5-phenylpyrazolo[1,5-a]pyrimidin-7-amine | 93669-80-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-phenylpyrazolo[1,5-a]pyrimidin-7-amine
• CAS: 93669-80-8
• 化学式: C₁₂H₁₀N₄
• 分子量: 210.238
• InChiKey: GGEVDDIFIGUHAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  210 °C
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-phenylpyrazolo[1,5-a]pyrimidin-7-amine 在 dipotassium peroxodisulfate 、 N-碘代丁二酰亚胺 作用下， 以 正己烷 、 乙腈 为溶剂， 反应 36.0h， 生成 6-iodo-5-phenyl-3-thiocyanatopyrazolo[1,5-a]pyrimidin-7-amine
  参考文献：
  名称：

  K2S2O8-promoted C3-thiocyanation of pyrazole [1,5-a] pyrimidine-7-amines

  摘要：

  DOI：

  10.1016/j.tet.2023.133324
• 作为产物：
  描述：

  5-phenyl-3-(p-tolylthio)pyrazolo[1,5-a]pyrimidin-7-amine 在 N-碘代丁二酰亚胺 、 2,2,6,6-四甲基哌啶氧化物 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 生成 5-phenylpyrazolo[1,5-a]pyrimidin-7-amine
  参考文献：
  名称：

  Highly selective C3-sulfenylation and C3-selenylation of 3-iodo-5-arylpyrazolo[1,5-a]pyrimidin-7-amine in water

  摘要：

  DOI：

  10.1016/j.molstruc.2023.136165

文献信息

• Heterocycles of biological importance. Part 1. Novel synthesis and biological activity study of 5-Alkyl and 5-Aryl-7-aminopyrazolo[1,5-<i>a</i>]-pyrimidines from allenic or acetylenic nitriles and 3-aminopyrazole
  作者：Z. Tanee Fomum、P. Forche Asobo、P. Ngozi Ifeadike

  DOI：10.1002/jhet.5570210439

  日期：1984.7

  Allenic nitriles react with 3-aminopyrazole in ethanol or dimethylformamide to give 5-alkyl-7-aminopyrazolo[1,5-a]pyrimidines 5 of pharmaceutical interest in good yields. 3-Phenylpropynenitrile reacts with 3-aminopyrazole in a similar manner to give the aryl compound 8.

  烯丙基腈与3-氨基吡唑在乙醇或二甲基甲酰胺中反应，以高收率得到具有药用价值的5-烷基-7-氨基吡唑并[1,5- a ]嘧啶5。3-苯基丙腈与3-氨基吡唑以类似方式反应，得到芳基化合物8。
• NOVEL FUSED HETEROCYCLIC COMPOUND AND USE THEREOF
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1671962A1

  公开（公告）日：2006-06-21

  The compound represented by the general formula (I): wherein, a fused ring AB represents a 5- to 10-membered fused heterocyclic ring; R1 represents (1) a hydrogen atom, (2) a halogen atom, (3) a cyano group, (4) an oxo group, (5) an optionally protected hydroxyl group, (6) an optionally protected carboxyl group, (7) an optionally protected amino group, (8) a cyclic group which may have a substituent (s), (9) an aliphatic hydrocarbon group which may have a substituent (s), or (10) an optionally protected thiol group; n represents 0 or an integer of 1 to 8; provided that n represents an integer of not less than 2, plural R1 are the same or different; a salt thereof, a solvate thereof or a prodrug thereof has a kinase(especially c-Jun N-terminalkinase) inhibitory activity and an inhibitory activity of a function of AP-1 as a transcription factor, it is useful as a preventive and/or therapeutic agent for a for example, a diabetes of metabolic disease, etc., a rheumatoid arthritis of inflammatory, etc.

  化合物的一般式（I）：其中，融合环AB代表一个5-至10-成员的融合杂环；R1代表（1）氢原子，（2）卤素原子，（3）氰基，（4）氧基，（5）可选保护的羟基，（6）可选保护的羧基，（7）可选保护的氨基，（8）可能具有取代基的环状基团，（9）可能具有取代基的脂肪烃基团或（10）可选保护的硫醇基团; n代表0或1至8的整数; 假设n代表不小于2的整数，则复数R1相同或不同;其盐，溶剂化物或前药具有激酶（尤其是c-Jun N末端激酶）抑制活性和AP-1作为转录因子的功能抑制活性，因此可用作预防和/或治疗代谢疾病（例如糖尿病等）和炎症性风湿性关节炎等的药物。
• Novel fused heterocyclic compound and use thereof
  申请人：Yoshizawa Toshio

  公开号：US20070060595A1

  公开（公告）日：2007-03-15

  The compound represented by the general formula (I): wherein, a fused ring AB represents a 5- to 10-membered fused heterocyclic ring; R 1 represents (1) a hydrogen atom, (2) a halogen atom, (3) a cyano group, (4) an oxo group, (5) an optionally protected hydroxyl group, (6) an optionally protected carboxyl group, (7) an optionally protected amino group, (8) a cyclic group which may have a substituent (s), (9) an aliphatic hydrocarbon group which may have a substituent (s), or (10) an optionally protected thiol group; n represents 0 or an integer of 1 to 8; provided that n represents an integer of not less than 2, plural R 1 are the same or different; a salt thereof, a solvate thereof or a prodrug thereof has a kinase (especially c-Jun N-terminal kinase) inhibitory activity and an inhibitory activity of a function of AP-1 as a transcription factor, it is useful as a preventive and/or therapeutic agent for a for example, a diabetes of metabolic disease, etc., a rheumatoid arthritis of inflammatory, etc.

