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焦袂康酸O-甲基醚 | 1193-64-2

中文名称
焦袂康酸O-甲基醚
中文别名
3-甲氧基-4H-吡喃-4-酮
英文名称
3-methoxy-4H-pyran-4-one
英文别名
3-Methoxypyran-4-one
焦袂康酸O-甲基醚化学式
CAS
1193-64-2
化学式
C6H6O3
mdl
——
分子量
126.112
InChiKey
WLONNGPPUOEELX-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    94.5-95.5 °C
  • 沸点:
    280.7±35.0 °C(Predicted)
  • 密度:
    1.19±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    0.3
  • 重原子数:
    9
  • 可旋转键数:
    1
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.17
  • 拓扑面积:
    35.5
  • 氢给体数:
    0
  • 氢受体数:
    3

安全信息

  • 海关编码:
    2932999099

SDS

SDS:23791bd277abd4a41b768798af09972b
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上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    焦袂康酸O-甲基醚 作用下, 以 乙醇 为溶剂, 反应 8.0h, 以94%的产率得到(9ci)-3-甲氧基-4-羟基吡啶
    参考文献:
    名称:
    Systematic comparison of the mono-, dimethyl- and trimethyl 3-hydroxy-4(1H)-pyridones – Attempted optimization of the orally active iron chelator, deferiprone
    摘要:
    A range of close analogues of deferiprone have been synthesised. The group includes mono-, di- and trimethyl-3-hydroxy-4(1H)-pyridones. These compounds were found to possess similar pFe(3+) values to that of deferiprone, with the exception of the 2.5-dimethylated derivatives. Surprisingly the NH-containing hydroxy-4(1H)-pyridones were found to be marginally more lipophilic than the corresponding N-Me containing analogues. This same group are also metabolised less efficiently by Phase 1 hydroxylating enzymes than the corresponding N-Me analogues.As result of this study, three compounds have been identified for further investigation centred on neutropenia and agranulocytosis. (C) 2016 Elsevier Masson SAS. All rights reserved.
    DOI:
    10.1016/j.ejmech.2016.03.014
  • 作为产物:
    描述:
    2-(羟基甲基)-5-甲氧基-4H-吡喃-4-酮 在 Jones reagent 作用下, 以 N-甲基吡咯烷酮丙酮 为溶剂, 反应 4.67h, 生成 焦袂康酸O-甲基醚
    参考文献:
    名称:
    Systematic comparison of the mono-, dimethyl- and trimethyl 3-hydroxy-4(1H)-pyridones – Attempted optimization of the orally active iron chelator, deferiprone
    摘要:
    A range of close analogues of deferiprone have been synthesised. The group includes mono-, di- and trimethyl-3-hydroxy-4(1H)-pyridones. These compounds were found to possess similar pFe(3+) values to that of deferiprone, with the exception of the 2.5-dimethylated derivatives. Surprisingly the NH-containing hydroxy-4(1H)-pyridones were found to be marginally more lipophilic than the corresponding N-Me containing analogues. This same group are also metabolised less efficiently by Phase 1 hydroxylating enzymes than the corresponding N-Me analogues.As result of this study, three compounds have been identified for further investigation centred on neutropenia and agranulocytosis. (C) 2016 Elsevier Masson SAS. All rights reserved.
    DOI:
    10.1016/j.ejmech.2016.03.014
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文献信息

