(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 | 273926-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (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
• CAS: 273926-52-6
• 化学式: C₂₂H₂₈O₁₀
• 分子量: 452.458
• InChiKey: IYPNACNFIAOGAL-BBSCWVFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  32.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  148.82
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (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 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 1:2,9:10 cyclic carbonate-2,9,10,13-pentadeacetyl-7-deacetoxy-13-oxo baccatine IV
  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：

  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