3-[(S)-2-(3-{3-[((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-(6-tert-butoxycarbonylamino-hexyl)-amino]-2-oxo-cyclohexyl}-propionylamino)-2-methoxycarbonyl-ethyl]-indole-1-carboxylic acid tert-butyl ester | 405555-30-8

• 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: 3-[(S)-2-(3-{3-[((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-(6-tert-butoxycarbonylamino-hexyl)-amino]-2-oxo-cyclohexyl}-propionylamino)-2-methoxycarbonyl-ethyl]-indole-1-carboxylic acid tert-butyl ester
• CAS: 405555-30-8
• 化学式: C₅₄H₇₁N₅O₁₁
• 分子量: 966.185
• InChiKey: PLEZDMBRKHKJNC-WNHYBSMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.59
• 重原子数：
  70.0
• 可旋转键数：
  21.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  200.67
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3-[(S)-2-(3-{3-[((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-(6-tert-butoxycarbonylamino-hexyl)-amino]-2-oxo-cyclohexyl}-propionylamino)-2-methoxycarbonyl-ethyl]-indole-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以25%的产率得到
  参考文献：
  名称：

  Inhibitors of Plasmin that Extend into Both the S and S‘ Binding Sites:  Cooperative Interactions between S1 and S2

  摘要：

  A new procedure for the synthesis of cyclohexanone-based inhibitors of serine proteases is reported. In this procedure the reactive ketone functionality is carried through the synthesis in masked form as a TBDMS-protected alcohol. Deprotection followed by oxidation of the alcohol generates the final form of the inhibitor. Two new inhibitors, which interact with the S1-S3 and S2' subsites of plasmin, are synthesized using this procedure. Inhibitors 1 and 2 have IC50 values against plasmin of 20 and 24 muM, respectively. The inhibition studies show that cooperative binding of inhibitors in the S1 and S2 subsites of plasmin is important for determining inhibitor selectivity.

  DOI：

  10.1021/jo0160569
• 作为产物：
  描述：

  在 aluminum oxide 、 sodium tetrahydroborate 、 zinc tetrafluoroborate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.5h， 生成 3-[(S)-2-(3-{3-[((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-(6-tert-butoxycarbonylamino-hexyl)-amino]-2-oxo-cyclohexyl}-propionylamino)-2-methoxycarbonyl-ethyl]-indole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Inhibitors of Plasmin that Extend into Both the S and S‘ Binding Sites:  Cooperative Interactions between S1 and S2

  摘要：

  A new procedure for the synthesis of cyclohexanone-based inhibitors of serine proteases is reported. In this procedure the reactive ketone functionality is carried through the synthesis in masked form as a TBDMS-protected alcohol. Deprotection followed by oxidation of the alcohol generates the final form of the inhibitor. Two new inhibitors, which interact with the S1-S3 and S2' subsites of plasmin, are synthesized using this procedure. Inhibitors 1 and 2 have IC50 values against plasmin of 20 and 24 muM, respectively. The inhibition studies show that cooperative binding of inhibitors in the S1 and S2 subsites of plasmin is important for determining inhibitor selectivity.

  DOI：

  10.1021/jo0160569