6-(1-ethoxyvinyl)-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine | 1241428-42-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(1-ethoxyvinyl)-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine
• 英文别名: 6-(1-ethoxyvinyl)-2-methoxy-3-(4-methylimidazol-1-yl)pyridine；6-(1-ethoxyethenyl)-2-methoxy-3-(4-methylimidazol-1-yl)pyridine
• CAS: 1241428-42-1
• 化学式: C₁₄H₁₇N₃O₂
• 分子量: 259.308
• InChiKey: ZEYIEJNESIVVLE-UHFFFAOYSA-N

物化性质

• 沸点：
  421.2±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(1-ethoxyvinyl)-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine 在 盐酸 、 水 、 氢溴酸 、 溴 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 、 乙酸乙酯 、 丙酮 为溶剂， 反应 40.0h， 生成 4-(6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-N-(2-methyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)thiazol-2-amine
  参考文献：
  名称：

  Design and synthesis of novel methoxypyridine-derived gamma-secretase modulators

  摘要：

  The evolution of gamma-secretase modulators (GSMs) through the introduction of novel heterocycles with the goal of aligning activity for reducing the levels of Aβ42 and properties consistent with a drug-like molecule are described. The insertion of a methoxypyridine motif within the tetracyclic scaffold provided compounds with improved activity for arresting Aβ42 production as well as improved properties, including solubility. In vivo pharmacokinetic analysis demonstrated that several compounds within the novel series were capable of crossing the BBB and accessing the therapeutic target. Treatment with methoxypyridine-derived compound 64 reduced Aβ42 levels in the plasma of J20 mice, in addition to reducing Aβ42 levels in the plasma and brain of Tg2576 mice.

  DOI：

  10.1016/j.bmc.2020.115734
• 作为产物：
  描述：

  N-(6-溴-2-甲氧基-3-吡啶)甲酰胺 在 bis-triphenylphosphine-palladium(II) chloride 、 ammonium acetate 、 溶剂黄146 、 potassium iodide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 6-(1-ethoxyvinyl)-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine
  参考文献：
  名称：

  Design and synthesis of novel methoxypyridine-derived gamma-secretase modulators

  摘要：

  The evolution of gamma-secretase modulators (GSMs) through the introduction of novel heterocycles with the goal of aligning activity for reducing the levels of Aβ42 and properties consistent with a drug-like molecule are described. The insertion of a methoxypyridine motif within the tetracyclic scaffold provided compounds with improved activity for arresting Aβ42 production as well as improved properties, including solubility. In vivo pharmacokinetic analysis demonstrated that several compounds within the novel series were capable of crossing the BBB and accessing the therapeutic target. Treatment with methoxypyridine-derived compound 64 reduced Aβ42 levels in the plasma of J20 mice, in addition to reducing Aβ42 levels in the plasma and brain of Tg2576 mice.

  DOI：

  10.1016/j.bmc.2020.115734

文献信息

• [EN] ARYL IMIDAZOLE COMPOUNDS AND THEIR USE AS BETA AMYLOID PRODUCTION INHIBITORS<br/>[FR] COMPOSÉ ARYLIMIDAZOLE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE PRODUCTION DE LA PROTÉINE AMYLOÏDE BÊTA
  申请人：EISAI R&D MAN CO LTD

  公开号：WO2010098488A1

  公开（公告）日：2010-09-02

  A compound represented by the formula (I): or a pharmacologically acceptable salt or ester thereof, wherein Ring A represents a triazolyl group or the like which may be substituted, Ring B represents a phenyl group or the like which may be substituted, X1 represents a single bond or the like, R1 and R2 each represent a C1-6 alkyl group or the like, m represents an integer of 0 to 3, and n represents an integer of 0 to 2, is effective as a therapeutic agent for a disease caused by Aβ.

