(2,2-diethoxy-ethyl)-pyridin-2-ylmethylene-amine | 6190-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (2,2-diethoxy-ethyl)-pyridin-2-ylmethylene-amine
• 英文别名: pyridin-2-ylmethyleneamino-acetaldehyde diethyl acetal；(2,2-diethoxy-ethyl)-[2]pyridylmethylen-amine；(2,2-Diaethoxy-aethyl)-[2]pyridylmethylen-amin；2--pyridin；(E)-N-(2,2-Diethoxyethyl)-1-(pyridin-2-yl)methanimine；N-(2,2-diethoxyethyl)-1-pyridin-2-ylmethanimine
• CAS: 6190-94-9
• 化学式: C₁₂H₁₈N₂O₂
• 分子量: 222.287
• InChiKey: YLTOKMFRXFNTHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2,2-diethoxy-ethyl)-pyridin-2-ylmethylene-amine 在 盐酸 、 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 1-(2-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：

  吡啶-2-甲醛 、 氨基乙醛缩二乙醇 以 甲苯 为溶剂， 反应 12.0h， 生成 (2,2-diethoxy-ethyl)-pyridin-2-ylmethylene-amine
  参考文献：
  名称：

  荧光三苯胺衍生物的收敛和实用合成及其在活细胞中的定位

  摘要：

  各种三苯胺衍生物的聚合合成导致了一个小型荧光团库，显示出不同的光物理特性。吡啶的位置（邻位、间位、对位）对荧光团的颜色（从黄色到红色）以及其细胞定位（线粒体或细胞核）有影响。

  DOI：

  10.1002/ejoc.202101397

文献信息

• Über Pyridyloxazole, eine neue Klasse Dipyridyl-ähnlicher Verbindungen
  作者：M. Dadkhah、B. Prijs

  DOI：10.1002/hlca.19620450143

  日期：——

  Pyridyl- and quinolyloxazoles have been synthesized by cyclodehydrogenation of azomethines of the corresponding heterocyclic aldehydes.

  吡啶基和喹啉基恶唑是通过相应杂环醛的偶氮次甲基的环脱氢反应合成的。
• Hart, Journal of the Chemical Society, 1954, p. 4030
  作者：Hart

  DOI：——

  日期：——
• Convergent and Practical Synthesis of Fluorescent Triphenylamine Derivatives and Their Localization in Living Cells
  作者：Romain Mougeot、Samuel Oger、Marie Auvray、Thibault Gallavardin、Stéphane Leleu、Florence Mahuteau‐Betzer、Xavier Franck

  DOI：10.1002/ejoc.202101397

  日期：2022.1.17

  A convergent synthesis of various triphenylamine derivatives led to a small library of fluorophores showing different photophysical properties. The position of the pyridinium (ortho, meta, para) has an influence on the color of the fluorophore (from yellow to red) as well as on its cellular localization (mitochondria or nucleus).

  各种三苯胺衍生物的聚合合成导致了一个小型荧光团库，显示出不同的光物理特性。吡啶的位置（邻位、间位、对位）对荧光团的颜色（从黄色到红色）以及其细胞定位（线粒体或细胞核）有影响。
• Inhibitors of dopamine .beta.-hydroxylase. 3. Some 1-(pyridylmethyl)imidazole-2-thiones
  作者：Stephen T. Ross、Lawrence I. Kruse、Eliot H. Ohlstein、Robert W. Erickson、Mildred Ezekiel、Kathryn E. Flaim、John L. Sawyer、Barry A. Berkowitz

  DOI：10.1021/jm00391a008

  日期：1987.8

  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.