3-(3-hydroxymethylphenyl)-5-isobutylthiophene-2-(N-tert-butyl)sulfonamide | 912942-72-4

• 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: 3-(3-hydroxymethylphenyl)-5-isobutylthiophene-2-(N-tert-butyl)sulfonamide
• 英文别名: 3-(3-hydroxymethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide；N-tert-butyl-3-[3-(hydroxymethyl)phenyl]-5-(2-methylpropyl)thiophene-2-sulfonamide
• CAS: 912942-72-4
• 化学式: C₁₉H₂₇NO₃S₂
• 分子量: 381.56
• InChiKey: LEYKPPRPUICCBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3-hydroxymethylphenyl)-5-isobutylthiophene-2-(N-tert-butyl)sulfonamide 在 四溴化碳 、 苯甲醚 、 三苯基膦 、 三氟乙酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 3-(3-((2-acetyl-1H-imidazol-1-yl)methyl)phenyl)-5-isobutylthiophene-2-sulfonamide
  参考文献：
  名称：

  From the First Selective Non-Peptide AT₂ Receptor Agonist to Structurally Related Antagonists

  摘要：

  A para substitution pattern of the phenyl ring is a characteristic feature of the first reported selective AT(2) receptor agonist M024/C21 (1) and all the nonpeptidic AT(2) receptor agonists described so far. Two series of compounds structurally related to 1 but with a meta substitution pattern have now been synthesized and biologically evaluated for their affinity to the AT(1) and AT(2) receptors. A high AT(2)/AT(1) receptor selectivity was obtained with all 41 compounds synthesized, and the majority exhibited K-i ranging from 2 to 100 nM. Five compounds were evaluated for their functional activity at the AT(2) receptor, applying a neurite outgrowth assay in NG108-15 cells.. Notably, four of the five compounds, with representatives from both series, acted as potent AT(2) receptor antagonists. These compounds were found to be considerably more effective than PD 123,319, the standard AT(2) receptor antagonist used in most laboratories. No AT(2) receptor antagonists were previously reported among the derivatives with a para substitution pattern. Hence, by a minor modification of the agonist 1 it could be transformed into the antagonist, compound 38. These compounds should serve as valuable tools in the assessment of the role of the AT(2) receptor in more complex physiological models.

  DOI：

  10.1021/jm2015099
• 作为产物：
  描述：

  3-溴苯甲醇 、 5-异丁基-2-(N-叔丁基氨基磺酰基)噻吩-3-硼酸 在 四(三苯基膦)钯 sodium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 4.0h， 以57%的产率得到3-(3-hydroxymethylphenyl)-5-isobutylthiophene-2-(N-tert-butyl)sulfonamide
  参考文献：
  名称：

  WO2006/109056

  摘要：

  公开号：

文献信息

• Tricyclic Angiotensin II Agonists
  申请人：Alterman Mathias

  公开号：US20090215847A1

  公开（公告）日：2009-08-27

  There is provided compounds of formula I, wherein the dotted line, X 1 , X 2 , X 3 , A, Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 2 , R 2 and R 3 have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful as selective agonists of the AT2 receptor, and thus, in particular, in the treatment of inter alia gastrointestinal conditions, such as dyspepsia, IBS and MOF, and cardiovascular disorders.

  提供了一些公式为I的化合物，其中虚线，X1，X2，X3，A，Y1，Y2，Y3，Y4，Z1，Z2，R2和R3的含义在说明中给出，并且其药学上可接受的盐，这些化合物可用作AT2受体的选择性激动剂，因此特别适用于治疗胃肠疾病，如消化不良，肠易激综合征和多器官功能障碍等，以及心血管疾病。
• Tricyclic angiotensin II agonists
  申请人：Vicore Pharma AB

  公开号：US08067418B2

  公开（公告）日：2011-11-29

  There is provided compounds of formula I, wherein the dotted line, X1, X2, X3, A, Y1, Y2, Y3, Y4, Z1, Z2, R2 and R3 have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful as selective agonists of the AT2 receptor, and thus, in particular, in the treatment of inter alia gastrointestinal conditions, such as dyspepsia, IBS and MOF, and cardiovascular disorders.

  提供了公式I的化合物，其中虚线、X1、X2、X3、A、Y1、Y2、Y3、Y4、Z1、Z2、R2和R3的含义在描述中给出，并且其药学上可接受的盐，这些化合物可用作AT2受体的选择性激动剂，因此，特别适用于治疗胃肠疾病，如消化不良、肠易激综合征和多器官功能障碍等，以及心血管疾病。
• WO2006/109056
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2006/109048
  申请人：——

  公开号：——

  公开（公告）日：——
• NEW TRICYCLIC ANGIOTENSIN II AGONISTS
  申请人：Vicore Pharma AB

  公开号：EP1869023B1

  公开（公告）日：2012-01-11