  一种由化学式(I)表示的化合物，或其药理学上可接受的盐或酯，其中环A代表可能被取代的三唑基团或类似物，环B代表可能被取代的苯基团或类似物，X1代表单键或类似物，R1和R2分别代表C1-6烷基或类似物，m代表0到3的整数，n代表0到2的整数，对于由Aβ引起的疾病具有治疗作用。
• [EN] NITROGEN-CONTAINING FUSED HETEROCYCLIC COMPOUNDS AND THEIR USE AS BETA AMYLOID PRODUCTION INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES CONDENSÉS CONTENANT DE L'AZOTE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE PRODUCTION DE LA BÊTA-AMYLOÏDE
  申请人：EISAI R&D MAN CO LTD

  公开号：WO2010098487A1

  公开（公告）日：2010-09-02

  A compound represented by the formula [I]: or a pharmacologically acceptable salt or ester thereof, wherein Ring A represents a five-membered aromatic heterocyclic group or the like fused with a non-aromatic ring group, which may be substituted, Ring B represents a phenyl group or the like which may be substituted, X1 represents a single bond or the like, R1 and R2 each represent a C1-6 alkyl group or the like, m represents an integer of 0 to 3, and n represents an integer of 0 to 2, is effective as a therapeutic agent for a disease caused by Aβ.

  化合物的分子式为[I]：或其药理学可接受的盐或酯，其中环A代表一个五元芳香杂环基团或类似于非芳香环基团的融合物，可以被取代，环B代表一个苯基或类似的基团，可以被取代，X1代表一个单键或类似物，R1和R2分别代表一个C1-6烷基基团或类似物，m表示0到3的整数，n表示0到2的整数，对由Aβ引起的疾病具有治疗作用。
• Nitrogen-Containing Fused Heterocyclic Compounds and Their use as Beta Amyloid Production Inhibitors
  申请人：Kitazawa Noritaka

  公开号：US20120053171A1

  公开（公告）日：2012-03-01

  A compound represented by the formula [I]: or a pharmacologically acceptable salt or ester thereof, wherein Ring A represents a five-membered aromatic heterocyclic group or the like fused with a non-aromatic ring group, which may be substituted, Ring B represents a phenyl group or the like which may be substituted, X1 represents a single bond or the like, R1 and R2 each represent a C1-6 alkyl group or the like, m represents an integer of 0 to 3, and n represents an integer of 0 to 2, is effective as a therapeutic agent for a disease caused by Aβ.

  化合物的化学式为[I]，或其药理学上可接受的盐或酯，其中环A代表一个五元芳香杂环基团或类似物，与非芳香环基团融合，可以被取代，环B代表苯基或类似物，可以被取代，X1代表单键或类似物，R1和R2各代表C1-6烷基或类似物，m代表0至3的整数，n代表0至2的整数，该化合物对由Aβ引起的疾病具有治疗作用。
• COMPOUNDS AND USES THEREOF IN MODULATING LEVELS OF VARIOUS AMYLOID BETA PEPTIDE ALLOFORMS
  申请人：Wagner Steven L.

  公开号：US20130165416A1

  公开（公告）日：2013-06-27

  The invention provides a novel compound having a structure corresponding to Formula (I): (A)-(B)—(C)-(D)  (I) or a pharmaceutically acceptable salt or prodrug thereof and methods for using them.

  本发明提供了一种新型化合物，其结构对应于公式（I）：（A）-（B）-（C）-（D）（I），或其药学上可接受的盐或前药，并提供其使用方法。
• Compounds and uses thereof in modulating levels of various amyloid beta peptide alloforms
  申请人：Wagner Steven L.

  公开号：US09403815B2

  公开（公告）日：2016-08-02

  The invention provides a novel compound having a structure corresponding to Formula (I): (A)-(B)-(C)-(D)  (I) or a pharmaceutically acceptable salt or prodrug thereof and methods for using them.

  本发明提供了一种新型化合物，其结构对应于公式(I):(A)-(B)-(C)-(D)  (I)或其药物可接受的盐或前药，以及使用它们的方法。