(S)-2-(2-(4-isobutylphenyl)propanamido)acetic acid | 390432-48-1

• 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: (S)-2-(2-(4-isobutylphenyl)propanamido)acetic acid
• 英文别名: 2-[[(2S)-2-[4-(2-methylpropyl)phenyl]propanoyl]amino]acetic acid
• CAS: 390432-48-1
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: LTAWAYHSIMQTJI-NSHDSACASA-N

物化性质

• 沸点：
  484.9±38.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-(4-isobutylphenyl)propanamido)acetic acid 在 4-二甲氨基吡啶 、 sodium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  (S)-(+)-Ibuprofen-based hydrogelators: an approach toward anti-inflammatory drug delivery

  摘要：

  We have synthesized (S)-(+)-ibuprofen-based hydrogelators that feature dipeptide linkages. In aqueous media, one of these hydrogelators formed robust gels that were stable for several months. Enzyme-mediated hydrolysis offers a route toward the sustained release of this anti-inflammatory agent. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.002
• 作为产物：
  描述：

  (S)-(+)-布洛芬 在 4-二甲氨基吡啶 、 sodium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 (S)-2-(2-(4-isobutylphenyl)propanamido)acetic acid
  参考文献：
  名称：

  (S)-(+)-Ibuprofen-based hydrogelators: an approach toward anti-inflammatory drug delivery

  摘要：

  We have synthesized (S)-(+)-ibuprofen-based hydrogelators that feature dipeptide linkages. In aqueous media, one of these hydrogelators formed robust gels that were stable for several months. Enzyme-mediated hydrolysis offers a route toward the sustained release of this anti-inflammatory agent. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.002

文献信息

• Synthesis of Ibuprofen Conjugated Molecular Transporter Capable of Enhanced Brain Penetration
  作者：Goutam Biswas、Wanil Kim、Kyong-Tai Kim、Junhwi Cho、Dongjun Jeong、Keon-Hyoung Song、Jungkyun Im

  DOI：10.1155/2017/4746158

  日期：——

  Based on the strong evidences between inflammation and neurodegeneration, nonsteroidal anti-inflammatory drugs (NSAIDs), such as ibuprofen, are considered as effective agents to reduce the risk of Alzheimer’s and Parkinson’s disease. However, the clinical use of NSAIDs in these diseases is limited by low brain distribution. In this study, we had synthesized ibuprofen conjugate which has good brain penetration.S-(+)-Ibuprofen was covalently attached to a molecular transporter having FITC and eight terminal guanidine groups. This conjugate showed good cellular uptake property in live cells. It was also injected into a mouse and the distribution of the compound was examined in each organ. The conjugate was well delivered to mouse brain indicating the conjugate is able to cross the blood-brain barrier. Our novel synthetic ibuprofen conjugate will hopefully deliver other NSAIDs into brain and is therefore applicable to the neurodegenerative diseases treatment or prevention.

  基于炎症和神经退行性之间的强烈证据，非甾体抗炎药（NSAIDs），如布洛芬，被认为是降低阿尔茨海默病和帕金森病风险的有效药物。然而，NSAIDs在这些疾病的临床应用受到脑分布低的限制。在这项研究中，我们合成了具有良好脑穿透性的布洛芬共轭物。S-(+)-布洛芬被共价地连接到具有FITC和八个末端鸟氨酸基团的分子转运体上。这种共轭物在活细胞中表现出良好的细胞摄取性能。它还被注入到小鼠体内，并检查了化合物在每个器官中的分布。共轭物被成功地输送到小鼠的大脑，表明该共轭物能够穿过血脑屏障。我们的新型合成布洛芬共轭物有望将其他NSAIDs输送到脑中，因此适用于神经退行性疾病的治疗或预防。
• 퇴행성 뇌질환 예방 또는 치료용 약학 조성물
  申请人：Soonchunhyang University Industry Academy Cooperation Foundation 순천향대학교 산학협력단(220040359422) BRN ▼312-82-10071

