tert-butyl N-[4-methyl-2-[(5-oxo-4H-1,2,4-oxadiazol-3-yl)methyl]pentyl]carbamate | 228104-51-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl N-[4-methyl-2-[(5-oxo-4H-1,2,4-oxadiazol-3-yl)methyl]pentyl]carbamate
• CAS: 228104-51-6
• 化学式: C₁₄H₂₅N₃O₄
• 分子量: 299.37
• InChiKey: OKKQTCQTJSYVQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  89
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[4-methyl-2-[(5-oxo-4H-1,2,4-oxadiazol-3-yl)methyl]pentyl]carbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-(2-aminomethyl-4-methyl-pentyl)-4H-[1,2,4]oxadiazol-5-one
  参考文献：
  名称：

  Oxadiazolone bioisosteres of pregabalin and gabapentin

  摘要：

  A series of oxadiazolone bioisosteres of pregabalin 1 and gabapentin 2 were prepared, and several were found to exhibit similar potency for the alpha(2)-delta subunit of voltage-gated calcium channels. Oxadiazolone 9 derived from 2 achieved low brain uptake but was nevertheless active in models of osteoarthritis. The high clearance associated with compound 9 was postulated to be a consequence of efflux by OAT and/or OCT, and was attenuated on co-administration with cimetidine or probenecid. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.10.101
• 作为产物：
  描述：

  tert-butyl N-[2-[(2Z)-2-amino-2-hydroxyiminoethyl]-4-methylpentyl]carbamate 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 生成 tert-butyl N-[4-methyl-2-[(5-oxo-4H-1,2,4-oxadiazol-3-yl)methyl]pentyl]carbamate
  参考文献：
  名称：

  Oxadiazolone bioisosteres of pregabalin and gabapentin

  摘要：

  A series of oxadiazolone bioisosteres of pregabalin 1 and gabapentin 2 were prepared, and several were found to exhibit similar potency for the alpha(2)-delta subunit of voltage-gated calcium channels. Oxadiazolone 9 derived from 2 achieved low brain uptake but was nevertheless active in models of osteoarthritis. The high clearance associated with compound 9 was postulated to be a consequence of efflux by OAT and/or OCT, and was attenuated on co-administration with cimetidine or probenecid. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.10.101

文献信息

• US7189747B2
  申请人：——

  公开号：US7189747B2

  公开（公告）日：2007-03-13