ethyl 5-phenyl-7-(trifluoromethyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylate | 312635-19-1

• 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-phenyl-7-(trifluoromethyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylate
• 英文别名: ethyl 7-(trifluoromethyl)-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxylate；ethyl 5-phenyl-7-trifluoromethylpyrazolo[1,5-a]pyrimidine-3-carboxylate；Ethyl 5-phenyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate
• CAS: 312635-19-1
• 化学式: C₁₆H₁₂F₃N₃O₂
• 分子量: 335.285
• InChiKey: DQWUKBFAOSIKEW-UHFFFAOYSA-N

物化性质

• 熔点：
  111-113 °C
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 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：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 5-phenyl-7-(trifluoromethyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以74%的产率得到5-苯基-7-(三氟甲基)吡唑并-[1,5-A]嘧啶-3-羧酸
  参考文献：
  名称：

  Novel and Efficient Synthesis of 7-Trifluoromethyl-Substituted Pyrazolo[1,5-a] Pyrimidines with Potent Antitumor Agents

  摘要：

  DOI：

  10.5012/jkcs.2011.55.4.719
• 作为产物：
  描述：

  苯甲酰三氟丙酮 、 3-氨基-4-乙氧羰基吡唑 在 溶剂黄146 作用下， 反应 4.0h， 以79%的产率得到ethyl 5-phenyl-7-(trifluoromethyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylate
  参考文献：
  名称：

  四氢吡唑并嘧啶衍生物的合成及其构效关系-一种新型的结构型强钙敏感受体拮抗剂

  摘要：

  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。

  DOI：

  10.1016/j.bmc.2010.10.035

文献信息

• Substituted pyrazolo[1,5-A] pyrimidines as calcium receptor modulating agents
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US09447100B2

  公开（公告）日：2016-09-20

  There is provided a calcium receptor modulator comprising a compound of the formula (I): wherein ring A is an optionally substituted 5- to 7-membered ring; ring B is an optionally substituted 5- to 7-membered heterocyclic ring; X1 is CR1, CR1R2, N or NR13; X2 is N or NR3; Y is C, CR4 or N, Z is CR5, CR5R6, N or NR7; Ar is an optionally substituted cyclic group; R is H, an optionally substituted hydrocarbon group, etc.; and is a single bond or a double bond; R1, R2, R3, R4, R5, R6, R7 and R13 are independently H, an optionally substituted hydrocarbon group; or a salt thereof or a prodrug thereof. Compounds of the formula (II) and (III): wherein ring A is an optionally substituted 5- to 7-membered ring; Q is C, CR5 or N; R8, R9, R10, R11 and R12 are independently, H, an optionally substituted hydrocarbon group, etc., or a salt thereof are also provided. Also specify X1, R3, R1, Y and X3 in formula (II) and (III) as before.

  提供了一种包括式(I)化合物的钙受体调节剂： 其中环A是可选择地取代的5-至7-成员环；环B是可选择地取代的5-至7-成员杂环；X1是CR1、CR1R2、N或NR13；X2是N或NR3；Y是C、CR4或N，Z是CR5、CR5R6、N或NR7；Ar是可选择地取代的环状基团；R是H、可选择地取代的碳氢基团等；和是单键或双键；R1、R2、R3、R4、R5、R6、R7和R13独立地是H、可选择地取代的碳氢基团；或其盐或前药。还提供了式(II)和(III)的化合物： 其中环A是可选择地取代的5-至7-成员环；Q是C、CR5或N；R8、R9、R10、R11和R12独立地是H、可选择地取代的碳氢基团等，或其盐。 还请在式(II)和(III)中指定X1、R3、R1、Y和X3。
• SUBSTITUTED PYRAZOLO[1,5-A] PYRIMIDINES AS CALCIUM RECEPTOR MODULATING AGENTS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US20140155416A1

  公开（公告）日：2014-06-05

  There is provided a calcium receptor modulator comprising a compound of the formula (I): wherein ring A is an optionally substituted 5- to 7-membered ring; ring B is an optionally substituted 5- to 7-membered heterocyclic ring; X 1 is CR 1 , CR 1 R 2 , N or NR 13 ; X 2 is N or NR 3 ; Y is C, CR 4 or N, Z is CR 5 , CR 5 R 6 , N or NR 7 ; Ar is an optionally substituted cyclic group; R is H, an optionally substituted hydrocarbon group, etc.; and is a single bond or a double bond; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 13 are independently H, an optionally substituted hydrocarbon group; or a salt thereof or a prodrug thereof. Compounds of the formula (II) and (III): wherein ring A is an optionally substituted 5- to 7-membered ring; Q is C, CR 5 or N; R 8 , R 9 , R 10 , R 11 and R 12 are independently, H, an optionally substituted hydrocarbon group, etc., or a salt thereof are also provided. Also specify X 1 , R 3 , R 1 , Y and X 3 in formula (II) and (III) as before.

