N-hexyl-N-(2-hydroxyethyl)-5-isoquinolinesulfonamide | 111541-55-0

• 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-hexyl-N-(2-hydroxyethyl)-5-isoquinolinesulfonamide
• 英文别名: N-hexyl-N-(2-hydroxyethyl)isoquinoline-5-sulfonamide
• CAS: 111541-55-0
• 化学式: C₁₇H₂₄N₂O₃S
• 分子量: 336.455
• InChiKey: PGOVORSXZMZVNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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-hexyl-N-(2-hydroxyethyl)-5-isoquinolinesulfonamide 在 邻苯二甲酸亚胺 、 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 N-(2-aminoethyl)-N-hexyl-5-isoquinolinesulfonamide hydrochloride
  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
• 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-hexyl-N-(2-hydroxyethyl)-5-isoquinolinesulfonamide
  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

• Isoquinoline derivatives
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：US04798897A1

  公开（公告）日：1989-01-17

  An isoquinoline derivative represented by the formula (I) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and A are as defined in the disclosure, or a pharmacologically acceptable acid salt thereof. These compounds have an excellent relaxation action on blood vessels, particularly coronary arteries, and on bronchial tubes. Accordingly, the compounds can be advantageously utilized as drugs for prevention and treatment of angina, myocardial infarction, cardiovascular thrombosis, cerebrovascular thrombosis, hypertonia, asthma and other various circulatory and respiratory organ diseases.

  一种以式(I)表示的异喹啉衍生物，其中R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.5和A如本文所定义，或其药学上可接受的酸盐。这些化合物对血管，特别是冠状动脉和支气管具有优异的松弛作用。因此，这些化合物可以优势地用作预防和治疗心绞痛、心肌梗塞、心血管血栓形成、脑血栓形成、高血压、哮喘和其他各种循环和呼吸器官疾病的药物。
• 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：——
• XIDAKA, XIROESI;MORIKAVA, YASURI
  作者：XIDAKA, XIROESI、MORIKAVA, YASURI

  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.