DL-3-(8-hydroxyquinolin-5-yl)alanine | 23279-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: DL-3-(8-hydroxyquinolin-5-yl)alanine
• 英文别名: 2-amino-3-(8-hydroxyquinolin-5-yl)propanoic acid；2-amino-3-(8-hydroxy-5-quinolyl)propanoic acid；2-Azaniumyl-3-(8-hydroxyquinolin-5-yl)propanoate
• CAS: 23279-45-0
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: LCHDHNGXRBTPLK-UHFFFAOYSA-N

物化性质

• 熔点：
  194 °C (decomp)
• 沸点：
  498.7±45.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  96.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  DL-3-(8-hydroxyquinolin-5-yl)alanine 在 氯化亚砜 、 α-chymotrypsin 作用下， 以 sodium hydroxide 、 水 为溶剂， 反应 6.0h， 生成 D-3-(8-hydroxyquinolin-5-yl)alanine ethyl ester
  参考文献：
  名称：

  Novel potential neuroprotective agents with both iron chelating and amino acid-based derivatives targeting central nervous system neurons

  摘要：

  Antioxidants and iron chelating molecules are known as neuroprotective agents in animal models of neurodegenerative disorders such as Alzheimer's disease (AD) and Parkinson's disease (PD). In this study, we designed and synthesized a novel bifunctional molecule (M10) with radical scavenging and iron chelating ability on an amino acid carrier likely to be a substrate for system L, thus targeting the compound to the central nervous system (CNS). M10 had a moderate iron affinity in HEPES buffer (pH 7.4) with log K-3 = 12.25 +/- 0.55 but exhibited highly inhibitory action against iron-induced lipid peroxidation, with an IC50 value (12 mu M) comparable to that of desferal (DFO). EPR studies indicated that M10 was a highly potent (center dot)0H scavenger with an IC50 of about 0.3 molar ratio of M10 to H2O2. In PC12 cell culture, M10 was at least as potent as the anti-Parkinson drug rasagiline in protecting against cell death induced by serum-deprivation and by 6-hydroxydopamine (6-OHDA). These results suggest that M10 deserves further investigation as a potential agent for the treatment of neurodegenerative disorders such as AD and PD. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2005.09.003
• 作为产物：
  描述：

  5-(氯甲基)-8-羟基喹啉盐酸盐 在 吡啶 、 盐酸 、 sodium 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 DL-3-(8-hydroxyquinolin-5-yl)alanine
  参考文献：
  名称：

  Novel potential neuroprotective agents with both iron chelating and amino acid-based derivatives targeting central nervous system neurons

  摘要：

  Antioxidants and iron chelating molecules are known as neuroprotective agents in animal models of neurodegenerative disorders such as Alzheimer's disease (AD) and Parkinson's disease (PD). In this study, we designed and synthesized a novel bifunctional molecule (M10) with radical scavenging and iron chelating ability on an amino acid carrier likely to be a substrate for system L, thus targeting the compound to the central nervous system (CNS). M10 had a moderate iron affinity in HEPES buffer (pH 7.4) with log K-3 = 12.25 +/- 0.55 but exhibited highly inhibitory action against iron-induced lipid peroxidation, with an IC50 value (12 mu M) comparable to that of desferal (DFO). EPR studies indicated that M10 was a highly potent (center dot)0H scavenger with an IC50 of about 0.3 molar ratio of M10 to H2O2. In PC12 cell culture, M10 was at least as potent as the anti-Parkinson drug rasagiline in protecting against cell death induced by serum-deprivation and by 6-hydroxydopamine (6-OHDA). These results suggest that M10 deserves further investigation as a potential agent for the treatment of neurodegenerative disorders such as AD and PD. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2005.09.003

文献信息

• Inhibitors of hepatitis C virus NS3 protease
  申请人：——

  公开号：US20020065248A1

  公开（公告）日：2002-05-30

  The present invention relates to compounds of Formula (I): 1 wherein A 1 is methylene, ethylene or propylene group and A 2 is N or CR 5 , or stereoisomeric forms, stereoisomeric mixtures, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of HCV NS3 protease, and to pharmaceutical compositions and diagnostic kits comprising the same, and methods of using the same for treating viral infection or as an assay standard or reagent.

