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

Ozyanik M., Demirci S., BEKTAŞ H., DEMİRBAŞ N., DEMİRBAŞ A., Karaoglu S. A.

TURKISH JOURNAL OF CHEMISTRY, vol.36, no.2, pp.233-246, 2012 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 36 Issue: 2
  • Publication Date: 2012
  • Doi Number: 10.3906/kim-1109-9
  • Journal Name: TURKISH JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.233-246
  • Keywords: Quinoline, 1,3,4-thiadiazole, 1,2,4-triazole, Mannich base, antimicrobial activity, HYBRID MOLECULES, AKT INHIBITORS, ANTICONVULSANT, ANTIMALARIALS, ANTIFUNGAL, ANALOGS, MANNICH, DESIGN, SERIES, BASES
  • Recep Tayyip Erdoğan University Affiliated: Yes

Abstract

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.