ethyl 1-[4-(aminosulfonyl)phenyl]-2-methyl-5-(4-biphenylyl)-1H-pyrrole-3-carboxylate | 1000279-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 1-[4-(aminosulfonyl)phenyl]-2-methyl-5-(4-biphenylyl)-1H-pyrrole-3-carboxylate
• 英文别名: 5-biphenyl-4-yl-2-methyl-1-(4-sulfamoyl-phenyl)-1H-pyrrole-3-carboxylic acid ethyl ester；Ethyl 2-methyl-5-(4-phenylphenyl)-1-(4-sulfamoylphenyl)pyrrole-3-carboxylate
• CAS: 1000279-39-9
• 化学式: C₂₆H₂₄N₂O₄S
• 分子量: 460.554
• InChiKey: SEKLEMBOYFZNPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  99.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 1-[4-(aminosulfonyl)phenyl]-2-methyl-5-(4-biphenylyl)-1H-pyrrole-3-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 25.0h， 以94%的产率得到1-[4-(aminosulfonyl)phenyl]-2-methyl-5-(4-biphenylyl)-1H-pyrrole-3-carboxylic acid
  参考文献：
  名称：

  Design, solid-phase synthesis, and biological evaluation of novel 1,5-diarylpyrrole-3-carboxamides as carbonic anhydrase IX inhibitors

  摘要：

  Following previous studies we herein report the synthesis and the pharmacological evaluation of a new class of human carbonic anhydrase (hCA) inhibitors, 1,5-diarylpyrrole-3-carboxamides prepared by a solid-phase strategy involving a PS(HOBt) resin. A molecular modeling study was conducted in order to simulate the binding mode of this new family of enzyme inhibitors within the active site of hCA IX. This study revealed that the 3-position of the pyrrole was opened to the solvent, so we introduced an amino side-chain, protonated at physiological pH both to enhance the aqueous solubility and to decrease the cell membrane penetration. This strategy consisted of preparing membrane-impermeant inhibitors that may selectively target the tumor-associated hCA IX. Physico-chemical characterizations including aqueous solubility and lipophilic parameters are described. Pharmacological studies revealed high hCA IX inhibitory potency in the nanomolar range. Some compounds are selective for hCA IX displaying hCA I/hCA IX and hCA II/hCA IX ratios higher than 20 and 5, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.007
• 作为产物：
  描述：

  ethyl 1-[4-(aminosulfonyl)phenyl]-5-(4-bromophenyl)-2-methyl-1H-pyrrole-3-carboxylate 、 苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride sodium carbonate 作用下， 以 水 、 异丙醇 为溶剂， 生成 ethyl 1-[4-(aminosulfonyl)phenyl]-2-methyl-5-(4-biphenylyl)-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  WO2008/2974

  摘要：

  公开号：

文献信息

• PYRROLE DERIVATIVES AND THEIR METHODS OF USE
  申请人：Faghih Ramin

  公开号：US20080064695A1

  公开（公告）日：2008-03-13

  The invention relates to a series of substituted pyrrole derivatives, compositions comprising the same, and methods of treating conditions and disorders using such compounds and compositions.

  本发明涉及一系列取代吡咯衍生物，包括这些衍生物的组合物以及使用这些化合物和组合物治疗疾病和疾病的方法。
• Pyrrole Derivatives and Their Methods of Use
  申请人：Faghih Ramin

  公开号：US20100216748A1

  公开（公告）日：2010-08-26

  The invention relates to a series of substituted pyrrole derivatives, compositions comprising the same, and methods of treating conditions and disorders using such compounds and compositions.

  本发明涉及一系列取代吡咯衍生物，包括这些衍生物的组合物以及使用这些化合物和组合物治疗疾病和障碍的方法。
• US7741364B2
  申请人：——

  公开号：US7741364B2

  公开（公告）日：2010-06-22
• US8609713B2
  申请人：——

  公开号：US8609713B2

  公开（公告）日：2013-12-17
• [EN] PYRROLE DERIVATIVES AND THEIR METHODS OF USE<br/>[FR] DÉRIVÉS DE PYRROLE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ABBOTT LAB

  公开号：WO2008002974A1

  公开（公告）日：2008-01-03

  [EN] The invention relates to a series of substituted pyrrole derivatives, compositions comprising the same, and methods of treating conditions and disorders using such compounds and compositions.
  [FR] L'invention concerne une série de dérivés de pyrrole substitués, des compositions incluant ces dérivés et des procédés de traitement des conditions et des troubles utilisant de tels composés et de telles compositions.