(S)-9-[(2S,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4,11-diethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione | 121080-61-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 喜树碱
• 英文名称: (S)-9-[(2S,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4,11-diethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione
• 英文别名: (19S)-7-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-10,19-diethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
• CAS: 121080-61-3
• 化学式: C₃₄H₄₀N₂O₁₅
• 分子量: 716.696
• InChiKey: AICFDENDAJHFAC-HNGVZWCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  51
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  258
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  7-乙基-10-羟基喜树碱 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 6.5h， 生成 (S)-9-[(2S,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4,11-diethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione
  参考文献：
  名称：

  Chemical Modification of an Antitumor Alkaloid, 20(S)-Camptothecin: Glycosides, Phosphates and Sulfates of 7-Ethyl-10-hydroxycamptothecin.

  摘要：

  从 7-乙基-10-羟基喜树碱（1）开始，合成了内酯环完整的水溶性衍生物。1 的酚羟基糖苷（2）是在丙酮或丙酮水溶液中，在碳酸钾的存在下，与乙酰化的 α-溴糖反应，然后进行脱保护而得到的。单磷酸盐（3p）和硫酸盐（4a 和 4b）的有机铵盐对体内的 L1210 具有显著的活性。

  DOI：

  10.1248/cpb.40.131

文献信息

• Chemical Modification of an Antitumor Alkaloid, 20(S)-Camptothecin: Glycosides, Phosphates and Sulfates of 7-Ethyl-10-hydroxycamptothecin.
  作者：Takashi YAEGASHI、Ken-ichiro NOKATA、Seigo SAWADA、Tomio FURUTA、Teruo YOKOKURA、Tadasi MIYASAKA

  DOI：10.1248/cpb.40.131

  日期：——

  Water-soluble derivatives having the lactone ring intact were synthesized starting from 7-ethyl-10-hydroxycamptothecin (1). Glycosides (2) of the phenolic hydroxyl group of 1 were obtained by reaction with acetylated α-bromosugars in acetone or aqueous acetone in the presence of potassium carbonate, followed by deprotection.Phosphates (3) were prepared by reaction of 1 with phosphoryl chloride in pyridine or with dibenzylchlorophosphoridate.Sulfates (4) were obtained by reaction of 1 with sulfur trioxide-pyridine complex in the presence of a tertiary amine.The organic ammonium salts of monophosphate (3p) and sulfates (4a and 4b) showed significant activity against L1210 in vivo.

  从 7-乙基-10-羟基喜树碱（1）开始，合成了内酯环完整的水溶性衍生物。1 的酚羟基糖苷（2）是在丙酮或丙酮水溶液中，在碳酸钾的存在下，与乙酰化的 α-溴糖反应，然后进行脱保护而得到的。单磷酸盐（3p）和硫酸盐（4a 和 4b）的有机铵盐对体内的 L1210 具有显著的活性。