Fused 2-thiohydantoin derivatives: Evaluation as potential antioxidants

被引：13

作者：

KiecKononowicz, K

KarolakWojciechowska, J

Robak, J

机构：

[1] TECH UNIV LODZ,INST GEN CHEM,PL-90924 LODZ,POLAND

[2] JAGIELLONIAN UNIV,COLL MED,DEPT PHARMACOL,KRAKOW,POLAND

来源：

ARCHIV DER PHARMAZIE | 1997年 / 330卷 / 04期

关键词：

fused-2-thiohydantoins; free radicals scavengers; semiempirical quantum-chemistry calculations; frontier orbital interactions;

D O I：

10.1002/ardp.19973300402

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of fused 5,5-diphenyl and 5-arylidene-2-thiohydantoin derivatives were examined for their oxygen free radical inhibitory and radical scavenging properties (RSC) using both an enzymic and non-enzymic biological generators of free radicals. Non-enzymic lipid peroxidation (OH . radicals) was assayed as the amount of malondialdehyde (MDA) that had been formed during incubation of boiled rat liver microsomes in the presence of ascorbic acid and ferric ions. Superoxide anions (. O-2(-) anion radicals) were generated enzymatically in the xanthine-xanthine oxidase system. Among the 20 investigated compounds only four fused arylidene 2-thiohydantoin derivatives showed weak antioxidant activity scavenging OH . radicals. There is a relationship between the electrophilic OH . radical scavenging properties (RSC) of the tested molecules and the value of their HOMO energy derived from semiempirical MO calculations.

引用

收藏

页码：85 / 90

页数：6

相关论文

共 25 条

[1]

ARMSTRONG D, 1985, FREE RADICALS MOL BI, V27, P8

[2]

BUKERT U, 1982, MOL MECH

[3] FREE-RADICALS IN BRAIN METABOLISM AND PATHOLOGY [J].

EVANS, PH .

BRITISH MEDICAL BULLETIN, 1993, 49 (03) :577-587

[4]

FLEMING I, 1976, FRONTIER ORBITALS OR, P208

[5] REACTION OF 5,5-DIPHENYL-2-THIOHYDANTOIN WITH 1,2-DIBROMOETHANE - CRYSTAL AND MOLECULAR-STRUCTURES OF 2,3-DIHYDRO-6,6-DIPHENYLIMIDAZO-[2,1-B]-THIAZOL-5(6H)-ONE AND 2,3-DIHYDRO-5,5-DIPHENYLIMIDAZO-[2,1-B]-THIAZOL-6(5H)-ONE AND THEIR REACTIVITY [J].

KAROLAKWOJCIECHOWSKA, J ;

MIKOLAJCZYK, M ;

ZATORSKI, A ;

KIECKONONOWICZ, K ;

ZEJC, A .

TETRAHEDRON, 1985, 41 (20) :4593-4602

[6] REACTION OF 5,5-DIPHENYL-2-THIOHYDANTOIN WITH ETHYL-2,3-DIBROMOPROPIONATE - CRYSTAL AND MOLECULAR-STRUCTURE OF ETHYL-2-(2,3-DIHYDRO-6,6-DIPHENYLIMIDAZO-[2,1-B]-THIAZOL-5(6H)-ONE)FORMATE [J].

KAROLAKWOJCIECHOWSKA, J ;

KIECKONONOWICZ, K .

JOURNAL OF CRYSTALLOGRAPHIC AND SPECTROSCOPIC RESEARCH, 1987, 17 (04) :485-494

[7] REACTION OF 5,5-DIPHENYL-2-THIOHYDANTOIN WITH 1,4-DIBROMOBUTANE - THE CRYSTAL AND MOLECULAR-STRUCTURE OF 2,3,4,5-TETRAHYDRO-7,7-DIPHENYLIMIDAZO-[2,1-B]-THIAZEPINE-8(7H)-ONE [J].

KIECKONONOWICZ, K ;

ZATORSKI, A ;

KAROLAKWOJCIECHOWSKA, J .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1989, 42 (3-4) :191-200

[8] REACTION OF 5,5-DIPHENYL-2-THIOHYDANTOIN WITH ETHYL CHLOROACETATE - SYNTHESIS AND CRYSTAL AND MOLECULAR-STRUCTURE OF 2,3,5,6-TETRAHYDROIMIDAZO-[2,1-B]-THIAZOL-3,6-DIONE [J].

KIECKONONOWICZ, K ;

KAROLAKWOJCIECHOWSKA, J ;

KWIATKOWSKI, W .

JOURNAL OF CRYSTALLOGRAPHIC AND SPECTROSCOPIC RESEARCH, 1988, 18 (05) :563-573

[9] REACTION OF 5,5-DIPHENYL-2-THIOHYDANTOIN WITH 1,3-DIBROMOPROPANE UNDER PHASE-TRANSFER CATALYTIC CONDITIONS - CRYSTAL AND MOLECULAR-STRUCTURE OF 2,3,4,5-TETRAHYDRO-7,7-DIPHENYLIMIDAZO-[2,1-B]-THIAZINE-6(7H)-ONE [J].

KIECKONONOWICZ, K ;

ZEJC, A ;

MIKOLAJCZYK, M ;

ZATORSKI, A ;

KAROLAKWOJCIECHOWSKA, J ;

WIECZOREK, MW .

TETRAHEDRON, 1981, 37 (02) :409-415

[10] SYNTHESIS AND SPECTROSCOPIC PROPERTIES OF FUSED 5-ARYLIDENE-2-THIOHYDANTOIN DERIVATIVES [J].

KIECKONONOWICZ, K ;

KAROLAKWOJCIECHOWSKA, J .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1992, 73 (1-4) :235-248