2-thiol (9) was performed from the reaction of 1 with CS2 in basic media. The Mannich reaction of compounds 4, 7, and 9 resulted in the formation of aminoalkylated derivatives 5a-c, 8, and 10a,b. The condensation of 1 with thiosemicarbazide, carbohydrazide, or thiocarbohydrazide gave the corresponding 1,2,4-triazole derivatives (11-13). The treatment of 4-amino-5-(quinolin-2-yl)-4H -1,2,4-triazole-3-thiol (13) with 4-chlorophenacyl bromide caused the formation of fused triazolothiadiazine 14. The condensation of 13 with 4-methoxybenzaldehyde generated the corresponding Schiff base 15. The newly synthesized compounds were characterized by elemental analyses, IR, $^1H-NMR$, $^{13} C-NMR$, and mass spectra. The antimicrobial activity study revealed that some of the newly synthesized compounds showed good to moderate activity against a variety of microorganisms.

Anahtar Kelime:

Konular: Mühendislik, Kimya

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

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APA	ÖZYANIK M, DEMİRCİ S, BEKTAŞ H, DEMİRBAŞ N, DEMİRBAŞ A, Alpay Karaoğlu Ş (2012). Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus. , 233 - 246.
Chicago	ÖZYANIK Muhammet,DEMİRCİ Serpil,BEKTAŞ Hakan,DEMİRBAŞ NESLİHAN,DEMİRBAŞ Ahmet,Alpay Karaoğlu Şengül Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus. (2012): 233 - 246.
MLA	ÖZYANIK Muhammet,DEMİRCİ Serpil,BEKTAŞ Hakan,DEMİRBAŞ NESLİHAN,DEMİRBAŞ Ahmet,Alpay Karaoğlu Şengül Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus. , 2012, ss.233 - 246.
AMA	ÖZYANIK M,DEMİRCİ S,BEKTAŞ H,DEMİRBAŞ N,DEMİRBAŞ A,Alpay Karaoğlu Ş Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus. . 2012; 233 - 246.
Vancouver	ÖZYANIK M,DEMİRCİ S,BEKTAŞ H,DEMİRBAŞ N,DEMİRBAŞ A,Alpay Karaoğlu Ş Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus. . 2012; 233 - 246.
IEEE	ÖZYANIK M,DEMİRCİ S,BEKTAŞ H,DEMİRBAŞ N,DEMİRBAŞ A,Alpay Karaoğlu Ş "Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus." , ss.233 - 246, 2012.
ISNAD	ÖZYANIK, Muhammet vd. "Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus". (2012), 233-246.

APA	ÖZYANIK M, DEMİRCİ S, BEKTAŞ H, DEMİRBAŞ N, DEMİRBAŞ A, Alpay Karaoğlu Ş (2012). Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus. Turkish Journal of Chemistry, 36(2), 233 - 246.
Chicago	ÖZYANIK Muhammet,DEMİRCİ Serpil,BEKTAŞ Hakan,DEMİRBAŞ NESLİHAN,DEMİRBAŞ Ahmet,Alpay Karaoğlu Şengül Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus. Turkish Journal of Chemistry 36, no.2 (2012): 233 - 246.
MLA	ÖZYANIK Muhammet,DEMİRCİ Serpil,BEKTAŞ Hakan,DEMİRBAŞ NESLİHAN,DEMİRBAŞ Ahmet,Alpay Karaoğlu Şengül Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus. Turkish Journal of Chemistry, vol.36, no.2, 2012, ss.233 - 246.
AMA	ÖZYANIK M,DEMİRCİ S,BEKTAŞ H,DEMİRBAŞ N,DEMİRBAŞ A,Alpay Karaoğlu Ş Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus. Turkish Journal of Chemistry. 2012; 36(2): 233 - 246.
Vancouver	ÖZYANIK M,DEMİRCİ S,BEKTAŞ H,DEMİRBAŞ N,DEMİRBAŞ A,Alpay Karaoğlu Ş Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus. Turkish Journal of Chemistry. 2012; 36(2): 233 - 246.
IEEE	ÖZYANIK M,DEMİRCİ S,BEKTAŞ H,DEMİRBAŞ N,DEMİRBAŞ A,Alpay Karaoğlu Ş "Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus." Turkish Journal of Chemistry, 36, ss.233 - 246, 2012.
ISNAD	ÖZYANIK, Muhammet vd. "Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus". Turkish Journal of Chemistry 36/2 (2012), 233-246.