Substituted indoloquinolines as new antifungal agents

被引:68
作者
Ablordeppey, SY [1 ]
Fan, PC
Li, SM
Clark, AM
Hufford, CD
机构
[1] Florida A&M Univ, Coll Pharm & Pharmaceut Sci, Tallahassee, FL 32307 USA
[2] Univ Mississippi, Pharmaceut Sci Res Inst, Natl Ctr Nat Prod Res, Sch Pharm, University, MS 38677 USA
[3] Univ Mississippi, Dept Pharmacognosy, Sch Pharm, University, MS 38677 USA
关键词
D O I
10.1016/S0968-0896(01)00401-1
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Cryptolepine (2) possesses desirable properties to serve as a lead in developing new antifungal agents. Using SAR techniques, several analogues of cryptolepine were designed to increase potency and to broaden the antifungal spectrum over several opportunistic microorganisms. A number of 2-substituted indoloquinolines have been synthesized and evaluated in antifungal screens and several have been shown to increase potency and expand the antifungal spectrum of cryptolepine. Comparison of MICs of a number of these analogues with standard antifungal agents, shows them to be comparable to Amphotericin B and Ketoconazole. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1337 / 1346
页数:10
相关论文
共 38 条
[1]   H-1-NMR AND C-13-NMR ASSIGNMENTS OF CRYPTOLEPINE, A 3 - 4-BENZ-DELTA-CARBOLINE DERIVATIVE ISOLATED FROM CRYPTOLEPIS-SANGUINOLENTA [J].
ABLORDEPPEY, SY ;
HUFFORD, CD ;
BORNE, RF ;
DWUMABADU, D .
PLANTA MEDICA, 1990, 56 (04) :416-417
[2]   Probing the N-5 region of the indoloquinoline alkaloid, cryptolepine for anticryptococcal activity [J].
Ablordeppey, SY ;
Fan, PC ;
Clark, AM ;
Nimrod, A .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (02) :343-349
[3]  
Ablordeppey SY, 1999, CURR MED CHEM, V6, P1151
[4]  
ANSAASAMOAH R, 1983, 1 INT C CRYPT, P52
[5]   New synthesis of benzo-δ-carbolines, cryptolepines, and their salts:: In vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of δ-caribolines, benzo-δ-carbolines, and cryptolepines [J].
Arzel, E ;
Rocca, P ;
Grellier, P ;
Labaeïd, M ;
Frappier, F ;
Guéritte, F ;
Gaspard, C ;
Marsais, F ;
Godard, A ;
Quéguiner, G .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (06) :949-960
[6]  
Bailly C, 2000, ANTI-CANCER DRUG DES, V15, P191
[7]   Antihyperglycemic activities of cryptolepine analogues:: An ethnobotanical lead structure isolated from Cryptolepis sanguinolenta [J].
Bierer, DE ;
Dubenko, LG ;
Zhang, PS ;
Lu, Q ;
Imbach, PA ;
Garofalo, AW ;
Phuan, PW ;
Fort, DM ;
Litvak, J ;
Gerber, RE ;
Sloan, B ;
Luo, J ;
Cooper, R ;
Reaven, GM .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (15) :2754-2764
[8]   Ethnobotanical-directed discovery of the antihyperglycemic properties of cryptolepine:: Its isolation from Cryptolepis sanguinolenta, synthesis, and in vitro and in vivo activities [J].
Bierer, DE ;
Fort, DM ;
Mendez, CD ;
Luo, J ;
Imbach, PA ;
Dubenko, LG ;
Jolad, SD ;
Gerber, RE ;
Litvak, J ;
Lu, Q ;
Zhang, PS ;
Reed, MJ ;
Waldeck, N ;
Bruening, RC ;
Noamesi, BK ;
Hector, RF ;
Carlson, TJ ;
King, SR .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (06) :894-901
[9]   CRYPTOLEPINE HYDROCHLORIDE EFFECT ON STAPHYLOCOCCUS-AUREUS [J].
BOAKYEYIADOM, K ;
HEMANACKAH, SM .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1979, 68 (12) :1510-1514
[10]   Synthesis of substituted indeno[1,2-b]quinoline-6-carboxamides, [1]benzothieno[3,2-b]quinoline-4-carboxamides and 10H-quindoline-4-carboxamides:: Evaluation of structure-activity relationships for cytotoxicity [J].
Chen, JJ ;
Deady, LW ;
Desneves, J ;
Kaye, AJ ;
Finlay, GJ ;
Baguley, BC ;
Denny, WA .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (10) :2461-2466