3-(aminomethyl)-1,5-dimethoxy-1,4-cyclohexadiene | 97294-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(aminomethyl)-1,5-dimethoxy-1,4-cyclohexadiene
• 英文别名: (3,5-Dimethoxycyclohexa-2,5-dien-1-yl)methanamine
• CAS: 97294-65-0
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: DTITVUVBUATMFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(aminomethyl)-1,5-dimethoxy-1,4-cyclohexadiene 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以900 mg的产率得到5-(aminomethyl)-1,3-cyclohexanedione hydrochloride
  参考文献：
  名称：

  Synthesis and activity of 5-(aminomethyl)-1,3-cyclohexanediones: enolic analogs of .gamma.-aminobutyric acid

  摘要：

  Eight 1,3-cyclohexanediones with an aminoalkyl side chain in the 5-position were synthesized as rigid enolic analogues of GABA (gamma-aminobutyric acid). Biochemical investigations about their abilities to displace [3H]GABA and [3H]baclofen [beta-(p-chlorophenyl)-gamma-aminobutyric acid] in binding studies or to inhibit the high-affinity sodium-dependent GABA uptake showed that these compounds were generally devoid of affinity for the two GABA receptors and for the GABA carrier. Only compound 1 exhibited a weak affinity in the GABA-A binding experiments (IC50 = 6.5 X 10(-5) M). Graphic computer modeling was applied in an attempt to explain this activity in comparison to some reference GABA agonists. Electrophysiological studies on dorsal root ganglia (DRG) also excluded agonistic or antagonistic properties on GABA-A or GABA-B receptor models but pointed out an atypical prolongation of Ca2+-dependent action potential for compound 1.

  DOI：

  10.1021/jm00148a012
• 作为产物：
  描述：

  3,5-二甲氧基苄胺 在 氨 、 lithium 、 叔丁醇 作用下， 反应 2.0h， 以78%的产率得到3-(aminomethyl)-1,5-dimethoxy-1,4-cyclohexadiene
  参考文献：
  名称：

  Synthesis and activity of 5-(aminomethyl)-1,3-cyclohexanediones: enolic analogs of .gamma.-aminobutyric acid

  摘要：

  Eight 1,3-cyclohexanediones with an aminoalkyl side chain in the 5-position were synthesized as rigid enolic analogues of GABA (gamma-aminobutyric acid). Biochemical investigations about their abilities to displace [3H]GABA and [3H]baclofen [beta-(p-chlorophenyl)-gamma-aminobutyric acid] in binding studies or to inhibit the high-affinity sodium-dependent GABA uptake showed that these compounds were generally devoid of affinity for the two GABA receptors and for the GABA carrier. Only compound 1 exhibited a weak affinity in the GABA-A binding experiments (IC50 = 6.5 X 10(-5) M). Graphic computer modeling was applied in an attempt to explain this activity in comparison to some reference GABA agonists. Electrophysiological studies on dorsal root ganglia (DRG) also excluded agonistic or antagonistic properties on GABA-A or GABA-B receptor models but pointed out an atypical prolongation of Ca2+-dependent action potential for compound 1.

  DOI：

  10.1021/jm00148a012

文献信息

• MANN, A.;HUMBLET, CH.;CHAMBON, J. -P.;SCHLICHTER, R.;DESARMENIEN, M.;FELT+, J. MED. CHEM., 1985, 28, N 10, 1440-1446
  作者：MANN, A.、HUMBLET, CH.、CHAMBON, J. -P.、SCHLICHTER, R.、DESARMENIEN, M.、FELT+

  DOI：——

  日期：——
• Synthesis and activity of 5-(aminomethyl)-1,3-cyclohexanediones: enolic analogs of .gamma.-aminobutyric acid
  作者：Andre Mann、Christine Humblet、Jean Pierre Chambon、Remy Schlichter、Michel Desarmenien、Paul Feltz、Camille Georges Wermuth

  DOI：10.1021/jm00148a012

  日期：1985.10

  Eight 1,3-cyclohexanediones with an aminoalkyl side chain in the 5-position were synthesized as rigid enolic analogues of GABA (gamma-aminobutyric acid). Biochemical investigations about their abilities to displace [3H]GABA and [3H]baclofen [beta-(p-chlorophenyl)-gamma-aminobutyric acid] in binding studies or to inhibit the high-affinity sodium-dependent GABA uptake showed that these compounds were generally devoid of affinity for the two GABA receptors and for the GABA carrier. Only compound 1 exhibited a weak affinity in the GABA-A binding experiments (IC50 = 6.5 X 10(-5) M). Graphic computer modeling was applied in an attempt to explain this activity in comparison to some reference GABA agonists. Electrophysiological studies on dorsal root ganglia (DRG) also excluded agonistic or antagonistic properties on GABA-A or GABA-B receptor models but pointed out an atypical prolongation of Ca2+-dependent action potential for compound 1.