tris(2-chlorobenzyl) (((12Z,52Z,92Z,2S,6S,10S)-4,8,12-trioxo-3,7,11-triaza-1(2,4),5,9(4,2)-trioxazolacyclododecaphane-2,6,10-triyl)tris(butane-4,1-diyl))tricarbamate | 1004055-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tris(2-chlorobenzyl) (((12Z,52Z,92Z,2S,6S,10S)-4,8,12-trioxo-3,7,11-triaza-1(2,4),5,9(4,2)-trioxazolacyclododecaphane-2,6,10-triyl)tris(butane-4,1-diyl))tricarbamate
• CAS: 1004055-04-2
• 化学式: C₅₁H₅₄Cl₃N₉O₁₂
• 分子量: 1091.4
• InChiKey: KFEBEKPJUXMOLW-IGMOWHQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.63
• 重原子数：
  75.0
• 可旋转键数：
  21.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  280.38
• 氢给体数：
  6.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  tris(2-chlorobenzyl) (((12Z,52Z,92Z,2S,6S,10S)-4,8,12-trioxo-3,7,11-triaza-1(2,4),5,9(4,2)-trioxazolacyclododecaphane-2,6,10-triyl)tris(butane-4,1-diyl))tricarbamate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以75%的产率得到(4S,11S,18R)-4,11,18-tris(4-aminobutyl)-6,13,20-trioxa-3,10,17,22,23,24-hexazatetracyclo[17.2.1.15,8.112,15]tetracosa-1(21),5(24),7,12(23),14,19(22)-hexaene-2,9,16-trione
  参考文献：
  名称：

  Oxazole-Based Peptide Macrocycles:  A New Class of G-Quadruplex Binding Ligands

  摘要：

  Herein we report on the synthesis and DNA binding properties of a new class of water soluble oxazole-based peptide macrocycles that bind selectively to quadruplex DNA, with no detectable binding to duplex DNA. We have recently identified one quadruplex in the proto-oncogene c-kit that is suspected to act as a regulatory element for the expression of the c-kit gene. Here we provide the first example of a ligand binding to and stabilizing the c-kit quadruplex. Moreover, we show that these macrocycles show a preference for the c-kit quadruplex as compared to the human telomeric quadruplex.

  DOI：

  10.1021/ja064713e
• 作为产物：
  描述：

  2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]-4,5-dihydrooxazole-4-carboxylic acid methyl ester 在 2,6-二甲基吡啶 、 sodium hydroxide 、 三氯溴甲烷 、 五氟苯基二苯基磷酸酯 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 29.0h， 生成 tris(2-chlorobenzyl) (((12Z,52Z,92Z,2S,6S,10S)-4,8,12-trioxo-3,7,11-triaza-1(2,4),5,9(4,2)-trioxazolacyclododecaphane-2,6,10-triyl)tris(butane-4,1-diyl))tricarbamate
  参考文献：
  名称：

  Oxazole-Based Peptide Macrocycles:  A New Class of G-Quadruplex Binding Ligands

  摘要：

  Herein we report on the synthesis and DNA binding properties of a new class of water soluble oxazole-based peptide macrocycles that bind selectively to quadruplex DNA, with no detectable binding to duplex DNA. We have recently identified one quadruplex in the proto-oncogene c-kit that is suspected to act as a regulatory element for the expression of the c-kit gene. Here we provide the first example of a ligand binding to and stabilizing the c-kit quadruplex. Moreover, we show that these macrocycles show a preference for the c-kit quadruplex as compared to the human telomeric quadruplex.

  DOI：

  10.1021/ja064713e