  提供了一种含有式(I)化合物的钙受体调节剂，其中环A是可选取代的5-至7元环；环B是可选取代的5-至7元杂环；X1是CR1，CR1R2，N或NR13；X2是N或NR3；Y是C，CR4或N，Z是CR5，CR5R6，N或NR7；Ar是可选取代的环状基团；R是H，可选取代的烃基团等；表示单键或双键；R1、R2、R3、R4、R5、R6、R7和R13独立地是H，可选取代的烃基团；或其盐或前药。还提供了式(II)和(III)的化合物：其中环A是可选取代的5-至7元环；Q是C，CR5或N；R8、R9、R10、R11和R12独立地是H，可选取代的烃基团等，或其盐。同样指定式(II)和(III)中的X1、R3、R1、Y和X3如前。
• SUBSTITUTED PYRAZOLO[1,5-A]PYRIMIDINES AS CALCIUM RECEPTOR MODULATING AGENTS
  申请人：Yasuma Tsuneo

  公开号：US20090215746A1

  公开（公告）日：2009-08-27

  There is provided a calcium receptor modulator comprising a compound of the formula (I): wherein ring A is an optionally substituted 5- to 7-membered ring; ring B is an optionally substituted 5- to 7-membered heterocyclic ring; X 1 is CR 1 , CR 1 R 2 , N or NR 13 ; X 2 is N or NR 3 ; Y is C, CR 4 or N, Z is CR 5 , CR 5 R 6 , N or NR 7 ; Ar is an optionally substituted cyclic group; R is H, an optionally substituted hydrocarbon group, etc.; and is a single bond or a double bond; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 13 are independently H, an optionally substituted hydrocarbon group; or a salt thereof or a prodrug thereof. Compounds of the formula (II) and (III): wherein ring A is an optionally substituted 5- to 7-membered ring; Q is C, CR 5 or N; R 8 , R 9 , R 10 , R 11 and R 12 are independently, H, an optionally substituted hydrocarbon group, etc., or a salt thereof are also provided. Also specify X 1 , R 3 , R 1 , Y and X 3 in formula (II) and (III) as before.

  提供了一种包含式(I)化合物的钙受体调节剂，其中环A是可选取代的5-至7-成员环；环B是可选取代的5-至7-成员杂环；X1是CR1、CR1R2、N或NR13；X2是N或NR3；Y是C、CR4或N，Z是CR5、CR5R6、N或NR7；Ar是可选取代的环状基团；R是H、可选取代的碳氢基团等；和是单键或双键；R1、R2、R3、R4、R5、R6、R7和R13独立地是H、可选取代的碳氢基团；或其盐或前药。还提供了式(II)和(III)化合物：其中环A是可选取代的5-至7-成员环；Q是C、CR5或N；R8、R9、R10、R11和R12独立地是H、可选取代的碳氢基团等，或其盐。同时，如前所述，还指定式(II)和(III)中的X1、R3、R1、Y和X3。
• Optimization of Small-Molecule Inhibitors of Influenza Virus Polymerase: From Thiophene-3-Carboxamide to Polyamido Scaffolds
  作者：Susan Lepri、Giulio Nannetti、Giulia Muratore、Gabriele Cruciani、Renzo Ruzziconi、Beatrice Mercorelli、Giorgio Palù、Arianna Loregian、Laura Goracci

  DOI：10.1021/jm500300r

  日期：2014.5.22

  Influenza virus infections represent a serious concern to public health, being characterized by high morbidity and significant mortality. To date, compounds targeting the viral ion-channel M2 or the viral neuraminidase are the drugs available for treatment of influenza, but the emergence of drug-resistant viral mutants renders the search for novel targets and their possible inhibitors a major priority. Recently, we I I demonstrated that the viral RNA-dependent RNA polymerase (RdRP) complex can be an optimal target of protein protein disruption by small molecules, with thiophene-3-carboxamide derivatives emerging as promising candidates for the development of new anti-influenza drugs with broad-spectrum activity. Here, we report a further dissection of the thiophene-3-carboxamide structure. By using a GRID molecular interaction field (MIF)-based scaffold-hopping approach, more potent and nontoxic polyamido derivatives were identified, highlighting a new space in the chemical variability of RdRP inhibitors. Finally, a possible pharmacophoric model highlighting the key features required for RdRP inhibition is proposed.
• ——
  作者：V. I. Filyakova、O. A. Kuznetsova、E. N. Ulomskii、T. V. Rybalova、Yu. V. Gatilov、M. I. Kodess、V. L. Rusinov、K. I. Pashkevich

  DOI：10.1023/a:1015420130033

  日期：——

  The reactions of Li enolates of fluorine-containing beta-diketones with 3-aminopyrazoles afforded (7-polyfluoroalkyl)pyrazolo[1,5-a]pyrimidines. The structure of 3-bromo-2-methyl-5-phenyl-7-trifluoromethylpyrazolo[1,5-a]pyrimidine was established by X-ray diffraction analysis.