5-Bromo-4-[2-(1-methyl-piperidin-4-yl)-ethoxy]-6-[(spiro[2.5]oct-6-ylmethyl)-amino]-pyrimidine-2-carbonitrile | 1062654-22-1

• 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: 5-Bromo-4-[2-(1-methyl-piperidin-4-yl)-ethoxy]-6-[(spiro[2.5]oct-6-ylmethyl)-amino]-pyrimidine-2-carbonitrile
• 英文别名: 5-bromo-4-[2-(1-methylpiperidin-4-yl)ethoxy]-6-(spiro[2.5]octan-6-ylmethylamino)pyrimidine-2-carbonitrile
• CAS: 1062654-22-1
• 化学式: C₂₂H₃₂BrN₅O
• 分子量: 462.433
• InChiKey: HJUPPNTXGDFNAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  74.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-[2-(1-Methyl-piperidin-4-yl)-ethoxy]-6-[(spiro[2.5]oct-6-ylmethyl)-amino]-pyrimidine-2-carbonitrile 在 pyridinium hydrobromide perbromide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以89%的产率得到5-Bromo-4-[2-(1-methyl-piperidin-4-yl)-ethoxy]-6-[(spiro[2.5]oct-6-ylmethyl)-amino]-pyrimidine-2-carbonitrile
  参考文献：
  名称：

  4-Amino-2-cyanopyrimidines: Novel scaffold for nonpeptidic cathepsin S inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.07.011

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.