2,3-aziridino-4-<2-ethoxy>-2,3-cis-dihydro-1H-cyclopentanthracene-6,11-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,3-aziridino-4-<2-ethoxy>-2,3-cis-dihydro-1H-cyclopentanthracene-6,11-dione
• 英文别名: 2,3-aziridino-4-[2-(N,N-bis(2-chloroethyl)amino)ethoxy]-2,3-cis-dihydro-1H-cyclopent[a]anthracene-6,11-dione；(4R,6S)-8-[2-[bis(2-chloroethyl)amino]ethoxy]-5-azapentacyclo[8.8.0.02,7.04,6.012,17]octadeca-1,7,9,12,14,16-hexaene-11,18-dione
• 化学式: C₂₃H₂₂Cl₂N₂O₃
• 分子量: 445.345
• InChiKey: XDBCWWAIEDSVFI-DYESRHJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  5

上下游信息

反应信息

• 作为产物：
  描述：

  三(2-氯乙基)胺盐酸盐 在 吡啶 、 叠氮化锂 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.0h， 生成 2,3-aziridino-4-<2-ethoxy>-2,3-cis-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

• 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.