2-n-propyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one | 934524-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并三嗪类
• 英文名称: 2-n-propyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one
• 英文别名: 2-propyl-3H,4H-pyrazolo[1,5-a][1,3,5]triazin-4-one；2-propyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one
• CAS: 934524-67-1
• 化学式: C₈H₁₀N₄O
• 分子量: 178.194
• InChiKey: MLGRZOIZAMNFHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-n-propyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one 在 四氯化锡 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 生成 [4-(N-methylanilino)-2-propylpyrazolo[1,5-a][1,3,5]triazin-8-yl]-phenylmethanone
  参考文献：
  名称：

  Efficient synthesis of 8-substituted pyrazolo[1,5-a]-1,3,5-triazines by regioselective acylation

  摘要：

  An efficient two-step synthesis of 8-acylated pyrazolo[1,5-a]-1,3,5-triazines has been accomplished. The key strategic elements of this novel synthetic approach involve the use of the N-methyl-N-phenylamino activating group, which was easily obtained in high yield by treatment of the pyrazolotriazin-4-one with phosphorus oxychloride and dimethylaniline through high pressure reaction coupled with a regioselective acylation at position 8 followed by the subsequent displacement of the N-methyl-N-phenylamino group upon treatment with various amines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02456-5
• 作为产物：
  描述：

  N-(1H-吡唑-3-基)丁脒 、 N,N'-羰基二咪唑 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 2-n-propyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one
  参考文献：
  名称：

  Pyrazolotriazines

  摘要：

  具有特定化学式I的化合物，其中R1、R2、A、R4、B、R5和R6的含义如描述中所示，是具有抗增殖和/或诱导凋亡活性的有效化合物。

  公开号：

  EP2070932A1

文献信息

• Synthesis of 8-Substituted Pyrazolo[1,5-<i>a</i>]-1,3,5-triazine Derivatives by Palladium-Catalyzed Cross-Coupling Reactions
  作者：Benoît Joseph、Florence Popowycz、Philippe Bernard、Pierre Raboisson

  DOI：10.1055/s-2006-958963

  日期：2007.2

  8-Substituted pyrazolo[1,5-a]-1,3,5-triazine derivatives 6 were prepared from the corresponding 8-iodopyrazolo[1,5-a]-1,3,5-triazines 5 through palladium-catalyzed cross-coupling reactions. Several bioisosteres of hypoxanthine drugs 2 were then prepared by final nucleophilic aromatic substitution.

  8-取代的吡唑并[1,5-a]-1,3,5-三嗪衍生物6由相应的8-碘吡唑并[1,5-a]-1,3,5-三嗪5通过钯催化交叉制备-偶联反应。然后通过最终的亲核芳香取代制备了几种次黄嘌呤药物 2 的生物等排体。
• Cyclic nucleotide phosphodiesterase type 4 inhibitors: Evaluation of pyrazolo[1,5-a]-1,3,5-triazine ring system as an adenine bioisostere
  作者：Pierre Raboisson、Dominique Schultz、Christian Muller、Jean-Marie Reimund、Guillaume Pinna、Romain Mathieu、Philippe Bernard、Quoc-Tuan Do、Renee L. DesJarlais、Hélène Justiano

  DOI：10.1016/j.ejmech.2007.05.016

  日期：2008.4

  5-a]-1,3,5-triazines were considered as a bioisosteric replacement for the 9-substituted adenine derivatives resulting in the discovery of 8-(2-methoxybenzyl)-4-(N-methylamino)-2-n-propylpyrazolo[1,5-a]-1,3,5-triazine (14d) and 2-trifluoromethyl-8-(2-methoxybenzyl)-4-(N-methylamino)pyrazolo[1,5-a]-1,3,5-tria zine (14e) as a new structural class of potent phosphodiesterase type 4 inhibitors (IC(50)=13

  一系列的8-取代的吡唑并[1,5-a] -1,3,5-三嗪被认为是9-取代的腺嘌呤衍生物的生物立体替代品，从而发现了8-（2-甲氧基苄基）-4- （N-甲基氨基）-2-正丙基吡唑并[1,5-a] -1,3,5-三嗪（14d）和2-三氟甲基-8-（2-甲氧基苄基）-4-（N-甲基氨基）吡唑并[1,5-a] -1,3,5-三嗪（14e）作为具有强同工酶选择性的新型4类有效磷酸二酯酶抑制剂（IC（50）= 13 nM和11 nM）。反应的原始串联涉及容易获得的8-碘-2-甲基-4-（N-甲基-N-苯基氨基）吡唑并[1,5-a] -1的钯介导的交叉偶联反应（PMCCR） ，3，5-三嗪（11a）和芳基硼酸或炔烃，然后置换N-甲基-N-苯基氨基，是本文开发的新型合成方法中的关键步骤。用n-BuLi和选定的醛处理11a-c代表了PMCCR有趣的替代方法，用于合成苄基衍生物14a-i。初步生物学测试表明
• [EN] PYRAZOLOTRIAZINES<br/>[FR] PYRAZOLOTRIAZINES
  申请人：4SC AG

  公开号：WO2009074677A2

  公开（公告）日：2009-06-18

  Compounds of a certain formula I, in which R1, R2, A, R4, B, R5 and R6 have the meanings indicated in the description, are effective compounds with antiproliferative and/or apoptosis inducing activity.
• Pyrazolotriazines
  申请人：4SC AG

  公开号：EP2070932A1

  公开（公告）日：2009-06-17

  Compounds of a certain formula I, in which R1, R2, A, R4, B, R5 and R6 have the meanings indicated in the description, are effective compounds with anti-proliferative and/or apoptosis inducing activity.

  具有特定化学式I的化合物，其中R1、R2、A、R4、B、R5和R6的含义如描述中所示，是具有抗增殖和/或诱导凋亡活性的有效化合物。
• Efficient synthesis of 8-substituted pyrazolo[1,5-a]-1,3,5-triazines by regioselective acylation
  作者：Pierre Raboisson、Dominique Schultz、Claire Lugnier、Jean-Jacques Bourguignon

  DOI：10.1016/s0040-4039(02)02456-5

  日期：2002.12

  An efficient two-step synthesis of 8-acylated pyrazolo[1,5-a]-1,3,5-triazines has been accomplished. The key strategic elements of this novel synthetic approach involve the use of the N-methyl-N-phenylamino activating group, which was easily obtained in high yield by treatment of the pyrazolotriazin-4-one with phosphorus oxychloride and dimethylaniline through high pressure reaction coupled with a regioselective acylation at position 8 followed by the subsequent displacement of the N-methyl-N-phenylamino group upon treatment with various amines. (C) 2002 Elsevier Science Ltd. All rights reserved.