2,2-diethoxy-N-(3-pyridylmethyl)ethanamine | 71172-67-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,2-diethoxy-N-(3-pyridylmethyl)ethanamine
• 英文别名: 2,2-Diethoxy-n-(pyridin-3-ylmethyl)ethanamine
• CAS: 71172-67-3
• 化学式: C₁₂H₂₀N₂O₂
• mdl: MFCD00023611
• 分子量: 224.303
• InChiKey: YXWKUCRKSMPHCE-UHFFFAOYSA-N

物化性质

• 沸点：
  313.3±32.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.583
• 拓扑面积：
  43.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  potassium thioacyanate 、 2,2-diethoxy-N-(3-pyridylmethyl)ethanamine 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 以67%的产率得到1-(3-吡啶基甲基)-1,3-二氢-2H-咪唑-2-硫酮
  参考文献：
  名称：

  Inhibitors of dopamine .beta.-hydroxylase. 3. Some 1-(pyridylmethyl)imidazole-2-thiones

  摘要：

  The 1-benzylimidazole-2-thione moiety has been previously shown by Kruse et al. to be broadly associated with dopamine beta-hydroxylase (DBH) inhibitory activity both in vitro and in vivo in spontaneously hypertensive rats (SHR). An extension of structure-activity studies to 1-(pyridylmethyl)- and 1-(oxypyridylmethyl)imidazole-2-thiones is reported here in an attempt to exploit the pH differential that exists across the chromaffin vesicle membrane. We hypothesized that the weakly basic pyridyl compounds would diffuse into the acidic vesicles in their neutral forms where protonation and concentration would occur to enhance their in vivo effectiveness as inhibitors. To test this hypothesis, isomeric 2-, 3- and 4-(1-pyridylmethyl)imidazole-2-thiones were synthesized from the appropriate pyridinecarboxaldehydes by reductive alkylation of aminoacetaldehyde dialkyl acetal followed by imidazole-2-thione formation using acidic potassium thiocyanate. Related oxypyridyl compounds were synthesized by first preparing the appropriate aldehyde intermediate followed by conversion to the imidazole-2-thione by the same procedure. The unsubstituted pyridylmethyl compounds showed modest DBH inhibition in vitro but, consistent with a transport-mediated increase in observed potency, showed significant effects in vivo to increase the vascular ratio of dopamine to norepinephrine and to lower blood pressure.

  DOI：

  10.1021/jm00391a008
• 作为产物：
  描述：

  3-吡啶甲醛 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 2,2-diethoxy-N-(3-pyridylmethyl)ethanamine
  参考文献：
  名称：

  Inhibitors of dopamine .beta.-hydroxylase. 3. Some 1-(pyridylmethyl)imidazole-2-thiones

  摘要：

  The 1-benzylimidazole-2-thione moiety has been previously shown by Kruse et al. to be broadly associated with dopamine beta-hydroxylase (DBH) inhibitory activity both in vitro and in vivo in spontaneously hypertensive rats (SHR). An extension of structure-activity studies to 1-(pyridylmethyl)- and 1-(oxypyridylmethyl)imidazole-2-thiones is reported here in an attempt to exploit the pH differential that exists across the chromaffin vesicle membrane. We hypothesized that the weakly basic pyridyl compounds would diffuse into the acidic vesicles in their neutral forms where protonation and concentration would occur to enhance their in vivo effectiveness as inhibitors. To test this hypothesis, isomeric 2-, 3- and 4-(1-pyridylmethyl)imidazole-2-thiones were synthesized from the appropriate pyridinecarboxaldehydes by reductive alkylation of aminoacetaldehyde dialkyl acetal followed by imidazole-2-thione formation using acidic potassium thiocyanate. Related oxypyridyl compounds were synthesized by first preparing the appropriate aldehyde intermediate followed by conversion to the imidazole-2-thione by the same procedure. The unsubstituted pyridylmethyl compounds showed modest DBH inhibition in vitro but, consistent with a transport-mediated increase in observed potency, showed significant effects in vivo to increase the vascular ratio of dopamine to norepinephrine and to lower blood pressure.

  DOI：

  10.1021/jm00391a008

文献信息

• Novel Benzothiazolone Derivatives
  申请人：Bonnert Roger

  公开号：US20080300275A1

  公开（公告）日：2008-12-04

  The present invention provides compounds of formula (I) wherein e, R 1 , R 2 , R 3 , R 4 , R 5 , R 4 , R 5 , R 6 , R 7 , R 7a , R 7b , A, D, m and n are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明提供了公式（I）化合物，其中e，R1，R2，R3，R4，R5，R4，R5，R6，R7，R7a，R7b，A，D，m和n如说明书中所定义，以及其制备方法，包含它们的制药组合物以及它们在治疗中的用途。
• WO2007/18461
  申请人：——

  公开号：——

  公开（公告）日：——
• ROSS, S. T.;KRUSE, L. I.;OHLSTEIN, E. H.;ERICKSON, R. W.;EZEKIEL, M.;FLAI+, J. MED. CHEM., 30,(1987) N 8, 1309-1313
  作者：ROSS, S. T.、KRUSE, L. I.、OHLSTEIN, E. H.、ERICKSON, R. W.、EZEKIEL, M.、FLAI+

  DOI：——

  日期：——
• NOVEL BENZOTHIAZOLONE DERIVATIVES
  申请人：AstraZeneca AB

  公开号：EP1915354A1

  公开（公告）日：2008-04-30
• US7709511B2
  申请人：——

  公开号：US7709511B2

  公开（公告）日：2010-05-04