(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 | 11034-45-0

• 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
• 中文名称: (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
• 英文名称: 1β,2α,9α,10β-tetrahydroxy-5α-cinnamoyloxytaxa-4(20),11-dien-13-one
• 英文别名: 5α-trans-cinnamoyloxy-1,2α,9α,10β-tetrahydroxy-taxa-4(20),11-dien-13-one；5α-trans-Cinnamoyloxy-1,2α,9α,10β-tetrahydroxy-taxa-4(20),11-dien-13-on；o-Cinnamoyltaxicin-i；[(1S,2S,3R,5S,8R,9R,10R)-1,2,9,10-tetrahydroxy-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: 11034-45-0
• 化学式: C₂₉H₃₆O₇
• 分子量: 496.601
• InChiKey: LMHMWINKBZRNRU-PDBYPBKASA-N

物化性质

• 熔点：
  233-234°
• 比旋光度：
  D21 +285° (chloroform)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  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 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 、 copper(II) sulfate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 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 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 以86%的产率得到(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
  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

文献信息

• Chemistry of taxoids: One-step functionalization of the positions 1, 2, 9 and 10 from the selectively protected 5-o-cinnamoyltaxicine I
  作者：A. Al Mourabit、H. Poujol、C. Poupat、A. Ahond、P. Potier

  DOI：10.1016/s0040-4039(96)02152-1

  日期：1996.12
• Baxter et al., Proceedings of the Chemical Society, London, 1958, p. 9,10
  作者：Baxter et al.

  DOI：——

  日期：——
• Baxter et al., Journal of the Chemical Society, 1962, p. 2964,2970
  作者：Baxter et al.

  DOI：——

  日期：——
• 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.
• 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.