2-ethyl-3-(benzyloxy)-4-hydroxypyridine | 143697-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-ethyl-3-(benzyloxy)-4-hydroxypyridine
• 英文别名: 3-(benzyloxy)-2-ethylpyridin-4(1H)-one；2-ethyl-3-benzyloxypyridin-4(1H)-one；3-benzyloxy-2-ethyl-4-pyridinone；2-ethyl-3-benzyloxypyridone；4(1H)-Pyridinone, 2-ethyl-3-(phenylmethoxy)-；2-ethyl-3-phenylmethoxy-1H-pyridin-4-one
• CAS: 143697-02-3；150630-14-1
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: GUWNDHOREAOGFH-UHFFFAOYSA-N

物化性质

• 沸点：
  400.4±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethyl-3-(benzyloxy)-4-hydroxypyridine 在 potassium carbonate 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 0.67h， 生成 3-(benzyloxy)-1-((7-(benzyloxy)-2-oxo-2H-chromen-3-yl)methyl)-2-ethylpyridin-4(1H)-one
  参考文献：
  名称：

  具有铁螯合和单胺氧化酶B抑制活性的香豆 素杂合吡啶酮类化合物及其制备与应用

  摘要：

  本发明公开了一种如式(Ⅰ)所示的香豆素/吡啶酮杂合衍生物或其药学上可接受的盐，所述的香豆素/吡啶酮杂合衍生物的制备方法为：以式1所示的不同取代基的羟基吡喃酮为原料通过一系列合成得到式3所示的吡啶酮衍生物；以式4所示的化合物经过缩合反应得到如式5所示的化合物经一步溴代得到式6所示的化合物与式3所示的吡啶酮衍生物经过一步亲核取代反应得到如式7所示的化合物，最后脱除吡啶酮结构中的烷基保护基团得到式(I)所示的目标化合物。本发明提供的化合物是一类全新的单分子多靶点系列药物，具有铁螯合性也有靶向MAO‑B抑制活性以及抗氧化活性，对于发病机理复杂的阿尔兹海默病具有独到的优势，作用机制明确，活性优异。

  公开号：

  CN110218207B
• 作为产物：
  描述：

  2-乙基-3-苯基甲氧基吡喃-4-酮 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以89%的产率得到2-ethyl-3-(benzyloxy)-4-hydroxypyridine
  参考文献：
  名称：

  N-取代的2-烷基-3-羟基-4（1H）-吡啶酮的合成，理化性质和生物学评估：具有临床潜力的口服活性铁螯合剂。

  摘要：

  描述了一系列包含螯合部分3-羟基-4（1H）-吡啶酮的新型双齿配体的合成。已经确定了配体的pKa值及其铁（III）配合物的稳定性常数。给出了一种配体和一种铁（III）配合物的晶体结构。报告了配体的分布系数，并且与配体从肝细胞中去除铁的能力有关。描述了3-羟基-4（1H）-吡啶酮对细胞氧化损伤的影响。与目前的铁螯合剂去铁胺-B相比，本研究中描述的许多双齿配体在铁超载小鼠中具有口服活性。

  DOI：

  10.1021/jm00069a002

文献信息

• Novel synthetic approach to 2-(1′-hydroxyalkyl)- and 2-amido-3-hydroxypyridin-4-ones
  作者：Sirivipa Piyamongkol、Zu D Liu、Robert C Hider

  DOI：10.1016/s0040-4020(01)00222-8

  日期：2001.4

  Novel methods for the synthesis of high pFe3+ iron chelators, 2-(1′-hydroxyalkyl)- and 2-amido-3-hydroxypyridin-4-ones, have been developed. The products are obtained, via N-oxide intermediates, from either maltol or ethyl maltol.

  已经开发出用于合成高pFe 3+铁螯合剂2-（1'-羟烷基）-和2-酰胺基-3-羟基吡啶-4--4-酮的新方法。产物通过N-氧化物中间体从麦芽酚或乙基麦芽酚获得。
• Synthesis, antimicrobial evaluation and QSAR study of some 3-hydroxypyridine-4-one and 3-hydroxypyran-4-one derivatives
  作者：Afshin Fassihi、Daryoush Abedi、Lotfollah Saghaie、Razieh Sabet、Hossein Fazeli、Ghasem Bostaki、Omid Deilami、Hekmatollah Sadinpour

  DOI：10.1016/j.ejmech.2008.10.022

  日期：2009.5

  A series of Mannich bases of 2-alkyl-3-hydroxy-pyridine-4-ones, namely 2-alkyl-3-hydroxy-5-N-piperidylmethyl or N,N-dialkylaminomethyl pyridine-4-ones 9, 10 and 15-18, two derivatives of N-aryl-2methyl-3-hydroxy-pyridine-4-ones 19, 20 and two N-alkyl derivatives of maltol, 21 and 22 were prepared. They were screened for their antibacterial and antifungal activities against a variety of microorganisms using micro plate Alamar Blues assay (MABA) method. Multiple linear regressions (MLR) analysis was performed for the synthesized compounds as well as a series of pyridinone and pyranone derivatives 23-43 which have been synthesized and evaluated for antimicrobial activity by other researchers previously. Studied compounds showed a better quantitative structure-activity relationship (QSAR) model for the antimicrobial activity against Candida albicans and Staphylococcus aureus in comparison with other tested microorganisms. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Design, synthesis and biological evaluation of hydroxypyridinone-coumarin hybrids as multimodal monoamine oxidase B inhibitors and iron chelates against Alzheimer's disease
  作者：Changjun Zhang、Ke Yang、Sihang Yu、Jing Su、Shengli Yuan、Jiaxin Han、Yan Chen、Jinping Gu、Tao Zhou、Renren Bai、Yuanyuan Xie

  DOI：10.1016/j.ejmech.2019.07.031

  日期：2019.10

  A series of hybrids of hydroxypyridinone and coumarin were rationally designed, synthesized and biologically evaluated for their iron ion chelating and MAO-B inhibitory activities. Most of the compounds displayed excellent iron ion chelating effects and moderate to good anti-MAO-B activities. Compound 27a exhibited the most potent activity against MAO-B, with an IC50 value of 14.7 nM. Importantly, 27a showed good U251 cell protective effect and significantly ameliorated the cognitive dysfunction of scopolamine-induced AD mice. Moreover, molecular docking was performed to elucidate the probable ligand-receptor interaction, and the structure-activity relationships were also summarized. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Synthesis of 2-Alkyl-3-hydroxy-4-pyridinone-ribonucleosides, Potential Oral Iron Chelators
  作者：Gang Liu、Fred W. Bruenger、Amy M. Barrios、Scott C. Miller

  DOI：10.1080/15257779508010712

  日期：1995.11

  Several ribonucleosides, named 2-alkyl-3-hydroxy-1-(beta-D-ribofuranosyl or pyranosyl)-4-pyridinones, were synthesized in good yield. The method provides a useful means to obtain alpha-ketohydroxypyridin derivatives with different sugar moieties that, if used as drugs, might enhance their absorption from the intestine and certain other desirable pharmacological properties.
• Efficient Synthesis of N-[(2-Hydroxyethoxy)methyl]-2-alkyl-3-hydroxy-4-pyridinone by a Modified Hilbert-Johnson Reaction
  作者：Liu、Gang、Miller、C. Scott、Bruenger、W. Fred

  DOI：10.1080/00397919608004584

  日期：1996.7