4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one | 77493-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one
• CAS: 77493-73-3
• 化学式: C₁₂H₉N₃O
• 分子量: 211.223
• InChiKey: SHSZMJPKJAGIND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.16
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one 在 盐酸 、 溶剂黄146 、 sodium nitrite 作用下， 以25%的产率得到Pyrazolo[1,5-a]pyrimidin-7(4H)-one, 3-nitroso-2-phenyl-
  参考文献：
  名称：

  2-Phenylpyrazolo[1,5-a]pyrimidin-7-ones. A new class of nonsteroidal antiinflammatory drugs devoid of ulcerogenic activity

  摘要：

  Syntheses of some pyrazolo[1,5-a]pyrimidines were performed in order to study the relationship between structural modifications on the parent 4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one (1) and their antiinflammatory properties. The modifications carried out were introduction and functionalization of a longer side chain at the 4-position, substitution of the hydrogen atom at the 3-position, and replacement of the phenyl group with a 4-methylphenyl, methyl, or hydrogen substituent. 4-Ethyl-4,7-dihydro-2-phenylpyrazolo [1,5-a]pyrimidin-7-one (3) showed the highest activity and a better therapeutic index than phenylbutazone and indomethacin, used as reference drugs. All other changes at the 3-, 5-, and 6-positions, as well as the replacement of the phenyl group at position 2, caused a marked decrease of activity. Compound 3 was found devoid of ulcerogenic activity and was probably endowed with antiulcerogenic properties.

  DOI：

  10.1021/jm00366a009
• 作为产物：
  描述：

  diethyl 2-<<(3-phenyl-5-pyrazolyl)amino>methylen>propandioate 在 喹啉 、 sodium hydroxide 、 铜 作用下， 以 水 为溶剂， 生成 4,7-dihydro-2-phenylpyrazolo[1,5-a]pyrimidin-7-one
  参考文献：
  名称：

  Pecori Vettori; Cecchi; Costanzo, Farmaco, Edizione Scientifica, 1981, vol. 36, # 6, p. 441 - 448

  摘要：

  DOI：

文献信息

• Synthesis of pyrazolo[1,5-<i>a</i>]pyrimidines in the reaction of 5-amino-3-arylpyrazoles with methoxymethylene meldrum's acid derivatives and thermolysis of their pyrazolylaminomethylene derivatives
  作者：Jairo Quiroga、Angelina Hormaza、Braulio Insuasty、Claudio Saitz、Alvaro Cañete、Carolina Jullian

  DOI：10.1002/jhet.5570350112

  日期：1998.1

  A series of pyrazolo[1,5-a]pyrimidin-3-ones 3 was prepared from Meldrum's acid and 5-amino-3-arylpyrazoles 1 by cyclization in nitrobenzene of the corresponding 5-pyrazolylaminomethylene Meldrum's acid derivatives 2. The structure of pyrazolo[1,5-a]pyrimidin-3-ones and their precursors were determined by nmr measurements.

  通过将相应的5-吡唑基氨基亚甲基Meldrum的酸衍生物2在硝基苯中环化，由Meldrum的酸和5-氨基-3-芳基吡唑1制备一系列吡唑并[1，5 - a ]嘧啶-3-酮3。吡唑并[1，5 - a ]嘧啶-3-酮的结构及其前体通过核磁共振测定。
• Gas-Phase Synthesis of Pyrazolo[3,4-b]pyridin-4-ones
  作者：Alison Hulme、Martha Mackay、Andrew Nortcliffe、Hamish McNab

  DOI：10.1055/s-0034-1378666

  日期：——

  Flash vacuum pyrolysis (FVP) at 500-600 degrees C of 1-substituted pyrazolylaminomethylene derivatives of Meldrum's acid provides 1-substituted pyrazolo[3,4-b]pyridin-4-ones in high yields. If the 1-substituent is a tert-butyl group, FVP at 750-850 degrees C causes elimination of 2-methyl-1-propene to give the parent pyrazolo[3,4-b]pyridin-4-one.
• Synthesis and antischistosomal activity of certain pyrazolo[1,5-a]pyrimidines
  作者：Keitaro Senga、Thomas Novinson、Henry R. Wilson、Roland K. Robins

  DOI：10.1021/jm00137a023

  日期：1981.5

  Several 7-hydroxypyrazolo[1,5-a]pyrimidines (1-21), 7-mercaptopyrazolo[1,5-a]pyrimidines (37-49), and 4-alkylpyrazolo[1,5-a]pyrimidin-7-ones (50-55) and the corresponding 4-alkylpyrazolo[1,5-a]pyrimidine-7-thiones (56-60) were synthesized and tested for antischistosomal activity against Schistosoma mansoni. Of the compounds examined, the greatest degree of activity in vitro was found with the 7-mercaptopyrazolo[1,5-a]pyrimidines. In particular, compounds 37 and 47 proved lethal at 100 micrograms/mL after an exposure of only 1 h. The 7-hydroxypyrazolo[1,5-a]-pyrimidines were not as active. None of the compounds exhibiting in vitro activity were active against S. mansoni in vivo.
• VETTORI L. P.; CECCHI L.; COSTANZO A.; AUZZI G.; BRUNI F., FARMACO ED. SCI., 1981, 36, NO 6, 441-448
  作者：VETTORI L. P.、 CECCHI L.、 COSTANZO A.、 AUZZI G.、 BRUNI F.

  DOI：——

  日期：——
• SENGA, KEITARO;NOVINSON, T.;WILSON, H. R.;ROBINS, R. K., J. MED. CHEM., 1981, 24, N 5, 610-613
  作者：SENGA, KEITARO、NOVINSON, T.、WILSON, H. R.、ROBINS, R. K.

  DOI：——

  日期：——