Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities

被引：108
作者：
Madrid, PB
Sherrill, J
Liou, AP
Weisman, JL
DeRisi, JL
Guy, RK [1 ]
机构：
[1] Univ Calif San Francisco, Dept Pharmaceut Chem, San Francisco, CA 94143 USA
[2] Univ Calif San Francisco, Dept Biochem & Biophys, San Francisco, CA 94143 USA
[3] Univ Calif San Francisco, Dept Cellular & Mol Pharmacol, San Francisco, CA 94143 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2005年 / 15卷 / 04期
关键词：
D O I：
10.1016/j.bmcl.2004.12.037
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A simple two-step synthesis method was used to make 51 B-ring-substituted 4-hydroxyquinolines allowing analysis of the effect of ring substitutions on inhibition of growth of chloroquine sensitive and resistant strains of Plasmodium falciparum, the dominant cause of malaria morbidity. Substituted quinoline rings other than the 7-chloroquinoline ring found in chloroquine were found to have significant activity against the drug-resistant strain of P. falciparum W2. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1015 / 1018
页数：4
相关论文
共 50 条
  • [41] TIN(IV) CHLORIDE-PROMOTED SYNTHESIS OF 4-AMINOPYRIDINES AND 4-AMINOQUINOLINES
    VERONESE, AC
    CALLEGARI, R
    MORELLI, CF
    TETRAHEDRON, 1995, 51 (45) : 12277 - 12284
  • [42] SPECTROPHOTOMETRIC AND POTENTIOMETRIC EVALUATION OF APPARENT ACID DISSOCIATION EXPONENTS OF VARIOUS 4-AMINOQUINOLINES
    IRVIN, JL
    IRVIN, EM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (05) : 1091 - 1099
  • [43] SYNTHESIS OF SOME RING-SUBSTITUTED [1]FERROCENOPHANES AND THE STRUCTURE OF 4 REPRESENTATIVE EXAMPLES
    BUTLER, IR
    CULLEN, WR
    EINSTEIN, FWB
    RETTIG, SJ
    WILLIS, AJ
    ORGANOMETALLICS, 1983, 2 (01) : 128 - 135
  • [44] THE MODE OF ACTION OF CHLOROQUINE - NON-WEAK BASE PROPERTIES OF 4-AMINOQUINOLINES AND ANTIMALARIAL EFFECTS ON STRAINS OF PLASMODIUM
    VEIGNIE, E
    MOREAU, S
    ANNALS OF TROPICAL MEDICINE AND PARASITOLOGY, 1991, 85 (02): : 229 - 237
  • [45] 4-Aminoquinolines Bearing a 1,3-Benzodioxole Moiety: Synthesis and Biological Evaluation as Potential Antifungal Agents
    Yang, Rui
    Li, Zhuolin
    Xie, Jialing
    Liu, Jianchuan
    Qin, Tianhong
    Liu, Junda
    Du, Haiying
    Ye, Haoyun
    CHEMISTRY & BIODIVERSITY, 2021, 18 (05)
  • [46] Antimalarial versus Cytotoxic Properties of Dual Drugs Derived From 4-Aminoquinolines and Mannich Bases: Interaction with DNA
    Wenzel, Nicole I.
    Chavain, Natascha
    Wang, Yulin
    Friebolin, Wolfgang
    Maes, Louis
    Pradines, Bruno
    Lanzer, Michael
    Yardley, Vanessa
    Brun, Reto
    Herold-Mende, Christel
    Biot, Christophe
    Toth, Katalin
    Davioud-Charvet, Elisabeth
    JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (08) : 3214 - 3226
  • [47] In vitro activities of piperaquine and other 4-aminoquinolines against clinical isolates of Plasmodium falciparum in Cameroon
    Basco, LK
    Ringwald, P
    ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2003, 47 (04) : 1391 - 1394
  • [48] SYNTHESIS AND BIOLOGICAL ACTIVITY OF SOME RING-SUBSTITUTED TRYPTAMINES
    HUNT, RR
    BRIMBLEC.RW
    JOURNAL OF MEDICINAL CHEMISTRY, 1967, 10 (04) : 646 - &
  • [49] Structure-activity relationships for antiplasmodial activity among 7-substituted 4-aminoquinolines
    De, DYD
    Krogstad, FM
    Byers, LD
    Krogstad, DJ
    JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (25) : 4918 - 4926
  • [50] Synthesis and antimycobacterial activities of ring-substituted quinolinecarboxylic acid/ester analogues. Part 1
    Vaitilingam, B
    Nayyar, A
    Palde, PB
    Monga, V
    Jain, R
    Kaur, S
    Singh, PP
    BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (15) : 4179 - 4188
12345