(2-Sec-butoxybenzyl)amine | 1042628-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-Sec-butoxybenzyl)amine
• 英文别名: (2-butan-2-yloxyphenyl)methanamine
• CAS: 1042628-16-9
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: XHKNZQJAMBTBKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  265.8±15.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  (2-Sec-butoxybenzyl)amine 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.34h， 生成 N-[(2S)-1-[[(2S,3S)-1-[(2-butan-2-yloxyphenyl)methylamino]-3-methyl-1-oxopentan-2-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]-1,2-oxazole-5-carboxamide
  参考文献：
  名称：

  Benzylamide antagonists of protease activated receptor 2 with anti-inflammatory activity

  摘要：

  Activation of protease activated receptor 2 (PAR2) has been implicated in inflammatory and metabolic disorders and its inhibition may yield novel therapeutics. Here, we report a series of PAR2 antagonists based on C-terminal capping of 5-isoxazolyl-L-cyclohexylalanine-L-isoleucine, with benzylamine analogues being effective new PAR2 antagonists. 5-Isoxazolyl-L-cyclohexylalanine-L-isoleucine-2-methoxy-benzylamine (10) inhibited PAR2-, but not PAR1-, induced release of Ca2+ (IC50 0.5 mu M) in human colon cells, IL-6 and TNF alpha secretion (IC50 1-5 mu M) from human kidney cells, and was anti-inflammatory in acute rat paw inflammation (ED50 5 mg/kg sc). These findings show that new benzylamide antagonists of PAR2 have anti-inflammatory activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.048

文献信息

• [1,8] NAPHTHYRIDINE DERIVATIVES HAVING ANTIVIRAL ACTIVITY
  申请人：Shire BioChem Inc.

  公开号：EP1155017B1

  公开（公告）日：2003-01-15
• Benzylamide antagonists of protease activated receptor 2 with anti-inflammatory activity
  作者：Mei-Kwan Yau、Ligong Liu、Junxian Lim、Rink-Jan Lohman、Adam J. Cotterell、Jacky Y. Suen、David A. Vesey、Robert C. Reid、David P. Fairlie

  DOI：10.1016/j.bmcl.2015.12.048

  日期：2016.2

  Activation of protease activated receptor 2 (PAR2) has been implicated in inflammatory and metabolic disorders and its inhibition may yield novel therapeutics. Here, we report a series of PAR2 antagonists based on C-terminal capping of 5-isoxazolyl-L-cyclohexylalanine-L-isoleucine, with benzylamine analogues being effective new PAR2 antagonists. 5-Isoxazolyl-L-cyclohexylalanine-L-isoleucine-2-methoxy-benzylamine (10) inhibited PAR2-, but not PAR1-, induced release of Ca2+ (IC50 0.5 mu M) in human colon cells, IL-6 and TNF alpha secretion (IC50 1-5 mu M) from human kidney cells, and was anti-inflammatory in acute rat paw inflammation (ED50 5 mg/kg sc). These findings show that new benzylamide antagonists of PAR2 have anti-inflammatory activity. (C) 2015 Elsevier Ltd. All rights reserved.