(1R,4R,7R,9R)-4-(hydroxymethyl)-9-[(1R,4R,7R,9R)-4-(hydroxymethyl)-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-trien-9-yl]-5-methyl-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione | 1219135-52-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (1R,4R,7R,9R)-4-(hydroxymethyl)-9-[(1R,4R,7R,9R)-4-(hydroxymethyl)-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-trien-9-yl]-5-methyl-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione
• CAS: 1219135-52-0
• 化学式: C₃₀H₃₂N₆O₆
• 分子量: 572.621
• InChiKey: VTKYLQGBLDNDHY-CCYLHAPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  tert-butyl (1S,4R,7R,9R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-9-[(1S,4R,7R,9R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-methyl-16-[(2-methylpropan-2-yl)oxycarbonyl]-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-trien-9-yl]-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-16-carboxylate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到(1R,4R,7R,9R)-4-(hydroxymethyl)-9-[(1R,4R,7R,9R)-4-(hydroxymethyl)-5-methyl-3,6-dioxo-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-trien-9-yl]-5-methyl-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione
  参考文献：
  名称：

  Total Synthesis of (+)-Chaetocin and its Analogues: Their Histone Methyltransferase G9a Inhibitory Activity

  摘要：

  The first total synthesis of (+)-chaetocin has been accomplished in nine steps starting from known N-Cbz-N-Me-serine using radical alpha-bromination reaction of diketopiperazine 10 and Co(I)-mediated reductive dimerization reaction of 12 as key reactions. The enantiomers show comparable inhibitory activity toward histone methyltransferase (HMT) G9a, but analogues without the sulfur functionality are inactive.

  DOI：

  10.1021/ja101280p

文献信息

• Total Synthesis of (+)-Chaetocin and its Analogues: Their Histone Methyltransferase G9a Inhibitory Activity
  作者：Eriko Iwasa、Yoshitaka Hamashima、Shinya Fujishiro、Eisuke Higuchi、Akihiro Ito、Minoru Yoshida、Mikiko Sodeoka

  DOI：10.1021/ja101280p

  日期：2010.3.31

  The first total synthesis of (+)-chaetocin has been accomplished in nine steps starting from known N-Cbz-N-Me-serine using radical alpha-bromination reaction of diketopiperazine 10 and Co(I)-mediated reductive dimerization reaction of 12 as key reactions. The enantiomers show comparable inhibitory activity toward histone methyltransferase (HMT) G9a, but analogues without the sulfur functionality are inactive.