Synthesis, spectroscopic characterizations, crystal structures and DFT studies of nalidixic acid carbonyl hydrazones derivatives

Autor(es)

Bergamini, F. R. G. ^[1] ; Ribeiro, M. A. ^[1] ; Lancellotti, M. ^[2] ; Machado, D. ^[2] ; Miranda, P. C. M. L. ^[3] ; Cuin, A. ^[4] ; Formiga, A. L. B. ^[1] ; Corbi, P. P. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Campinas UNICAMP, Inst Chem, Dept Inorgan Chem, POB 6154, BR-13083970 Campinas, SP - Brazil

^[2] Univ Campinas UNICAMP, Inst Biol, Biotechnol Lab, POB 6154, BR-13083970 Campinas, SP - Brazil

^[3] Univ Campinas UNICAMP, Inst Chem, Dept Organ Chem, POB 6154, BR-13083970 Campinas, SP - Brazil

^[4] Univ Fed Juiz de Fora, LQBin Lab Quim BioInorgan, Dept Quim, BR-36036330 Juiz de Fora, MG - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Molecular Structure; v. 1120, p. 115-124, SEP 15 2016.
• Citações Web of Science: 2

Resumo

This article describes the synthesis and characterization of the 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbohydrazide (hzd) and six carbonyl hydrazones derivatives of the nalidixic with 1H-pyrrol-2-ylmethylidene (hpyrr), 1H-imidazol-2-ylmethylidene (h2imi), pyridin-2-ylmethylidene (h2py), pyridin-3-ylmethylidene (h3py), pyridin-4-ylmethylidene(h4py) and (2-hydroxyphenyl)methylidene (hsali). The carbonyl hydrazones were characterized by elemental and ESI-QTOF-MS analyses, IR and detailed NMR spectroscopic measurements. The 2D NMR experiments allowed the unambiguous assignment of the hydrogen, carbon and nitrogen atoms, which have not been reported for nalidixic acid carbonyl hydrazone derivatives so far. Crystal structures of hzd and the new carbonyl hydrazones h2imi, hpyrr and h3py were determined by X-ray diffraction studies. Although the synthesis of hzd was reported decades ago, the hzd crystal structure have not been reported yet. Geometric optimizations of all the characterized structures were performed with the aid of DFT studies. Despite the fact that the hydrazones with 2-pyridine carboxylic acid (h2py) and salicyl aldehyde (hsali) were already reported by literature, a detailed spectroscopic study followed by DFT studies are also reported for such compounds in this manuscript. Antimicrobial studies of the compounds are also presented. (C) 2016 Elsevier B.V. All rights reserved. (AU)

• Processo FAPESP: 12/08230-2 - Síntese, caracterização e estudo das atividades farmacológicas de complexos metálicos de Ag(I), Au(I), Pt(II) e Pd(II) com ligantes bioativos
• Beneficiário: Pedro Paulo Corbi
• Modalidade de apoio: Auxílio à Pesquisa - Regular