A simple and efficient synthesis of the ras farnesyl-protein transferase inhibitor chaetomellic acid A

被引:24
作者
Argade, NP [1 ]
Naik, RH [1 ]
机构
[1] NATL CHEM LAB,DIV ORGAN CHEM SYNTH,PUNE 411008,MAHARASHTRA,INDIA
关键词
D O I
10.1016/0968-0896(96)00076-4
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
A simple and efficient synthesis of the ras farnesyl-protein transferase inhibitor chaetomellic acid A anhydride (1) is reported. The imidazopyridinium bromide 5 obtained from the reaction of 2-bromopalmioyl chloride and 2-aminopyridine was reacted with maleic anhydride in the presence of NaOAc/AcOH to form 1 in 62% overall yield in three steps. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:881 / 883
页数:3
相关论文
共 15 条
  • [1] DECARBOXYLATIVE DIMERIZATION OF MALEIC-ANHYDRIDE TO DIMETHYLMALEIC ANHYDRIDE
    BAUMANN, ME
    BOSSHARD, H
    [J]. HELVETICA CHIMICA ACTA, 1978, 61 (07) : 2751 - 2753
  • [2] PREPARATION OF DISUBSTITUTED MALEIC ANHYDRIDES FROM REACTIVE 2-OXO-3H-IMIDAZO[1,2-ALPHA]PYRIDINIUM COMPOUNDS
    BAUMANN, ME
    BOSSHARD, H
    BREITENSTEIN, W
    RIST, G
    [J]. HELVETICA CHIMICA ACTA, 1986, 69 (02) : 396 - 403
  • [3] MECHANISM OF THE DECARBOXYLATIVE DIMERIZATION OF MALEIC-ANHYDRIDE TO DIMETHYLMALEIC ANHYDRIDE UNDER THE INFLUENCE OF 2-AMINOPYRIDINE
    BAUMANN, ME
    BOSSHARD, H
    BREITENSTEIN, W
    RIHS, G
    WINKLER, T
    [J]. HELVETICA CHIMICA ACTA, 1984, 67 (07) : 1897 - 1905
  • [4] A COBALOXIME-MEDIATED RADICAL ROUTE TO BUTENOLIDES
    BRANCHAUD, BP
    SLADE, RM
    JANISSE, SK
    [J]. TETRAHEDRON LETTERS, 1993, 34 (49) : 7885 - 7888
  • [5] A COBALOXIME-MEDIATED SYNTHESIS OF THE RAS FARNESYL-PROTEIN TRANSFERASE INHIBITOR CHAETOMELLIC ACID-A
    BRANCHAUD, BP
    SLADE, RM
    [J]. TETRAHEDRON LETTERS, 1994, 35 (24) : 4071 - 4072
  • [6] IRIDIUM-MALEOYL COMPLEXES FROM TRICARBONYLIRIDIUM HALIDES AND ACETYLENES
    CANZIANI, F
    MALATESTA, MC
    LONGONI, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (07) : 267 - 268
  • [7] RAS C-TERMINAL PROCESSING ENZYMES - MINIREVIEW NEW DRUG TARGETS
    GIBBS, JB
    [J]. CELL, 1991, 65 (01) : 1 - 4
  • [8] GIBBS JB, 1993, J BIOL CHEM, V268, P7617
  • [9] A STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED MALEIC ESTERS BY USE OF PHOSPHONATES
    HUFF, RK
    MOPPETT, CE
    SUTHERLA.JK
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (22): : 2725 - &
  • [10] JANITSCHKE L, 1976, SYNTHESIS-STUTTGART, P314