Efficient microwave-assisted synthesis of new sulfonylbenzimidazole-4,7-diones: heterocyclic quinones with potential antitumor activity

被引:50
作者
Boufatah, N [1 ]
Gellis, A [1 ]
Maldonado, J [1 ]
Vanelle, P [1 ]
机构
[1] Univ Mediterranee, Fac Pharm, Lab Chim Organ Pharmaceut, CNRS,UM R6517,LCOP, F-13385 Marseille 5, France
关键词
benzimidazole-4,7-diones; microwave irradiation; S-alkylation; sulfones;
D O I
10.1016/j.tet.2004.07.070
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New benzimidazoloquinones substituted at 2-position by a sulfonyl group have been synthesized via a final microwave assisted step using 2-chloromethyl-1,5,6-trimethylbenzimidazole-4,7-dione 7 as starting material. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9131 / 9137
页数:7
相关论文
共 41 条
  • [1] Benzimidazole-4,7-diones as inhibitors of protozoal (Toxoplasma gondii) purine nucleoside phosphorylase
    Alvarez, F
    Ghérardi, A
    Nebois, P
    Sarciron, ME
    Pétavy, AF
    Walchshofer, N
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (06) : 977 - 979
  • [2] HETEROCYCLIC QUINONES WITH POTENTIAL ANTITUMOR-ACTIVITY .2. SYNTHESIS AND ANTITUMOR-ACTIVITY OF SOME BENZIMIDAZOLE-4,7-DIONE DERIVATIVES
    ANTONINI, I
    CLAUDI, F
    CRISTALLI, G
    FRANCHETTI, P
    GRIFANTINI, M
    MARTELLI, S
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (01) : 260 - 264
  • [3] Indolequinone antitumor agents: Relationship between quinone structure and rate of metabolism by recombinant human NQO1
    Beall, HD
    Hudnott, AR
    Winski, S
    Siegel, D
    Swann, E
    Ross, D
    Moody, CJ
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (05) : 545 - 548
  • [4] Multistep synthesis of thiazoloquinazolines under microwave irradiation in solution
    Besson, T
    Guillard, J
    Rees, CW
    [J]. TETRAHEDRON LETTERS, 2000, 41 (07) : 1027 - 1030
  • [5] Expeditious routes to 4-alkoxyquinazoline-2-carbonitriles and thiocarbamates via N-arylimino-1,2,3-dithiazoles using microwave irradiation
    Besson, T
    Dozias, MJ
    Guillard, J
    Jacquault, P
    Legoy, MD
    Rees, CW
    [J]. TETRAHEDRON, 1998, 54 (23) : 6475 - 6484
  • [6] MICROWAVE-ASSISTED ORGANIC-REACTIONS
    CADDICK, S
    [J]. TETRAHEDRON, 1995, 51 (38) : 10403 - 10432
  • [7] CHAI SY, 2002, Patent No. 6444694
  • [8] Application of focused microwaves to the scale-up of solvent-free organic reactions
    Cléophax, J
    Liagre, M
    Loupy, A
    Petit, A
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2000, 4 (06) : 498 - 504
  • [9] EO9 phase II study in advanced breast, gastric, pancreatic and colorectal carcinoma by the EORTC early clinical studies group
    Dirix, LY
    Tonnesen, F
    Cassidy, J
    Epelbaum, R
    Huinink, WWT
    Pavlidis, N
    Sorio, R
    Gamucci, T
    Wolff, I
    TeVelde, A
    Lan, J
    Verweij, J
    [J]. EUROPEAN JOURNAL OF CANCER, 1996, 32A (11) : 2019 - 2022
  • [10] Development of novel quinone phosphorodiamidate prodrugs targeted to DT-diaphorase
    Flader, C
    Liu, JW
    Borch, RF
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (16) : 3157 - 3167