3-amino-N-methylpropane-1-sulfonamide | 860111-98-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 3-amino-N-methylpropane-1-sulfonamide
• 英文别名: 3-aminopropane-N-methylsulfonamide
• CAS: 860111-98-4
• 化学式: C₄H₁₂N₂O₂S
• 分子量: 152.217
• InChiKey: OXIUGKFUBWICRY-UHFFFAOYSA-N

物化性质

• 沸点：
  262.9±42.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-N-methylpropane-1-sulfonamide 、 4-acetyl-1(2H)isoquinolone 在 titanium(IV) isopropylate 、 sodium tetrahydroborate 、 乙醇 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以27%的产率得到N-methyl-3-((1-(1-oxo-1,2-dihydroisoquinolin-4-yl)ethyl)amino)propane-1-sulfonamide
  参考文献：
  名称：

  WO2020123674A5

  摘要：

  公开号：

  WO2020123674A5
• 作为产物：
  描述：

  3-phthalimidopropane-N-methylsulfonamide 在 水 、 肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 3-amino-N-methylpropane-1-sulfonamide
  参考文献：
  名称：

  Synthesis and QSAR of Quinazoline Sulfonamides As Highly Potent Human Histamine H₄ Receptor Inverse Agonists

  摘要：

  Hit optimization of the class of quinazoline containing histamine H-4 receptor (H4R) ligands resulted in a sulfonamide substituted analogue with high affinity for the H4R. This moiety leads to improved physicochemical properties and is believed to probe a distinct H4R binding pocket that was previously identified using pharmacophore modeling. By introducing a variety of sulfonamide substituents, the H4R affinity was optimized. The interaction of the new ligands, in combination with a set of previously published quinazoline compounds, was described by a QSAR equation. Pharmacological studies revealed that the sulfonamide analogues have excellent H4R affinity and behave as inverse agonists at the human H4R. In vivo evaluation of the potent 2-(6-chloro-2-(4-methylpiperazin-1-yl)quinazoline-4-amino)-N-phenylethanesulfonamide (54) (pK(i) = 8.31 +/- 0.10) revealed it to have anti-inflammatory activity in an animal model of acute inflammation.

  DOI：

  10.1021/jm901379s

文献信息

• INDOLEAMINE-2,3-DIOXYGENASE INHIBITOR, PREPARATION METHOD THEREFOR AND USE THEREOF
  申请人：Hinova Pharmaceuticals Inc.

  公开号：EP3747875B1

  公开（公告）日：2022-12-07
• WO2020123674A5
  申请人：——

  公开号：WO2020123674A5

  公开（公告）日：2022-05-27
• Synthesis and QSAR of Quinazoline Sulfonamides As Highly Potent Human Histamine H₄ Receptor Inverse Agonists
  作者：Rogier A. Smits、Maristella Adami、Enade P. Istyastono、Obbe P. Zuiderveld、Cindy M. E. van Dam、Frans J. J. de Kanter、Aldo Jongejan、Gabriella Coruzzi、Rob Leurs、Iwan J. P. de Esch

  DOI：10.1021/jm901379s

  日期：2010.3.25

  Hit optimization of the class of quinazoline containing histamine H-4 receptor (H4R) ligands resulted in a sulfonamide substituted analogue with high affinity for the H4R. This moiety leads to improved physicochemical properties and is believed to probe a distinct H4R binding pocket that was previously identified using pharmacophore modeling. By introducing a variety of sulfonamide substituents, the H4R affinity was optimized. The interaction of the new ligands, in combination with a set of previously published quinazoline compounds, was described by a QSAR equation. Pharmacological studies revealed that the sulfonamide analogues have excellent H4R affinity and behave as inverse agonists at the human H4R. In vivo evaluation of the potent 2-(6-chloro-2-(4-methylpiperazin-1-yl)quinazoline-4-amino)-N-phenylethanesulfonamide (54) (pK(i) = 8.31 +/- 0.10) revealed it to have anti-inflammatory activity in an animal model of acute inflammation.