(19b)-(2S,4S,5S)-5-amino-4-hydroxy-2-isopropyl-6-[4-(3-methoxyphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]hexanoic acid (2-aminoformyl-2-methylpropyl)amide | 1000047-53-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (19b)-(2S,4S,5S)-5-amino-4-hydroxy-2-isopropyl-6-[4-(3-methoxyphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]hexanoic acid (2-aminoformyl-2-methylpropyl)amide
• 英文别名: (19b)-(2S,4S,5S)-5-Amino-4-hydroxy-2-isopropyl-6-[4-(3-methoxyphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]hexanoic acid (2-carbamoyl-2-methylpropyl)amide；(2S,4S,5S)-5-amino-4-hydroxy-2-isopropyl-6-[4-(3-methoxyphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]hexanoic acid (2-aminoformyl-2-methylpropyl)amide；(2S,4S,5S)-5-amino-4-hydroxy-2-isopropyl-6-[4-(3-methoxyphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]hexanoic acid (2-carbamoyl-2-methylpropyl)amide；(2S,4S,5S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-6-[4-(3-methoxyphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-2-propan-2-ylhexanamide
• CAS: 1000047-53-9
• 化学式: C₂₇H₄₅N₅O₅
• 分子量: 519.685
• InChiKey: GYUXQXHWHMVAMV-FKBYEOEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  富马酸 、 (19b)-(2S,4S,5S)-5-amino-4-hydroxy-2-isopropyl-6-[4-(3-methoxyphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]hexanoic acid (2-aminoformyl-2-methylpropyl)amide 以 甲醇 为溶剂， 生成 (2S,4S,5S)-5-amino-4-hydroxy-2-isopropyl-6-[4-(3-methoxyphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]hexanoic acid (2-carbamoyl-2-methylpropyl)amide hemifumarate
  参考文献：
  名称：

  Design and optimization of novel (2S,4S,5S)-5-amino-6-(2,2-dimethyl-5-oxo-4-phenylpiperazin-1-yl)-4-hydroxy-2-isopropylhexanamides as renin inhibitors

  摘要：

  Introduction of the 2,2-dimethyl-4-phenylpiperazin-5-one scaffold into the P-3-P-1 portion of the (2S,4S,5S)-5-amino-6-dialkylamino-4-hydroxy-2-isopropylhexanamide backbone dramatically increased the renin inhibitory activity without using the interaction to the S-3(sp) pocket. Compound 31 exhibited >10,000-fold selectivity over other human proteases, and 18.5% oral bioavailability in monkey. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.092

文献信息

• CYCLIC AMINE COMPOUND
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2036896B1

  公开（公告）日：2012-03-14
• US8158790B2
  申请人：——

  公开号：US8158790B2

  公开（公告）日：2012-04-17
• Design and optimization of novel (2S,4S,5S)-5-amino-6-(2,2-dimethyl-5-oxo-4-phenylpiperazin-1-yl)-4-hydroxy-2-isopropylhexanamides as renin inhibitors
  作者：Yuji Nakamura、Chie Sugita、Masaki Meguro、Shojiro Miyazaki、Kazuhiko Tamaki、Mizuki Takahashi、Yoko Nagai、Takahiro Nagayama、Mikio Kato、Hiroshi Suemune、Takahide Nishi

  DOI：10.1016/j.bmcl.2012.05.092

  日期：2012.7

  Introduction of the 2,2-dimethyl-4-phenylpiperazin-5-one scaffold into the P-3-P-1 portion of the (2S,4S,5S)-5-amino-6-dialkylamino-4-hydroxy-2-isopropylhexanamide backbone dramatically increased the renin inhibitory activity without using the interaction to the S-3(sp) pocket. Compound 31 exhibited >10,000-fold selectivity over other human proteases, and 18.5% oral bioavailability in monkey. (C) 2012 Elsevier Ltd. All rights reserved.