(4-nitrophenyl)methyl N-[(1R,7R,11R,14R,20R,24R)-2,12,15,25-tetramethyl-11,24-bis(methylsulfanylmethyl)-20-[(4-nitrophenyl)methoxycarbonylamino]-3,6,10,13,16,19,23,26-octaoxo-9,22-dioxa-28,29-dithia-2,5,12,15,18,25-hexazabicyclo[12.12.4]triacontan-7-yl]carbamate | 939431-76-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4-nitrophenyl)methyl N-[(1R,7R,11R,14R,20R,24R)-2,12,15,25-tetramethyl-11,24-bis(methylsulfanylmethyl)-20-[(4-nitrophenyl)methoxycarbonylamino]-3,6,10,13,16,19,23,26-octaoxo-9,22-dioxa-28,29-dithia-2,5,12,15,18,25-hexazabicyclo[12.12.4]triacontan-7-yl]carbamate
• CAS: 939431-76-2
• 化学式: C₄₄H₅₆N₁₀O₁₈S₄
• 分子量: 1141.25
• InChiKey: KSPKNJQQGMVMQG-ZRBWWFCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  76
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  462
• 氢给体数：
  4
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  (4-nitrophenyl)methyl N-[(1R,7R,11R,14R,20R,24R)-2,12,15,25-tetramethyl-11,24-bis(methylsulfanylmethyl)-20-[(4-nitrophenyl)methoxycarbonylamino]-3,6,10,13,16,19,23,26-octaoxo-9,22-dioxa-28,29-dithia-2,5,12,15,18,25-hexazabicyclo[12.12.4]triacontan-7-yl]carbamate 在 sodium dithionite 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Solid-Phase Synthesis of Oxathiocoraline by a Key Intermolecular Disulfide Dimer

  摘要：

  Oxathiocoraline, a member of the quinoxaline antibiotic family, has been synthesized on solid-phase. The depsipeptide exhibits high synthetic complexity owing to the presence of consecutive NMe amino acids, two ester moieties, a disulfide bridge, and two SMe Cys residues. Because of internal diketopiperazine formation, standard stepwise or convergent approaches failed to deliver the linear octadepsipeptide precursor. Therefore, an alternative methodology where an intermolecular disulfide dimer is formed on solid-phase was developed. Cleavage of the dimer from the solid-phase and subsequent bismacrolactamization followed by incorporation of the heterocyclic unit afforded the target compound. Oxathiocoraline showed antitumoral activity in three tumor cell lines.

  DOI：

  10.1021/ja0686312
• 作为产物：
  描述：

  2-[[(2R)-3-[(2R)-2-[[(2R)-3-[[(2R)-3-[[(2R)-1-[(2R)-3-(carboxymethylamino)-2-[(4-nitrophenyl)methoxycarbonylamino]-3-oxopropoxy]-3-methylsulfanyl-1-oxopropan-2-yl]-methylamino]-2-(methylamino)-3-oxopropyl]disulfanyl]-2-(methylamino)propanoyl]-methylamino]-3-methylsulfanylpropanoyl]oxy-2-[(4-nitrophenyl)methoxycarbonylamino]propanoyl]amino]acetic acid 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (4-nitrophenyl)methyl N-[(1R,7R,11R,14R,20R,24R)-2,12,15,25-tetramethyl-11,24-bis(methylsulfanylmethyl)-20-[(4-nitrophenyl)methoxycarbonylamino]-3,6,10,13,16,19,23,26-octaoxo-9,22-dioxa-28,29-dithia-2,5,12,15,18,25-hexazabicyclo[12.12.4]triacontan-7-yl]carbamate
  参考文献：
  名称：

  Solid-Phase Synthesis of Oxathiocoraline by a Key Intermolecular Disulfide Dimer

  摘要：

  Oxathiocoraline, a member of the quinoxaline antibiotic family, has been synthesized on solid-phase. The depsipeptide exhibits high synthetic complexity owing to the presence of consecutive NMe amino acids, two ester moieties, a disulfide bridge, and two SMe Cys residues. Because of internal diketopiperazine formation, standard stepwise or convergent approaches failed to deliver the linear octadepsipeptide precursor. Therefore, an alternative methodology where an intermolecular disulfide dimer is formed on solid-phase was developed. Cleavage of the dimer from the solid-phase and subsequent bismacrolactamization followed by incorporation of the heterocyclic unit afforded the target compound. Oxathiocoraline showed antitumoral activity in three tumor cell lines.

  DOI：

  10.1021/ja0686312