4-[[(1S,2S,3R,4S,7R,10R,11R,12R,15S)-4,12-diacetyloxy-15-[(2S,4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carbonyl]oxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-11-yl]oxy]-4-oxobutanoic acid | 266676-48-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-[[(1S,2S,3R,4S,7R,10R,11R,12R,15S)-4,12-diacetyloxy-15-[(2S,4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carbonyl]oxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-11-yl]oxy]-4-oxobutanoic acid
• CAS: 266676-48-6
• 化学式: C₅₉H₆₃NO₁₇
• 分子量: 1058.15
• InChiKey: PYYCWQPPTJMCNM-NMCFRGRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  77
• 可旋转键数：
  19
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  237
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  4-[[(1S,2S,3R,4S,7R,10R,11R,12R,15S)-4,12-diacetyloxy-15-[(2S,4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carbonyl]oxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-11-yl]oxy]-4-oxobutanoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 生成 1-O-[[(2R,3S,4R,5R)-5-(6-chloropurin-9-yl)-3,4-dihydroxyoxolan-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：

  (7R,12S,15S)-2,7,8-三羟基-4-羰基-12-{[(2Z)-3-苯基丙-2-烯酰]氧代}-13,20-二脱氢-7,8,9,10,11,12,13,14-八氢-2,15:9,14-二环视网膜醇 在 palladium on activated charcoal 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四氧化锇 、 N-甲基吲哚酮 、 盐酸羟胺 、 四丁基氟化铵 、 氢气 、 sodium acetate 、 四丁基醋酸铵 、 copper(II) sulfate 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 丁酮 为溶剂， 反应 48.0h， 生成 4-[[(1S,2S,3R,4S,7R,10R,11R,12R,15S)-4,12-diacetyloxy-15-[(2S,4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carbonyl]oxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-11-yl]oxy]-4-oxobutanoic acid
  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