  • Identification of N-phenyl-3-methoxy-4-pyridinones as orally bioavailable H3 receptor antagonists and β-amyloid aggregation inhibitors for the treatment of Alzheimer’s disease
    作者:Minkui Zhang、Li Tang、Liu Jiang、Jun Wei、Yongzhou Hu、Rong Sheng
    DOI:10.1016/j.ejmech.2020.113096
    日期:2021.2
    functional agents for therapy of Alzheimer’s disease, through introducing alkyloxy moiety into 4-pyridinone ring to avoid the possible phase II metabolism of 3-hydroxy-4-pyridinone in lead compound 3-hydroxy-2-methyl-1-(4-(3-(pyrrolidin-1-yl)propoxy)phenyl)-pyridin-4(1H)-one (4). In vitro studies indicated that most of these compounds exhibit excellent H3 receptor antagonistic activities and potent
    根据我们以前的工作,通过将烷氧基部分引入4-吡啶酮环中以避免可能的II期,设计了一系列N-苯基-3-甲氧基-4-吡啶酮衍生物作为口服生物可利用的双重功能药物,用于治疗阿尔茨海默氏病化合物的3-羟基-4-吡啶酮的代谢3-羟基-2-甲基-1-(4-(3-(吡咯烷-1-基)丙氧基)苯基) -吡啶-4-(1 ħ) -酮( 4)。体外研究表明,这些化合物大多数都具有出色的H 3受体拮抗活性和强力的自诱导Aβ1-40 / Aβ1-42聚集抑制活性。特别是,3-甲氧基-1-(4-(3-(吡咯烷基-1-基)丙氧基)苯基)-吡啶-4(1H)-一(7i)在H 3 R拮抗作用中显示IC 50值为0.52 nM。对其他组胺受体亚型具有良好的选择性。透射电子显微镜(TEM)图像显示化合物7i可有效抑制自我介导的Aβ1-40 / Aβ1-42聚集。如预期的那样,它在血浆中表现出理想的药代动力学性质和良好的BBB渗透
  • 具潜在抗AD活性的香豆素杂合吡啶酮酰胺衍 生物及其制备方法与应用
    申请人:浙江工业大学
    公开号:CN110804045B
    公开(公告)日:2021-07-27
    本发明公开了一种香豆素杂合吡啶酮酰胺衍生物及其制备方法与应用。所述的香豆素杂合吡啶酮酰胺衍生物及其药学上可接受的盐如式(I)或式(II)所示,其可应用于制备抗阿尔兹海默症、抗帕森病或通过抑制单胺氧化酶、螯合离子、抗Aβ及抗氧化来治疗的其它疾病或病症药物方面的用途。
  • Tetrahydropyranyl cyclopentyl tetrahydropyridopyridine modulators of chemokine receptor activity
    申请人:Jiao Richard
    公开号:US20050101628A1
    公开(公告)日:2005-05-12
    The present invention is directed to compounds of the formula I: (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , X, n and the dashed line are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptor CCR-2. The present invention is also directed to intermediates useful in the preparation of formula I compounds.
    本发明涉及式 I 的化合物: (其中 R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 X、n 和虚线的定义),可用作趋化因子受体活性的调节剂。特别是,这些化合物可用作趋化因子受体 CCR-2 的调节剂。本发明还涉及用于制备式 I 化合物的中间体。
  • Rational design, synthesis and biological evaluation of novel multitargeting anti-AD iron chelators with potent MAO-B inhibitory and antioxidant activity
    作者:Xiaoying Jiang、Jianan Guo、Yangjing Lv、Chuansheng Yao、Changjun Zhang、Zhisheng Mi、Yuan Shi、Jinping Gu、Tao Zhou、Renren Bai、Yuanyuan Xie
    DOI:10.1016/j.bmc.2020.115550
    日期:2020.6
    A series of (3-hydroxypyridin-4-one)-coumarin hybrids were developed and investigated as potential multi targeting candidates for the treatment of Alzheimer's disease (AD) through the incorporation of iron-chelating and monoamine oxidase B (MAO-B) inhibition. This combination endowed the hybrids with good capacity to inhibit MAO-B as well as excellent iron-chelating effects. The pFe(3+) values of the compounds were ranging from 16.91 to 20.16, comparable to more potent than the reference drug deferiprone (DFP). Among them, compound 18d exhibited the most promising activity against MAO-B, with an IC50 value of 87.9 nM. Moreover, compound 18d exerted favorable antioxidant activity, significantly reversed the amyloid-beta(1-42) (A beta(1-42)) induced PC12 cell damage. More importantly, 18d remarkably ameliorated the cognitive dysfunction in a scopolamine-induced mice AD model. In brief, a series of hybrids with potential anti-AD effect were successfully obtained, indicating that the design of iron chelators with MAO-B inhibitory and antioxidant activities is an attractive strategy against AD progression.
  • The Structure of Leucenol. IV
    作者:Roger Adams、V. V. Jones、J. L. Johnson
    DOI:10.1021/ja01199a071
    日期:1947.7
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同类化合物

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