[4S-[4R*,7S*,8R*,9R*,14S*,16R*(E)]]-14-bromo-4,8-bis(triethylsilyloxy)-5,5,7,9-tetramethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-1-oxacyclohexadecane-2,6,13-trione | 247232-08-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: [4S-[4R*,7S*,8R*,9R*,14S*,16R*(E)]]-14-bromo-4,8-bis(triethylsilyloxy)-5,5,7,9-tetramethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-1-oxacyclohexadecane-2,6,13-trione
• 英文别名: (4S,7R,8S,9S,14R,16S)-14-bromo-5,5,7,9-tetramethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,8-bis(triethylsilyloxy)-oxacyclohexadecane-2,6,13-trione
• CAS: 247232-08-2
• 化学式: C₃₈H₆₆BrNO₆SSi₂
• 分子量: 801.086
• InChiKey: XRIRRWSSIOVEKX-PGGYCCPKSA-N

物化性质

• 沸点：
  744.9±60.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.71
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [4S-[4R*,7S*,8R*,9R*,14S*,16R*(E)]]-14-bromo-4,8-bis(triethylsilyloxy)-5,5,7,9-tetramethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-1-oxacyclohexadecane-2,6,13-trione 在 18-冠醚-6 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 [1S,5S,6S,7R,10S,14S(E),16S]-1-cyano-6,10-dihydroxy-5,7,9,9-tetramethyl-14-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-13,17-dioxa-bicyclo[14.1.0]heptadecane-8,12-dione
  参考文献：
  名称：

  SAR and pH Stability of Cyano-Substituted Epothilones

  摘要：

  graphic3-Cyano epothilones 15-18 are the only examples of non-hydroxy C-3-substituted analogues. Their tubulin binding affinity and cytotoxicity provide meaningful structure-activity relationship information on the dependence of C-1/C-3 conformation upon activity. 12-Cyano epothilone 24 has improved pH stability over epothilone B, and its activity further supports the hypothesis that C-12 stereochemistry is not critical for tubulin affinity.

  DOI：

  10.1021/ol026589j
• 作为产物：
  描述：

  bis-TES-epothilone A 在 吡啶 、 pyridinium chlorochromate 、 magnesium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 [4S-[4R*,7S*,8R*,9R*,14S*,16R*(E)]]-14-bromo-4,8-bis(triethylsilyloxy)-5,5,7,9-tetramethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-1-oxacyclohexadecane-2,6,13-trione
  参考文献：
  名称：

  SAR and pH Stability of Cyano-Substituted Epothilones

  摘要：

  graphic3-Cyano epothilones 15-18 are the only examples of non-hydroxy C-3-substituted analogues. Their tubulin binding affinity and cytotoxicity provide meaningful structure-activity relationship information on the dependence of C-1/C-3 conformation upon activity. 12-Cyano epothilone 24 has improved pH stability over epothilone B, and its activity further supports the hypothesis that C-12 stereochemistry is not critical for tubulin affinity.

  DOI：

  10.1021/ol026589j

文献信息

• SAR and pH Stability of Cyano-Substituted Epothilones
  作者：Alicia Regueiro-Ren、Kenneth Leavitt、Soong-Hoon Kim、Gerhard Höfle、Michael Kiffe、Jack Z. Gougoutas、John D. DiMarco、Francis Y. F. Lee、Craig R. Fairchild、Byron H. Long、Gregory D. Vite

  DOI：10.1021/ol026589j

  日期：2002.10.1

  graphic3-Cyano epothilones 15-18 are the only examples of non-hydroxy C-3-substituted analogues. Their tubulin binding affinity and cytotoxicity provide meaningful structure-activity relationship information on the dependence of C-1/C-3 conformation upon activity. 12-Cyano epothilone 24 has improved pH stability over epothilone B, and its activity further supports the hypothesis that C-12 stereochemistry is not critical for tubulin affinity.