2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)ethanesulfonic acid butylamide | 81428-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)ethanesulfonic acid butylamide
• 英文别名: N-butyl-2-(1,3-dioxoisoindolin-2-yl)ethanesulfonamide；N-butyl-2-(1,3-dioxoisoindol-2-yl)ethanesulfonamide
• CAS: 81428-05-9
• 化学式: C₁₄H₁₈N₂O₄S
• 分子量: 310.374
• InChiKey: WXDXIUOLCGZNJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  91.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)ethanesulfonic acid butylamide 在 一水合肼 作用下， 以 乙醇 为溶剂， 以37 %的产率得到2-amino-ethanesulfonic acid butylamide
  参考文献：
  名称：

  Synthesis of New Amidoethanesulfonamides of Betulonic Acid

  摘要：

  DOI：

  10.1007/s10600-023-03983-z
• 作为产物：
  描述：

  2-苯二(甲)酰亚氨基乙烷磺酰氯 生成 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)ethanesulfonic acid butylamide
  参考文献：
  名称：

  ANDERSEN, L. H.;HILDEN, L. A. I.

  摘要：

  DOI：

文献信息

• Novel 2,7-Dialkyl-Substituted 5(<i>S</i>)-Amino-4(<i>S</i>)-hydroxy-8-phenyl-octanecarboxamide Transition State Peptidomimetics Are Potent and Orally Active Inhibitors of Human Renin
  作者：Richard Göschke、Stefan Stutz、Vittorio Rasetti、Nissim-Claude Cohen、Joseph Rahuel、Pascal Rigollier、Hans-Peter Baum、Peter Forgiarini、Christian R. Schnell、Trixie Wagner、Markus G. Gruetter、Walter Fuhrer、Walter Schilling、Frédéric Cumin、Jeanette M. Wood、Jürgen Maibaum

  DOI：10.1021/jm070314y

  日期：2007.10.1

  The action of renin is the rate-limiting step of the renin-angiotensin system (RAS), a key regulator of blood pressure. Effective renin inhibitors directly block the RAS entirely at source and, thus, may provide a vital weapon for hypertension therapy. Our efforts toward identifying novel small-molecule peptidomimetic renin inhibitors have resulted in the design of transition-state isosteres such as I bearing an all-carbon 8-phenyl-octanecarboxamide framework. Optimization of the extended P3 portion of I and extensive P2' modifications provided analogues with improved in vitro potencies in the presence of plasma. X-ray resolution of rhrenin/38a in the course of SAR work surprisingly unveiled the exploitation of a previously unexplored pocket (S3(SP)) important for strong binding affinities. Several inhibitors demonstrated oral efficacy in sodium-depleted marmosets. The most potent, 38a, induced dose-dependently a pronounced reduction in mean arterial blood pressure, paralleled by complete blockade of active plasma renin, up to 8 h post-dose. Oral bioavailability of 38a was 16% in marmosets.
• ANDERSEN, L. H.;HILDEN, L. A. I.
  作者：ANDERSEN, L. H.、HILDEN, L. A. I.

  DOI：——

  日期：——
• Synthesis of New Amidoethanesulfonamides of Betulonic Acid
  作者：N. G. Komissarova、A. V. Orlov、L. V. Spirikhin

  DOI：10.1007/s10600-023-03983-z

  日期：2023.3