thiophene-3-carboxylic acid {(R)-1-[1-(1-cyano-cyclopropyl)-1H-[1,2,3]triazol-4-yl]-2-methylsulfanyl-ethyl}-amide | 1333426-22-4

• 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: thiophene-3-carboxylic acid {(R)-1-[1-(1-cyano-cyclopropyl)-1H-[1,2,3]triazol-4-yl]-2-methylsulfanyl-ethyl}-amide
• 英文别名: N-[(1R)-1-[1-(1-cyanocyclopropyl)triazol-4-yl]-2-methylsulfanylethyl]thiophene-3-carboxamide
• CAS: 1333426-22-4
• 化学式: C₁₄H₁₅N₅OS₂
• 分子量: 333.438
• InChiKey: KZKLUYRROHPHRK-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  thiophene-3-carboxylic acid {(R)-1-[1-(1-cyano-cyclopropyl)-1H-[1,2,3]triazol-4-yl]-2-methylsulfanyl-ethyl}-amide 在 sodium tungstate 、 双氧水 、 四丁基硫酸氢铵 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以52%的产率得到thiophene-3-carboxylic acid {(R)-1-[1-(1-cyano-cyclopropyl)-1H-[1,2,3]triazol-4-yl]-2-methanesulfonyl-ethyl}-amide
  参考文献：
  名称：

  Exploration of cathepsin S inhibitors characterized by a triazole P1–P2 amide replacement

  摘要：

  This paper details exploration of a class of triazole-based cathepsin S inhibitors originally reported by Ellman and co-workers. SAR studies involving modifications across the whole inhibitor provide a perspective on the strengths and weaknesses of this class of inhibitors. In addition, we put the unique characteristics of this class of compounds into perspective with other classes of cathepsin S inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.054
• 作为产物：
  描述：

  tert-butyl N-[(2R)-1-methylsulfanylbut-3-yn-2-yl]carbamate 在 盐酸 、 三聚氯氰 、 sodium ascorbate 、 copper(II) sulfate 、 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 1.0h， 生成 thiophene-3-carboxylic acid {(R)-1-[1-(1-cyano-cyclopropyl)-1H-[1,2,3]triazol-4-yl]-2-methylsulfanyl-ethyl}-amide
  参考文献：
  名称：

  Exploration of cathepsin S inhibitors characterized by a triazole P1–P2 amide replacement

  摘要：

  This paper details exploration of a class of triazole-based cathepsin S inhibitors originally reported by Ellman and co-workers. SAR studies involving modifications across the whole inhibitor provide a perspective on the strengths and weaknesses of this class of inhibitors. In addition, we put the unique characteristics of this class of compounds into perspective with other classes of cathepsin S inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.054

文献信息

• [EN] HETEROARYL NITRILE COMPOUNDS USEFUL AS INHIBITORS OF CATHEPSIN-S<br/>[FR] COMPOSÉS D'HÉTÉROARYL-NITRILE UTILES COMME INHIBITEURS DE CATHEPSINE-S
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2011109470A1

  公开（公告）日：2011-09-09

  Disclosed are Cathepsin-S reversible inhibitor compounds of the formula (I) which are useful in the treatment of autoimmune and other diseases. Also disclosed are pharmaceutical compositions containing the same, and methods of making and using the same.

  揭示了具有以下化学式（I）的Cathepsin-S可逆抑制剂化合物，可用于治疗自身免疫和其他疾病。还揭示了含有这些化合物的药物组合物，以及制备和使用这些化合物的方法。
• Heteroaryl Nitrile Compounds Useful as Inhibitors of Cathepsin-S
  申请人：Burke Michael J.

  公开号：US20130158018A1

  公开（公告）日：2013-06-20

  Disclosed are Cathepsin-S reversible inhibitor compounds of the formula (I) which are useful in the treatment of autoimmune and other diseases. Also disclosed are pharmaceutical compositions containing the same, and methods of making and using the same.
• US8729114B2
  申请人：——

  公开号：US8729114B2

  公开（公告）日：2014-05-20
• Exploration of cathepsin S inhibitors characterized by a triazole P1–P2 amide replacement
  作者：Neil Moss、Zhaoming Xiong、Mike Burke、Derek Cogan、Donghong A. Gao、Kathleen Haverty、Alexander Heim-Riether、Eugene R. Hickey、Raj Nagaraja、Matthew Netherton、Kathy O’Shea、Philip Ramsden、Racheline Schwartz、Daw-Tsun Shih、Yancey Ward、Erick Young、Qing Zhang

  DOI：10.1016/j.bmcl.2012.09.054

  日期：2012.12

  This paper details exploration of a class of triazole-based cathepsin S inhibitors originally reported by Ellman and co-workers. SAR studies involving modifications across the whole inhibitor provide a perspective on the strengths and weaknesses of this class of inhibitors. In addition, we put the unique characteristics of this class of compounds into perspective with other classes of cathepsin S inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.