(1S,2S)-1,2-Dihydroxy-3,3,12-trimethyl-1,2,3,12-tetrahydro-pyrano[2,3-c]acridin-7-one | 169956-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (1S,2S)-1,2-Dihydroxy-3,3,12-trimethyl-1,2,3,12-tetrahydro-pyrano[2,3-c]acridin-7-one
• 英文别名: 7H-Pyrano[2,3-c]acridin-7-one, 1,2,3,12-tetrahydro-1,2-dihydroxy-3,3,12-trimethyl-, cis-；(1S,2S)-1,2-dihydroxy-3,3,12-trimethyl-1,2-dihydropyrano[2,3-c]acridin-7-one
• CAS: 169956-95-0
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: XWRPQXPIFGFDFJ-ROUUACIJSA-N

物化性质

• 沸点：
  509.0±50.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N'-羰基二咪唑 、 (1S,2S)-1,2-Dihydroxy-3,3,12-trimethyl-1,2,3,12-tetrahydro-pyrano[2,3-c]acridin-7-one 以 丁酮 为溶剂， 反应 3.0h， 以61%的产率得到(+/-)-cis-1,2-di-O-carbonyl-1,2-dihydroxy-1,2-dihydro-6-demethoxyacronycine
  参考文献：
  名称：

  Synthesis and Cytotoxic and Antitumor Activity of Esters in the 1,2-Dihydroxy-1,2-dihydroacronycine Series

  摘要：

  Seven 1,2-dihydroxy-1,2-dihydroacronycine and 1,2-dihydroxy-1,2-dihydro-6-demethoxyacronycine esters and diesters were synthesized via osmic oxidation of acronycine or 6-demethoxyacronycine followed by acylation. The 6-demethoxyacronycine derivatives were found to be inactive, whereas in contrast, all of the acronycine derivatives were more potent than acronycine itself when tested against L1210 cells in vitro. Four selected acronycine derivatives (17, 19, 21, and 22) were evaluated in vivo against murine P388 leukemia and colon 38 adenocarcinoma implanted in mice. All compounds were markedly active against P388 at doses 4-16-fold lower than acronycine itself. Against the colon 38 adenocarcinoma, the three compounds 17, 21, and 22 were highly efficient. 1,2-Diacetoxy-1,2-dihydroacronycine (17) was the most active, all the treated mice being tumor-free on day 23.

  DOI：

  10.1021/jm9602975
• 作为产物：
  描述：

  6-demethoxyacronycine 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 2.0h， 以65%的产率得到(1S,2S)-1,2-Dihydroxy-3,3,12-trimethyl-1,2,3,12-tetrahydro-pyrano[2,3-c]acridin-7-one
  参考文献：
  名称：

  Synthesis and Cytotoxic and Antitumor Activity of Esters in the 1,2-Dihydroxy-1,2-dihydroacronycine Series

  摘要：

  Seven 1,2-dihydroxy-1,2-dihydroacronycine and 1,2-dihydroxy-1,2-dihydro-6-demethoxyacronycine esters and diesters were synthesized via osmic oxidation of acronycine or 6-demethoxyacronycine followed by acylation. The 6-demethoxyacronycine derivatives were found to be inactive, whereas in contrast, all of the acronycine derivatives were more potent than acronycine itself when tested against L1210 cells in vitro. Four selected acronycine derivatives (17, 19, 21, and 22) were evaluated in vivo against murine P388 leukemia and colon 38 adenocarcinoma implanted in mice. All compounds were markedly active against P388 at doses 4-16-fold lower than acronycine itself. Against the colon 38 adenocarcinoma, the three compounds 17, 21, and 22 were highly efficient. 1,2-Diacetoxy-1,2-dihydroacronycine (17) was the most active, all the treated mice being tumor-free on day 23.

  DOI：

  10.1021/jm9602975