Azolidene carbenes derived from biologically relevant molecules. Synthesis and characterization of iridium complexes of imidazolidene ligands based upon the antifungal drugs econazole and miconazole

被引:14
作者
Davis, JH [1 ]
Lake, CM
Bernard, MA
机构
[1] Univ S Alabama, Dept Chem, Mobile, AL 36688 USA
[2] Univ Alabama Birmingham, Dept Chem, Birmingham, AL 35294 USA
关键词
D O I
10.1021/ic9806277
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The azole-based antifungal drugs econazole and miconazole are readily converted into imidazolidene carbenes, which are trapped by coordination to iridium(I). The resulting complexes are the first antifungal drug-metal conjugates incorporating an M-C sigma bond. This demonstration of the capacity of azole-containing bioactive molecules to form carbene ligands may open the door to the investigation of complexes derived from such species for a variety of biological and medicinal purposes.
引用
收藏
页码:5412 / +
页数:3
相关论文
共 20 条
[1]   STABLE CARBENES AS STRONG BASES [J].
ALDER, RW ;
ALLEN, PR ;
WILLIAMS, SJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (12) :1267-1268
[2]   ELECTRON-DISTRIBUTION IN A STABLE CARBENE [J].
ARDUENGO, AJ ;
DIAS, HVR ;
DIXON, DA ;
HARLOW, RL ;
KLOOSTER, WT ;
KOETZLE, TF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6812-6822
[3]   A STABLE CRYSTALLINE CARBENE [J].
ARDUENGO, AJ ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363
[4]   Computer modelling of electron paramagnetic resonance-active molybdenum(v) species in xanthine oxidase [J].
Bray, MR ;
Deeth, RJ .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1997, (21) :4005-4009
[6]   SOME COMMENTS ON CARBON-HYDROGEN AND NITROGEN-HYDROGEN DISTANCES ASSUMED IN, AND DETERMINED FROM, RECENT X-RAY-DIFFRACTION STUDIES ON INORGANIC COMPLEXES [J].
CHURCHILL, MR .
INORGANIC CHEMISTRY, 1973, 12 (05) :1213-1214
[7]   N-heterocyclic carbenes [J].
Herrmann, WA ;
Kocher, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (20) :2162-2187
[8]  
Joule J. A., 1995, HETEROCYCLIC CHEM, DOI DOI 10.1007/978-1-4899-3222-8
[9]   Heterocyclic carbenes. One-pot synthesis of rhodium and iridium carbene complexes [J].
Kocher, C ;
Herrmann, WA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 532 (1-2) :261-265
[10]   Toward a novel metal-based chemotherapy against tropical diseases .3. Synthesis and antimalarial activity in vitro and in vivo of the new gold-chloroquine complex [Au(PPh3)(CQ)]PF6 [J].
Navarro, M ;
Perez, H ;
SanchezDelgado, RA .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (12) :1937-1939