Preparation and antimicrobial activity evaluation of some new bi- and triheterocyclic azoles
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Med Chem Res (2013) 22:4930–4945 DOI 10.1007/s00044-013-0498-3
ORIGINAL RESEARCH
Preparation and antimicrobial activity evaluation of some new bi- and triheterocyclic azoles Serpil Demirci • Serap Basoglu • Arif Bozdereci Neslihan Demirbas
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Received: 14 November 2012 / Accepted: 16 January 2013 / Published online: 3 February 2013 Ó Springer Science+Business Media New York 2013
Abstract Synthesis of the carbothioamides (5, 13, 22) was performed starting from 3H-1,2,4-triazol-3-ones (2, 17) by several steps, and then, these carbothioamides was converted to triheterocyclic compounds incorporating 1,2,4-triazole, imidazole and 1,3-thiazol(idinone) moieties. The reaction of compound 2 with 3,4-difluoronitrobenzene afforded the 2-(2-fluoro-4-nitrophenyl) derivative, 10. Compound 10 was converted to the arylideneamino derivatives (12a, b) via the reduction of nitro group. On the other hand, the treatment of the hydrazide (20) that was obtained starting from 17, with several aromatic aldehydes generated the corresponding arylidenhydrazides (21a–c). Mannich reaction between compound 2 and a suitable heterocyclic amine resulted in the N-alkylation of 2. All newly synthesized compounds were screened for their antimicrobial activities. In general, most compounds except 22 were Found (%) to be active against Mycobacterium smegmatis, Candida albicans and/or Saccharomyces cerevisiae. Furthermore, 9a and b, which are Mannich bases incorporating morpholine or piperazine nucleus, exhibited excellent antimicrobial activity on test microorganisms. In addition, the hydrazide, 4, was Found (%) to have activity towards Ec and Yp. Keywords 1,2,4-Triazole 1,3-Thiazole 1,3-Thiazolidinone Arylidenhydrazide Mannich base Antimicrobial activity S. Demirci S. Basoglu N. Demirbas (&) Department of Chemistry, Faculty of Art and Sciences, Karadeniz Technical University, 61080 Trabzon, Turkey e-mail: [email protected] A. Bozdereci Department of Biology, Recep Tayyip Erdog˘an University, 53100 Rize, Turkey
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Introduction The limitations in the use of the existing antibacterial drugs due to various reasons such as drug resistance, the serious side effects and/or lack of efficacy made infectious diseases a vicious cycle. In addition, the treatment of resistant strains requires a prolonged therapy containing the use of more toxic drugs and increases the financial burden. One of the infections leading to death is tuberculosis (TB). According to the survey reported by Global Alliances, there are 8–10 million new active cases of TB with approximately 3 million deaths each year (Mallikarjuna et al., 2009; Kumar et al., 2010; Silverman, 2004; Pablos-Mendez et al., 1998). Therefore, it is inevitable to discover and develop new drugs for the treatment of dreadful infections, which have spread worldwide now. To search and synthesize of combinational chemotherapeutic drugs with different mechanisms of action and low side effects constitutes an important part of the methods aiming to overcome the antimicrobial resistance. Beside the expl
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