2-{4-[(E)-(9S,10S,14R,18S)-18-Carbamoylmethyl-9-carboxymethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-10-yl]-phenyl}-malonic acid | 852714-80-8

• 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: 2-{4-[(E)-(9S,10S,14R,18S)-18-Carbamoylmethyl-9-carboxymethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-10-yl]-phenyl}-malonic acid
• 英文别名: 2-[4-[(9S,10S,11E,14R,18S)-18-(2-amino-2-oxoethyl)-9-(carboxymethyl)-14-[(5-methylindol-1-yl)methyl]-8,17,20-trioxo-7,16,19-triazaspiro[5.14]icos-11-en-10-yl]phenyl]propanedioic acid
• CAS: 852714-80-8
• 化学式: C₄₀H₄₇N₅O₁₀
• 分子量: 757.841
• InChiKey: ZUXPTLXJHBSAQT-YUAXJFSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  55
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  247
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-{4-[(E)-(9S,10S,14R,18S)-18-Carbamoylmethyl-9-carboxymethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-10-yl]-phenyl}-malonic acid 在 lithium hydroxide 作用下， 反应 4.0h， 以19%的产率得到[(E)-(9S,10S,14R,18S)-18-Carbamoylmethyl-10-(4-carboxymethyl-phenyl)-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-9-yl]-acetic acid
  参考文献：
  名称：

  Examination of Phosphoryl-Mimicking Functionalities within a Macrocyclic Grb2 SH2 Domain-Binding Platform

  摘要：

  Reported herein are the design, synthesis, and Grb2 SH2 domain-binding affinities of several phosphoryl-mimicking groups displayed within the context of a conformationally constrained macrocyclic platform. With use of surface plasmon resonance techniques, single-digit nanomolar affinities were exhibited by phosphonic acid and malonyl-containing diacidic phosphoryl mimetics (for 4h and 4g, K-D = 1.47 and 3.62 nM, respectively). Analogues containing monoacidic phosphoryl mimetics provided affinities of K-D = 16-67 nM. Neutral phosphoryl-mimicking groups did not show appreciable binding.

  DOI：

  10.1021/jm050059m
• 作为产物：
  描述：

  (2S,3S)-3-(4-{bis[(tert-butyl)oxycarbonyl]methyl}-phenyl)-2-{[(tert-butyl)oxycarbonyl]methyl}-pent-4-enoic acid 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 ethandithiol 、 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 97.1h， 生成 2-{4-[(E)-(9S,10S,14R,18S)-18-Carbamoylmethyl-9-carboxymethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-10-yl]-phenyl}-malonic acid
  参考文献：
  名称：

  Examination of Phosphoryl-Mimicking Functionalities within a Macrocyclic Grb2 SH2 Domain-Binding Platform

  摘要：

  Reported herein are the design, synthesis, and Grb2 SH2 domain-binding affinities of several phosphoryl-mimicking groups displayed within the context of a conformationally constrained macrocyclic platform. With use of surface plasmon resonance techniques, single-digit nanomolar affinities were exhibited by phosphonic acid and malonyl-containing diacidic phosphoryl mimetics (for 4h and 4g, K-D = 1.47 and 3.62 nM, respectively). Analogues containing monoacidic phosphoryl mimetics provided affinities of K-D = 16-67 nM. Neutral phosphoryl-mimicking groups did not show appreciable binding.

  DOI：

  10.1021/jm050059m