1-methyl-2-chloromethyl-5-benzyloxypyridin-4(1H)-one hydrochloride | 481726-31-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methyl-2-chloromethyl-5-benzyloxypyridin-4(1H)-one hydrochloride
• 英文别名: 5-(benzyloxy)-2-(chloromethyl)-1-methylpyridin-4(1H)-one hydrochloride；5-(Benzyloxy)-2-(chloromethyl)-1-methyl-1,4-dihydropyridin-4-one hydrochloride；2-(chloromethyl)-1-methyl-5-phenylmethoxypyridin-4-one;hydrochloride
• CAS: 481726-31-2
• 化学式: C₁₄H₁₄ClNO₂*ClH
• mdl: MFCD22056384
• 分子量: 300.185
• InChiKey: OEQAAZTZELJHTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.214
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-2-chloromethyl-5-benzyloxypyridin-4(1H)-one hydrochloride 在 ammonium hydroxide 作用下， 以81%的产率得到2-(aminomethyl)-5-(benzyloxy)-1-methyl-1,4-dihydropyridin-4-one
  参考文献：
  名称：

  Design, Synthesis, Physicochemical Properties, and Evaluation of Novel Iron Chelators with Fluorescent Sensors

  摘要：

  The synthesis of a range of novel 3-hydroxypyridin-4-ones and 3-hydroxypyran-4-ones linked with different coumarin substituents is described. These compounds have been developed in order to provide a series of molecular probes for the quantification of intracellular labile iron pools. An evaluation of the effect of iron(III) on fluorescence intensity was undertaken. Chelation of iron(III) causes quenching of fluorescence. The relationship between iron(III) concentration and the extent of fluorescence quenching indicates that the metal is chelated in a complex with a metal-to-ligand stoichiometry of 1:3. The fluorescence of hydroxypyridinone compounds was found to be more efficiently quenched by iron(III) than were the hydroxypyranones. The metal-to-ligand stoichiometry at which maximum quenching is observed was found to depend on the site at which coumarin is attached. The efficiency of fluorescence quenching by iron(III) is markedly influenced by solvent polarity and pH. The permeability of two representative fluorescent chelators across human erythrocyte ghost membranes was investigated. The rate of permeability for a series of probes was found to be related to the corresponding ClogP values.

  DOI：

  10.1021/jm049751s
• 作为产物：
  描述：

  曲酸 在 sodium hydroxide 、 氯化亚砜 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 1-methyl-2-chloromethyl-5-benzyloxypyridin-4(1H)-one hydrochloride
  参考文献：
  名称：

  Design, Synthesis, Physicochemical Properties, and Evaluation of Novel Iron Chelators with Fluorescent Sensors

  摘要：

  The synthesis of a range of novel 3-hydroxypyridin-4-ones and 3-hydroxypyran-4-ones linked with different coumarin substituents is described. These compounds have been developed in order to provide a series of molecular probes for the quantification of intracellular labile iron pools. An evaluation of the effect of iron(III) on fluorescence intensity was undertaken. Chelation of iron(III) causes quenching of fluorescence. The relationship between iron(III) concentration and the extent of fluorescence quenching indicates that the metal is chelated in a complex with a metal-to-ligand stoichiometry of 1:3. The fluorescence of hydroxypyridinone compounds was found to be more efficiently quenched by iron(III) than were the hydroxypyranones. The metal-to-ligand stoichiometry at which maximum quenching is observed was found to depend on the site at which coumarin is attached. The efficiency of fluorescence quenching by iron(III) is markedly influenced by solvent polarity and pH. The permeability of two representative fluorescent chelators across human erythrocyte ghost membranes was investigated. The rate of permeability for a series of probes was found to be related to the corresponding ClogP values.

  DOI：

  10.1021/jm049751s

文献信息

• [EN] FLUORINATED DERIVATIVES OF 3-HYDROXYPYRIDIN-4-ONES<br/>[FR] DÉRIVÉS FLUORÉS DE 3-HYDROXYPYRIDIN-4-ONES
  申请人：APOTEX TECHNOLOGIES INC

  公开号：WO2011000104A1

  公开（公告）日：2011-01-06

  Provided are compounds of Formula I which are derivatives of 3-Hydroxypyridin-4-ones. The compounds may be used in treatment of a medical condition related to a toxic concentration of iron. The compounds may be used for preparation of a medicament for treatment of a medical condition related to a toxic concentration of iron. The medical condition related to a toxic concentration of iron may be selected from the group consisting of: cancer, pulmonary disease, progressive kidney disease and Frederich's Ataxia.

