ethyl ((3-(4-((1H-imidazol-1-yl)methyl)phenyl)-5-isobutylthiophen-2-yl)sulfonyl)carbamate

• 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: ethyl ((3-(4-((1H-imidazol-1-yl)methyl)phenyl)-5-isobutylthiophen-2-yl)sulfonyl)carbamate
• 英文别名: N-ethyloxycarbonyl-3-(4-imidazol-1-ylmethylphenyl)-5-iso-butylthiophene-2-sulfonamide；ethyl N-[3-[4-(imidazol-1-ylmethyl)phenyl]-5-(2-methylpropyl)thiophen-2-yl]sulfonylcarbamate
• 化学式: C₂₁H₂₅N₃O₄S₂
• 分子量: 447.579
• InChiKey: LPYXRTXXLKVWKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl ((3-(4-((1H-imidazol-1-yl)methyl)phenyl)-5-isobutylthiophen-2-yl)sulfonyl)carbamate 、 甲基丁胺 以 甲苯 为溶剂， 反应 3.0h， 以60%的产率得到N-(N-butyl-N-methylamino)carbonyl-3-(4-imidazol-1-ylmethyl-phenyl)-5-iso-butylthiophene-2-sulfonamide
  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：

  氯甲酸乙酯 、 3-[4-[(1H-imidazol-1-yl)methyl]phenyl]-5-isobutylthiophene-2-sulfonamide 在 吡啶 、 2-(吡咯烷-1-基)吡啶 作用下， 以78 mg的产率得到ethyl ((3-(4-((1H-imidazol-1-yl)methyl)phenyl)-5-isobutylthiophen-2-yl)sulfonyl)carbamate
  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

• Rapid and straightforward transesterification of sulfonyl carbamates
  作者：Rebecka Isaksson、Ilze Kumpiņa、Mats Larhed、Johan Wannberg

  DOI：10.1016/j.tetlet.2016.02.071

  日期：2016.3

  A fast and convenient method for the alkoxy exchange of sulfonyl carbamates by simply heating in a chosen alkyl alcohol is described. No catalysts or additives are required. Microwave heating at 100–120 °C for 20–60 min resulted in good to excellent yields (53–93%) of alkyl (arylsulfonyl)carbamates where the alkyl part originates from the alcohol solvent. The developed protocol was applied to the synthesis

  描述了一种通过简单地在选择的烷基醇中加热来进行磺酰基氨基甲酸酯的烷氧基交换的快速方便的方法。不需要催化剂或添加剂。微波在100–120°C的温度下加热20–60分钟，得到的烷基（芳基磺酰基）氨基甲酸酯烷基化物的收率好至极好（53–93％），其中烷基部分来自醇溶剂。该开发的协议被应用于血管紧张素II 2型受体（AT2R）配体的合成。
• 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。
• Microwave Promoted Transcarbamylation Reaction of Sulfonylcarbamates under Continuous-Flow Conditions
  作者：Ilze Kumpiņa、Rebecka Isaksson、Jonas Sävmarker、Johan Wannberg、Mats Larhed

  DOI：10.1021/acs.oprd.5b00323

  日期：2016.2.19

  Successful conditions for the transcarbamylation/transesterification reaction of sulfonylcarbamates with alcohols by microwave heating under continuous flow conditions were developed. After optimization of the processes, two series of O-alkylsulfonylcarbamates were obtained in high yields and purities using microwave transparent borosilicate tube reactors. In order to also illustrate the usefulness of the protocol in a medicinal chemistry context, the methodology was used for the synthesis of three angiotensin II type 2 receptor ligands.
• 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