C7-trimethylsilyloxy-2,3-dehydro-epothilone A | 476623-84-4

• 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: C7-trimethylsilyloxy-2,3-dehydro-epothilone A
• 英文别名: (1S,3S,6E,10R,11S,12S,16R)-8,8,10,12-tetramethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-11-triethylsilyloxy-4,17-dioxabicyclo[14.1.0]heptadec-6-ene-5,9-dione
• CAS: 476623-84-4
• 化学式: C₃₂H₅₁NO₅SSi
• 分子量: 589.912
• InChiKey: QDYMMNJTEZDZPT-MOGLNCCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.92
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  C7-trimethylsilyloxy-2,3-dehydro-epothilone A 在 18-冠醚-6 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 94.0h， 生成 [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：

  Formic acid (E)-(1S,3S,10R,11S,12S,16R)-8,8,10,12-tetramethyl-3-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-5,9-dioxo-4,17-dioxa-bicyclo[14.1.0]heptadec-6-en-11-yl ester 在 4-二甲氨基吡啶 、 氨 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 C7-trimethylsilyloxy-2,3-dehydro-epothilone A
  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.