5α-hydroxy-2α,10β-diacetoxy-4(20),11-taxadien-13-one | 444307-65-7

• 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: 5α-hydroxy-2α,10β-diacetoxy-4(20),11-taxadien-13-one
• 英文别名: [(1R,2R,3S,5S,8S,10S)-2-acetyloxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylidene-13-oxo-10-tricyclo[9.3.1.03,8]pentadec-11-enyl] acetate
• CAS: 444307-65-7
• 化学式: C₂₄H₃₄O₆
• 分子量: 418.53
• InChiKey: CKDZQNVEBOIINN-MWYQPOEZSA-N

物化性质

• 熔点：
  153 °C
• 沸点：
  522.8±50.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5α-hydroxy-2α,10β-diacetoxy-4(20),11-taxadien-13-one 在 四氧化锇 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 水 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 61.33h， 生成 2α,20-diacetoxy-13α-(acetylacetoxy)-10β-(triethylsilyloxy)-4α,5α-(dimethylmethylenedioxy)-11-taxene
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New 4‐Deacety‐1,7,9‐trideoxy‐10‐oxopaclitaxel via Sinenxan A

  摘要：

  A new 4-deacety-1,7,9-trideoxy-10-oxopaclitaxel (compound 1) was prepared in 21 steps via sinenxan A, a biosynthetic taxane. The biological evaluation in vitro against human cancer lines showed compound 1 to be devoid of cytotoxicity.

  DOI：

  10.1080/00397910701569767
• 作为产物：
  描述：

  2α,5α,10β-triacetoxy-taxa-4(20),11-diene 在 chromium(VI) oxide 、 叔丁基过氧化氢 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 5α-hydroxy-2α,10β-diacetoxy-4(20),11-taxadien-13-one
  参考文献：
  名称：

  Synthesis and biological evaluation of taxinine analogues as orally active multidrug resistance reversal agents in cancer

  摘要：

  Three novel taxinine analogues were prepared and tested for their activity as multidrug resistance (MDR) reversal agents in comparison with verapamil. In vitro testing demonstrated that compounds 8-10 possess MDR-reversal activity in the KB/V cell line. Half-hour after treatment with 5, 10, and 20 mumol/L compound 9, the intracellular rhodamine 123 concentration increased 2.3, 2.9, and 3.2-fold, respectively, higher than 1.88-fold of 10 mumol/L verapamil in KB/V cell line. In vivo studies with VCR-resistant KB/V tumor xenografts showed that compound 9 in combination with VCR significantly inhibited tumor growth. Treatment with VCR or 9 alone did not result in growth inhibition. These results reveal that three taxinine analogues are good modifiers of MDR in tumor cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.089

文献信息

• Synthesis of 7,9-dideoxybaccatin IV analogs from sinenxan A
  作者：Meng Zhang、Dali Yin、Ji-Yu Guo、Xiao-Tian Liang

  DOI：10.1016/j.tet.2005.03.137

  日期：2005.6

  Sinenxan A, a taxoid isolated from callus tissue cultures of Taxus yunnanensis was converted into 13-oxo-7,9-dideoxy-2-debenzoyl-2-acetyl-baccatin IV and 7.9-dideoxy-2-debenzoyl-4-deacetyl-baccatin IV, a key framework of 1,7,9-trideoxypaclitaxel. Several special steps in this transformation are worthy of note: (1) deoxygenation by treatment with hypophosphorous acid at C-14 positions (2) a highly regioselective O-deacetylation of taxane:, at C-5 position; and (3) stereoselective reduction of the 13-carbonyl group by transannular assistance from the C-4-hydroxyl. (c) 2005 Published by Elsevier Ltd.
• Synthetic study of 1,7,9-trideoxypaclitaxel via sinenxan A
  作者：Meng Zhang、Dali Yin、Ji-Yu Guo、Xiao-Tian Liang

  DOI：10.1016/s0040-4039(02)02330-4

  日期：2002.12

  Sinenxan A, a biosynthetic taxane, was converted into compound 9, a key intermediate of 1,7,9-trideoxypaclitaxel. Two special steps in this transformation are worthy of note: (1) regioselective removal of C-5-acetyl; and (2) stereoselective reduction of the 13-carbonyl group by transannular assistance from the C-4-hydroxyl. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and structure–activity relationships of sinenxan A derivatives as multidrug resistance reversal agents
  作者：Meng Huang、Xin Zhao、Meng Zhang、Jun Gu、Xiaoguang Chen、Dali Yin

  DOI：10.1016/j.bmcl.2010.07.099

  日期：2010.9

  Two types of sinenxan A derivatives with different side chains at C-5 were synthesized and evaluated for their in vitro multidrug resistant reversal activities. Several derivatives exhibited better activities than the positive control verapamil. The structure-activity relationships of these derivatives suggested that a carbonyl group at C-13 and the length of side chain at C-5 are important for the activity. (c) 2010 Elsevier Ltd. All rights reserved.