Acetic acid (1R,2R,3R,5S,8R,9R,10R)-2,10-diacetoxy-8,12,15,15-tetramethyl-4-methylene-13-oxo-5-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-9-yl ester | 204572-86-1

• 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: Acetic acid (1R,2R,3R,5S,8R,9R,10R)-2,10-diacetoxy-8,12,15,15-tetramethyl-4-methylene-13-oxo-5-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-9-yl ester
• 英文别名: [(1R,2R,3R,5S,8R,9R,10R)-9,10-diacetyloxy-8,12,15,15-tetramethyl-4-methylidene-13-oxo-5-triethylsilyloxy-2-tricyclo[9.3.1.03,8]pentadec-11-enyl] acetate
• CAS: 204572-86-1
• 化学式: C₃₂H₅₀O₈Si
• 分子量: 590.83
• InChiKey: CLIVETVICYKYSS-QZMRLLAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Acetic acid (1R,2R,3R,5S,8R,9R,10R)-2,10-diacetoxy-8,12,15,15-tetramethyl-4-methylene-13-oxo-5-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-9-yl ester 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以31%的产率得到2-O-deacetyl-5-O-triethylsilyl-taxinine A
  参考文献：
  名称：

  Modulation of multidrug resistance in tumor cells by taxinine derivatives

  摘要：

  Among a series of taxinine (1) and its designed derivatives (2 similar to 33), two taxoids (29 and 33) increased cellular accumulation of vincristine in multidrug-resistant tumor cells more potently than verapamil, while the activities of eight taxoids (11, 14 similar to 16, 22, and 30 similar to 32) were comparable with that of verapamil. These results reveal that some taxinine derivatives are good modifiers of multidrug resistance in tumor cells. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00009-8
• 作为产物：
  描述：

  taxinine 在 咪唑 、 硫酸羟胺 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 Acetic acid (1R,2R,3R,5S,8R,9R,10R)-2,10-diacetoxy-8,12,15,15-tetramethyl-4-methylene-13-oxo-5-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-9-yl ester
  参考文献：
  名称：

  Modulation of multidrug resistance in tumor cells by taxinine derivatives

  摘要：

  Among a series of taxinine (1) and its designed derivatives (2 similar to 33), two taxoids (29 and 33) increased cellular accumulation of vincristine in multidrug-resistant tumor cells more potently than verapamil, while the activities of eight taxoids (11, 14 similar to 16, 22, and 30 similar to 32) were comparable with that of verapamil. These results reveal that some taxinine derivatives are good modifiers of multidrug resistance in tumor cells. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00009-8

文献信息

• Stereoselective epoxidation of 4(20)-exomethylene in taxinine derivatives and assignment of the epoxide orientation by NMR
  作者：Hirokazu Hosoyama、Hideyuki Shigemori、Yasuko In、Toshimasa Ishida、Jun'ichi Kobayashi

  DOI：10.1016/s0040-4020(98)00018-0

  日期：1998.3

  Epoxidation of taxinine (1), taxinine A (2), and taxinine derivative 7 with m-chloroperbenzoic acid afforded the α-4(20)-epoxides selectively (α : β = 99 : 1), while epoxidation of taxinine derivatives 7 and 8 with dimethyldioxirane gave the β-4(20)-epoxides predominantly (α : β = 1 : 4∼5). The epoxide orientation was found to be assignable by magnitude of chemical shift differences between the geminal

  taxinine（环氧化1），taxinine A（2），和taxinine衍生物7与米，得到氯过苯甲酸的α-4（20） -环氧化物选择性（α：β = 99：1），而taxinine衍生物的环氧化7和8与二甲基二，得到β-4（20） -环氧化物主要（α：β = 1：4〜5）。发现环氧化物的取向可通过1 H NMR光谱中双环环氧质子之间的化学位移差异的大小来确定。1β-羟基浆果赤霉素I的相对立体化学（9通过X射线分析确定具有β-4（20）-环氧部分的），以提供环氧方向的有效分配。
• Synthesis and biological evaluation of 4-Deacetoxy-1,7-dideoxy azetidine paclitaxel analogues
  作者：Qian Cheng、Hiromasa Kiyota、Marina Yamaguchi、Tohru Horiguchi、Takayuki Oritani

  DOI：10.1016/s0960-894x(03)00054-4

  日期：2003.3

  Three novel 4-deacetoxy-1,7-dideoxy azetidine paclitaxel analogues were synthesized through a convenient route that employed hydroboration-amination and intramolecular S(N)2-type substitution reaction from a natural taxoid taxinine. All analogues have been tested for cytotoxicity against three human tumor cell lines. None of them showed remarkable cytotoxicity compared to paclitaxel against tested tumor cell lines. (C) 2003 Elsevier Science Ltd. All rights reserved.