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金属基生物活性化合物:三唑衍生希夫碱及其氧钒(IV)配合物的设计、合成及抗菌/抗真菌/细胞毒性性质。

Metal based biologically active compounds: design, synthesis, and antibacterial/antifungal/cytotoxic properties of triazole-derived Schiff bases and their oxovanadium(IV) complexes.

机构信息

Department of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan.

出版信息

Eur J Med Chem. 2010 Jul;45(7):2739-47. doi: 10.1016/j.ejmech.2010.02.053. Epub 2010 Mar 1.

DOI:10.1016/j.ejmech.2010.02.053
PMID:20338672
Abstract

A new series of oxovanadium(IV) complexes have been designed and synthesized with a new class of triazole Schiff bases derived from the reaction of 3,5-diamino-1,2,4-triazole with 2-hydroxy-1-naphthaldehyde, pyrrole-2-carboxaldehyde, pyridine-2-carboxaldehyde and acetyl pyridine-2-carboxaldehyde, respectively. Physical (magnetic susceptibility, molar conductance), spectral (IR, (1)H NMR, (13)C NMR, mass and electronic) and analytical data have established the structures of these synthesized Schiff bases and their oxovanadium(IV) complexes. The Schiff bases, predominantly act as bidentate and coordinate with the vanadium(IV) metal to give a stoichiometric ratio of 1:2 [M:L], forming a general formulae, [M(L-H)(2)] and [M(L)(2)]SO(4) where L = (L(1))-(L(4)) and M = VO(IV) of these complexes in a square-pyramidal geometry. In order to evaluate the biological activity of Schiff bases and to assess the role of vanadium(IV) metal on biological activity, the triazole Schiff bases and their oxovanadium(IV) complexes have been studied for in vitro antibacterial activity against four Gram-negative (Escherichia coli, Shigella flexenari, Pseudomonas aeruginosa, Salmonella typhi) and two Gram-positive (Staphylococcus aureus, Bacillus subtilis) bacterial strains, in vitro antifungal activity against Trichophyton longifucus, Candida albican, Aspergillus flavus, Microscopum canis, Fusarium solani and Candida glaberata. The simple Schiff bases showed weaker to significant activity against one or more bacterial and fungal strains. In most of the cases higher activity was exhibited upon coordination with vanadium(IV) metal. Brine shrimp bioassay was also carried out for in vitro cytotoxic properties against Artemia salina.

摘要

设计并合成了一系列新型的氧钒(IV)配合物,这些配合物是由 3,5-二氨基-1,2,4-三唑与 2-羟基-1-萘醛、吡咯-2-甲醛、吡啶-2-甲醛和乙酰吡啶-2-甲醛反应得到的新型三唑席夫碱衍生而来。物理(磁化率、摩尔电导率)、光谱(IR、(1)H NMR、(13)C NMR、质谱和电子)和分析数据确定了这些合成席夫碱及其氧钒(IV)配合物的结构。席夫碱主要作为双齿配体与钒(IV)金属配位,形成摩尔比为 1:2 [M:L]的配合物,形成一个通用化学式[M(L-H)(2)]和[M(L)(2)]SO(4),其中 L = (L(1))-(L(4)),M = VO(IV),这些配合物在四方锥几何形状中。为了评估席夫碱的生物活性,并评估钒(IV)金属对生物活性的作用,研究了三唑席夫碱及其氧钒(IV)配合物对四种革兰氏阴性(大肠杆菌、志贺氏菌、铜绿假单胞菌、伤寒沙门氏菌)和两种革兰氏阳性(金黄色葡萄球菌、枯草芽孢杆菌)细菌菌株的体外抗菌活性,对 Trichophyton longifucus、Candida albican、Aspergillus flavus、Microscopum canis、Fusarium solani 和 Candida glaberata 的体外抗真菌活性。简单的席夫碱对一种或多种细菌和真菌菌株表现出较弱到显著的活性。在大多数情况下,与钒(IV)金属配位后表现出更高的活性。还进行了盐水虾生物测定,以评估对 Artemia salina 的体外细胞毒性。

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