  本发明涉及化合物的结构公式（I）：其中A1为亚甲基、乙烯基或丙烯基，A2为N或CR5，或其立体异构体形式、立体异构体混合物或药用盐形式，用作HCV NS3蛋白酶的抑制剂，以及包含相同化合物的药物组合物和诊断试剂盒，以及用于治疗病毒感染或作为测定标准或试剂的方法。
• Incorporation of metal-chelating unnatural amino acids into halotag for allylic deamination
  作者：Alina Stein、Alexandria Deliz Liang、Reyhan Sahin、Thomas R. Ward

  DOI：10.1016/j.jorganchem.2022.122272

  日期：2022.3

  The potential of artificial metalloenzymes has led to an increase in interest for the design of novel metal-binding sites in proteins. Metal-chelating unnatural amino acids offer an auspicious solution to engineer active metal sites in a defined way. Herein, we describe the introduction of four metal-chelating unnatural amino acids into HaloTag, an attractive scaffold for the assembly of functional

  人工金属酶的潜力导致人们对设计蛋白质中新型金属结合位点的兴趣增加。金属螯合非天然氨基酸为以明确的方式设计活性金属位点提供了一种吉祥的解决方案。在这里，我们描述了将四种金属螯合非天然氨基酸引入 HaloTag，这是一种用于组装功能性人工金属酶的有吸引力的支架。用 2-氨基-3-(8-羟基喹啉-5-基)丙酸 (HQ-Ala-1) 改造的 HaloTag 用于组装人工金属酶，以在与 [(η 5 -C 5 H ) 互补时改善烯丙基脱氨5 )Ru(MeCN) 3 ] + .
• Peptide inhibitors of hepatitis C virus NS3 protein
  申请人：——

  公开号：US20020177725A1

  公开（公告）日：2002-11-28

  This invention relates to a novel class of peptides having the Formula (I): 1 Which are useful as serine protease inhibitors, and more particularly as Hepatitis C virus(HCV) NS3 protease inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of using the same in the treatment of HCV infection.

  本发明涉及一类新型肽的公式(I)：1，其作为丝氨酸蛋白酶抑制剂具有用途，更具体地作为丙型肝炎病毒（HCV）NS3蛋白酶抑制剂。本发明还涉及包含这些化合物的制药组合物以及使用它们治疗HCV感染的方法。
• [EN] ALPHA-KETOAMIDE INHIBITORS OF HEPATITIS C VIRUS NS3 PROTEASE<br/>[FR] INHIBITEURS D'ALPHA-CETOAMIDES DE LA PROTEASE NS3 DU VIRUS DE L'HEPATITE C
  申请人：DU PONT PHARM CO

  公开号：WO2001040262A1

  公开（公告）日：2001-06-07

  The present invention relates to ketoamide and ketoester compounds of Formula (I): where W is -NH- or -O-, or stereoisomeric forms, stereoisomeric mixtures, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of HCV NS3 protease, and to pharmaceutical compositions and diagnostic kits comprising the same, and methods of using the same for treating viral infection or as an assay standard or reagent.

  本发明涉及式(I)的酮酰胺和酮酯化合物：其中W为-NH-或-O-，或其立体异构体、立体异构体混合物或药学上可接受的盐形式，它们可用作HCV NS3蛋白酶的抑制剂，以及包含它们的制药组合物和诊断试剂盒，以及将它们用于治疗病毒感染或作为测定标准或试剂的方法。
• Alpha-ketoamide inhibitors of hepatitis C virus NS3 protease
  申请人：——

  公开号：US20020123468A1

  公开（公告）日：2002-09-05

  The present invention relates to ketoamide and ketoester compounds of Formula (I): 1 wherein W is —NH— or —O—, or stereoisomeric forms, stereoisomeric mixtures, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of HCV NS3 protease, and to pharmaceutical compositions and diagnostic kits comprising the same, and methods of using the same for treating viral infection or as an assay standard or reagent.

  本发明涉及公式（I）的酮酰胺和酮酯化合物：1其中W为-NH-或-O-，或其立体异构体形式，立体异构体混合物或其药学上可接受的盐形式，它们可用作HCV NS3蛋白酶的抑制剂，以及包含它们的制药组合物和诊断试剂盒，以及将它们用于治疗病毒感染或作为测定标准或试剂的方法。