1-O-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl] 4-O-[(1S,2S,3R,4S,7R,10R,11R,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-1,15-dihydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-11-yl] butanedioate | 266676-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl] 4-O-[(1S,2S,3R,4S,7R,10R,11R,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-1,15-dihydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-11-yl] butanedioate
• CAS: 266676-52-2
• 化学式: C₄₅H₅₅N₅O₁₆
• 分子量: 921.956
• InChiKey: OVGDRZHISSTLGL-MCBAAKIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  66.0
• 可旋转键数：
  12.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  294.04
• 氢给体数：
  3.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  1-O-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl] 4-O-[(1S,2S,3R,4S,7R,10R,11R,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-1,15-dihydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-11-yl] butanedioate 在 盐酸 、 4-二甲氨基吡啶 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 1-O-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl] 4-O-[(1S,2S,3R,4S,7R,10R,11R,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-11-yl] butanedioate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 9-functional heterocyclic coupled 7-deoxy-9-Dihydropaclitaxel analogue

  摘要：

  Novel 9-functional heterocyclic coupled 7-deoxy-9-dihydropaclitaxel analogues 17 and 22-24 synthesized from a natural taxoid 5-cinnamoyltriacetyltaxicin-I (3) and their biological evaluation in tubulin assembly activity and cytotoxicity in vitro against several human tumor cell lines are first presented. The biologically tested results show that 17, 22 and 23 are inactive in tubulin assembly assay and have no more remarkable cytotoxicities against human tumor cell lines SK-0V3, WIDR and MCF-7, though 22 and 23 exhibit more potent cytotoxicity against human liver cancer and human esophagus cancer cell lines (BEL-7402 and ECa-109) than paclitaxel. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00031-7
• 作为产物：
  描述：

  (1S,5S,6R,7S,8S,11R,12R,16R)-7-[[tert-butyl(dimethyl)silyl]oxymethyl]-7,8-dihydroxy-11,14,14,18,21,21-hexamethyl-2,4,13,15-tetraoxapentacyclo[15.3.1.01,5.06,11.012,16]henicos-17-ene-3,19-dione 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四丁基氟化铵 、 四丁基醋酸铵 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 丁酮 为溶剂， 反应 48.0h， 生成 1-O-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl] 4-O-[(1S,2S,3R,4S,7R,10R,11R,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-1,15-dihydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-11-yl] butanedioate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 9-functional heterocyclic coupled 7-deoxy-9-Dihydropaclitaxel analogue

  摘要：

  Novel 9-functional heterocyclic coupled 7-deoxy-9-dihydropaclitaxel analogues 17 and 22-24 synthesized from a natural taxoid 5-cinnamoyltriacetyltaxicin-I (3) and their biological evaluation in tubulin assembly activity and cytotoxicity in vitro against several human tumor cell lines are first presented. The biologically tested results show that 17, 22 and 23 are inactive in tubulin assembly assay and have no more remarkable cytotoxicities against human tumor cell lines SK-0V3, WIDR and MCF-7, though 22 and 23 exhibit more potent cytotoxicity against human liver cancer and human esophagus cancer cell lines (BEL-7402 and ECa-109) than paclitaxel. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00031-7