2,9,10-triacetyl-5-O-cinnamoyltaxicin-I | 13452-36-3

• 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: 2,9,10-triacetyl-5-O-cinnamoyltaxicin-I
• 英文别名: 5-cinnamoyltaxicin I triacetate；5-cinnamoyltriacetyltaxicin I；O-cinnamoyltaxicin；1-hydroxytaxinine；5-Cinnamoyltaxicin-I 2,9,10-triacetate；o-Cinnamoyltaxicin-i triacetate；[(1S,2S,3R,5S,8R,9R,10R)-2,9,10-triacetyloxy-1-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxo-5-tricyclo[9.3.1.03,8]pentadec-11-enyl] (E)-3-phenylprop-2-enoate
• CAS: 13452-36-3
• 化学式: C₃₅H₄₂O₁₀
• 分子量: 622.712
• InChiKey: VBLNERPSGWCFQJ-NINUBRFRSA-N

物化性质

• 熔点：
  237-239°
• 比旋光度：
  D18 +218° (chloroform)
• 沸点：
  690.2±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,9,10-triacetyl-5-O-cinnamoyltaxicin-I 在 吡啶 、 四氧化锇 、 盐酸羟胺 、 四丁基氟化铵 、 sodium methylate 、 sodium acetate 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 70.17h， 生成 (3aS,7aR,10aR,10bR,13S,14S,14aR,14bS)-13,14-dihydroxy-14-(hydroxymethyl)-6,10b,15,15-tetramethyl-10a,10b,11,12,13,14,14a,14b-octahydro-4H-3a,7-methanobenzo[3,4]cyclodeca[1,2-d:5,6-d']bis([1,3]dioxole)-2,5,9(7aH)-trione
  参考文献：
  名称：

  The Synthesis and Biological Activity of 9- and 2′-cAMP 7-Deoxypaclitaxel Analogues from 5-Cinnamoyltriacetyltaxicin-I

  摘要：

  The synthesis and biological activity of new 7-deoxypaclitaxel analogues 3 and 4 in which the hydroxy group at C-2' of the sidechain, C-9 and C-10 in the B-ring are substituted by cAMP and benozoyloxy group respectively are presented. These derivatives have been first synthesized from a natural taxoid 5-cinnamoyltriacetyltaxicin-1 5 and tested in vitro for cytotoxicity against three human tumor cell lines. The biologically tested results indicate 3 having more potent cytotoxicity and 4 having a remarkably reduced cytotoxicity as well as 33 having no much effect on cytotoxicity against all human tumor cell lines tested in comparison to that of paclitaxel. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00073-9
• 作为产物：
  描述：

  在 咪唑 、 4-二甲氨基吡啶 、 四氧化锇 、 伯吉斯试剂 、 2,4,6-三氯苯甲酰氯 、 氟化氢吡啶 、 N-甲基吗啉氧化物 、 三乙胺 、 pyridinium chlorochromate 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 95.5h， 生成 2,9,10-triacetyl-5-O-cinnamoyltaxicin-I
  参考文献：
  名称：

  Total Synthesis of 1‐Hydroxytaxinine

  摘要：

  Abstract1‐Hydroxytaxinine (1) is a cytotoxic taxane diterpenoid. Its central eight‐membered B‐ring possesses four oxygen‐functionalized centers (C1, C2, C9, and C10) and two quaternary carbon centers (C8 and C15), and is fused with six‐membered A‐ and C‐rings. The densely functionalized and intricately fused structure of 1 makes it a highly challenging synthetic target. Reported here is an efficient radical‐based strategy for assembling 1 from A‐ and C‐ring fragments. The A‐ring bearing an α‐alkoxyacyl telluride moiety underwent intermolecular coupling with the C‐ring fragment by a Et3B/O2‐promoted decarbonylative radical formation. After construction of the C8‐quaternary stereocenter, a pinacol coupling reaction using a low‐valent titanium reagent formed the B‐ring with stereoselective installation of the C1,C2‐diol. Subsequent manipulations at the A‐ and C‐rings furnished 1 in 26 total steps.

