2-氨基-3-乙基苯磺酰胺 | 194020-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氨基-3-乙基苯磺酰胺
• 英文名称: 3-ethyl-2-aminobenzenesulfonamide
• 英文别名: 2-amino-3-ethylbenzenesulfonamide
• CAS: 194020-05-8
• 化学式: C₈H₁₂N₂O₂S
• 分子量: 200.261
• InChiKey: MXUOCYOEJLHSPP-UHFFFAOYSA-N

物化性质

• 沸点：
  404.5±55.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  94.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基-3-乙基苯磺酰胺 在 N-氯代丁二酰亚胺 、 D(+)-10-樟脑磺酸 作用下， 以 乙腈 为溶剂， 反应 13.75h， 生成
  参考文献：
  名称：

  5′-Alkyl-benzothiadiazides: A New Subgroup of AMPA Receptor Modulators with Improved Affinity

  摘要：

  AMPA receptors form a major subdivision of the glutamate receptor family that mediates excitatory synaptic transmission in the brain, Currents through AMPA receptors can be up- or down-regulated by compounds that allosterically modulate receptor kinetics through binding sites distinct from that for glutamate. One of those modulators is the benzothiadiazide IDRA-21 which has been reported to enhance synaptic transmission and be effective in behavioral tests, but typically requires threshold concentrations of at least 100 muM to be active in vitro. In this study, new benzothiadiazides were developed with IDRA-21 as lead compound and examined for their potency in modulating AMPA receptor kinetics. A significant increase in drug affinity was obtained by alkyl substitution at the 5'-position of IDRA-21; substitutions at other positions of the benzothiadiazide core generally did not yield a further gain in affinity and in some cases abolished drug binding. The 5'-ethyl derivative exhibited an EC50 value in the order of 22 muM which represents about a 30-fold gain in affinity over that of IDRA-21. The EC50 value is comparable to that of cyclothiazide, the most potent benzothiadiazide drug, but the effects on AMPA receptors differed substantially between these two compounds in that the 5'-ethyl derivative of IDRA-21 greatly increased the binding affinity for receptor agonists whereas cyclothiazide is known to reduce agonist binding. The structure-activity relationships reported here thus offer to provide new insights how receptor kinetics is linked to particular aspects of receptor-drug interactions. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(01)00405-9
• 作为产物：
  描述：

  2-乙基苯胺 在 三氯化铝 、 硫酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 2-氨基-3-乙基苯磺酰胺
  参考文献：
  名称：

  5′-Alkyl-benzothiadiazides: A New Subgroup of AMPA Receptor Modulators with Improved Affinity

  摘要：

  AMPA receptors form a major subdivision of the glutamate receptor family that mediates excitatory synaptic transmission in the brain, Currents through AMPA receptors can be up- or down-regulated by compounds that allosterically modulate receptor kinetics through binding sites distinct from that for glutamate. One of those modulators is the benzothiadiazide IDRA-21 which has been reported to enhance synaptic transmission and be effective in behavioral tests, but typically requires threshold concentrations of at least 100 muM to be active in vitro. In this study, new benzothiadiazides were developed with IDRA-21 as lead compound and examined for their potency in modulating AMPA receptor kinetics. A significant increase in drug affinity was obtained by alkyl substitution at the 5'-position of IDRA-21; substitutions at other positions of the benzothiadiazide core generally did not yield a further gain in affinity and in some cases abolished drug binding. The 5'-ethyl derivative exhibited an EC50 value in the order of 22 muM which represents about a 30-fold gain in affinity over that of IDRA-21. The EC50 value is comparable to that of cyclothiazide, the most potent benzothiadiazide drug, but the effects on AMPA receptors differed substantially between these two compounds in that the 5'-ethyl derivative of IDRA-21 greatly increased the binding affinity for receptor agonists whereas cyclothiazide is known to reduce agonist binding. The structure-activity relationships reported here thus offer to provide new insights how receptor kinetics is linked to particular aspects of receptor-drug interactions. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(01)00405-9

文献信息

• Method for treating sexual dysfunctions
  申请人：The Regents of the University of California

  公开号：US06083947A1

  公开（公告）日：2000-07-04

  This invention is a novel treatment for sexual dysfunctions by administering to a subject exhibiting a sexual dysfunction compounds that upmodulate the AMPA receptor. Methods and compositions for treating sexual dysfunction are provided. Kits containing the compositions in appropriate form for administration are also provided.

  这项发明是一种通过向表现出性功能障碍的主体施用上调AMPA受体的化合物来治疗性功能障碍的新方法。提供了治疗性功能障碍的方法和组合物。还提供了包含适于给药形式的组合物的试剂盒。
• Anti-infective agents
  申请人：——

  公开号：US20040087577A1

  公开（公告）日：2004-05-06

  Compounds having the formula 1 are hepatitis C (HCV) polymerase inhibitors. Also disclosed are a composition and method for inhibiting hepatitis C (HCV) polymerase, processes for making the compounds, and synthetic intermediates employed in the processes.

  具有公式1的化合物是丙型肝炎（HCV）聚合酶抑制剂。还公开了一种用于抑制丙型肝炎（HCV）聚合酶的组成和方法，用于制造这些化合物的过程，以及在这些过程中使用的合成中间体。
• METHOD FOR TREATING SEXUAL DYSFUNCTIONS
  申请人：The Regents of The University of California

  公开号：EP0883403B1

  公开（公告）日：2010-08-25
• EP0883403A4
  申请人：——

  公开号：EP0883403A4

  公开（公告）日：2002-03-06
• N-ACYLSULFONAMIDE APOPTOSIS PROMOTERS
  申请人：Abbott Laboratories

  公开号：EP1318978A2

  公开（公告）日：2003-06-18