6-phenyl-3-(pyridin-2-yl)-1,2,4-triazin-5(4H)-one | 49772-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 6-phenyl-3-(pyridin-2-yl)-1,2,4-triazin-5(4H)-one
• 英文别名: 6-Phenyl-3-(2'-pyridyl)-1,2,4-triazin-5-on；6-phenyl-3-pyridin-2-yl-4H-[1,2,4]triazin-5-one；6-Phenyl-3-(pyridin-2-yl)-1,2,4-triazin-5(2H)-one；6-phenyl-3-pyridin-2-yl-4H-1,2,4-triazin-5-one
• CAS: 49772-15-8
• 化学式: C₁₄H₁₀N₄O
• 分子量: 250.26
• InChiKey: ZASIMEKMAIDNRW-UHFFFAOYSA-N

物化性质

• 熔点：
  175 °C(Solv: methanol (67-56-1))
• 沸点：
  414.9±37.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-phenyl-3-(pyridin-2-yl)-1,2,4-triazin-5(4H)-one 在 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 48.17h， 生成 N-(3-morpholin-4-ylpropyl)-6-phenyl-3-pyridin-2-yl-1,2,4-triazin-5-amine
  参考文献：
  名称：

  Discovery of a new molecular probe ML228: An activator of the hypoxia inducible factor (HIF) pathway

  摘要：

  Hypoxia and ischemia are linked to several serious public health problems that affect most major organ systems. Specific examples include diseases of the cardiovascular, pulmonary, renal, neurologic, and musculoskeletal systems. The most significant pathway for cellular response to hypoxia is the hypoxia inducible factor (HIF) pathway. HIFs are transcription factors responsible for the activation of genes which encode proteins that mediate adaptive responses to reduced oxygen availability. A high-throughput cell-based HIF-mediated gene reporter screen was carried out using the NIH's Molecular Libraries Small Molecule Repository to identify activators of the HIF pathway. This communication describes the subsequent medicinal chemistry optimization of a triazine scaffold that led to the identification of the new molecular probe ML228. A discussion of HIF activation SAR within this chemotype as well as detailed in vitro characterization of the probe molecule is presented here. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.077
• 作为产物：
  描述：

  6-phenyl-3-(2-pyridyl)-1,2,4-triazine-5-carbonitrile 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.17h， 以77%的产率得到6-phenyl-3-(pyridin-2-yl)-1,2,4-triazin-5(4H)-one
  参考文献：
  名称：

  从6-芳基1,2,4-丁三嗪-5-酮高效一步合成3-芳基-2-吡啶酮

  摘要：

  一种有效的合成取代的2-吡啶酮的方法，它基于1,2,4-三嗪-5-酮与二烯，2,5-降冰片二烯和4-（环戊-1-烯-）的氮杂-狄尔斯-阿尔德反应提出了1-基）吗啉。

  DOI：

  10.1007/s10593-019-02566-7

文献信息

• Neunhoeffer, Hans; Reichel, Diethard; Cullmann, Birgit, Liebigs Annalen der Chemie, 1990, # 7, p. 631 - 640
  作者：Neunhoeffer, Hans、Reichel, Diethard、Cullmann, Birgit、Rehn, Ingrid

  DOI：——

  日期：——
• NEUNHOEFFER, HANS;REICHEL, DIETHARD;CULLMANN, BIRGIT;REHN, INGRID, LIEBIGS ANN. CHEM.,(1990) N, C. 631-460
  作者：NEUNHOEFFER, HANS、REICHEL, DIETHARD、CULLMANN, BIRGIT、REHN, INGRID

  DOI：——

  日期：——
• 1,2,4-Triazine derivatives, process for their production and pharmaceutical composition
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0030038B1

  公开（公告）日：1983-10-05
• [EN] METHOD OF PROMOTING EXPRESSION OF LDL RECEPTOR GENE<br/>[FR] PROCEDE PERMETTANT DE FAVORISER L'EXPRESSION DU GENE DU RECEPTEUR DE LA LIPOPROTEINE DE BASSE DENSITE (LDL)
  申请人：——

  公开号：WO1999007352A2

  公开（公告）日：1999-02-18

  [EN] Method of promoting expression of LDL receptor gene and an agent therefor, which comprises as an active ingredient a 1,2,4-triazin-5-one derivative of formula (I), wherein R<1> is unsubstituted or substituted phenyl, unsubstituted or substituted heterocycle; R<2> is unsubstituted or substituted phenyl, unsubstituted or substituted naphthyl, unsubstituted or substituted aralkyl, unsubstituted or substituted 5- to 6-membered aromatic heteromonocycle, unsubstituted or substituted C1-C6alkyl, or unsubstituted or substituted C2-C6alkenyl, or pharmaceutically acceptable salt thereof, said active compound (I) increasing the LDL receptor amount by promoting expression of LDL receptor gene (amount of mRNA), by which showing activity of reducing cholesterol level in the blood, and therefore being useful in the prophylaxis or treatment of hyperlipidemia.
  [FR] L'invention concerne un procédé permettant de favoriser l'expression du gène du récepteur de la LDL et un agent utilisé à cet effet, lequel comprend, comme principe actif, un dérivé de 1,2,4-triazin-5-one correspondant à la formule (I) où un sel pharmaceutiquement acceptable de celui-ci. Dans ladite formule: R<1> représente phényle non substitué ou substitué, ou un hétérocycle non substitué ou substitué; R<2> représente phényle non substitué ou substitué, naphtyle non substitué ou substitué, aralkyle non substitué ou substitué, un hétéromonocycle aromatique à 5 ou 6 éléments, non substitué ou substitué, alkyle C1-C6 non substitué ou substitué, ou bien alcényle C2-C6 non substitué ou substitué. Ledit composé actif (I) augmente la quantité de récepteur de LDL en favorisant l'expression du gène du récepteur de LDL (quantité d'ARNm), ce qui lui permet de réduire le niveau de cholestérol dans le sang. Ce composé peut donc être utilisé pour prévenir ou traiter l'hyperlipidémie.
• Discovery of a new molecular probe ML228: An activator of the hypoxia inducible factor (HIF) pathway
  作者：Jimmy R. Theriault、Andrew S. Felts、Brittney S. Bates、Jose R. Perez、Michelle Palmer、Shawn R. Gilbert、Eric S. Dawson、Julie L. Engers、Craig W. Lindsley、Kyle A. Emmitte

  DOI：10.1016/j.bmcl.2011.11.077

  日期：2012.1

  Hypoxia and ischemia are linked to several serious public health problems that affect most major organ systems. Specific examples include diseases of the cardiovascular, pulmonary, renal, neurologic, and musculoskeletal systems. The most significant pathway for cellular response to hypoxia is the hypoxia inducible factor (HIF) pathway. HIFs are transcription factors responsible for the activation of genes which encode proteins that mediate adaptive responses to reduced oxygen availability. A high-throughput cell-based HIF-mediated gene reporter screen was carried out using the NIH's Molecular Libraries Small Molecule Repository to identify activators of the HIF pathway. This communication describes the subsequent medicinal chemistry optimization of a triazine scaffold that led to the identification of the new molecular probe ML228. A discussion of HIF activation SAR within this chemotype as well as detailed in vitro characterization of the probe molecule is presented here. (C) 2011 Elsevier Ltd. All rights reserved.