[1R,3S(E),7S,10S,11S,12R,16R]-11-triethylsilyloxy-8,8,10,12-tetramethyl-3-[1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-5,9-dioxo-4,17-dioxa-bicyclo[14.1.0]heptadecane-7-carbonitrile | 476623-85-5

• 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: [1R,3S(E),7S,10S,11S,12R,16R]-11-triethylsilyloxy-8,8,10,12-tetramethyl-3-[1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-5,9-dioxo-4,17-dioxa-bicyclo[14.1.0]heptadecane-7-carbonitrile
• CAS: 476623-85-5
• 化学式: C₃₃H₅₂N₂O₅SSi
• 分子量: 616.938
• InChiKey: ONADZFFDVADBMB-WEWJYGKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  42.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  101.81
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [1R,3S(E),7S,10S,11S,12R,16R]-11-triethylsilyloxy-8,8,10,12-tetramethyl-3-[1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-5,9-dioxo-4,17-dioxa-bicyclo[14.1.0]heptadecane-7-carbonitrile 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以44%的产率得到[1R,3S(E),7S,10S,11S,12R,16R]-11-hydroxy-8,8,10,12-tetramethyl-3-[1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-5,9-dioxo-4,17-dioxa-bicyclo[14.1.0]heptadecane-7-carbonitrile
  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：

  2,3-dehydro-epothilone A 在 4-二甲氨基吡啶 、 18-冠醚-6 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 [1R,3S(E),7S,10S,11S,12R,16R]-11-triethylsilyloxy-8,8,10,12-tetramethyl-3-[1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-5,9-dioxo-4,17-dioxa-bicyclo[14.1.0]heptadecane-7-carbonitrile
  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