Fluoro-artemisinins:: When a gem-difluoroethylene replaces a carbonyl group

被引：170
作者：
Magueur, Guillaume [1 ]
Crousse, Benoit [1 ]
Ourevitch, Michle [1 ]
Bonnet-Delpon, Danile [1 ]
Begue, Jean-Pierre [1 ]
机构：
[1] Ctr Etud Pharmaceut, Biocis CNRS, UMR 8076, F-92296 Chatenay Malabry, France
来源：
JOURNAL OF FLUORINE CHEMISTRY | 2006年 / 127卷 / 4-5期
关键词：
gem-difluoroolefin; artemisinin; malaria; mimic effect; carbohydrate lactone;
D O I：
10.1016/j.jfluchem.2005.12.013
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Exo gem-difluoromethylene-artemisinins (8) has been designed to mimic artemisinin. The classical Wittig olefination reaction applied to artemisinin failed. An alternative reaction involving the generation of an alpha-CF3 carbanion, from the corresponding bromide 6, allowed the access to the target compound 8, and could also be exemplified in sugar series. The replacement of the carbonyl function by a difluoroethylene moiety resulted in a better antimalarial activity. (C) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码：637 / 642
页数：6
相关论文
共 34 条
  • [1] Synthesis and in vivo antimalarial activity of 12 alpha-trifluoromethyl-hydroartemisinin
    Abouabdellah, A
    Begue, JP
    BonnetDelpon, D
    Gantier, JC
    Nga, TTT
    Thac, TD
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (22) : 2717 - 2720
  • [2] The future of antimalarials:: artemisinins and synthetic endoperoxides
    Bégué, JP
    Bonnet-Delpon, D
    [J]. DRUGS OF THE FUTURE, 2005, 30 (05) : 509 - 518
  • [3] BEGUE JP, 2005, CHIMIE BIOORGANIQUE
  • [4] The effect of 10α-trifluoromethylhydroartemisinin on Plasmodium berghei infection and its toxicity in experimental animals
    Binh, PD
    Cong, LD
    Van Nhu, T
    Tien, NT
    Nhan, DH
    Bégue, JP
    Bonnet-Delpon, D
    Nga, TTT
    [J]. TRANSACTIONS OF THE ROYAL SOCIETY OF TROPICAL MEDICINE AND HYGIENE, 2002, 96 (06) : 677 - 683
  • [5] Fluorinated ylides and related compounds
    Burton, DJ
    Yang, ZY
    Qiu, WM
    [J]. CHEMICAL REVIEWS, 1996, 96 (05) : 1641 - 1715
  • [6] Fluoro artemisinins:: Difluoromethylene ketones
    Chorki, F
    Grellepois, F
    Crousse, B
    Ourévitch, M
    Bonnet-Delpon, D
    Bégué, JP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) : 7858 - 7863
  • [7] QUANTITATIVE ASSESSMENT OF ANTI-MALARIAL ACTIVITY INVITRO BY A SEMIAUTOMATED MICRODILUTION TECHNIQUE
    DESJARDINS, RE
    CANFIELD, CJ
    HAYNES, JD
    CHULAY, JD
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 16 (06) : 710 - 718
  • [8] Artemisinins target the SERCA of Plasmodium falciparum
    Eckstein-Ludwig, U
    Webb, RJ
    van Goethem, IDA
    East, JM
    Lee, AG
    Kimura, M
    O'Neill, PM
    Bray, PG
    Ward, SA
    Krishna, S
    [J]. NATURE, 2003, 424 (6951) : 957 - 961
  • [9] 2,2,2-Trifluoroethyl iodide
    Gilman, H
    Jones, RG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1943, 65 : 2037 - 2038
  • [10] Orally active antimalarials:: Hydrolytically stable derivatives of 10-trifluoromethyl anhydrodihydroartemisinin
    Grellepois, F
    Chorki, F
    Ourévitch, M
    Charneau, S
    Grellier, P
    McIntosh, KA
    Charman, WN
    Pradines, B
    Crousse, B
    Bonnet-Delpon, D
    Bégué, JP
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (06) : 1423 - 1433
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