ISRN Organic Chemistry最新文献

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Synthesis, physiochemical properties, photochemical probe, and antimicrobial effects of novel norfloxacin analogues. 新型诺氟沙星类似物的合成、理化性质、光化学探针及抗菌作用。

ISRN Organic Chemistry

Pub Date : 2011-03-06 eCollection Date: 2011-01-01 DOI: 10.5402/2011/184754

Dina A Bakhotmah, Reda M Abdul-Rahman, Mohammad S Makki, Mohamed A El-Zahabi, Mansor Suliman

The emerging resistance to antimicrobial drugs demands the synthesis of new remedies for microbial infections. Attempts have been made to prepare new compounds by modifications in the quinolone structure. An important method for the synthesis of new quinolone is using Vilsmeier approach but has its own limitations. The present work aimed to synthesize novel norfloxacin analogues using modified Vilsmeier approach and conduct preliminary investigations for the evaluation of their physicochemical properties, photochemical probe, and antimicrobial effects. In an effort to synthesize norfloxacin analogues, only 7-bromo-6-N-benzyl piperazinyl-4-oxoquinoline-3-carboxylic acid was isolated using Vilsmeier approach at high temperature, where N, N'-bis-(4-fluoro-3-nitrophenyl)-oxalamide and N, N'-bis-(3-chloro-4-fluorophenyl)-malonamide were obtained at low temperature. Correlation results showed that lipophilicity, molecular mass, and electronic factors might influence the activity. The synthesized compounds were evaluated for their antimicrobial effects against important pathogens, for their potential use in the inhibition of vitiligo.

对抗菌药物的耐药性要求合成新的治疗微生物感染的药物。已尝试通过对喹诺酮结构的修饰来制备新的化合物。维斯迈耶法是合成新喹诺酮的一种重要方法，但有其局限性。本工作旨在利用改进的Vilsmeier法合成新型诺氟沙星类似物，并对其理化性质、光化学探针和抗菌作用进行初步研究。为了合成诺氟沙星类似物，在高温下采用Vilsmeier法分离得到7-溴-6-N-苄基哌嗪基-4-氧喹啉-3-羧酸，在低温下得到N, N'-双-(4-氟-3-硝基苯基)-草酰胺和N, N'-双-(3-氯-4-氟苯基)-丙二胺。相关结果表明，亲脂性、分子质量和电子因素可能影响其活性。合成的化合物对重要病原体的抑菌效果进行了评价，并对其在抑制白癜风方面的潜在应用进行了评价。

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引用次数: 3

A Study of Solvent Effects in the Solvolysis of Propargyl Chloroformate. 氯甲酸丙炔溶剂分解的溶剂效应研究。

ISRN Organic Chemistry

Pub Date : 2011-01-01 DOI: 10.5402/2011/767141

Malcolm J D'Souza, Anthony M Darrington, Dennis N Kevill

The specific rates of solvolysis of propargyl chloroformate (1) are analyzed in 22 solvents of widely varying nucleophilicity and ionizing power values at 25.0 °C using the extended Grunwald-Winstein equation. Sensitivities to solvent nucleophilicity (l) of 1.37 and to solvent ionizing power (m) of 0.47 suggest a bimolecular process with the formation of a tetrahedral intermediate. A plot of the rates of solvolysis of 1 against those previously reported for phenyl chloroformate (2) results in a correlation coefficient (R) of 0.996, a slope of 0.86, and an F-test value of 2161. The unequivocal correlation between these two substrates attest that the stepwise association-dissociation (A(N) + D(N)) mechanism previously proposed for 2 is also operative in 1.

利用扩展的Grunwald-Winstein方程，在25.0°C下，分析了氯甲酸丙炔酯(1)在22种亲核性和电离功率值变化很大的溶剂中的溶剂溶解比速率。对溶剂亲核性(l)的敏感性为1.37，对溶剂电离力(m)的敏感性为0.47，表明这是一个形成四面体中间体的双分子过程。将1的溶剂溶解速率与先前报道的氯甲酸苯酯(2)的溶剂溶解速率进行对比，得出相关系数(R)为0.996，斜率为0.86,f检验值为2161。这两种底物之间的明确相关性证明，先前为2提出的逐步结合-解离(A(N) + D(N))机制也适用于1。

引用次数: 4

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