2-bromo-1-[(2S,4S)-2-(5-tert-butyl-[1,2,4]oxadiazole-3-carbonyl)-4-fluoro-pyrrolidine-1-yl]-ethanone | 851029-82-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-1-[(2S,4S)-2-(5-tert-butyl-[1,2,4]oxadiazole-3-carbonyl)-4-fluoro-pyrrolidine-1-yl]-ethanone
• 英文别名: 2-bromo-1-[(2S,4S)-2-(5-tert-butyl-1,2,4-oxadiazole-3-carbonyl)-4-fluoropyrrolidin-1-yl]ethanone
• CAS: 851029-82-8
• 化学式: C₁₃H₁₇BrFN₃O₃
• 分子量: 362.199
• InChiKey: BZWOLCCSRSMHMN-YUMQZZPRSA-N

物化性质

• 沸点：
  485.8±55.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  76.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-bromo-1-[(2S,4S)-2-(5-tert-butyl-[1,2,4]oxadiazole-3-carbonyl)-4-fluoro-pyrrolidine-1-yl]-ethanone 、 叔丁胺 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 2-tert-butylamino-1-[(2S,4S)-2-(5-tert-butyl-[1,2,4]oxadiazole-3-carbonyl)-4-fluoro-pyrrolidine-1-yl]-ethanone
  参考文献：
  名称：

  Synthesis, SAR, and X-ray structure of novel potent DPPIV inhibitors: Oxadiazolyl ketones

  摘要：

  Synthesis of a novel series of DPPIV inhibitors with 1,2,4- and 1,3,4-oxadiazolyl ketone derivatives and its structure-activity relationships are discussed. Compound 18h showed good inhibitory activity against DPPIV and favorable pharmacokinetic properties. In vivo pharmacodynamic efficacy and co-crystal structure of compound 18h with DPPIV is also described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.046
• 作为产物：
  描述：

  Boc-L-脯氨酸甲酯 在 盐酸 、 盐酸羟胺 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 sodium hydrogensulfite 、 N,N-二异丙基乙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-bromo-1-[(2S,4S)-2-(5-tert-butyl-[1,2,4]oxadiazole-3-carbonyl)-4-fluoro-pyrrolidine-1-yl]-ethanone
  参考文献：
  名称：

  Synthesis, SAR, and X-ray structure of novel potent DPPIV inhibitors: Oxadiazolyl ketones

  摘要：

  Synthesis of a novel series of DPPIV inhibitors with 1,2,4- and 1,3,4-oxadiazolyl ketone derivatives and its structure-activity relationships are discussed. Compound 18h showed good inhibitory activity against DPPIV and favorable pharmacokinetic properties. In vivo pharmacodynamic efficacy and co-crystal structure of compound 18h with DPPIV is also described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.046

文献信息

• Synthesis, SAR, and X-ray structure of novel potent DPPIV inhibitors: Oxadiazolyl ketones
  作者：Ki Dong Koo、Min Jung Kim、Sungsub Kim、Kyoung-Hee Kim、Sang Yong Hong、Gwong-Cheung Hur、Hyeon Joo Yim、Geun Tae Kim、Hee Oon Han、O Hwan Kwon、Tae Sik Kwon、Jong Sung Koh、Chang-Seok Lee

  DOI：10.1016/j.bmcl.2007.05.046

  日期：2007.8

  Synthesis of a novel series of DPPIV inhibitors with 1,2,4- and 1,3,4-oxadiazolyl ketone derivatives and its structure-activity relationships are discussed. Compound 18h showed good inhibitory activity against DPPIV and favorable pharmacokinetic properties. In vivo pharmacodynamic efficacy and co-crystal structure of compound 18h with DPPIV is also described. (c) 2007 Elsevier Ltd. All rights reserved.