A facile synthesis of antitumoral indeno[1,2-c]pyrazole-4-one by mild oxidation with molecular oxygen

被引:22
|
作者
Tao, ZF [1 ]
Sowin, TJ [1 ]
Lin, NH [1 ]
机构
[1] Abbott Labs, Canc Res, Global Pharmaceut Res & Dev, Abbott Pk, IL 60064 USA
关键词
indenopyrazole; pyrazoloindenone; oxidation; molecular oxygen; Suzuki coupling; Mitsunobu reaction; antitumor activity;
D O I
10.1016/j.tetlet.2005.08.147
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, convenient, and general synthetic method for indeno[1,2-c]pyrazole-4-ones through oxidation of indeno-pyrazoles by treatment with a base and molecular oxygen is described, and a possible mechanism for the oxidation is proposed. The product indeno[1,2-c]pyrazole-4-ones were elaborated further by Suzuki coupling and Mitsunobu reaction. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7615 / 7618
页数:4
相关论文
共 50 条
  • [41] SYNTHESIS OF PYRAZOLONE DERIVATIVES .22. SYNTHESIS OF BENZO-[4,5]CYCLOHEPTA[1,2-C]PYRAZOLE-DIONES
    ITO, I
    NAGAI, S
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1974, 22 (09) : 2131 - 2135
  • [42] Nano-Fe3O4-Cysteine as a Superior Catalyst for the Synthesis of Indeno[1,2-c]pyrazol-4(1H)-ones
    Safaei-Ghomi, Javad
    Ebrahimi, Seyyed Mohammad
    POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (05) : 2693 - 2703
  • [43] Design, Synthesis and Biological Evaluation of Novel Selective Thiol-based Histone Deacetylase(HDAC) VI Inhibitors Bearing Indeno[1,2-c]pyrazole or Benzoindazole Scaffold
    Xu Qihao
    Yu Shujia
    Cai Yijun
    Yang Jinyu
    Zhao Linxiang
    Liu Dan
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2018, 34 (01) : 75 - 83
  • [44] Design, synthesis and biological evaluation of novel selective thiol-based histone deacetylase(HDAC) VI inhibitors bearing indeno[1,2-c]pyrazole or benzoindazole scaffold
    Qihao Xu
    Shujia Yu
    Yijun Cai
    Jinyu Yang
    Linxiang Zhao
    Dan Liu
    Chemical Research in Chinese Universities, 2018, 34 : 75 - 83
  • [45] SYNTHESIS OF INDENO[1,2-C][1,2-LAMBDA-4,6]THIADIAZINES FROM S,S-DI-ALKYLSULFUR DIIMIDES
    RIED, W
    JACOBI, MA
    CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (04): : 805 - 808
  • [47] 2-Oxobenzo[h]chromene:: a novel entry for the concise and efficient synthesis of indeno[1,2-c]phenanthrenes
    Pratap, Ramendra
    Ram, Vishnu Ji
    TETRAHEDRON LETTERS, 2007, 48 (25) : 4379 - 4382
  • [48] Design, synthesis and biological evaluation of 1, 4-dihydro indeno[1,2-c] pyrazole linked oxindole analogues as potential anticancer agents targeting tubulin and inducing p53 dependent apoptosis
    Khan, Irfan
    Garikapati, Koteswara Rao
    Shaik, Anver Basha
    Makani, Venkata Krishna Kanth
    Rahim, Abdul
    Shareef, Mohd Adil
    Reddy, V. Ganga
    Pal-Bhadra, Manika
    Kamal, Ahmed
    Kumar, C. Ganesh
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 144 : 104 - 115
  • [49] Pentaleno[1,2-c:4,5-c′]dithiophene Derivatives: First Synthesis, Properties, and a Molecular Structure
    Konishi, Akihito
    Fujiwara, Takeru
    Ogawa, Noriko
    Hirao, Yasukazu
    Matsumoto, Kouzou
    Kurata, Hiroyuki
    Kubo, Takashi
    Kitamura, Chitoshi
    Kawase, Takeshi
    CHEMISTRY LETTERS, 2010, 39 (03) : 300 - 301
  • [50] SYNTHESIS, BENZODIAZEPINE RECEPTOR AFFINITY AND ANTICONVULSANT ACTIVITY OF 5-H-INDENO[1,2-C]PYRIDAZINE DERIVATIVES
    ALTOMARE, C
    CAMPAGNA, F
    CARTA, V
    CELLAMARE, S
    CAROTTI, A
    GENCHI, G
    DESARRO, G
    FARMACO, 1994, 49 (05): : 313 - 323