(5E)-5-(羟基亚胺)-5,6,7,8-四氢-1-萘甲酸 | 187389-78-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (5E)-5-(羟基亚胺)-5,6,7,8-四氢-1-萘甲酸
• 英文名称: 5-hydroxyimino-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid
• 英文别名: 5-hydroxyimino-7,8-dihydro-6H-naphthalene-1-carboxylic acid
• CAS: 187389-78-2
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: MPQHQQMNIVLXIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5E)-5-(羟基亚胺)-5,6,7,8-四氢-1-萘甲酸 在 palladium on activated charcoal 氨 、 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 氯仿 为溶剂， 25.0~50.0 ℃ 、206.84 kPa 条件下， 反应 6.5h， 生成 5-[N-(t-butoxycarbonyl)amino]-5,6,7,8-tetrahydro-1-naphthalenecarboxamide
  参考文献：
  名称：

  Ade NovoDesign Probe of a Dopamine Receptor Ligand Based on a Theoretical Approach

  摘要：

  A trial to design de novo a dopamine (DA) receptor ligand was made, taking as the base four structural and electrostatic requirements: (1) a group simulating the interaction of the DA amino group with the TM3 aspartic acid of the receptor, (2) a group that can simulate the interaction of the DA m-hydroxyl group with the TM5 serine of the receptor, (3) a distance between these groups similar to that of the DA anti-coplanar conformer, and (4) a rigid structure keeping the distance between the groups right. After the design ''on paper'' of the models of four structures, quantum chemistry calculations were performed to check the properties of the molecules, and then the most encouraging ones were synthesized. None of the compounds synthesized was able to bind D-1- and D-2-dopamine receptor subtypes; this shows that the structural and electrostatic requirements considered in this work are insufficient. In particular, the presence of an arylethylamine moiety seems to be essential for the interaction of a ligand with the DA receptor. (C) 1996 Academic Press, Inc.

  DOI：

  10.1006/bioo.1996.0031

文献信息

• Ade NovoDesign Probe of a Dopamine Receptor Ligand Based on a Theoretical Approach
  作者：M. Baginski、F. Claudi、G. Giorgioni、J.A. Fontenla、E. Rosa、M. Cardellini

  DOI：10.1006/bioo.1996.0031

  日期：1996.12

  A trial to design de novo a dopamine (DA) receptor ligand was made, taking as the base four structural and electrostatic requirements: (1) a group simulating the interaction of the DA amino group with the TM3 aspartic acid of the receptor, (2) a group that can simulate the interaction of the DA m-hydroxyl group with the TM5 serine of the receptor, (3) a distance between these groups similar to that of the DA anti-coplanar conformer, and (4) a rigid structure keeping the distance between the groups right. After the design ''on paper'' of the models of four structures, quantum chemistry calculations were performed to check the properties of the molecules, and then the most encouraging ones were synthesized. None of the compounds synthesized was able to bind D-1- and D-2-dopamine receptor subtypes; this shows that the structural and electrostatic requirements considered in this work are insufficient. In particular, the presence of an arylethylamine moiety seems to be essential for the interaction of a ligand with the DA receptor. (C) 1996 Academic Press, Inc.