13-氧代-10-去乙酰基浆果赤霉素III | 92950-42-0

• 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: 13-氧代-10-去乙酰基浆果赤霉素III
• 中文别名: 13-氧-10-去乙酰浆果赤霉素III；13-氧化-1-DAB；13-氧化-10-DAB
• 英文名称: 13-dehydro-10-deacetylbaccatin III
• 英文别名: 10-deacetyl-13-oxobaccatin III；13-oxo,10-deacetylbaccatin III；13-oxo-10-deacetylbaccatin III；[(1S,2S,3R,4S,7R,9S,10S,12R)-4-acetyloxy-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11,15-dioxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 92950-42-0
• 化学式: C₂₉H₃₄O₁₀
• 分子量: 542.583
• InChiKey: WMZBAMYUOYXRSF-RIFKXWPOSA-N

物化性质

• 熔点：
  205-207 °C
• 沸点：
  720.7±60.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  157
• 氢给体数：
  3
• 氢受体数：
  10

制备方法与用途

10-脱乙酰基-13-氧代巴卡亭Ⅲ是一种紫杉烷，可以从税托纳树中分离得到。该化合物在不同细胞系中的细胞毒性测试结果显示：对A498、NCI-H226、A549和PC-3细胞的抑制率分别为29.7%、49.2%、43.9%和65.3%。

反应信息

• 作为反应物：
  描述：

  13-氧代-10-去乙酰基浆果赤霉素III 在 N-甲基咪唑 、 ytterbium trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 多西他赛杂质57
  参考文献：
  名称：

  Diastereoselective 14β-Hydroxylation of Baccatin III Derivatives

  摘要：

  14beta-Hydroxybaccatin III, a compound with limited availability by natural sources, is the starting material for the synthesis of the second-generation anticancer taxoid ortataxel. The 7-tertbutoxycarbonyl. (1a) and 7-triethylsilyl (1b) derivatives of 14beta-hydroxybaccatin III 1,14-carbonate were synthesized from 10-deacetylbaccatin III (3). The crucial steps were (a) the C(14)beta hydroxylation of the corresponding 13-oxobaccatin III derivatives by oxaziridine-mediated electrophilic oxidation and (b) the reduction of the C-13 carbonyl group with sodium or alkylammonium borohydrides. This protocol provides a practical way for the semisynthesis of ortataxel from 10-deacetylbaccatin III, a compound readily available from various yews.

  DOI：

  10.1021/jo0347112
• 作为产物：
  描述：

  10-脱乙酰基巴卡丁 III 在 间氯过氧苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 生成 13-氧代-10-去乙酰基浆果赤霉素III
  参考文献：
  名称：

  紫杉烷二萜的化学：10-脱乙酰氧基-11,12-环氧紫杉醇的立体选择性合成

  摘要：

  用间氯过苯甲酸完成10-deacetoxybaccatin III（6）和10-deacetoxypaclitaxel（9）中烯烃的环氧化反应，产生了新的五环体系。由于在分子的β-面发生环氧化，因此环氧直接引导的环氧化剂似乎没有在反应的立体选择性中起作用。在微管组装试验中，10 -Deacetoxy-11,12-epoxypaclitaxel（10）比紫杉醇（1）更具活性，对紫杉醇对B16黑色素瘤细胞的毒性比紫杉醇低三倍。

  DOI：

  10.1016/0040-4039(95)01928-b

文献信息

• Semisynthesis of D-Ring Modified Taxoids:  Novel Thia Derivatives of Docetaxel
  作者：Ludovic Mercklé,、Joëlle Dubois、Estelle Place、Sylviane Thoret、Françoise Guéritte、Daniel Guénard、Christiane Poupat、Alain Ahond、Pierre Potier

  DOI：10.1021/jo015539+

  日期：2001.7.1

  Two novel 5(20)-thia analogues of docetaxel have been synthesized from 10-deacetylbaccatin III or taxine B and isotaxine B. The key step of these syntheses is the concomitant thietane ring formation and acetylation of the tertiary alcohol at C-4. Both compounds are less cytotoxic than docetaxel but have divergent activity on microtubule disassembly.
• Baccatin III derivatives: Reduction of the C-11, C-12 double bond
  作者：Raphaële Marder、Joëlle Dubois、Daniel Guénard、Françoise Guéritte-Voegelein、Pierre Potier

  DOI：10.1016/0040-4020(94)01078-e

  日期：1995.2

  Zinc-promoted reduction of 13-oxobaccatin III derivatives leads to 11,12-dihydro analogs. The reduced products are unstable and a skeleton rearrangement occurs leading to the cleavage of the C-10, C-11 bond. The 11,12-dihydrobaccatin III derivatives do not retain antitubulin activity.
• Appendino, Giovanni; Fenoglio, Ivana; Cravotto, Giancarlo, Gazzetta Chimica Italiana, 1994, vol. 124, # 6, p. 253 - 258
  作者：Appendino, Giovanni、Fenoglio, Ivana、Cravotto, Giancarlo、Varese, Marcella、Gariboldi, Pierluigi、Gabetta, Bruno

  DOI：——

  日期：——
• Synthesis of 5(20)deoxydocetaxel, a new active docetaxel analogue
  作者：Joëlle Dubois、Sylviane Thoret、Françoise Guéritte、Daniel Guénard

  DOI：10.1016/s0040-4039(00)00379-8

  日期：2000.4

  5(20)Deoxydocetaxel was prepared from 13-oxo-10-deacetyl baccatin III. This compound is the first docetaxel analogue with a modified D-ring which is as active as paclitaxel on microtubules. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Diastereoselective 14β-Hydroxylation of Baccatin III Derivatives
  作者：Eleonora Baldelli、Arturo Battaglia、Ezio Bombardelli、Giacomo Carenzi、Gabriele Fontana、Andrea Gambini、Maria Luisa Gelmi、Andrea Guerrini、Donato Pocar

  DOI：10.1021/jo0347112

  日期：2003.12.1

  14beta-Hydroxybaccatin III, a compound with limited availability by natural sources, is the starting material for the synthesis of the second-generation anticancer taxoid ortataxel. The 7-tertbutoxycarbonyl. (1a) and 7-triethylsilyl (1b) derivatives of 14beta-hydroxybaccatin III 1,14-carbonate were synthesized from 10-deacetylbaccatin III (3). The crucial steps were (a) the C(14)beta hydroxylation of the corresponding 13-oxobaccatin III derivatives by oxaziridine-mediated electrophilic oxidation and (b) the reduction of the C-13 carbonyl group with sodium or alkylammonium borohydrides. This protocol provides a practical way for the semisynthesis of ortataxel from 10-deacetylbaccatin III, a compound readily available from various yews.