(5,7-dimethyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)acetic acid | 142653-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (5,7-dimethyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)acetic acid
• 英文别名: 5,7-dimethyl-2-phenylpyrazolo[1,5-a]pyrimidine-3-acetic acid；2-(5,7-dimethyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)acetic acid
• CAS: 142653-49-4
• 化学式: C₁₆H₁₅N₃O₂
• 分子量: 281.314
• InChiKey: UGZOIPROCZTNSW-UHFFFAOYSA-N

物化性质

• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  67.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5,7-dimethyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)acetic acid 、 N-乙基苄胺 在 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以20%的产率得到
  参考文献：
  名称：

  Insight into 2-phenylpyrazolo[1,5-a]pyrimidin-3-yl acetamides as peripheral benzodiazepine receptor ligands: Synthesis, biological evaluation and 3D-QSAR investigation

  摘要：

  The present paper reports the synthesis and binding studies of new 2-phenylpyrazolo[1,5-alpha]pyrimidin-3-yl acetamides as selective Peripheral Benzodiazepine Receptor (PBR) ligands. The variability of substituents at the 3-position was investigated and a 3D-QSAR model was proposed to evaluate the effect of different substitutions on the acetamide moiety. In addition, a subset of the novel compounds showing high affinity for PBR was tested for their ability to modulate the steroid biosynthesis in C6 glioma cells. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.015
• 作为产物：
  描述：

  3-cyano-4-oxo-4-phenylbutanoic acid 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 (5,7-dimethyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)acetic acid
  参考文献：
  名称：

  Insight into 2-phenylpyrazolo[1,5-a]pyrimidin-3-yl acetamides as peripheral benzodiazepine receptor ligands: Synthesis, biological evaluation and 3D-QSAR investigation

  摘要：

  The present paper reports the synthesis and binding studies of new 2-phenylpyrazolo[1,5-alpha]pyrimidin-3-yl acetamides as selective Peripheral Benzodiazepine Receptor (PBR) ligands. The variability of substituents at the 3-position was investigated and a 3D-QSAR model was proposed to evaluate the effect of different substitutions on the acetamide moiety. In addition, a subset of the novel compounds showing high affinity for PBR was tested for their ability to modulate the steroid biosynthesis in C6 glioma cells. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.015

文献信息

• 2-phenylpyrazolo[1,5-a]pyrimidine-3-acetic acid derivatives exhibiting
  申请人：A. H. Robins Company Incorporated

  公开号：US05114944A1

  公开（公告）日：1992-05-19

  This invention provides a 2-arylpyrazolo[1,5-a]pyrimidine-3-acetic acid corresponding to the formula: ##STR1## where X is hydrogen or a halogen, hydroxy, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy substituent; Y is hydrogen or a halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy substituent; Z is a hydroxy, C.sub.1 -C.sub.4 alkoxy or --NRR substituent; and R is hydrogen or a C.sub.1 -C.sub.4 alkyl substituent; or a pharmaceutically acceptable salt thereof which is useful as a therapeutic agent which exhibits anxiolytic, anticonvulsant and muscle relaxant effects in a warm blooded animal.

  这项发明提供了一种2-芳基吡唑并[1,5-a]嘧啶-3-乙酸，其对应于以下式子：##STR1##其中X是氢或卤素，羟基，C.sub.1-C.sub.4烷基或C.sub.1-C.sub.4烷氧基取代基；Y是氢或卤素，C.sub.1-C.sub.4烷基或C.sub.1-C.sub.4烷氧基取代基；Z是羟基，C.sub.1-C.sub.4烷氧基或--NRR取代基；R是氢或C.sub.1-C.sub.4烷基取代基；或其药学上可接受的盐，用作在温血动物中表现出抗焦虑、抗惊厥和肌肉松弛作用的治疗剂。
• US5114944A
  申请人：——

  公开号：US5114944A

  公开（公告）日：1992-05-19
• Insight into 2-phenylpyrazolo[1,5-a]pyrimidin-3-yl acetamides as peripheral benzodiazepine receptor ligands: Synthesis, biological evaluation and 3D-QSAR investigation
  作者：Silvia Selleri、Paola Gratteri、Camilla Costagli、Claudia Bonaccini、Annarella Costanzo、Fabrizio Melani、Gabriella Guerrini、Giovanna Ciciani、Barbara Costa、Francesca Spinetti、Claudia Martini、Fabrizio Bruni

  DOI：10.1016/j.bmc.2005.05.015

  日期：2005.8

  The present paper reports the synthesis and binding studies of new 2-phenylpyrazolo[1,5-alpha]pyrimidin-3-yl acetamides as selective Peripheral Benzodiazepine Receptor (PBR) ligands. The variability of substituents at the 3-position was investigated and a 3D-QSAR model was proposed to evaluate the effect of different substitutions on the acetamide moiety. In addition, a subset of the novel compounds showing high affinity for PBR was tested for their ability to modulate the steroid biosynthesis in C6 glioma cells. (c) 2005 Elsevier Ltd. All rights reserved.