1-Acetoxy-1-(cyclopent-1-enyl)ethene | 69289-13-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-Acetoxy-1-(cyclopent-1-enyl)ethene
• 英文别名: 1-(Cyclopenten-1-yl)ethenyl acetate
• CAS: 69289-13-0
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: ZIDZPFHEWDXSJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Acetoxy-1-(cyclopent-1-enyl)ethene 在 palladium on activated charcoal 作用下， 以 甲苯 为溶剂， 生成 4-acetoxy-2,3-dihydro-1H-cyclopentanthracene-6,11-dione
  参考文献：
  名称：

  Synthesis of cyclopentanthraquinones: analogs of mitomycin C

  摘要：

  2,3-Dihydro-1H-cyclopent[a]anthracene-6,11-dione (cyclopentanthraquinone) derivatives bearing a mustard side chain at C-4 and an aziridine ring at the cyclopentene moiety were synthesized. Such a compound may be viewed as an analogue of mitomycin C (MC) and may exhibit bifunctional DNA-alkylating and DNA-intercalating agent. The key intermediate, 4-hydroxy-2,3-di-O-substituted cyclopentanthraquinone, was synthesized by Deils-Alder reaction of naphthoquinone with various 4,5-dihydroxy-1-vinylcyclopent-1-ene derivatives. Introduction of a mustard side chain to the OH group at C-4 and subsequent construction of an aziridine-ring on C2-C3 of the cyclopentanthraquinone molecule furnished the target compound, 2,3-aziridino-4-[2-[NN-bis(2-chloroethyl)amino]ethoxy]-2,3-dihydro-1H-cyclopent [a] anthracene-6,11-dione (37). It was found that both the aziridine function and the mustard side chain play a significant role in their cytotoxicity against leukemic L1210 and HL-60 cell growth in culture and the inhibition of topoisomerase II kDNA decatenation.

  DOI：

  10.1021/jo00059a014

文献信息

• Diels-alder reactions of 2-carbomethoxy-4,4-dimethylcyclopentenone
  作者：Drury Caine、Charles R. Harrison、Donald G. VanDerveer

  DOI：10.1016/s0040-4039(00)81654-8

  日期：1983.1
• US5476952A
  申请人：——

  公开号：US5476952A

  公开（公告）日：1995-12-19
• [EN] ANTITUMOR CYCLOPENTANPHTHOQUINONE AND CYCLOPENTANTHRAQUINONE DERIVATIVES<br/>[FR] DERIVES DE CYCLOPENTANAPHTOQUINONE ET DE CYCLOPENTANTHRAQUINONE A ACTION ANTITUMORALE
  申请人：SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH

  公开号：WO1994020094A1

  公开（公告）日：1994-09-15

  (EN) The present invention provides compounds having structure (I) or having structure (II). The present invention also provides a pharmaceutical composition containing the compounds, methods of synthesizing the compounds, as well as methods of inhibiting growth of tumor cells and of treating a subject having a disease characterized by the proliferation of tumor cells.(FR) L'invention se rapporte à des composés ayant la structure (I) ou la structure (II). L'invention décrit également une composition pharmaceutique contenant ces composés, des procédés de synthèse de ces composés, ainsi que des procédés pour inhiber la croissance de cellules tumorales et pour traiter un sujet atteint d'une maladie se caractérisant par une prolifération de cellules tumorales.
• Synthesis of cyclopentanthraquinones: analogs of mitomycin C
  作者：Bernd Kohler、Tsann Long Su、Ting Chao Chou、Xiang Jun Jiang、Kyoichi A. Watanabe

  DOI：10.1021/jo00059a014

  日期：1993.3

  2,3-Dihydro-1H-cyclopent[a]anthracene-6,11-dione (cyclopentanthraquinone) derivatives bearing a mustard side chain at C-4 and an aziridine ring at the cyclopentene moiety were synthesized. Such a compound may be viewed as an analogue of mitomycin C (MC) and may exhibit bifunctional DNA-alkylating and DNA-intercalating agent. The key intermediate, 4-hydroxy-2,3-di-O-substituted cyclopentanthraquinone, was synthesized by Deils-Alder reaction of naphthoquinone with various 4,5-dihydroxy-1-vinylcyclopent-1-ene derivatives. Introduction of a mustard side chain to the OH group at C-4 and subsequent construction of an aziridine-ring on C2-C3 of the cyclopentanthraquinone molecule furnished the target compound, 2,3-aziridino-4-[2-[NN-bis(2-chloroethyl)amino]ethoxy]-2,3-dihydro-1H-cyclopent [a] anthracene-6,11-dione (37). It was found that both the aziridine function and the mustard side chain play a significant role in their cytotoxicity against leukemic L1210 and HL-60 cell growth in culture and the inhibition of topoisomerase II kDNA decatenation.