5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-pentylcarbamoyl-ethyl]-2-methoxycarbonylmethoxy-benzoic acid methyl ester | 553668-07-8

• 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: 5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-pentylcarbamoyl-ethyl]-2-methoxycarbonylmethoxy-benzoic acid methyl ester
• CAS: 553668-07-8
• 化学式: C₂₇H₄₁N₃O₁₀
• 分子量: 567.637
• InChiKey: PDEPENSGVIAKIU-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  40.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  178.59
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-pentylcarbamoyl-ethyl]-2-methoxycarbonylmethoxy-benzoic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-pentylcarbamoyl-ethyl]-2-carboxymethoxy-benzoic acid
  参考文献：
  名称：

  Modification of the N-terminus of peptidomimetic protein tyrosine phosphatase 1B (PTP1B) inhibitors: identification of analogues with cellular activity

  摘要：

  Low molecular weight peptidomimetic compounds based on 0-malonyl tyrosine and 0-carboxymethyl salicylic acid are potent inhibitors of PTP1B. Modifications of the N-terminal Boc-Phe moiety were undertaken in an effort to improve physical chemical properties and to achieve cellular activity. Although Phe ultimately proved to be the optimal N-terminal amino acid, several viable replacements for the Boc group were identified, two of which afforded analogues that were effective at enhancing the insulin-stimulated uptake of 2-deoxyglucose by L6 myocytes. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01065-x
• 作为产物：
  描述：

  methyl 5-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-(2-methoxy-2-oxoethoxy)benzoate 在 TEA 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-pentylcarbamoyl-ethyl]-2-methoxycarbonylmethoxy-benzoic acid methyl ester
  参考文献：
  名称：

  Modification of the N-terminus of peptidomimetic protein tyrosine phosphatase 1B (PTP1B) inhibitors: identification of analogues with cellular activity

  摘要：

  Low molecular weight peptidomimetic compounds based on 0-malonyl tyrosine and 0-carboxymethyl salicylic acid are potent inhibitors of PTP1B. Modifications of the N-terminal Boc-Phe moiety were undertaken in an effort to improve physical chemical properties and to achieve cellular activity. Although Phe ultimately proved to be the optimal N-terminal amino acid, several viable replacements for the Boc group were identified, two of which afforded analogues that were effective at enhancing the insulin-stimulated uptake of 2-deoxyglucose by L6 myocytes. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01065-x