N,N'-bis-tert-butoxycarbonyl-4-(5-guanidino-pentanoylamino)-benzoic acid methyl ester | 936571-58-3

• 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: N,N'-bis-tert-butoxycarbonyl-4-(5-guanidino-pentanoylamino)-benzoic acid methyl ester
• 英文别名: Methyl 4-[5-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]pentanoylamino]benzoate
• CAS: 936571-58-3
• 化学式: C₂₄H₃₆N₄O₇
• 分子量: 492.572
• InChiKey: GCCZUTXNORBYGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-bis-tert-butoxycarbonyl-4-(5-guanidino-pentanoylamino)-benzoic acid methyl ester 在 lithium hydroxide 、 sodium hydride 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.77h， 生成 N-[(benzylcarbamoyl-methyl)-(5-guanidino-pentanoyl)-amino]-N-[1(S)-(1(S)-benzylcarbamoyl-2-phenyl-ethylcarbamoyl)-2-methyl-propyl]-benzamide
  参考文献：
  名称：

  Modifications of the GSK3β substrate sequence to produce substrate-mimetic inhibitors of Akt as potential anti-cancer therapeutics

  摘要：

  Amplification, overexpression, and elevated activation of Akt have been detected in many human malignancies making it an important target for cancer therapy. The Akt substrate-binding site offers a large number of potential interactions to an appropriately designed small molecule and can form the basis for the development of selective inhibitors. Here, we report the progression of GSK3 beta substrate-mimetic inhibitors towards the development of a potent, small molecule substrate-mimetic inhibitor of Akt. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.004
• 作为产物：
  描述：

  5-氨基颉草酸 在 达卡巴嗪 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 44.08h， 生成 N,N'-bis-tert-butoxycarbonyl-4-(5-guanidino-pentanoylamino)-benzoic acid methyl ester
  参考文献：
  名称：

  Modifications of the GSK3β substrate sequence to produce substrate-mimetic inhibitors of Akt as potential anti-cancer therapeutics

  摘要：

  Amplification, overexpression, and elevated activation of Akt have been detected in many human malignancies making it an important target for cancer therapy. The Akt substrate-binding site offers a large number of potential interactions to an appropriately designed small molecule and can form the basis for the development of selective inhibitors. Here, we report the progression of GSK3 beta substrate-mimetic inhibitors towards the development of a potent, small molecule substrate-mimetic inhibitor of Akt. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.004

文献信息

• WO2008/70823
  申请人：——

  公开号：——

  公开（公告）日：——
• SUBSTRATE-MIMETIC AKT INHIBITOR
  申请人：Sebti Said M.

  公开号：US20160369247A1

  公开（公告）日：2016-12-22

  Disclosed herein is a species of peptide and non-peptide inhibitors of Akt, an oncogenic protein. Beginning with a residue of Akt target substrate GSK-3, the functional domains of the GSK-3 residue were characterized. Functionally homologous non-peptide groups were substituted for the amino acids of the GSK-3 creating a hybrid peptide-non-peptide and non-peptide compounds capable of binding to Akt. The non-peptide compounds show increased stability and rigidity compared to peptide counterparts and are less susceptible to degradation. The bound non-peptide compounds exhibit an inhibitory effect on Akt, similar to peptide-based Akt inhibitors.