5-methyl-7-phenyl-N-p-tolylpyrazolo[1,5-a]pyrimidine-3-carboxamide | 1380716-63-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-methyl-7-phenyl-N-p-tolylpyrazolo[1,5-a]pyrimidine-3-carboxamide
• 英文别名: 5-methyl-N-(4-methylphenyl)-7-phenylpyrazolo[1,5-a]pyrimidine-3-carboxamide
• CAS: 1380716-63-1
• 化学式: C₂₁H₁₈N₄O
• 分子量: 342.4
• InChiKey: MUFXADBLCQQICZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 5-methyl-7-phenylpyrazolo<1,5-a>pyrimidine-3-carboxylate 在 水 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-methyl-7-phenyl-N-p-tolylpyrazolo[1,5-a]pyrimidine-3-carboxamide
  参考文献：
  名称：

  Discovery, Structure–Activity Relationship, and Biological Evaluation of Noninhibitory Small Molecule Chaperones of Glucocerebrosidase

  摘要：

  A major challenge in the field of Gaucher disease has been the development of new therapeutic strategies including molecular chaperones. All previously described chaperones of glucocerebrosidase are enzyme inhibitors, which complicates their clinical development because their chaperone activity must be balanced against the functional inhibition of the enzyme. Using a novel high throughput screening methodology, we identified a chemical series that does not inhibit the enzyme but can still facilitate its translocation to the lysosome as measured by immunostaining of glucocerebrosidase in patient fibroblasts. These compounds provide the basis for the development of a novel approach toward small molecule treatment for patients with Gaucher disease.

  DOI：

  10.1021/jm300063b

文献信息

• [EN] SUBSTITUTED PYRAZOLOPYRIMIDINES AS GLUCOCEREBROSIDASE ACTIVATORS<br/>[FR] UTILISATION DES PYRAZOLOPYRIMIDINES SUBSTITUÉES COMME ACTIVATEURS DE GLUCOCÉRÉBROSIDASE
  申请人：US HEALTH

  公开号：WO2012078855A1

  公开（公告）日：2012-06-14

  Substituted pyrazolopyrimidines and dihydropyrazolopyrimidines and related compounds, their methods of manufacture, compositions containing these compounds, and methods of use of these compounds in treating lysosomal storage disorders such as Gaucher disease are described herein. The compounds are of general Formula (I) in which variables R1-R7 and X are described in the application.

  本文描述了取代吡唑吡咯嘧啶和二氢吡唑吡咯嘧啶及相关化合物，它们的制备方法，含有这些化合物的组合物，以及这些化合物在治疗高雪氏病等溶酶体贮积症中的使用方法。这些化合物属于一般式(I)，其中变量R1-R7和X在申请中有描述。
• Ultrasound-Assisted 3-Component Reaction in Acetic Acid Alone: Catalyst / Promoter / Ligand Free Synthesis of Bioactive Pyrazolo[1,5-a]pyrimidines
  作者：Namburi Suresh、Bodapati Veera Durgarao、A. Ratnakar、Sunder Kumar Kolli、Mohd Ashraf Ashfaq、Mandava V. Basaveswara Rao、Manojit Pal

  DOI：10.2174/1570180814666170126120408

  日期：2017.9.8

  under ultrasound irradiation has been found to be effective for the three-component reaction involving ethyl-5- amino-1H-pyrazole-4-carboxylate, aromatic aldehydes and terminal alkynes in the presence of aerial oxygen. Methods: The catalyst / promoter / ligand free method afforded a range of pyrazolo[1,5-a] pyrimidines as potential and new cytotoxic agents. Results and Conclusion: While some of these

  背景：发现乙酸在超声辐射下用作溶剂时，对于在空气中存在的5-氨基-1H-吡唑-4-羧酸乙酯，芳族醛和末端炔烃的三组分反应有效氧。 方法：无催化剂/无助催化剂/无配体的方法提供了一系列潜在的吡唑并[1,5-a]嘧啶和新的细胞毒性剂。 结果与结论：尽管这些化合物中的某些对两种乳腺癌细胞系显示出细胞毒性，但发现其中一种是有前途的。
• SUBSTITUTED PYRAZOLOPYRIMIDINES AS GLUCOCEREBROSIDASE ACTIVATORS
  申请人：Marugan Juan Jose

  公开号：US20140249145A1

  公开（公告）日：2014-09-04

  Substituted pyrazolopyrimidines and dihydropyrazolopyrimidines and related compounds, their methods of manufacture, compositions containing these compounds, and methods of use of these compounds in treating lysosomal storage disorders such as Gaucher disease are described herein. The compounds are of general Formula (I) in which variables R 1 -R 7 and X are described in the application.

  本文描述了替代的吡唑并嘧啶和二氢吡唑并嘧啶及相关化合物，它们的制造方法，含有这些化合物的组合物，以及在治疗溶酶体贮积病如高氏病等方面使用这些化合物的方法。这些化合物的一般式（I）中的变量R1-R7和X在本申请中描述。
• Substituted pyrazolopyrimidines as glucocerebrosidase activators
  申请人：The United States of America, as Represented by the Secretary, Department of Health and Human Service

  公开号：US10925874B2

  公开（公告）日：2021-02-23

  Substituted pyrazolopyrimidines and dihydropyrazolopyrimidines and related compounds, their methods of manufacture, compositions containing these compounds, and methods of use of these compounds in treating lysosomal storage disorders such as Gaucher disease are described herein. The compounds are of general Formula (I) in which variables R1-R7 and X are described in the application.

  本文描述了取代的吡唑并嘧啶和二氢吡唑并嘧啶及相关化合物、它们的制造方法、含有这些化合物的组合物以及使用这些化合物治疗溶酶体贮积症（如戈谢病）的方法。这些化合物的通式为 (I) 其中变量 R1-R7 和 X 已在申请中说明。
• US9353117B2
  申请人：——

  公开号：US9353117B2

  公开（公告）日：2016-05-31