Toluene-4-sulfonic acid 2-(isoquinoline-5-sulfonylamino)-ethyl ester | 129305-12-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Toluene-4-sulfonic acid 2-(isoquinoline-5-sulfonylamino)-ethyl ester
• 英文别名: 5-Isoquinolinesulfonamide,n-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-；2-(isoquinolin-5-ylsulfonylamino)ethyl 4-methylbenzenesulfonate
• CAS: 129305-12-0
• 化学式: C₁₈H₁₈N₂O₅S₂
• 分子量: 406.483
• InChiKey: NNBOAJUYJBANFP-UHFFFAOYSA-N

物化性质

• 沸点：
  639.3±65.0 °C(Predicted)
• 密度：
  1.388±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid 2-(isoquinoline-5-sulfonylamino)-ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 1-[2-(Isoquinolin-5-ylsulfonylamino)ethyl]-1-methylguanidine;hydrochloride
  参考文献：
  名称：

  5-Isoquinolinesulfonamide derivatives. 1. Synthesis and vasodilatory activity of N-(2-guanidinoethyl)-5-isoquinolinesulfonamide derivatives

  摘要：

  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.

  DOI：

  10.1021/jm00121a009
• 作为产物：
  描述：

  异喹啉-5-磺酰氯盐酸盐 在 吡啶 、 碳酸氢钠 作用下， 反应 2.0h， 生成 Toluene-4-sulfonic acid 2-(isoquinoline-5-sulfonylamino)-ethyl ester
  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.

  本发明涉及一种磺酰胺衍生物，其表示为以下式（I），以及一种治疗哮喘的药物，其中该磺酰胺衍生物作为活性成分表现出支气管扩张作用。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R1是氢原子、卤素原子、低级烷基或低级烷氧基，或其中之一：其中R2是氢原子或羟基；当X为喹啉残基（II）时，n为零或1，在其中，当n为零时，R4是未取代或取代的二氮环烷基，当n为1时，R3是氢原子或低级烷基，R4是未取代或取代的芳基烷氨基或未取代或取代的二氮环烷基；当X为异喹啉残基（III）时，n为1，在其中，R3是氢原子或低级烷基，R4是3,4-亚甲二氧基苯乙胺基、3,4-亚甲二氧基苄胺基或未取代或取代的二氮环烷基，但当R4是未取代或取代的二氮环烷基时，该二氮环烷基与其中的氮原子相连。
• Isoquinoline derivatives
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP0287696B1

  公开（公告）日：1991-01-02
• MIESI, SIRO;ASANO, TOSIO
  作者：MIESI, SIRO、ASANO, TOSIO

  DOI：——

  日期：——
• 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.
• 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.