4-acetoxy-2,3-dihydro-1H-cyclopentanthracene-6,11-dione | 146518-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-acetoxy-2,3-dihydro-1H-cyclopentanthracene-6,11-dione
• 英文别名: 2,3-dihydro-4-acetoxy-1H-cyclopent[a]anthracene-6,11-dione；(6,11-dioxo-2,3-dihydro-1H-cyclopenta[a]anthracen-4-yl) acetate
• CAS: 146518-19-6
• 化学式: C₁₉H₁₄O₄
• 分子量: 306.318
• InChiKey: OQLWGFURNOXVIL-UHFFFAOYSA-N

物化性质

• 沸点：
  532.2±50.0 °C(predicted)
• 密度：
  1.356±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

上下游信息

反应信息

• 作为反应物：
  描述：

  4-acetoxy-2,3-dihydro-1H-cyclopentanthracene-6,11-dione 在 ammonium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 5.0h， 生成 4-<2-ethoxy>-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
• 作为产物：
  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

• Antitumor cyclopentnaphthoquinone and cyclopentanthraquinone derivatives
  申请人：Sloan-Kettering Institute for Cancer Research

  公开号：US05476952A1

  公开（公告）日：1995-12-19

  The present invention provides compounds having the structure: ##STR1## or having the structure: ##STR2## The present invention also provides a pharmaceutical compostion 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.

  本发明提供具有以下结构的化合物：##STR1## 或具有以下结构的化合物：##STR2## 本发明还提供含有这些化合物的药物组合物，合成这些化合物的方法，以及抑制肿瘤细胞生长和治疗患有肿瘤细胞增殖性疾病的受试者的方法。
• 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.