2-[(3-cyanofuroxan-4-yl)methoxy]benzaldehyde | 692756-19-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[(3-cyanofuroxan-4-yl)methoxy]benzaldehyde
• 英文别名: 4-[(2-Formylphenoxy)methyl]-2-oxido-1,2,5-oxadiazol-2-ium-3-carbonitrile
• CAS: 692756-19-7
• 化学式: C₁₁H₇N₃O₄
• 分子量: 245.194
• InChiKey: NCSVMTTWMPXXCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(3-cyanofuroxan-4-yl)methoxy]benzaldehyde 在 三甲氧基磷 作用下， 以 异丙醇 为溶剂， 反应 85.0h， 生成 (+)-methyl 4-[2-[(4-cyanofurazan-3-yl)methoxy]phenyl]-2,6-dimethyl-5-nitro-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  New 1,4-Dihydropyridines Endowed with NO-Donor and Calcium Channel Agonist Properties

  摘要：

  A new series of calcium channel agonists structurally related to Bay K8644, containing NO donor furoxans and the related furazans unable to release NO, is described. The racemic mixtures were studied for their action on L-type Ca2+ channels expressed in cultured rat insulinoma RINm5F cells. All the products proved to be potent calcium channel agonists. All the racemic mixtures, with the only exception of the carbamoyl derivatives 9, 12 endowed with scanty solubility, were separated by chiral chromatography into the corresponding enantiomers; the (+) enantiomers were found to be potent agonists while the (-) ones were feeble antagonists. The racemic mixtures were also assessed for their positive inotropic activity on electrically stimulated rat papillary muscle and for their ability to increase Ca2+ entry into the vascular smooth muscle of rat aorta strips. The cyanofuroxan 8 proved to be an interesting product with dual Ca2+-dependent positive inotropic and NO-dependent vasodilating activity.

  DOI：

  10.1021/jm031109v
• 作为产物：
  描述：

  邻甲基苄醇 、 4-(bromomethyl)furoxan-3-carbonitrile 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以87%的产率得到2-[(3-cyanofuroxan-4-yl)methoxy]benzaldehyde
  参考文献：
  名称：

  New 1,4-Dihydropyridines Endowed with NO-Donor and Calcium Channel Agonist Properties

  摘要：

  A new series of calcium channel agonists structurally related to Bay K8644, containing NO donor furoxans and the related furazans unable to release NO, is described. The racemic mixtures were studied for their action on L-type Ca2+ channels expressed in cultured rat insulinoma RINm5F cells. All the products proved to be potent calcium channel agonists. All the racemic mixtures, with the only exception of the carbamoyl derivatives 9, 12 endowed with scanty solubility, were separated by chiral chromatography into the corresponding enantiomers; the (+) enantiomers were found to be potent agonists while the (-) ones were feeble antagonists. The racemic mixtures were also assessed for their positive inotropic activity on electrically stimulated rat papillary muscle and for their ability to increase Ca2+ entry into the vascular smooth muscle of rat aorta strips. The cyanofuroxan 8 proved to be an interesting product with dual Ca2+-dependent positive inotropic and NO-dependent vasodilating activity.

  DOI：

  10.1021/jm031109v

文献信息

• New 1,4-Dihydropyridines Endowed with NO-Donor and Calcium Channel Agonist Properties
  作者：Sonja Visentin、Barbara Rolando、Antonella Di Stilo、Roberta Fruttero、Monica Novara、Emilio Carbone、Christian Roussel、Nicolas Vanthuyne、Alberto Gasco

  DOI：10.1021/jm031109v

  日期：2004.5.1

  A new series of calcium channel agonists structurally related to Bay K8644, containing NO donor furoxans and the related furazans unable to release NO, is described. The racemic mixtures were studied for their action on L-type Ca2+ channels expressed in cultured rat insulinoma RINm5F cells. All the products proved to be potent calcium channel agonists. All the racemic mixtures, with the only exception of the carbamoyl derivatives 9, 12 endowed with scanty solubility, were separated by chiral chromatography into the corresponding enantiomers; the (+) enantiomers were found to be potent agonists while the (-) ones were feeble antagonists. The racemic mixtures were also assessed for their positive inotropic activity on electrically stimulated rat papillary muscle and for their ability to increase Ca2+ entry into the vascular smooth muscle of rat aorta strips. The cyanofuroxan 8 proved to be an interesting product with dual Ca2+-dependent positive inotropic and NO-dependent vasodilating activity.