8-(5-chloromethyl)quinolyl acetate | 444792-19-2

• 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: 8-(5-chloromethyl)quinolyl acetate
• 英文别名: [5-(Chloromethyl)quinolin-8-yl] acetate
• CAS: 444792-19-2
• 化学式: C₁₂H₁₀ClNO₂
• 分子量: 235.67
• InChiKey: PDLZRMZZCCTNRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 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：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-(5-chloromethyl)quinolyl acetate 在 盐酸 、 氯化亚砜 、 sodium 、 α-chymotrypsin 作用下， 以 sodium hydroxide 、 水 为溶剂， 反应 21.0h， 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：

  8-羟基喹啉 在 吡啶 、 盐酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 8-(5-chloromethyl)quinolyl acetate
  参考文献：
  名称：

  将金属螯合非天然氨基酸掺入卤代标签中进行烯丙基脱氨

  摘要：

  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 ] + .

  DOI：

  10.1016/j.jorganchem.2022.122272