N-(2-hydroxyethyl)-N-methylisoquinoline-5-sulfonamide | 116700-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-(2-hydroxyethyl)-N-methylisoquinoline-5-sulfonamide
• CAS: 116700-34-6
• 化学式: C₁₂H₁₄N₂O₃S
• 分子量: 266.321
• InChiKey: VVKNWERLSZDYAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxyethyl)-N-methylisoquinoline-5-sulfonamide 以44%的产率得到
  参考文献：
  名称：

  MORIKAWA, ANRI;SONE, TAKANORI;ASANO, TOSHIO, J. MED. CHEM., 32,(1989) N, C. 42-46

  摘要：

  DOI：
• 作为产物：
  描述：

  5-异喹啉磺酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 氯化亚砜 、 碳酸氢钠 、 N,N-二甲基甲酰胺 作用下， 反应 3.0h， 生成 N-(2-hydroxyethyl)-N-methylisoquinoline-5-sulfonamide
  参考文献：
  名称：

  5-Isoquinolinesulfonamide derivatives. 2. Synthesis and vasodilatory activity of N-(2-aminoethyl)-5-isoquinoline sulfonamide derivatives

  摘要：

  A new series of aromatic sulfonamides, the N-(2-aminoethyl)-5-isoquinolinesulfonamide derivatives, 3, was synthesized from 5-isoquinolinesulfonic acid and shown to possess vasodilatory action. Vasodilatory activity was evaluated in vivo in terms of increases in arterial blood flow in dogs after local injection in the femoral and/or vertebral arteries. When the alkylene group between the two nonaromatic nitrogen atoms was ethylene, the most potent activity was obtained. Alkylations of either of the two nonaromatic nitrogens yielded more active compounds, although bulky or excessively long alkyl groups reduced the potency. Among these derivatives, 27 and 47 were equipotent to diltiazem, which is used clinically as a cardiovascular drug. These two compounds also had antihypertensive and vasodilatory activities when administered intravenously, although the activities were less than that of diltiazem when given by this route.

  DOI：

  10.1021/jm00121a010

文献信息

• 5-Isoquinolinesulfonamide derivatives. 1. Synthesis and vasodilatory activity of N-(2-guanidinoethyl)-5-isoquinolinesulfonamide derivatives
  作者：Anri Morikawa、Takanori Sone、Toshio Asano

  DOI：10.1021/jm00121a009

  日期：1989.1

  Two novel series of N-(2-guanidinoalkyl)-5-isoquinolinesulfonamides, 2 and 3, were prepared. Many of the compounds possessed vasodilatory activity when injected locally into the femoral artery of dogs. The most potent compound, 1-amidino-4-(5-isoquinolylsulfonyl)-1,4-perhydrodiazepine, 33, was comparable to diltiazem, which is used clinically as a vasodilator.
• MORIKAWA, ANRI;SONE, TAKANORI;ASANO, TOSHIO, J. MED. CHEM., 32,(1989) N, C. 46-50
  作者：MORIKAWA, ANRI、SONE, TAKANORI、ASANO, TOSHIO

  DOI：——

  日期：——
• MORIKAWA, ANRI;SONE, TAKANORI;ASANO, TOSHIO, J. MED. CHEM., 32,(1989) N, C. 42-46
  作者：MORIKAWA, ANRI、SONE, TAKANORI、ASANO, TOSHIO

  DOI：——

  日期：——
• US4798897A
  申请人：——

  公开号：US4798897A

  公开（公告）日：1989-01-17
• 5-Isoquinolinesulfonamide derivatives. 2. Synthesis and vasodilatory activity of N-(2-aminoethyl)-5-isoquinoline sulfonamide derivatives
  作者：Anri Morikawa、Takanori Sone、Toshio Asano

  DOI：10.1021/jm00121a010

  日期：1989.1

  A new series of aromatic sulfonamides, the N-(2-aminoethyl)-5-isoquinolinesulfonamide derivatives, 3, was synthesized from 5-isoquinolinesulfonic acid and shown to possess vasodilatory action. Vasodilatory activity was evaluated in vivo in terms of increases in arterial blood flow in dogs after local injection in the femoral and/or vertebral arteries. When the alkylene group between the two nonaromatic nitrogen atoms was ethylene, the most potent activity was obtained. Alkylations of either of the two nonaromatic nitrogens yielded more active compounds, although bulky or excessively long alkyl groups reduced the potency. Among these derivatives, 27 and 47 were equipotent to diltiazem, which is used clinically as a cardiovascular drug. These two compounds also had antihypertensive and vasodilatory activities when administered intravenously, although the activities were less than that of diltiazem when given by this route.