2-propyl-6-methyl-3-hydroxy-4-pyrone | 40861-87-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-propyl-6-methyl-3-hydroxy-4-pyrone
• 英文别名: 3-hydroxy-6-methyl-2-propyl-4H-pyran-4-one；3-Hydroxy-6-methyl-2-propylpyran-4-one
• CAS: 40861-87-8
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: MXVOQRVMUZXLTN-UHFFFAOYSA-N

物化性质

• 沸点：
  306.6±42.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-propyl-6-methyl-3-hydroxy-4-pyrone 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 18.0h， 生成 3-Benzyloxy-1,6-dimethyl-2-propyl-1H-pyridin-4-one
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Novel 2-Substituted 3-Hydroxypyridin-4-ones:  Structure−Activity Investigation of Metalloenzyme Inhibition by Iron Chelators

  摘要：

  A range of novel 3-hydroxypyridin-4-ones with different R(2) substitutents has been synthesized for the investigation of the structure-activity relationship between the chemical nature of the ligand and the inhibitory activity of the iron-containing metalloenzyme 5-lipoxygenase. Results indicate that the molecular dimensions, together with the lipophilicity, have a critical impact on the ability of this class of chelator to inhibit 5-lipoxygenase. Hydrophilic ligands with a bulky R(2) substitutent tend to be weak inhibitors; thus 1,6-dimethyl-2-(4'-N-n-propylsuccinamido)methyl-3-hydroxypyridin-4(1H)-one (22b) which has the largest R(2) substitutent only caused 2% inhibition of the enzyme activity after 30 min incubation at 110 muM IBE (iron-binding equivalents), as compared with deferiprone which caused 40% inhibition of the enzyme activity, under the same conditions.

  DOI：

  10.1021/jm010817i
• 作为产物：
  描述：

  2-(1-Hydroxypropyl)-3-hydroxy-6-methyl-pyran-4(1H)-one 在 盐酸 、 锌 作用下， 反应 24.0h， 以50%的产率得到2-propyl-6-methyl-3-hydroxy-4-pyrone
  参考文献：
  名称：

  羟基吡喃酮和羟基吡啶酮的合成，理化性质和生物学评估：用于细胞标记的新型双齿配体。

  摘要：

  描述了一系列可能与铟（III）螯合的羟基吡喃酮和羟基吡啶酮。给出了两种铟配合物的晶体结构。报告了配体和相应的铁（III），镓（III）和铟（III）配合物的分布系数。在铁和镓配合物与铁和铟配合物的分布系数之间获得了良好的线性关系。相反，在游离配体的分布系数与三组配合物的分布系数之间获得了非线性关系。后一种关系用于鉴定具有最佳细胞标记特性的化合物。已经将两种这样的化合物（6-（烷氧基甲基）-3-羟基-4H-吡喃-4-酮）与托酚酮比较了它们用111 In标记人白细胞的能力。所选配体的白细胞标记效率更高，体外血浆稳定性与111In-对羟基苯甲酸类似。这些结果表明，新的双齿配体可能比目前用于细胞标记的配体具有优势。

  DOI：

  10.1021/jm960220g

文献信息

• DRUG FOR AMELIORATING BRAIN DISEASES
  申请人：WAKUNAGA PHARMACEUTICAL CO., LTD.

  公开号：EP0838220A1

  公开（公告）日：1998-04-29

  The present invention discloses a drug for ameliorating brain diseases which comprises as an active ingredient a compound represented by the following formula (1): [wherein R1 represents H, OH, a lower alkoxyl group, or a lower alkyl group; each of R2 and R3 represents H, a (substituted) lower alkyl group, a lower alkenyl group, a (substituted) phenyl group, or a (substituted) styryl group; and X represents O or a nitrogen atom which may be substituted by a lower alkyl group] or a salt thereof. Because of inhibiting a decrease in brain neurons and promoting branching of neurites, this drug is efficacious in the prevention and treatment of dementia, etc. in association with degeneration and sloughing of brain neurons.

