[(1S,5S,6R,8S,11R,12R,16R)-11,14,14,18,21,21-hexamethyl-7-methylidene-3,19-dioxo-2,4,13,15-tetraoxapentacyclo[15.3.1.01,5.06,11.012,16]henicos-17-en-8-yl] (E)-3-phenylprop-2-enoate | 532402-59-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: [(1S,5S,6R,8S,11R,12R,16R)-11,14,14,18,21,21-hexamethyl-7-methylidene-3,19-dioxo-2,4,13,15-tetraoxapentacyclo[15.3.1.01,5.06,11.012,16]henicos-17-en-8-yl] (E)-3-phenylprop-2-enoate
• CAS: 532402-59-8
• 化学式: C₃₃H₃₈O₈
• 分子量: 562.66
• InChiKey: DNMAUPBSXWQUPL-GRNHTALPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  41
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(1S,5S,6R,8S,11R,12R,16R)-11,14,14,18,21,21-hexamethyl-7-methylidene-3,19-dioxo-2,4,13,15-tetraoxapentacyclo[15.3.1.01,5.06,11.012,16]henicos-17-en-8-yl] (E)-3-phenylprop-2-enoate 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吲哚酮 、 盐酸羟胺 、 四丁基氟化铵 、 sodium acetate 、 四丁基醋酸铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 48.0h， 生成 4-[[(1S,2S,3R,4S,7R,10R,11R,12R)-4,12-diacetyloxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-15-oxo-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
• 作为产物：
  描述：

  2,9,10-triacetyl-5-O-cinnamoyltaxicin-I 在 吡啶 、 sodium methylate 、 copper(II) sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 [(1S,5S,6R,8S,11R,12R,16R)-11,14,14,18,21,21-hexamethyl-7-methylidene-3,19-dioxo-2,4,13,15-tetraoxapentacyclo[15.3.1.01,5.06,11.012,16]henicos-17-en-8-yl] (E)-3-phenylprop-2-enoate
  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

文献信息

• Semisynthesis of 7-Deoxypaclitaxel Derivatives Devoid of an Oxetane D-Ring, Starting from Taxine B
  作者：Patrick H. Beusker、Harald Veldhuis、Johan Brinkhorst、Dennis G. H. Hetterscheid、Nicolas Feichter、Anthony Bugaut、Hans W. Scheeren

  DOI：10.1002/ejoc.200390109

  日期：2003.2

  Six 7-deoxypaclitaxel derivatives have been prepared from taxine B; they contribute to understanding of the effect of the oxetane D-ring in paclitaxel on the cytotoxic activity of paclitaxel. Three of these analogues each contain a double bond instead of a D-ring at the C-4 position, while two others each contain a three-membered ring in place of the oxetane ring. Both the C-4 double bond and the small

  以紫杉碱B为原料制备了6种7-脱氧紫杉醇衍生物；它们有助于了解紫杉醇中的氧杂环丁烷 D 环对紫杉醇细胞毒活性的影响。这些类似物中的三个在 C-4 位置各自包含一个双键而不是 D 环，而另外两个每个包含一个三元环代替氧杂环丁烷环。这些紫杉醇衍生物中的 C-4 双键和小 D 环都旨在作为紫杉醇氧杂环丁烷 D 环的替代物，并预期将一种刚性和类似的构象施加到紫杉烷骨架和侧基上紫杉醇中的氧杂环丁烷环产生的。相对于紫杉醇，所有衍生物都表现出显着降低的体外细胞毒活性——对一组七种充分表征的人类肿瘤细胞系。从这里报道的紫杉醇衍生物的构效关系得出的一般情况是，如果紫杉醇衍生物要保留在与紫杉醇氧杂环丁烷环中氧原子相似的空间位置上，则氧原子的存在很重要。相当大的细胞毒活性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003) 从这