N-(2-hydroxyethyl)-5-isoquinolinesulfonamide | 116700-33-5

• 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)-5-isoquinolinesulfonamide
• 英文别名: N-(2-hydroxyethyl)isoquinoline-5-sulfonamide
• CAS: 116700-33-5
• 化学式: C₁₁H₁₂N₂O₃S
• mdl: MFCD12439954
• 分子量: 252.294
• InChiKey: RELBLPIODCGVOB-UHFFFAOYSA-N

物化性质

• 熔点：
  144-145 °C(Solv: ethanol (64-17-5))
• 沸点：
  500.8±56.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxyethyl)-5-isoquinolinesulfonamide 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 N-[2-(methylamino)ethyl]-5-isoquinoline sulfonamide 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-(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-or quinoline-sulfonamide derivative and a pharmaceutical
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：US05340811A1

  公开（公告）日：1994-08-23

  Disclosed is a sulfonamide derivative represented by following formula (I) and a medicine for the treatment of asthma comprising the sulfonamide derivative as an active ingredient which exhibits bronchodilation effect. ##STR1## wherein X represents a quinoline residue represented by formula (II) or an isoquinoline residue represented by formula (III) ##STR2## where R.sup.1 is a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, or ##STR3## where R.sup.2 is a hydrogen atom or a hydroxyl group, and wherein: when X is quinoline residue (II), n is zero or 1, in which, when n is zero, R.sup.4 is an unsubstituted or substituted diazacycloalkyl group, and when n is 1, R.sup.3 is a hydrogen atom or a lower alkyl group and R.sup.4 is an unsubstituted or substituted aralkylamino group or an unsubstituted or substituted diazacycloalkyl group; and when X is isoquinoline residue (III), n is 1, in which, R.sup.3 is a hydrogen atom or a lower alkyl group and R.sup.4 is a 3,4-methylenedioxyphenethylamino group, a 3,4-methylenedioxybenzylamino group or an unsubstituted or substituted diazacycloalkyl group, with the proviso that when R.sup.4 is an unsubstituted or substituted diazacycloalkyl group, the diazacycloalkyl group is bonded at a nitrogen atom thereof.

  本发明公开了一种磺胺衍生物，其表示为以下式（I），以及包含所述磺胺衍生物作为活性成分的治疗哮喘的药物，该药物具有支气管扩张作用。其中，X代表由式（II）表示的喹啉残基或由式（III）表示的异喹啉残基。其中，R.sup.1是氢原子、卤素原子、低碳基团或低烷氧基团，或者R.sup.2是氢原子或羟基，且当X为喹啉残基（II）时，n为零或1，其中当n为零时，R.sup.4是未取代或取代的二氮杂环烷基团，当n为1时，R.sup.3是氢原子或低碳基团，R.sup.4是未取代或取代的芳基氨基团或未取代或取代的二氮杂环烷基团；当X为异喹啉残基（III）时，n为1，其中，R.sup.3是氢原子或低碳基团，R.sup.4是3,4-亚甲二氧基苯乙胺基团、3,4-亚甲二氧基苄胺基团或未取代或取代的二氮杂环烷基团，但当R.sup.4是未取代或取代的二氮杂环烷基团时，该二氮杂环烷基团与其氮原子结合。
• 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.
• Isoquinoline derivatives
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP0287696B1

  公开（公告）日：1991-01-02
• SULFONAMIDE DERIVATIVE AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP0471841B1

  公开（公告）日：1995-11-02
• 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：——