  提供的是Formula I的化合物，它们是3-羟基吡啶-4-酮的衍生物。这些化合物可用于治疗与铁的毒性浓度有关的医疗状况。这些化合物可用于制备用于治疗与铁的毒性浓度有关的医疗状况的药物。与铁的毒性浓度有关的医疗状况可从以下组中选择：癌症、肺部疾病、进行性肾病和弗里德里希共济失调。
• FLUORINATED DERIVATES OF 3-HYDROXYPYRIDIN-4-ONES
  申请人：Tam Tim Fat

  公开号：US20120270882A1

  公开（公告）日：2012-10-25

  Provided are compounds of Formula I which are derivatives of 3-Hydroxypyridin-4-ones. The compounds may be used in treatment of a medical condition related to a toxic concentration of iron. The compounds may be used for preparation of a medicament for treatment of a medical condition related to a toxic concentration of iron. The medical condition related to a toxic concentration of iron may be selected from the group consisting of: cancer, pulmonary disease, progressive kidney disease and Frederich's Ataxia.

  提供的是公式I的化合物，它们是3-羟基吡啶-4-酮的衍生物。这些化合物可以用于治疗与铁的毒性浓度相关的医疗状况。这些化合物可以用于制备治疗与铁的毒性浓度相关的医疗状况的药物。与铁的毒性浓度相关的医疗状况可以从以下组中选择：癌症、肺部疾病、进行性肾脏疾病和弗里德里希共济失调症。
• Fluorinated derivates of 3-hydroxypyridin-4-ones
  申请人：Tam Tim Fat

  公开号：US09073865B2

  公开（公告）日：2015-07-07

  Provided are compounds of Formula I which are derivatives of 3-Hydroxypyridin-4-ones. The compounds may be used in treatment of a medical condition related to a toxic concentration of iron. The compounds may be used for preparation of a medicament for treatment of a medical condition related to a toxic concentration of iron. The medical condition related to a toxic concentration of iron may be selected from the group consisting of: cancer, pulmonary disease, progressive kidney disease and Frederich's Ataxia.

  提供的化合物为公式I的衍生物，属于3-羟基吡啶-4-酮类。这些化合物可用于治疗与铁毒性浓度相关的医疗状况。这些化合物可用于制备治疗与铁毒性浓度相关的医疗状况的药物。与铁毒性浓度相关的医疗状况可以从以下一组中选择：癌症、肺部疾病、进行性肾脏疾病和弗雷德里希共济失调症。
• FLUORINATED DERIVATIVES OF 3-HYDROXYPYRIDIN-4-ONES
  申请人：APOTEX TECHNOLOGIES INC.

  公开号：US20150335626A1

  公开（公告）日：2015-11-26

  Provided are compounds of Formula I which are derivatives of 3-Hydroxypyridin-4-ones. The compounds may be used in treatment of a medical condition related to a toxic concentration of iron. The compounds may be used for preparation of a medicament for treatment of a medical condition related to a toxic concentration of iron. The medical condition related to a toxic concentration of iron may be selected from the group consisting of: cancer, pulmonary disease, progressive kidney disease and Frederich's Ataxia.

  提供的是I式化合物，它们是3-羟基吡啶-4-酮的衍生物。这些化合物可用于治疗与铁的毒性浓度相关的医疗状况。这些化合物可用于制备治疗与铁的毒性浓度相关的医疗状况的药物。与铁的毒性浓度相关的医疗状况可从以下组中选择：癌症，肺部疾病，进行性肾脏疾病和弗里德里希共济失调症。
• Fluorinated Derivatives of 3-Hydroxypyridin-4-Ones
  申请人：Apotex Technologies Inc.

  公开号：US20160083346A1

  公开（公告）日：2016-03-24

  Compounds of Formula I which are derivatives of 3-Hydroxypyridin-4-ones. The compounds may be used in treatment of a medical condition related to a toxic concentration of iron. The compounds may be used for preparation of a medicament for treatment of a medical condition related to a toxic concentration of iron. The medical condition related to a toxic concentration of iron may be selected from the group consisting of: cancer, pulmonary disease, progressive kidney disease and Friedreich's ataxia.

  公式I的衍生物化合物是3-羟基吡啶-4-酮的衍生物。这些化合物可用于治疗与铁的毒性浓度相关的医疗状况。这些化合物可用于制备治疗与铁的毒性浓度相关的医疗状况的药物。与铁毒性浓度相关的医疗状况可以从以下组中选择：癌症、肺病、进行性肾病和弗里德赫氏共济失调。