杂环化合物的研究：螺[吲哚-3,2'-噻唑烷]衍生物。单卤代3'-苯基螺[3H-吲哚-3,2'-噻唑烷-2,4'(1H)-二酮]的抗菌活性。

Studies on heterocyclic compounds: spiro [indole-3,2'-thiazolidine] derivatives. Antimicrobial activity of monohalogenated 3'-phenylspiro 3H-indole-3,2'-thiazolidine-2,4' (1H)-diones.

作者信息

Piscopo E, Diurno M V, Mazzoni O, Ciaccio A M

机构信息

Department of Pharmaceutical and Toxicological Chemistry, Faculty of Pharmacy, University of Naples, Italy.

出版信息

Boll Soc Ital Biol Sper. 1990 Dec;66(12):1181-6.

PMID:2100530

Abstract

The following halogenated 3'-phenyl [3H-indole-3,2'-thiazolidine]-2,4'(1H)-dione of general formula (A) were synthesized and screened for antimicrobial activity. (formula: see text) where: X = H (I, III, V, VII, IX, XI, XIII, XV), CH3 (II, IV, VI, VIII, X, XII, XIV, XVI); Y = H (I, II), 3-F (III, IV), 2-Cl (V, VI), 3-Cl (VII, VIII), 4-Cl (IX, X), 2-Br (XI, XII), 3-Br (XIII, XIV), 4-Br (XV, XVI). The synthetic approach involves the preparation of variously substituted Schiff-bases of indol-2,3-dione, which then are subjected to cyclocondensation with alpha-mercaptoalkanoic acids, to give spirothiazolidinones of type (A). The prepared compounds were screened against S. aureus, B. cereus, M. paratuberculosis, E. coli, S. typhi, Pr. mirabilis, Ps. aeruginosa, C. albicans, S. cerevisiae, A. niger by a disk-diffusion assay (Kirby-Bauer modified. The results of the antimicrobial screening showed that the prepared compounds exhibited varying degrees of activity against Gram-positive, Gram-negative bacteria, and fungi. 3-Fluoro-derivative (III) showed inhibitory activity especially toward S. aureus and C. albicans. Chloroderivatives (VII) and (VIII) showed broad-spectrum "in vitro" antimicrobial activity, and were especially inhibitory toward S. aureus, E. coli, and S. Typhi. Fluoro-derivative (IV) and bromo-derivatives (XIII) and (XIV) possessed marked antimicrobial activity against M. paratuberculosis.

摘要

合成了通式为(A)的以下卤代3'-苯基[3H-吲哚-3,2'-噻唑烷]-2,4'(1H)-二酮，并对其进行了抗菌活性筛选。(化学式：见原文) 其中：X = H (I、III、V、VII、IX、XI、XIII、XV)，CH3 (II、IV、VI、VIII、X、XII、XIV、XVI)；Y = H (I、II)，3-F (III、IV)，2-Cl (V、VI)，3-Cl (VII、VIII)，4-Cl (IX、X)，2-Br (XI、XII)，3-Br (XIII、XIV)，4-Br (XV、XVI)。合成方法包括制备各种取代的吲哚-2,3-二酮席夫碱，然后使其与α-巯基链烷酸进行环缩合，得到(A)型螺噻唑烷酮。通过纸片扩散法（改良的Kirby-Bauer法）对制备的化合物针对金黄色葡萄球菌、蜡样芽孢杆菌、副结核分枝杆菌、大肠杆菌、伤寒沙门氏菌、奇异变形杆菌、铜绿假单胞菌、白色念珠菌、酿酒酵母、黑曲霉进行筛选。抗菌筛选结果表明，制备的化合物对革兰氏阳性菌、革兰氏阴性菌和真菌表现出不同程度的活性。3-氟衍生物(III)表现出抑制活性，尤其对金黄色葡萄球菌和白色念珠菌。氯衍生物(VII)和(VIII)表现出广谱的“体外”抗菌活性，尤其对金黄色葡萄球菌、大肠杆菌和伤寒沙门氏菌有抑制作用。氟衍生物(IV)以及溴衍生物(XIII)和(XIV)对副结核分枝杆菌具有显著的抗菌活性。