N-((5-(4-chlorophenyl)furan-2-yl)methyl)(3,4,5-trimethoxyphenyl)methanamine

• 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-((5-(4-chlorophenyl)furan-2-yl)methyl)(3,4,5-trimethoxyphenyl)methanamine
• 英文别名: 1-[5-(4-chlorophenyl)furan-2-yl]-N-[(3,4,5-trimethoxyphenyl)methyl]methanamine
• 化学式: C₂₁H₂₂ClNO₄
• 分子量: 387.863
• InChiKey: LENNSQATENOTQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苄胺 、 5-(4-氯苯基)-2-呋喃甲醛 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以37%的产率得到N-((5-(4-chlorophenyl)furan-2-yl)methyl)(3,4,5-trimethoxyphenyl)methanamine
  参考文献：
  名称：

  3-Benzamides and 3,4,5-trimethoxyphenyl amines as calcium channel blockers

  摘要：

  T- and N-type calcium channels have known for relating to therapy of neuropathic pain which is chronic, debilitating pain state. Neuropathic pain is caused by damage of the somatosensory system. It may be associated with abnormal sensations and pain produced by normally non-painful stimuli (allodynia). Neuropathic pain is very difficult to treat, and only some 40-60% of patients achieve partial relief. For a neuropathic pain therapy, anticonvulsant like Lamotrigine, Carbamazepine and a topical anesthetic such as Lidocaine are used. We synthesized 15 novel amine derivatives and evaluated their activities against T-type and N-type calcium channels by whole-cell patch clamp recording on HEK293 cells. Among the tested compounds, compound 10 showed good inhibitory activity for both T-type and N-type calcium channels with the IC50 value of 1.9 mu M and 4.3 mu M, respectively. Compound 10 also showed good analgesic activity on rat spinal cord injury model. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.067

文献信息

• A one-pot, multi-component reaction cascade for the rapid synthesis of diversely functionalized heteroaryl methyl substrates
  作者：Daniel E. Jeffries、Craig W. Lindsley

  DOI：10.1016/j.tetlet.2016.11.120

  日期：2017.1

  A novel one-pot, “green” protocol to rapidly access pharmaceutically relevant heteroaryl methyl substrates is described. This process allows for a tandem SN2/Suzuki-Miyaura reaction or Sonogashira reaction across a breadth of chemical diversity with yields ranging between 31 and 87% for the tandem Suzuki-Miyaura process and 50–66% for the tandem Sonogashira process. This procedure tolerates S, N, and

  描述了一种新颖的一锅“绿色”协议，可快速访问药学上相关的杂芳基甲基底物。此过程允许在整个化学多样性范围内进行串联S N 2 / Suzuki-Miyaura反应或Sonogashira反应，串联Suzuki-Miyaura过程的收率介于31％至87％之间，而串联Sonogashira过程的收率介于50％至66％之间。此程序可耐受S，N和O杂原子连接子，并且适用于快速和稳健的铅开发筛选。此外，T型和N型钙通道阻滞剂（15使用该方法以43％的收率合成了α-β），这代表了先前报道的合成的产率和反应时间的改进。一锅协议还允许15的支架内包含更大的化学多样性。
• 3-Benzamides and 3,4,5-trimethoxyphenyl amines as calcium channel blockers
  作者：Bohee Kang、Jung Ae Oh、Jee Youn Lee、Hyewhon Rhim、Tae Young Yune、Hea-Young Park Choo

  DOI：10.1016/j.bmc.2015.07.067

  日期：2015.9

  T- and N-type calcium channels have known for relating to therapy of neuropathic pain which is chronic, debilitating pain state. Neuropathic pain is caused by damage of the somatosensory system. It may be associated with abnormal sensations and pain produced by normally non-painful stimuli (allodynia). Neuropathic pain is very difficult to treat, and only some 40-60% of patients achieve partial relief. For a neuropathic pain therapy, anticonvulsant like Lamotrigine, Carbamazepine and a topical anesthetic such as Lidocaine are used. We synthesized 15 novel amine derivatives and evaluated their activities against T-type and N-type calcium channels by whole-cell patch clamp recording on HEK293 cells. Among the tested compounds, compound 10 showed good inhibitory activity for both T-type and N-type calcium channels with the IC50 value of 1.9 mu M and 4.3 mu M, respectively. Compound 10 also showed good analgesic activity on rat spinal cord injury model. (c) 2015 Elsevier Ltd. All rights reserved.