Antifungal activity of organobismuth compounds against the yeast Saccharomyces cerevisiae:: structure-activity relationship
Antifungal activity of organobismuth compounds against the yeast Saccharomyces cerevisiae:: structure-activity relationship
复制标题
DOI：
10.1016/j.jinorgbio.2003.12.024
复制
发表时间：
2004-03-01
影响因子：
3.9
通讯作者：
Uno, H
中科院分区：
文献类型：
--
作者：
Murafuji, T;Miyoshi, Y;Uno, H
检测了有机铋（III）和（V）化合物1-9对酵母酿酒酵母的抗真菌活性。在这些化合物中观察到明确的结构-活性关系。因此，三芳基铋二氯化物2 {（4-YC 6 H 4）（3）BiCl 2：Y = MeO，F，Cl，CF 3，CN，NO 2}和卤代铋烷6 {2-（BuSO2C6H4）-Bu-t（4-YC6H4）I3iX：Y = MeO，Me，H，Cl; X = Cl，Br，I}，7 {Bi（X）（C6H4-2- SO2C6H4-1'-）：X = Cl，Br，I，8 {2-Me2NCH2C6H4（Ph）BiX：X = Cl，Br}和9 {4-MeC 6 H4（8-Me_2NC_（10）H_（6 -1-）BiCl}对生长有抑制作用，而三芳基二氟化铋3 {（4-YC_（6 H_4））（3）BiF_2}和三芳基铋烷1 {（4-YC_（6 H_4）（3）Bi}，4 {2-（BuSO_2C_6 H_4）-Bu-t（4-YC_6 H_4）（2）Bi}和5 {4-YC_6 H_4 Bi（C_6 H_4 -2-SO_2C_6 H_4 - 1 ′-）}无论取代基的性质如何都没有活性。抑制作用的产生是由铋中心的亲核反应能力决定的，其中刘易斯酸性铋中心是一个活性中心。在所有的铋化合物中，二苯砜衍生的卤代铋烷7表现出最高的活性。X射线晶体学研究表明，Bi（Cl）（C6 H4 -2-SO2 C6 H4 - 1 '-）通过分子内和分子间的配位作用，形成了7配位构型，这在有机铋（III）化合物中是罕见的。7的显著抑制作用可能归因于这种高度配位的几何构型，其允许铋中心与在S生长中起重要作用的一些生物分子紧密结合。啤酒。(C)2004年爱思唯尔公司All rights reserved.
Antifungal activity of organobismuth(III) and (V) compounds 1-9 was examined against the yeast, Saccharomyces cerevisiae. A clear structure-activity relationship was observed in these compounds. Thus, triarylbismuth dichlorides 2 {(4-YC6H4)(3)BiCl2: Y = MeO, F, Cl, CF3, CN, NO2} and halobismuthanes 6 {2-(BuSO2C6H4)-Bu-t(4-YC6H4)I3iX: Y = MeO, Me, H, Cl; X = Cl, Br, I}, 7 {Bi(X)(C6H4-2- SO2C6H4-1'-): X = Cl, Br, I, 8 {2-Me2NCH2C6H4(Ph)BiX: X = Cl, Br} and 9 {4-MeC6H4(8-Me2NC10H6-1-)BiCl} showed the growth inhibition effect, while triarylbismuth difluorides 3 {(4-YC6H4)(3)BiF2} and triarylbismuthanes 1 {(4-YC6H4)(3)Bi}, 4 {2-(BuSO2C6H4)-Bu-t(4-YC6H4)(2)Bi} and 5 {4-YC6H4Bi(C6H4-2-SO2C6H4-1'-)} were not active at all irrespective of the nature of the substituents. Generation of the inhibition effect is governed by the facility of nucleophilic reaction at the bismuth center and the Lewis acidic bismuth center is an active site. Of all the bismuth compounds attempted, halobismuthanes 7 derived from diphenyl sulfone exhibited the highest activities. An X-ray crystallographic study of 7a {Bi(Cl)(C6H4-2-SO2C6H4-1'-)} revealed that the bismuth center adopts a seven-coordinated geometry, which is unusual in organobismuth(III) compounds, through the intramolecular and intermolecular coordination between the bismuth and oxygen atoms. The marked inhibition effect of 7 may be attributed to such a highly coordinated geometry, which allows the bismuth center to bind tightly with some biomolecules playing important roles in the growth of S. cerevisiae. (C) 2004 Elsevier Inc. All rights reserved.