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

• 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-hydroxy-8,8,10,12,16-pentamethyl-3-[1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-5,9-dioxo-4,17-dioxa-bicyclo[14.1.0]heptadecane-7-carbonitrile
• 英文别名: (3S)-cyano epothilone；(1S,3S,7S,10R,11S,12S,16R)-11-hydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-5,9-dioxo-4,17-dioxabicyclo[14.1.0]heptadecane-7-carbonitrile
• 化学式: C₂₈H₄₀N₂O₅S
• 分子量: 516.702
• InChiKey: UCIWKAZENXIOAQ-CIBOUACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (1S,3S,7S,10R,11S,12S,16R)-8,8,10,12,16-Pentamethyl-3-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-5,9-dioxo-11-triethylsilanyloxy-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17%的产率得到[1R,3S(E),7S,10S,11S,12R,16R]-11-hydroxy-8,8,10,12,16-pentamethyl-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

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.