  本发明公开了一种用于改善脑部疾病的药物，其活性成分包括下式（1）所代表的化合物： [其中 R1 代表 H、OH、低级烷氧基或低级烷基；R2 和 R3 各代表 H、（取代的）低级烷基、低级烯基、（取代的）苯基或（取代的）苯乙烯基；X 代表 O 或可被低级烷基取代的氮原子]或其盐。由于这种药物能抑制脑神经元的减少并促进神经元的分枝，因此对预防和治疗与脑神经元退化和脱落有关的痴呆症等具有疗效。
• METAL COMPLEXES
  申请人：Hider, Robert Charles

  公开号：EP0473764A1

  公开（公告）日：1992-03-11
• US5962480A
  申请人：——

  公开号：US5962480A

  公开（公告）日：1999-10-05
• [EN] METAL COMPLEXES
  申请人：——

  公开号：WO1991014664A1

  公开（公告）日：1991-10-03

  [FR] Complexes ligand:métal (III) neutres 3:1 dans lesquels le cation métallique trivalent est un isotope radioactif d'indium ou de galium et chaque ligand consiste séparément en un composé de: (1) 3-hydroxy-4-pyrone dans lequel un des atomes d'hydrogène, ou davantage, fixé à des atomes de carbone cycliques est remplacé par un groupe hydrocarbure aliphatique constitué de un à six atomes de carbone ou un groupe semblable substitué par un groupe, ou davantage, sélectionné(s) à partir de groupes fluoro, hydroxy et hydrocarbyloxy aliphatique mais excluant 3-hydroxy-2-méthyle-4-pyrone; ou (2) un 3-hydroxypyridine-2-one ou un 3-hydroxypyridine-2-one dans lequel l'atome d'hydrogène fixé à l'atome d'azote est remplacé par un groupe acyle aliphatique, par un groupe hydrocarbure aliphatique constitué de 1 à 6 atomes de carbone ou par un groupe hydrocarbure aliphatique substitué par un substituant, ou davantage, sélectionné(s) à partir de groupes d'acyle aliphatique, alkoxy, cycloalkoxy, amide aliphatique, ester aliphatique, halogène et hydroxy et, éventuellement, dans lequel un, ou davantage, des atomes d'hydrogène fixé(s) aux atomes de carbone cyclique est (sont) remplacé(s) par l'un desdits substituents, par un groupe hydrocarbure aliphatique constitué de 1 à 6 atomes de carbone ou par un groupe hydrocarbure aliphatique substitué par un groupe alkoxy, cycloalkoxy, ester aliphatique ou hydroxy ou par un groupe halogène, ou davantage; s'adressant à la thérapie et, particulièrement, au diagnostic basé sur la désignation cellulaire.
  [EN] Neutral 3:1 ligand:metal (III) complexes, in which the trivalent metal cation is a radioactive isotope of indium or gallium and each ligand is separately provided by a compound being: (1) a 3-hydroxy-4-pyrone in which one or more of the hydrogen atoms attached to ring carbon atoms is replaced by an aliphatic hydrocarbon group of one to six carbon atoms or such a group substituted by one or more groups selected from fluoro, hydroxy and aliphatic hydrocarbyloxy groups but excluding 3-hydroxy-2-methyl-4-pyrone; or (2) 3-hydroxypyridin-2-one or a 3-hydroxypyridin-2-one in which the hydrogen atom attached to the nitrogen atom is replaced by an aliphatic acyl group, by an aliphatic hydrocarbon group of 1 to 6 carbon atoms, or by an aliphatic hydrocarbon group substituted by one or more substituents selected from aliphatic acyl, alkoxy, cycloalkoxy, aliphatic amide, aliphatic ester, halogen and hydroxy groups and optionally, in which one or more of the hydrogen atoms attached to ring carbon atoms is replaced by one of said substituents, by an aliphatic hydrocarbon group of 1 to 6 carbon atoms, or by an aliphatic hydrocarbon group substituted by an alkoxy, cycloalkoxy, aliphatic ester or hydroxy group or by one or more halogen groups; are of value in therapy and particularly in diagnosis, especially in the context of cell labelling.
• Design, Synthesis, and Evaluation of Novel 2-Substituted 3-Hydroxypyridin-4-ones:  Structure−Activity Investigation of Metalloenzyme Inhibition by Iron Chelators
  作者：Zu D. Liu、Reem Kayyali、Robert C. Hider、John B. Porter、Anthony E. Theobald

  DOI：10.1021/jm010817i

  日期：2002.1.1

  A range of novel 3-hydroxypyridin-4-ones with different R(2) substitutents has been synthesized for the investigation of the structure-activity relationship between the chemical nature of the ligand and the inhibitory activity of the iron-containing metalloenzyme 5-lipoxygenase. Results indicate that the molecular dimensions, together with the lipophilicity, have a critical impact on the ability of this class of chelator to inhibit 5-lipoxygenase. Hydrophilic ligands with a bulky R(2) substitutent tend to be weak inhibitors; thus 1,6-dimethyl-2-(4'-N-n-propylsuccinamido)methyl-3-hydroxypyridin-4(1H)-one (22b) which has the largest R(2) substitutent only caused 2% inhibition of the enzyme activity after 30 min incubation at 110 muM IBE (iron-binding equivalents), as compared with deferiprone which caused 40% inhibition of the enzyme activity, under the same conditions.