(3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-5-phenylpentanoic acid | 862388-09-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-5-phenylpentanoic acid
• 英文别名: (3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoic acid
• CAS: 862388-09-8
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: KKAKUZKLCKSLRK-UEWDXFNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-5-phenylpentanoic acid 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3S)-3-amino-N-ethyl-2-hydroxy-5-phenylpentanamide hydrochloride
  参考文献：
  名称：

  Exploration of orally available calpain inhibitors: Peptidyl α-ketoamides containing an amphiphile at P3 site

  摘要：

  A novel series of dipeptidyl alpha-ketoamide derivatives with amphiphile was designed and synthesized as water-soluble calpain inhibitors. The introduction of amphiphiles at the P3 site increased water solubility without loss of membrane permeability and provided the oral available inhibitors. Extension of the ethylene glycol chain at the P3 site led to an improvement in persistence of plasma levels. In particular, introduction of a combination of a diethylene glycol methyl ether moiety at the P3 site, a phenylalanine residue at the P1 site and a cyclopropyl moiety at the P' site was the most effective modification for an increase in plasma drug exposure. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.059
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-L-homophenylalaninal 生成 (3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-5-phenylpentanoic acid
  参考文献：
  名称：

  LISSENCEPHALY THERAPEUTIC AGENT

  摘要：

  公开号：

  EP2647386B1

文献信息

• [EN] ALPHA-KETOAMIDE DERIVATIVE, AND PRODUCTION METHOD AND USE THEREOF<br/>[FR] DERIVE D'ALPHA-CETOAMIDE, SON PROCEDE DE PRODUCTION ET D'UTILISATION
  申请人：SENJU PHARMA CO

  公开号：WO2005056519A1

  公开（公告）日：2005-06-23

  The present invention provides a compound represented by the formula (I): (INSERT CHEMICAL FORMULA) (wherein R1 is a lower alkyl substituted by a lower alkoxy or a heterocyclic group, or a heterocyclic group; R2 is a lower alkyl optionally substituted by a phenyl; and R3 is a lower alkyl optionally substituted by a halogen, a lower alkoxy or a phenyl, or a fused polycyclic hydrocarbon group), which is well absorbed orally, exhibits durability of good blood level and has potent calpain inhibitory activity.

  本发明提供了一种化合物，其化学式表示为（I）：（插入化学式）（其中R1是由低烷基取代的低烷氧基或杂环基，或者是杂环基；R2是可选择地由苯基取代的低烷基；R3是可选择地由卤素、低烷氧基或苯基取代的低烷基，或者是融合的多环碳氢基），该化合物在口服后被很好地吸收，表现出良好的血液水平持久性，并具有强大的钙蛋白酶抑制活性。
• COMPOSITION FOR TREATMENT AND/OR PREVENTION OF PERIPHERAL NERVE DISORDER
  申请人：OSAKA CITY UNIVERSITY

  公开号：US20190314320A1

  公开（公告）日：2019-10-17

  The present invention provides a means for treating and/or preventing peripheral nerve disorder by facilitating regeneration of peripheral nerves. Specifically, the present invention provides a composition for treating and/or preventing peripheral nerve disorder comprising a compound represented by the general formula (I): wherein R 1 is lower alkyl substituted with lower alkoxy, lower alkyl substituted with a heterocyclic group, a heterocyclic group, or a group represented by the formula (IIa): R 4 O—R 5  m (IIa) wherein R 4 is lower alkyl, R 5 is lower alkylene, and m is an integer of 1 to 6; R 2 is lower alkyl optionally substituted with phenyl; and R 3 is lower alkyl optionally substituted with halogen, lower alkoxy, or phenyl; condensed polycyclic hydrocarbon; or hydrogen.

  本发明提供了一种治疗和/或预防外周神经障碍的方法，通过促进外周神经再生。具体地，本发明提供了一种用于治疗和/或预防外周神经障碍的组合物，包括由通式（I）表示的化合物： 其中R1为与低烷氧基取代的低烷基，与杂环基取代的低烷基，杂环基，或由式（IIa）表示的基团： R4O—R5m（IIa） 其中R4为低烷基，R5为低烷基烯，m为1至6的整数； R2为可选择地取代苯基的低烷基；和 R3为可选择地取代卤素，低烷氧基，或苯基的低烷基；缩合多环碳氢化合物；或氢。
• Structure–activity relationship of HIV-1 protease inhibitors containing α-hydroxy-β-amino acids. Detailed study of P 1 site
  作者：Eiji Takashiro、Ichiro Hayakawa、Tamayo Nitta、Atsushi Kasuya、Shuichi Miyamoto、Yuji Ozawa、Ryuichi Yagi、Ikue Yamamoto、Takahiro Shibayama、Akihiko Nakagawa、Yuichiro Yabe

  DOI：10.1016/s0968-0896(99)00127-3

  日期：1999.9

  The structure-activity relationship of HIV-1 protease (HIV-1 PR) inhibitors containing alpha-hydroxy-beta-amino acids is discussed. We demonstrated that substituent groups on the P1 aromatic rings of the inhibitors exert significant influence on their biological activity. Inhibitors bearing an alkyl or a fluorine atom at the meta and para position on their P1 benzene ring were found to be good inhibitors

  讨论了含有α-羟基-β-氨基酸的HIV-1蛋白酶（HIV-1 PR）抑制剂的构效关系。我们证明了抑制剂的P1芳环上的取代基对其生物学活性具有重要影响。发现在它们的P1苯环的间位和对位带有烷基或氟原子的抑制剂是良好的抑制剂。我们还发现，P2苯甲酰胺的取代位置对于良好的抗病毒效力至关重要。在这项研究中，抑制剂48是最有效的[IC90（CEM / HIV-1 IIIB）27 nM]，在大鼠中显示出良好的药代动力学。
• Alpha-ketoamide derivative, and production method and use thereof
  申请人：Shirasaki Yoshihisa

  公开号：US20070004643A1

  公开（公告）日：2007-01-04

  The present invention provides a compound represented by the formula (I): (wherein R 1 is a lower alkyl substituted by a lower alkoxy or a heterocyclic group, or a heterocyclic group; R 2 is a lower alkyl optionally substituted by a phenyl; and R 3 is a lower alkyl optionally substituted by a halogen, a lower alkoxy or a phenyl, or a fused polycyclic hydrocarbon group), which is well absorbed orally, exhibits durability of good blood level and has potent calpain inhibitory activity.

  本发明提供了一种化合物，其化学式表示为(I):(其中，R1是一个低烷基，该低烷基被低烷氧基或杂环基取代，或者是一个杂环基；R2是一个低烷基，可选地被苯基取代；R3是一个低烷基，可选地被卤素、低烷氧基或苯基取代，或者是一个融合的多环碳氢基)，该化合物口服吸收良好，血液水平持久，具有强大的钙蛋白酶抑制活性。
• ALPHA-KETOAMIDE DERIVATIVE, AND PRODUCTION METHOD AND USE THEREOF
  申请人：Senju Pharmaceutical Co., Ltd.

  公开号：EP1692098A1

  公开（公告）日：2006-08-23