S-[(E)-4-[(5R,8S,11S)-5,8-dimethyl-6,9,13-trioxo-10-oxa-3,17-dithia-7,14,19,20-tetrazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-trien-11-yl]but-3-enyl] octanethioate | 1056880-57-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: S-[(E)-4-[(5R,8S,11S)-5,8-dimethyl-6,9,13-trioxo-10-oxa-3,17-dithia-7,14,19,20-tetrazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-trien-11-yl]but-3-enyl] octanethioate
• CAS: 1056880-57-9
• 化学式: C₂₇H₃₈N₄O₅S₃
• 分子量: 594.821
• InChiKey: PFCJSJVBQDDCGE-RAPWVNHYSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  206
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  S-butyl 3-enyloctanethioate 、 (12Z,22Z,24R,5S,8S)-24,5-dimethyl-8-vinyl-24,25-dihydro-7-oxa-4,11-diaza-1(4,2),2(2,4)-dithiazolacyclododecaphane-3,6,10-trione 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以61%的产率得到S-[(E)-4-[(5R,8S,11S)-5,8-dimethyl-6,9,13-trioxo-10-oxa-3,17-dithia-7,14,19,20-tetrazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-trien-11-yl]but-3-enyl] octanethioate
  参考文献：
  名称：

  Synthesis and Activity of Largazole Analogues with Linker and Macrocycle Modification

  摘要：

  To characterize largazole's structural requirements for histone deacetylase (HDAC) inhibitory and anti proliferative activities, a series of analogues with modifications to the side chain or 16-membered macrocycle were prepared and biologically evaluated. Structure-activity relationships suggested that the four-atom linker between the macrocycle and octanoyl group in the side chain and the (S)-configuration at the C17 position are critical to repression of HDAC activity. However, the valine residue in the macrocycle can be replaced with alanine without significant loss of activity.

  DOI：

  10.1021/ol801532s