Efficient synthesis of nevirapine analogs to study its metabolic profile by click fishing

被引:7
作者
Bernard, Sylvain [1 ]
Defoy, Daniel [2 ]
Dory, Yves L. [1 ]
Klarskov, Klaus [2 ]
机构
[1] Univ Sherbrooke, Dept Chim, Inst Pharmacol Sherbrooke, Sherbrooke, PQ J1H 5N4, Canada
[2] Univ Sherbrooke, Dept Pharmacol, Inst Pharmacol Sherbrooke, Sherbrooke, PQ J1H 5N4, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
Nevirapine; Synthesis; 5-Exo-dig cyclization; Click coupling; INDUCED SKIN RASH; REVERSE-TRANSCRIPTASE; CYCLOADDITION; INHIBITORS; CHEMISTRY;
D O I
10.1016/j.bmcl.2009.09.011
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Knowledge of the biotransformation and pharmacokinetics of the antiretroviral agent nevirapine is still insufficient. In order to trace rash inducing metabolites of nevirapine, we devised a short and efficient multi-gram synthesis of a nevirapine analog that can be coupled to azide containing compounds by click chemistry. (c) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6127 / 6130
页数:4
相关论文
共 30 条
  • [1] Preparation of 4-substituted 3-amino-2-chloropyridines, synthesis of a Nevirapine analogue
    Bakke, JM
    Riha, J
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (01) : 99 - 104
  • [2] RULES FOR RING-CLOSURE
    BALDWIN, JE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) : 734 - 736
  • [3] Rhodium(I)-catalyzed carbonyl allenylation versus propargylation via redox transmetalation across tetragonal tin(II) oxide
    Banerjee, M
    Roy, S
    [J]. ORGANIC LETTERS, 2004, 6 (13) : 2137 - 2140
  • [4] BOSWELL RF, 2004, Patent No. 2004002603
  • [5] CHANTANA SL, 2006, J MACROMOL SCI CHEM, V43, P1929
  • [6] Demonstration of the metabolic pathway responsible for nevirapine-induced skin rash
    Chen, Jie
    Mannargudi, Baskar M.
    Xu, Ling
    Uetrecht, Jack
    [J]. CHEMICAL RESEARCH IN TOXICOLOGY, 2008, 21 (09) : 1862 - 1870
  • [7] CUIHONG L, 2007, LANGMUIR, V23, P6754
  • [8] SYNTHESIS OF NEVIRAPINE AND ITS MAJOR METABOLITE
    GROZINGER, KG
    FUCHS, V
    HARGRAVE, KD
    MAULDIN, S
    VITOUS, J
    CAMPBELL, S
    ADAMS, J
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (01) : 259 - 263
  • [9] Synthesis of five nevirapine metabolites
    Grozinger, KG
    Byrne, DP
    Nummy, LJ
    Ridges, MD
    Salvagno, A
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (02) : 229 - 239
  • [10] NOVEL NONNUCLEOSIDE INHIBITORS OF HIV-1 REVERSE-TRANSCRIPTASE .1. TRICYCLIC PYRIDOBENZODIAZEPINONES AND DIPYRIDODIAZEPINONES
    HARGRAVE, KD
    PROUDFOOT, JR
    GROZINGER, KG
    CULLEN, E
    KAPADIA, SR
    PATEL, UR
    FUCHS, VU
    MAULDIN, SC
    VITOUS, J
    BEHNKE, ML
    KLUNDER, JM
    PAL, K
    SKILES, JW
    MCNEIL, DW
    ROSE, JM
    CHOW, GC
    SKOOG, MT
    WU, JC
    SCHMIDT, G
    ENGEL, WW
    EBERLEIN, WG
    SABOE, TD
    CAMPBELL, SJ
    ROSENTHAL, AS
    ADAMS, J
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (07) : 2231 - 2241