  公开号：KR101795302B1

  公开（公告）日：2017-11-09

  본 발명은 구아니딘 (guanidine) 말단기가 결합된 당 알콜 유도체에 이부프로펜 (S-(+)-ibuprofen)을 공유 결합시킨 이부프로펜 컨쥬게이트 (ibuprofen conjugate) 및 이를 포함하는 약학 조성물에 관한 것이다. 본 발명에 의한 구아니딘 말단기가 결합된 당 알콜 유도체에 이부프로펜을 공유 결합시킨 이부프로펜 컨쥬게이트는 혈액뇌장벽 (BBB)의 통과로 인해 뇌 침투력이 증가하여 뇌에 효율적인 약물 전달이 가능하며, 이로 인해 최적의 복용량으로 비스테로이드 항염증제 (NSAIDs)에 대한 부작용을 최소화하고 퇴행성 뇌질환의 진행을 예방 또는 치료할 수 있다.

  本发明涉及一种将胍啉（guanidine）末端基与糖醇衍生物共价结合的S-(+)-布洛芬（S-(+)-ibuprofen）共轭物以及包含它的药学组合物。本发明所述的将胍啉末端基与糖醇衍生物共价结合的S-(+)-布洛芬共轭物，由于通过血脑屏障（BBB）的通透性增加而具有更高的脑渗透力，从而可以有效地传递药物到大脑，从而最小化非甾体类抗炎药（NSAIDs）的副作用并预防或治疗退行性脑疾病的进展。
• PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING DEGENERATIVE BRAIN DISEASE
  申请人：SOONCHUNHYANG UNIVERSITY INDUSTRY ACADEMY COOPERATION FOUNDATION

  公开号：US20190216752A1

  公开（公告）日：2019-07-18

  The present invention relates to an ibuprofen conjugate in which ibuprofen (S-(+)-ibuprofen) is covalently linked to a guanidine-terminal-group-bound sugar alcohol derivative and to a pharmaceutical composition containing the same. The ibuprofen conjugate in which ibuprofen is covalently linked to a guanidine-terminal-group-bound sugar alcohol derivative can more effectively penetrate into the brain by passing through the blood-brain barrier (BBB), thus enabling efficient drug delivery to the brain, whereby administration of the ibuprofen conjugate in an optimal dose can minimize side effects of nonsteroidal anti-inflammatory drugs (NSAIDs) and can prevent or treat degenerative brain disease.
• [EN] PHARMACEUTICAL COMPOSITION FOR PREVENTION OR TREATMENT OF DEGENERATIVE BRAIN DISEASE<br/>[FR] COMPOSITION PHARMACEUTIQUE POUR LA PRÉVENTION OU LE TRAITEMENT D'UNE MALADIE CÉRÉBRALE DÉGÉNÉRATIVE<br/>[KO] 퇴행성 뇌질환 예방 또는 치료용 약학 조성물
  申请人：UNIV SOONCHUNHYANG IND ACAD COOP FOUND

  公开号：WO2018056530A1

  公开（公告）日：2018-03-29

  본 발명은 구아니딘 (guanidine) 말단기가 결합된 당 알콜 유도체에 이부프로펜 (S-(+)-ibuprofen)을 공유 결합시킨 이부프로펜 컨쥬게이트 (ibuprofen conjugate) 및 이를 포함하는 약학 조성물에 관한 것이다. 본 발명에 의한 구아니딘 말단기가 결합된 당 알콜 유도체에 이부프로펜을 공유 결합시킨 이부프로펜 컨쥬게이트는 혈액뇌장벽 (BBB)의 통과로 인해 뇌 침투력이 증가하여 뇌에 효율적인 약물 전달이 가능하며, 이로 인해 최적의 복용량으로 비스테로이드 항염증제 (NSAIDs)에 대한 부작용을 최소화하고 퇴행성 뇌질환의 진행을 예방 또는 치료할 수 있다.