3-[3-(Adamantan-1-ylamino)-propyl]-7,8-dimethoxy-1,3-dihydro-benzo[d]azepin-2-one | 847737-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 3-[3-(Adamantan-1-ylamino)-propyl]-7,8-dimethoxy-1,3-dihydro-benzo[d]azepin-2-one
• CAS: 847737-86-4
• 化学式: C₂₅H₃₄N₂O₃
• 分子量: 410.557
• InChiKey: CTUKAUPGPNIALT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  50.8
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-[3-(Adamantan-1-ylamino)-propyl]-7,8-dimethoxy-1,3-dihydro-benzo[d]azepin-2-one 在 palladium on activated charcoal 甲酸 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Design, synthesis and preliminary biological evaluation of zatebradine analogues as potential blockers of the hyperpolarization-activated current

  摘要：

  A series of zatebradine analogues, differing in the basic moiety and in the methylene spacer, have been synthesized; their negative chronotropic activity has been determined in guinea pig atria. The most active compounds have been studied for their blocking properties on the hyperpolarization-activated current If (which is one of the main currents underlying automatic activity in the sinus node) measured on ventricular myocytes of old spontaneously-hypertensive rats (SHR) by means of the patch-clamp technique. The majority of the substances were able to block If, with one of them (15) being slightly more potent than zatebradine. Surprisingly one analogue (6), while showing good negative chronotropic activity, was found to inhibit I-r only at high concentration and to markedly reduce outward currents, suggesting for this substance a different mechanism of action responsible for the negative chronotropic effect. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.017
• 作为产物：
  描述：

  金刚烷胺 、 7,8-二甲氧基-3-(3-碘代丙基)-1,3-二氢-2H-3-苯并氮杂卓-2-酮 以 乙腈 为溶剂， 反应 4.0h， 以33%的产率得到3-[3-(Adamantan-1-ylamino)-propyl]-7,8-dimethoxy-1,3-dihydro-benzo[d]azepin-2-one
  参考文献：
  名称：

  Design, synthesis and preliminary biological evaluation of zatebradine analogues as potential blockers of the hyperpolarization-activated current

  摘要：

  A series of zatebradine analogues, differing in the basic moiety and in the methylene spacer, have been synthesized; their negative chronotropic activity has been determined in guinea pig atria. The most active compounds have been studied for their blocking properties on the hyperpolarization-activated current If (which is one of the main currents underlying automatic activity in the sinus node) measured on ventricular myocytes of old spontaneously-hypertensive rats (SHR) by means of the patch-clamp technique. The majority of the substances were able to block If, with one of them (15) being slightly more potent than zatebradine. Surprisingly one analogue (6), while showing good negative chronotropic activity, was found to inhibit I-r only at high concentration and to markedly reduce outward currents, suggesting for this substance a different mechanism of action responsible for the negative chronotropic effect. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.017