  化合物的一般式(I)表示的化合物：其中，融合环AB表示一个5-至10-成员的融合杂环；R1表示（1）氢原子，（2）卤原子，（3）氰基，（4）氧代基，（5）可选保护的羟基，（6）可选保护的羧基，（7）可选保护的氨基，（8）可能具有取代基（s）的环状基团，（9）可能具有取代基（s）的脂肪烃基团，或（10）可选保护的硫醇基团；n表示0或1至8的整数；但是，如果n表示不少于2的整数，则复数R1相同或不同；其盐、溶剂化物或前药具有激酶（特别是c-Jun N末端激酶）抑制活性和AP-1作为转录因子的功能抑制活性，因此它对于例如代谢性疾病的糖尿病等，炎症性的类风湿性关节炎等的预防和/或治疗剂是有用的。
• PYRAZOLO [1,5-a]PYRIMIDINE DERIVATIVE
  申请人：OTSUKA PHARMACEUTICAL FACTORY, INC.

  公开号：EP0714898A1

  公开（公告）日：1996-06-05

  The invention provides a pyrazolo[1,5-a]pyrimidine derivative of the following formula (1): wherein R¹ is hydrogen, lower alkyl which may have thienyl, lower alkoxy, lower alkylthio, oxo or hydroxyl as a substituent, cycloalkyl, thienyl, furyl, lower alkenyl, or phenyl which may have 1 to 3 substituents selected from the group consisting of lower alkyl, lower alkoxy, phenylthio and halogen; R² is naphthyl, cycloalkyl, furyl, thienyl, optionally halogen-substituted pyridyl, optionally halogen-substituted phenoxy, or phenyl which may have 1 to 3 substituents selected from the group consisting of lower alkyl, lower alkoxy, halogen, nitro, halogen-substituted lower alkyl, halogen-substituted lower alkoxy, lower alkoxycarbonyl, hydroxyl, phenyl(lower)alkoxy, amino, cyano, lower alkanoyloxy, phenyl and di(lower)alkoxyphosphoryl(lower)alkyl; R³ is hydrogen, phenyl or lower alkyl; R⁴ is hydrogen, lower alkyl, lower alkoxycarbonyl, phenyl(lower)alkyl, optionally phenylthio-substituted phenyl, or halogen; R⁵ is hydrogen or lower alkyl; R⁶ is hydrogen, lower alkyl, phenyl(lower)alkyl, or benzoyl having 1 to 3 substituents selected from the group consisting of lower alkoxy, halogen-substituted lower alkyl and halogen; R¹ and R⁵ may conjointly form lower alkylene; Q is carbonyl or sulfonyl; A is a single bond, lower alkylene or lower alkenylene; and n is 0 or 1. This derivative is useful as a potent analgesic.

  本发明提供了下式（1）的吡唑并[1,5-a]嘧啶衍生物： 其中 R¹ 是氢、可具有噻吩基、低级烷氧基、低级烷硫基、氧代或羟基作为取代基的低级烷基、环烷基、噻吩基、呋喃基、低级烯基或可具有 1 至 3 个选自低级烷基、低级烷氧基、苯硫基和卤素的取代基的苯基；R² 是萘基、环烷基、呋喃基、噻吩基、任选卤素取代的吡啶基、任选卤素取代的苯氧基或苯基，可具有 1 至 3 个取代基，这些取代基可从低级烷基、低级烷氧基、卤素、硝基和卤素组成的组中选出、低级烷氧基、卤素、硝基、卤素取代的低级烷基、卤素取代的低级烷氧基、低级烷氧基羰基、羟基、苯基（低级）烷氧基、氨基、氰基、低级烷酰氧基、苯基和二（低级）烷氧基磷酰（低级）烷基；R³ 是氢、苯基或低级烷基；R⁴ 是氢、低级烷基、低级烷氧基羰基、苯基（低级）烷基、任选的苯硫基取代苯基或卤素；R⁵ 是氢或低级烷基；R⁶ 是氢、低级烷基、苯基（低级）烷基或具有 1 至 3 个取代基的苯甲酰基，取代基可从低级烷氧基、卤素取代的低级烷基和卤素组成的组中选出；R¹ 和 R⁵ 可共同形成低级亚烷基；Q 是羰基或磺酰基；A 是单键、低级亚烷基或低级亚烯基；n 是 0 或 1。这种衍生物可用作强效镇痛剂。
• Regioselective C3-halogenations of N-(pyrazolo[1,5-a]pyrimidin-7-yl)acetamides
  作者：Ting Pang、Tian Sang、Jing He、Jichang Liu、Ping Liu

  DOI：10.1016/j.tet.2023.133775

  日期：2024.1

  Regioselective C3-halogenations of N-(pyrazolo [1,5-a]pyrimidin-7-yl)acetamide with N-halosuccinimides (NBS or NCS) have been achieved. A diverse array of C3-halogenated products are provided in high yields with excellent regioselectivity. The practicability of this approach is highlighted by simple condition reactions, broad substrate scope, gram-scale reaction. Moreover, further derivatization reactions

  已经实现了N- (吡唑并[1,5- a ]嘧啶-7-基)乙酰胺与N-卤代琥珀酰亚胺（NBS 或 NCS）的区域选择性 C3 卤化。以高产率提供多种 C3 卤化产品，并具有出色的区域选择性。该方法的特点是反应条件简单、底物范围广、反应规模可达到克级。此外，进一步的衍生化反应证明了产品的多功能性。