N-(2-aminoethyl)-N-methyl-5-isoquinolinesulfonamide | 116700-40-4

• 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-aminoethyl)-N-methyl-5-isoquinolinesulfonamide
• 英文别名: N-(2-aminoethyl)-N-methylisoquinoline-5-sulfonamide
• CAS: 116700-40-4
• 化学式: C₁₂H₁₅N₃O₂S
• mdl: MFCD13430857
• 分子量: 265.336
• InChiKey: XLGGURACJIPJCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 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：
  84.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-甲基异硫脲硫酸盐 、 N-(2-aminoethyl)-N-methyl-5-isoquinolinesulfonamide 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.0h， 以44%的产率得到2-[2-[Isoquinolin-5-ylsulfonyl(methyl)amino]ethyl]guanidine;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 在 吡啶 、 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-(2-aminoethyl)-N-methyl-5-isoquinolinesulfonamide
  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

文献信息

• Rationally designed PKA inhibitors for positron emission tomography: Synthesis and cerebral biodistribution of N-(2-(4-bromocinnamylamino)ethyl)-N-[11C]methyl-isoquinoline-5-sulfonamide
  作者：Neil Vasdev、Frank J. LaRonde、James R. Woodgett、Armando Garcia、Elizabeth A. Rubie、Jeffrey H. Meyer、Sylvain Houle、Alan A. Wilson

  DOI：10.1016/j.bmc.2008.03.013

  日期：2008.5

  and N-(2-(4-bromocinnamylamino)ethyl)isoquinoline-5-sulfonamide (H-89, 2), (yielding N-(2-aminoethyl)-N-methyl-isoquinoline-5-sulfonamide (4) and N-(2-(4-bromocinnamylamino)ethyl)-N-methyl-isoquinoline-5-sulfonamide (5), respectively) does not appreciably reduce in vitro potency toward PKA. We have facilitated the synthesis of 4 by reacting isoquinoline-5-sulfonyl chloride with N-methylethylenediamine

  蛋白激酶 A (PKA) 是药物开发的重要信号转导靶标，因为它影响与神经精神疾病（如重度抑郁症）有关的关键细胞过程。本研究的目标是开发第一种用正电子发射断层扫描 (PET) 测量 PKA 水平的显像剂。通过对 5-异喹啉磺酰胺的合理衍生，发现在已知的 PKA 抑制剂 N-(2-氨基乙基)isoquinoline-5-sulfonamide (H-9, 1) 和 N- (2-(4-bromocinnamylamino)ethyl)isoquinoline-5-sulfonamide (H-89, 2), (产生 N-(2-aminoethyl)-N-methyl-isoquinoline-5-sulfonamide (4) 和 N-(2) -(4-bromocinnamylamino)ethyl)-N-methyl-isoquinoline-5-sulfonamide (5), 分别）不会明显降低体外对
• Isoquinoline derivatives
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP0287696B1

  公开（公告）日：1991-01-02
• Methods and compositions for the treatment of neurodegenerative disorders
  申请人：Jin Xiaowei

  公开号：US20080044390A1

  公开（公告）日：2008-02-21

  The present invention features compositions, kits, and methods for treating, preventing, and ameliorating neurodegenerative disorders, e.g., Huntington's disease.
• US4798897A
  申请人：——

  公开号：US4798897A

  公开（公告）日：1989-01-17
• [EN] METHODS AND COMPOSITIONS FOR THE TREATMENT OF NEURODEGENERATIVE DISORDERS<br/>[FR] MÉTHODES ET COMPOSITIONS POUR LE TRAITEMENT DE TROUBLES NEURODÉGÉNÉRATIFS
  申请人：COMBINATORX INC

  公开号：WO2008021210A2

  公开（公告）日：2008-02-21

  [EN] The present invention features compositions, kits, and methods for treating, preventing, and ameliorating neurodegenerative disorders, e.g., Huntington's disease.
  [FR] La présente invention comporte des compositions, des kits et des méthodes pour traiter, prévenir et guérir des troubles neurodégénératifs, par exemple, la maladie de Huntington.