N,N-Dimethyl-4,4-diphenylbut-3-enamide | 915318-08-0

• 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-Dimethyl-4,4-diphenylbut-3-enamide
• 英文别名: N,N-dimethyl-4,4-diphenylbut-3-enamide
• CAS: 915318-08-0
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: RRKSZNBZZXQHCB-UHFFFAOYSA-N

物化性质

• 熔点：
  67-71 °C
• 沸点：
  423.7±45.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  联苯乙醛 在 哌啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 N,N-Dimethyl-4,4-diphenylbut-3-enamide
  参考文献：
  名称：

  Discovery of diphenyl amine based sodium channel blockers, effective against hNav1.2

  摘要：

  The development of new therapies for chronic pain is an area of unmet medical need. Central to pathways of chronic pain is the upregulation of voltage-gated sodium channels. The use of tricyclic antidepressants, which also have sodium channel activity, in chronic pain therapy prompted us to develop novel compounds from this scaffold. Herein, we show that the tricyclic moiety is not needed for effective inhibition of the [H-3]-BTX binding site and sodium currents of hNa(v)1.2. Our lead compound 6, containing a diphenyl amine motif, demonstrated a 53% inhibitory block of Na(v)1.2 currents at 10 mu M, which is greater than 50% increase in current block in comparison to the amitriptyline standard. Altogether our study establishes that the tricyclic motif is unnecessary for hNa(v)1.2 activity and modification of the amine portion is detrimental to sodium channel block. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.010

文献信息

• Cobalt‐Catalyzed Enantioselective Reductive α‐Chloro‐Carbonyl Addition of Ketimine to Construct the β‐Tertiary Amino Acid Analogues
  作者：Tingting Xia、Wenwen Wu、Xianqing Wu、Jingping Qu、Yifeng Chen

  DOI：10.1002/anie.202318991

  日期：——

  Cobalt-catalyzed enantioselective reductive addition reaction of ketimine using α-chloro carbonyl electrophile has been developed to access diversified enantioenriched β-tertiary amino acid with excellent enantioselectivity and broad functional group tolerance. The synthetic utility of this protocol includes the efficient assembly of iterative amino acid units and oligopeptide.

  开发了使用α-氯羰基亲电子试剂的钴催化酮亚胺对映选择性还原加成反应，以获得具有优异对映选择性和广泛官能团耐受性的多样化对映体富集的β-叔氨基酸。该协议的合成用途包括迭代氨基酸单元和寡肽的有效组装。
• Discovery of diphenyl amine based sodium channel blockers, effective against hNav1.2
  作者：Debjani P. Hudgens、Catherine Taylor、Timothy W. Batts、Manoj K. Patel、Milton L. Brown

  DOI：10.1016/j.bmc.2006.09.010

  日期：2006.12

  The development of new therapies for chronic pain is an area of unmet medical need. Central to pathways of chronic pain is the upregulation of voltage-gated sodium channels. The use of tricyclic antidepressants, which also have sodium channel activity, in chronic pain therapy prompted us to develop novel compounds from this scaffold. Herein, we show that the tricyclic moiety is not needed for effective inhibition of the [H-3]-BTX binding site and sodium currents of hNa(v)1.2. Our lead compound 6, containing a diphenyl amine motif, demonstrated a 53% inhibitory block of Na(v)1.2 currents at 10 mu M, which is greater than 50% increase in current block in comparison to the amitriptyline standard. Altogether our study establishes that the tricyclic motif is unnecessary for hNa(v)1.2 activity and modification of the amine portion is detrimental to sodium channel block. (c) 2006 Elsevier Ltd. All rights reserved.