L-Prolyl-anthranilsaeure-methylester | 63254-87-5

• 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: L-Prolyl-anthranilsaeure-methylester
• 英文别名: (S)-proline 2-methoxycarbonylphenylamide；methyl 2-[[(2S)-pyrrolidine-2-carbonyl]amino]benzoate
• CAS: 63254-87-5
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: CUFCKQMDVKQGCU-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-Prolyl-anthranilsaeure-methylester 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 生成 (S)-2-(1-methylpyrrolidine-2-carboxamido)benzoic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel stachydrine derivatives as potent neuroprotective agents for cerebral ischemic stroke

  摘要：

  Stachydrine is a natural product with multiple protective biological activities, including those involved in preventing cancer, ischemia, and cardiovascular disease. However, its use has been limited by low bioavailability and unsatisfactory efficacy. To address this problem, a series of stachydrine derivatives (A1/A2/A3/A4/B1/B2/B3/B4) were designed and synthesized, and biological studies were carried out in vitro and in vivo. When compared with stachydrine, Compound B1 exhibited better neuroprotective effects in vitro, and significantly reduced infarction size in the model of the middle cerebral artery occlusion rat model. Therefore, Compound B1 was selected for further research on ischemic stroke.

  DOI：

  10.1007/s00210-020-01868-4
• 作为产物：
  描述：

  Boc-Pro-ONp 在 碳酸氢钠 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 L-Prolyl-anthranilsaeure-methylester
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel stachydrine derivatives as potent neuroprotective agents for cerebral ischemic stroke

  摘要：

  Stachydrine is a natural product with multiple protective biological activities, including those involved in preventing cancer, ischemia, and cardiovascular disease. However, its use has been limited by low bioavailability and unsatisfactory efficacy. To address this problem, a series of stachydrine derivatives (A1/A2/A3/A4/B1/B2/B3/B4) were designed and synthesized, and biological studies were carried out in vitro and in vivo. When compared with stachydrine, Compound B1 exhibited better neuroprotective effects in vitro, and significantly reduced infarction size in the model of the middle cerebral artery occlusion rat model. Therefore, Compound B1 was selected for further research on ischemic stroke.

  DOI：

  10.1007/s00210-020-01868-4

文献信息

• Proline derivatives
  申请人：Otsuka Pharmaceutical Factory, Inc.

  公开号：US04886813A1

  公开（公告）日：1989-12-12

  Disclosed is a proline derivative of the formula ##STR1## or a pharmaceutically acceptable salt thereof. These derivatives have useful utilities such as activity of inhibiting angiotensin converting enzyme.

  本发明涉及一种赖氨酸衍生物，其化学式为##STR1##或其药学上可接受的盐。这些衍生物具有有用的实用性，如抑制血管紧张素转换酶的活性。
• US4886813A
  申请人：——

  公开号：US4886813A

  公开（公告）日：1989-12-12
• Design, synthesis, and biological evaluation of novel stachydrine derivatives as potent neuroprotective agents for cerebral ischemic stroke
  作者：Liang Zhang、Feng Li、Chenhui Hou、Sifeng Zhu、Lili Zhong、Jianchun Zhao、Cai Song、Wenbao Li

  DOI：10.1007/s00210-020-01868-4

  日期：2020.12

  Stachydrine is a natural product with multiple protective biological activities, including those involved in preventing cancer, ischemia, and cardiovascular disease. However, its use has been limited by low bioavailability and unsatisfactory efficacy. To address this problem, a series of stachydrine derivatives (A1/A2/A3/A4/B1/B2/B3/B4) were designed and synthesized, and biological studies were carried out in vitro and in vivo. When compared with stachydrine, Compound B1 exhibited better neuroprotective effects in vitro, and significantly reduced infarction size in the model of the middle cerebral artery occlusion rat model. Therefore, Compound B1 was selected for further research on ischemic stroke.