Synthesis, structural studies and antituberculosis evaluation of new hydrazone derivatives of quinoline and their Zn(II) complexes

Journal of Saudi Chemical Society

卷:22

Ramesh Yamgar¹  Bapu Thorat²  Ram Jadhav²  Mustapha C. Mandewale²  Aarti Nagarsekar²  Y. Nivid³ 

[1] Department of Chemistry, Chikitsak Samuha’s Patkar-Varde College of Arts, Science and Commerce, Goregaon (West), Mumbai 400 062, India;

[2] P.G. and Research Centre, Department of Chemistry, Government of Maharashtra, Ismail Yusuf College of Arts, Science and Commerce, Jogeshwari (East), Mumbai 400 060, India;

[3] Terna Medical College, Nerul, Navi Mumbai 400706, India;

关键词: Quinoline;    Hydrazone;    Metal complex;    Antituberculosis;    Fluorescence;   

DOI  :  10.1016/j.jscs.2016.04.003

来源: DOAJ

【 摘 要 】

The quinoline hydrazone ligands were synthesized through multi-step reactions. The 2-hydroxy-3-formylquinoline derivatives (1a–1c) were prepared from acetanilide derivatives as starting materials using Vilsmeier–Haack reaction. Then the condensation of 2-hydroxy-3-formylquinoline derivatives with hydrazide derivatives (2a–2c) yielded quinoline hydrazone ligands (3a–3i). The synthesis of a new series of Zn(II) complexes carried out by refluxing with these quinoline hydrazone ligands (3a–3i) is reported. The molecular structures of the ligands (3a–3i) and the Zn complexes were characterized by elemental analysis and spectral studies like FT-IR, 1H and 13C NMR, MS, UV–Visible and fluorescence. The preliminary results of antituberculosis study showed that most of the Zn(II) complexes 4a–4i demonstrated very good antituberculosis activity while the ligands 3a–3i showed moderate activity. Among the tested compounds 4e and 4g were found to be most active with minimum inhibitory concentration (MIC) of 8.00μM and 7.42 μM respectively against Mycobacterium tuberculosis (H37 RV strain) ATCC No-27294 which is comparable to “first and second line” drugs used to treat tuberculosis.

【 授权许可】

Unknown