ethyl 5-methyl-7-phenylpyrazolo<1,5-a>pyrimidine-3-carboxylate | 140706-33-8

• 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: ethyl 5-methyl-7-phenylpyrazolo<1,5-a>pyrimidine-3-carboxylate
• 英文别名: ethyl 5-methyl-7-phenylpyrazolo[1,5-a]pyrimidine-3-carboxylate；Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid,5-methyl-7-phenyl-,ethyl ester
• CAS: 140706-33-8
• 化学式: C₁₆H₁₅N₃O₂
• 分子量: 281.314
• InChiKey: ZJARMAWYESAFCK-UHFFFAOYSA-N

物化性质

• 熔点：
  119.9-121.4 °C
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-methyl-7-phenylpyrazolo<1,5-a>pyrimidine-3-carboxylate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以92%的产率得到5-methyl-7-phenylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid
  参考文献：
  名称：

  单独乙酸中的超声辅助3组分反应：生物活性吡唑并[1,5-a]嘧啶的催化剂/助催化剂/无配体合成

  摘要：

  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。

  DOI：

  10.2174/1570180814666170126120408
• 作为产物：
  描述：

  3-氨基-4-乙氧羰基吡唑 、 3-amino-1-phenylbut-2-en-1-one 在 溶剂黄146 作用下， 以85%的产率得到ethyl 5-methyl-7-phenylpyrazolo<1,5-a>pyrimidine-3-carboxylate
  参考文献：
  名称：

  Maquestiau, A.; Taghret, H.; Eynde, J.-J. vanden, Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 2, p. 131 - 136

  摘要：

  DOI：

文献信息

• Synthesis and structure–activity relationship of tetrahydropyrazolopyrimidine derivatives—A novel structural class of potent calcium-sensing receptor antagonists
  作者：Masato Yoshida、Akira Mori、Atsuhiro Inaba、Masahiro Oka、Haruhiko Makino、Masashi Yamaguchi、Hisashi Fujita、Tomohiro Kawamoto、Mika Goto、Hiroyuki Kimura、Atsuo Baba、Tsuneo Yasuma

  DOI：10.1016/j.bmc.2010.10.035

  日期：2010.12

  derivatives containing an adamantyl group were synthesized and evaluated as potential calcium-sensing receptor (CaSR) antagonists. After chemical modification of 9a, which was identified as a hit compound in a random screening of CaSR antagonist assay, 7,7-dimethyl derivative 16c was found to be the most active compound of this new series (IC50 = 10 nM). We report the synthesis of this series and their

  合成了一系列含有金刚烷基的新型四氢吡唑并嘧啶衍生物，并将其评估为潜在的钙敏感受体（CaSR）拮抗剂。在对9a进行化学修饰后，发现该化合物在CaSR拮抗剂测定的随机筛选中被鉴定为命中化合物，之后发现7,7-二甲基衍生物16c是该新系列中活性最高的化合物（IC 50  = 10 nM）。我们报告了该系列的合成及其生物学活性和结构-活性关系。
• Discovery, Structure–Activity Relationship, and Biological Evaluation of Noninhibitory Small Molecule Chaperones of Glucocerebrosidase
  作者：Samarjit Patnaik、Wei Zheng、Jae H. Choi、Omid Motabar、Noel Southall、Wendy Westbroek、Wendy A. Lea、Arash Velayati、Ehud Goldin、Ellen Sidransky、William Leister、Juan J. Marugan

  DOI：10.1021/jm300063b

  日期：2012.6.28

  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.
• 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。
• Maquestiau, A.; Taghret, H.; Eynde, J.-J. vanden, Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 2, p. 131 - 136
  作者：Maquestiau, A.、Taghret, H.、Eynde, J.-J. vanden

  DOI：——

  日期：——