  DOI：

  10.1002/anie.201906872

文献信息

• A 3,11-cyclotaxane from Taxus baccata
  作者：Giovanni Appendino、Patrizia Lusso、Pierluigi Gariboldi、Ezio Bombardelli、Bruno Gabetta

  DOI：10.1016/0031-9422(92)80455-n

  日期：1992.12

  Abstract A collection of yew needles afforded a taxane diester characterized by an additional bond between C-3 and C-11. The structure was elucidated by spectral methods, and further confirmed by synthesis from a known taxane derivative. A general procedure for the photocyclization of taxicins is reported.

  摘要 一组红豆杉针叶提供了一种紫杉烷二酯，其特征在于 C-3 和 C-11 之间的附加键。该结构通过光谱方法阐明，并通过由已知紫杉烷衍生物的合成进一步证实。报告了紫杉素光环化的一般程序。
• Synthesis and biological evaluation of novel 9-functional heterocyclic coupled 7-deoxy-9-Dihydropaclitaxel analogue
  作者：Qian Cheng、Takayuki Oritani、Tohru Horiguchi、Teiko Yamada、Yan Mong

  DOI：10.1016/s0960-894x(00)00031-7

  日期：2000.3

  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.
• Synthetic Studies Towards Taxol Analogs: Chemoselective Cleavage of C-5 Cinnamoyl Group in Taxane Group of Diterpenoids with Hydroxylamine
  作者：Yadagiri Bathini、Ronald G. Micetich、Mohsen Daneshtalab

  DOI：10.1080/00397919408010151

  日期：1994.6

  Taxane group of diterpenoids 2 and 3 which possess cinnamoyl moiety at C-5 position underwent selective cleavage to C-5 hydroxy compounds 4 and 5 on treatment with hydroxylamine. The resulting compounds were characterised based on their spectral data.
• Total Synthesis of 1‐Hydroxytaxinine
  作者：Yusuke Imamura、Shun Yoshioka、Masanori Nagatomo、Masayuki Inoue

  DOI：10.1002/anie.201906872

  日期：2019.8.26

  Abstract1‐Hydroxytaxinine (1) is a cytotoxic taxane diterpenoid. Its central eight‐membered B‐ring possesses four oxygen‐functionalized centers (C1, C2, C9, and C10) and two quaternary carbon centers (C8 and C15), and is fused with six‐membered A‐ and C‐rings. The densely functionalized and intricately fused structure of 1 makes it a highly challenging synthetic target. Reported here is an efficient radical‐based strategy for assembling 1 from A‐ and C‐ring fragments. The A‐ring bearing an α‐alkoxyacyl telluride moiety underwent intermolecular coupling with the C‐ring fragment by a Et3B/O2‐promoted decarbonylative radical formation. After construction of the C8‐quaternary stereocenter, a pinacol coupling reaction using a low‐valent titanium reagent formed the B‐ring with stereoselective installation of the C1,C2‐diol. Subsequent manipulations at the A‐ and C‐rings furnished 1 in 26 total steps.
• The Synthesis and Biological Activity of 9- and 2′-cAMP 7-Deoxypaclitaxel Analogues from 5-Cinnamoyltriacetyltaxicin-I
  作者：Qian Cheng、Takayuki Oritani、Tohru Horiguchi

  DOI：10.1016/s0040-4020(00)00073-9

  日期：2000.3

  The synthesis and biological activity of new 7-deoxypaclitaxel analogues 3 and 4 in which the hydroxy group at C-2' of the sidechain, C-9 and C-10 in the B-ring are substituted by cAMP and benozoyloxy group respectively are presented. These derivatives have been first synthesized from a natural taxoid 5-cinnamoyltriacetyltaxicin-1 5 and tested in vitro for cytotoxicity against three human tumor cell lines. The biologically tested results indicate 3 having more potent cytotoxicity and 4 having a remarkably reduced cytotoxicity as well as 33 having no much effect on cytotoxicity against all human tumor cell lines tested in comparison to that of paclitaxel. (C) 2000 Elsevier Science Ltd. All rights reserved.