3-(naphth-1-yl)propyl 1-azide | 220193-49-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(naphth-1-yl)propyl 1-azide
• 英文别名: 3-(Naphth-1-yl)propyl-1-azide；1-(3-Azidopropyl)naphthalene
• CAS: 220193-49-7
• 化学式: C₁₃H₁₃N₃
• 分子量: 211.266
• InChiKey: ATCKGXPMVREFHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(naphth-1-yl)propyl 1-azide 在 sodium hydroxide 、 LiAlH4 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到1-萘丙胺
  参考文献：
  名称：

  Acylated oligopeptide derivatives having cell signal inhibiting activity

  摘要：

  该发明涉及一种酰化肽，即式（I）的化合物，其中n为0至15，X为草酸基，PTI为酪氨酸的双价基团或（更好地）磷酸酪氨酸的双价基团或磷酸酪氨酸类似物，AA代表天然或非天然氨基酸的双价基团，Y为次级氨基团或其盐，所述化合物用于治疗对抗（具有）SH2结构域的（一种）蛋白质和蛋白酪氨酸激酶或其修饰版本之间的相互作用有反应的疾病。

  公开号：

  US06307090B1
• 作为产物：
  描述：

  ethyl 3-(naphth-1-yl)propanoate 在 LiAlH4 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 3-(naphth-1-yl)propyl 1-azide
  参考文献：
  名称：

  Acylated oligopeptide derivatives having cell signal inhibiting activity

  摘要：

  该发明涉及一种酰化肽，即式（I）的化合物，其中n为0至15，X为草酸基，PTI为酪氨酸的双价基团或（更好地）磷酸酪氨酸的双价基团或磷酸酪氨酸类似物，AA代表天然或非天然氨基酸的双价基团，Y为次级氨基团或其盐，所述化合物用于治疗对抗（具有）SH2结构域的（一种）蛋白质和蛋白酪氨酸激酶或其修饰版本之间的相互作用有反应的疾病。

  公开号：

  US06307090B1

文献信息

• Acylated oligopeptide derivatives having cell signal inhibiting activity
  申请人：The United States of America as represented by the Department of Health and Human Services

  公开号：US06307090B1

  公开（公告）日：2001-10-23

  The invention relates to an acylated peptide, namely a compound of formula (I), wherein n is 0 to 15, X is oxalyl PTI is the bivalent radical of tyrosine or (preferably) the bivalent radical of phosphotyrosine or a phosphotyrosine mimetic, AA stands for a bivalent radical of a natural or unnatural amino acid, and Y is secondary amino group, or a salt thereof, said compound being useful for the treatment of diseases that respond to inhibition of the interaction of (a) protein(s) comprising (an) SH2 domain(s) and a protein tyrosine kinase or a modified version thereof.

  该发明涉及一种酰化肽，即式（I）的化合物，其中n为0至15，X为草酸基，PTI为酪氨酸的双价基团或（更好地）磷酸酪氨酸的双价基团或磷酸酪氨酸类似物，AA代表天然或非天然氨基酸的双价基团，Y为次级氨基团或其盐，所述化合物用于治疗对抗（具有）SH2结构域的（一种）蛋白质和蛋白酪氨酸激酶或其修饰版本之间的相互作用有反应的疾病。
• US6307090B1
  申请人：——

  公开号：US6307090B1

  公开（公告）日：2001-10-23
• Potent Inhibition of Grb2 SH2 Domain Binding by Non-Phosphate-Containing Ligands
  作者：Zhu-Jun Yao、C. Richter King、Tin Cao、James Kelley、George W. A. Milne、Johannes H. Voigt、Terrence R. Burke

  DOI：10.1021/jm980388x

  日期：1999.1.1

  Development of Grb2 Src homology 2 (SH2) domain binding inhibitors has important implications for treatment of a variety of diseases, including several cancers. In cellular studies, inhibitors of Grb2 SH2 domain binding have to date been large, highly charged peptides which relied on special transport devices for cell membrane penetration. Work presented in the current study examines a variety of pTyr mimetics in the context of a high-affinity Grb2 binding platform. Among the analogues studied are new norm-phosphorus-containing pTyr mimetics 23a and 23b which, when incorporated into tripeptide structures 18f and 20f, are able to inhibit Grb2 SH2 domain binding with affinities among the best yet reported for non-phosphorus-containing SH2 domain inhibitors (IC50 values of 6.7 and 1.3 mu M, respectively). The present study has also demonstrated the usefulness of the Na-oxalyl group as an auxiliary which enhances the binding potency of both phosphorus- and non-phosphorus-containing pTyr mimetics. When combined with the (phosphonomethyl)phenylalanine (Pmp) residue to give analogues such as L-20d, potent inhibition of Grb2 SH2 domain binding can be achieved both in extracellular assays using isolated Grb2 SH2 domain protein and in intracellular systems measuring the association of endogenous Grb2 with its cognate p185(erbB-2) ligand. These latter effects can be achieved at micromolar to submicromolar concentrations without prodrug derivatization. The oxalyl-containing pTyr mimetics presented in this study should be of general usefulness for the development of other Grb2 SH2 domain antagonists, independent of the beta-bend-mimicking platform utilized for their display.