3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-carboxamide | 477775-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-carboxamide
• 英文别名: 3-[4-(imidazol-1-ylmethyl)phenyl]-5-(2-methylpropyl)thiophene-2-carboxamide
• CAS: 477775-51-2
• 化学式: C₁₉H₂₁N₃OS
• 分子量: 339.461
• InChiKey: UAAAANWBZZFBPR-UHFFFAOYSA-N

物化性质

• 沸点：
  495.0±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  89.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-carboxamide 在 吡啶 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以40%的产率得到3-(4-imidazol-1-ylmethylphenyl)-5-isobutylthiophene-2-carbonitrile
  参考文献：
  名称：

  Selective Angiotensin II AT₂ Receptor Agonists:  Arylbenzylimidazole Structure−Activity Relationships

  摘要：

  Structural alterations in the 2- and 5-positions of the first drug-like selective angiotensin II AT(2) receptor agonist (1) have been performed. The imidazole ring system was proven to be a strong determinant for the AT(2) selectivity, and with few exceptions all variations gave good AT(2) receptor affinities and with retained high AT(2)/AT(1) selectivities. On the contrary to the findings with AT(1) receptor agonists, the impact of structural modifications in the 5-position of the AT(2) selective compounds were less pronounced regarding activation of the AT(2) receptor. The butyloxyphenyl (56) and the propylthienyl (50) derivatives were found to exert a high agonistic effect as deduced from their capacity to induce neurite elongation in neuronal cells, as does angiotensin II.

  DOI：

  10.1021/jm0606185
• 作为产物：
  描述：

  3-(4-imidazol-1-ylmethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-carboxamide 在 苯甲醚 、 三氟乙酸 作用下， 反应 17.0h， 以83%的产率得到3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-carboxamide
  参考文献：
  名称：

  Selective Angiotensin II AT₂ Receptor Agonists:  Arylbenzylimidazole Structure−Activity Relationships

  摘要：

  Structural alterations in the 2- and 5-positions of the first drug-like selective angiotensin II AT(2) receptor agonist (1) have been performed. The imidazole ring system was proven to be a strong determinant for the AT(2) selectivity, and with few exceptions all variations gave good AT(2) receptor affinities and with retained high AT(2)/AT(1) selectivities. On the contrary to the findings with AT(1) receptor agonists, the impact of structural modifications in the 5-position of the AT(2) selective compounds were less pronounced regarding activation of the AT(2) receptor. The butyloxyphenyl (56) and the propylthienyl (50) derivatives were found to exert a high agonistic effect as deduced from their capacity to induce neurite elongation in neuronal cells, as does angiotensin II.

  DOI：

  10.1021/jm0606185

文献信息

• Tricyclic compounds useful as angiotensin II agonists
  申请人：——

  公开号：US20040167176A1

  公开（公告）日：2004-08-26

  There is provided compounds of formula (I), wherein X 1 , X 2 , X 3 , Y 4 , Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 2 , R 4 and R 5 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X1、X2、X3、Y1、Y2、Y3、Y4、Z1、Z2、R4和R5在说明中给出了它们的含义，以及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道疾病（如消化不良、肠易激综合征和多器官衰竭等）和心血管疾病。
• Tricyclic Compounds Useful as Angiotensin II Agonists
  申请人：ALTERMAN Mathias

  公开号：US20090326026A1

  公开（公告）日：2009-12-31

  There is provided compounds of formula (I), wherein X 1 , X 2 , X 3 , Y 4 , Y 1 , Y 2 , Y 3 , Y 4 , Z 1 , Z 2 , R 4 and R 5 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.

  提供公式（I）的化合物，其中X1、X2、X3、Y1、Y2、Y3、Y4、Z1、Z2、R4和R5的含义如描述中所述，并且其药学上可接受的盐，这些化合物在AT2受体的选择性激动剂中有用，因此特别适用于治疗胃肠道疾病，如消化不良、肠易激综合征和多器官功能障碍，以及心血管疾病。
• Convenient removal of N-tert-butyl from amides with scandium triflate
  作者：A.K. Mahalingam、Xiongyu Wu、Mathias Alterman

  DOI：10.1016/j.tetlet.2006.03.010

  日期：2006.5

  Scandium triflate has been used as a convenient and efficient catalyst for removal of N-tert-butyl from amide groups. A variety of N-tert-butyl aryl and alkyl amides under these conditions gave the corresponding primary amide in high yields. With the use of microwave heating the deprotection reaction could be completed within I h. (c) 2006 Elsevier Ltd. All rights reserved.
• TRICYCLIC COMPOUNDS USEFUL AS ANGIOTENSIN II AGONISTS
  申请人：Vicore Pharma AB

  公开号：EP1395566B1

  公开（公告）日：2007-09-12
• US7652054B2
  申请人：——

  公开号：US7652054B2

  公开（公告）日：2010-01-26