2,4-dichloro-pyrimidine-5-carboxylic acid phenethylamide | 927176-99-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,4-dichloro-pyrimidine-5-carboxylic acid phenethylamide
• 英文别名: 2,4-Dichloro-N-phenethylpyrimidine-5-carboxamide；2,4-dichloro-N-(2-phenylethyl)pyrimidine-5-carboxamide
• CAS: 927176-99-6
• 化学式: C₁₃H₁₁Cl₂N₃O
• 分子量: 296.156
• InChiKey: CKOOSABKPPYPNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-pyrimidine-5-carboxylic acid phenethylamide 在 三乙烯二胺 、 三乙胺 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-cyano-4-(cyclohexylamino)-N-(2-phenylethyl)pyrimidine-5-carboxamide
  参考文献：
  名称：

  2-Cyano-pyrimidines:  A New Chemotype for Inhibitors of the Cysteine Protease Cathepsin K

  摘要：

  Starting from the purine lead structure 1, a new series of cathepsin K inhibitors based on a pyrimidine scaffold have been explored. Investigations of P3 and P2 substituents based on molecular modeling suggestions resulted in potent cathepsin K inhibitors with an improved selectivity profile over other cathepsins.

  DOI：

  10.1021/jm0613525
• 作为产物：
  描述：

  脲嘧啶-5-羧酸 在 五氯化磷 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 34.0h， 生成 2,4-dichloro-pyrimidine-5-carboxylic acid phenethylamide
  参考文献：
  名称：

  2-Cyano-pyrimidines:  A New Chemotype for Inhibitors of the Cysteine Protease Cathepsin K

  摘要：

  Starting from the purine lead structure 1, a new series of cathepsin K inhibitors based on a pyrimidine scaffold have been explored. Investigations of P3 and P2 substituents based on molecular modeling suggestions resulted in potent cathepsin K inhibitors with an improved selectivity profile over other cathepsins.

  DOI：

  10.1021/jm0613525

文献信息

• 4-Amino-2-cyanopyrimidines: Novel scaffold for nonpeptidic cathepsin S inhibitors
  作者：Osamu Irie、Fumiaki Yokokawa、Takeru Ehara、Atsuko Iwasaki、Yuki Iwaki、Yuko Hitomi、Kazuhide Konishi、Masashi Kishida、Atsushi Toyao、Keiichi Masuya、Hiroki Gunji、Junichi Sakaki、Genji Iwasaki、Hajime Hirao、Takanori Kanazawa、Keiko Tanabe、Takatoshi Kosaka、Terance W. Hart、Allan Hallett

  DOI：10.1016/j.bmcl.2008.07.011

  日期：2008.8

  We describe here a novel 4-amino-2-cyanopyrimidine scaffold for nonpeptidomimetic cathepsin S selective inhibitors. Some of the synthesized compounds have sub-nanomolar potency and high selectivity toward cathepsin S along with promising pharmacokinetic and physicochemical properties. The key structural features of the inhibitors consist of a combination of a spiro[2.5]oct-6-ylmethylamine P2 group at the 4-position, a small or polar P3 group at the 5-position and/or a polar group at the 6-position of the pyrimidine. (C) 2008 Elsevier Ltd. All rights reserved.
• 2-Cyano-pyrimidines:  A New Chemotype for Inhibitors of the Cysteine Protease Cathepsin K
  作者：Eva Altmann、Reiner Aichholz、Claudia Betschart、Thomas Buhl、Jonathan Green、Osamu Irie、Naoki Teno、René Lattmann、Marina Tintelnot-Blomley、Martin Missbach

  DOI：10.1021/jm0613525

  日期：2007.2.1

  Starting from the purine lead structure 1, a new series of cathepsin K inhibitors based on a pyrimidine scaffold have been explored. Investigations of P3 and P2 substituents based on molecular modeling suggestions resulted in potent cathepsin K inhibitors with an improved selectivity profile over other cathepsins.