1,6-二氢-4-甲基-6-氧代-2-苯基- 5-嘧啶甲腈 | 82114-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 1,6-二氢-4-甲基-6-氧代-2-苯基- 5-嘧啶甲腈
• 中文别名: 1,6-二氢-4-甲基-6-氧代-2-苯基-5-嘧啶甲腈
• 英文名称: 1,6-dihydro-4-methyl-6-oxo-2-phenyl-5-pyrimidinecarbonitrile
• 英文别名: 6-methyl-4-oxo-2-phenyl-3,4-dihydropyrimidine-5-carbonitrile；5-Cyan-6-methyl-2-phenyl-pyrimid-4(3H)-on；4-methyl-6-oxo-2-phenyl-1,6-dihydro-pyrimidine-5-carbonitrile；4-methyl-6-oxo-2-phenyl-pyrimidine-5-carbonitrile；4-Hydroxy-6-methyl-2-phenylpyrimidine-5-carbonitrile；4-methyl-6-oxo-2-phenyl-1H-pyrimidine-5-carbonitrile
• CAS: 82114-04-3
• 化学式: C₁₂H₉N₃O
• 分子量: 211.223
• InChiKey: XPRIKNMRRNFONW-UHFFFAOYSA-N

物化性质

• 熔点：
  295-296 °C(Solv: methanol (67-56-1))
• 沸点：
  346.5±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  1,6-二氢-4-甲基-6-氧代-2-苯基- 5-嘧啶甲腈 在 sodium ethanolate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 5-amino-4-methyl-2-phenyl-pyrrolo[2,3-d]pyrimidine-6-carboxamide
  参考文献：
  名称：

  WO2006/100095

  摘要：

  公开号：
• 作为产物：
  描述：

  6-甲基-4-苯基-2-硫代-1,2-二氢嘧啶-5-甲腈 在 氨 、 双氧水 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 48.0h， 以89%的产率得到1,6-二氢-4-甲基-6-氧代-2-苯基- 5-嘧啶甲腈
  参考文献：
  名称：

  WO2006/100095

  摘要：

  公开号：

文献信息

• Discovery of selective PDE4B inhibitors
  作者：Kenji Naganuma、Akifumi Omura、Naomi Maekawara、Masahiro Saitoh、Naoto Ohkawa、Takashi Kubota、Hiromitsu Nagumo、Toshiyuki Kodama、Masayoshi Takemura、Yuji Ohtsuka、Junji Nakamura、Ryuichi Tsujita、Koh Kawasaki、Hirotsugu Yokoi、Masashi Kawanishi

  DOI：10.1016/j.bmcl.2009.04.121

  日期：2009.6

  In this study the first PDE4B selective inhibitor is described. Optimization of lead 2-arylpyrimidine derivatives afforded a series of potent PDE4B inhibitors with >100-fold selectivity over the PDE4D isozyme. With a good pharmacokinetic profile, a selected compound exhibited potent anti-inflammatory effects in vivo and showed less emesis compared with Cilomilast. (C) 2009 Elsevier Ltd. All rights reserved.
• Golec, Julian M. C.; Scrowston, Richard M., Journal of Chemical Research, Miniprint, 1988, # 1, p. 326 - 345
  作者：Golec, Julian M. C.、Scrowston, Richard M.

  DOI：——

  日期：——
• Cuadrado, Francisco J.; Perez, Miguel A.; Soto, Jose L., Journal of the Chemical Society. Perkin transactions I, 1984, p. 2447 - 2450
  作者：Cuadrado, Francisco J.、Perez, Miguel A.、Soto, Jose L.

  DOI：——

  日期：——
• (Pyrimidinyloxy)acetic acids and pyrimidineacetic acids as a novel class of aldose reductase inhibitors
  作者：John Ellingboe、Thomas Alessi、Jane Millen、Janet Sredy、Andrew King、Candace Prusiewicz、Frieda Guzzo、Donna VanEngen、Jehan Bagli

  DOI：10.1021/jm00172a034

  日期：1990.10

  Pyrimidineacetic acids and (pyrimidinyloxy)acetic acids were synthesized by alkylation, with methyl bromoacetate or tert-butyl bromoacetate as alkylating agents. Alkylation reaction at the nitrogen or oxygen atom for different substrates was found to be solvent dependent. N-Alkylation was favored in ethereal solvent, e.g., tetrahydrofuran and dimethoxyethane, whereas O-alkylation was predominant in dimethylformamide. These compounds were tested in vitro to determine their ability to inhibit bovine lens aldose reductase. Selected compounds were assayed in vivo, in a 4-day galactose-fed rat model. The decrease in galactitol from the control was determined in lens, nerve, and diaphragm. Several of the 6-oxopyrimidine-1-acetic acids and (pyrimidinyl-4-oxy)acetic acids were found to be potent inhibitors of bovine lens aldose reductase. A study was also undertaken to determine in vitro the transport behavior of selected compounds in the isolated rat sciatic nerve. A discussion of the structure-activity relationship of this class of compounds with reference to their intrinsic biochemical activity is reported. It is concluded, in general, that ability of a compound to penetrate the tissue membrane plays an important role in the genesis of in vivo lens aldose reductase (LAR) inhibitory activity.
• CUADRADO, F. J.;PEREZ, M. A.;SOTO, J. L., J. CHEM. SOC. PERKIN TRANS., 1984, N 10, 2447-2449
  作者：CUADRADO, F. J.、PEREZ, M. A.、SOTO, J. L.

  DOI：——

  日期：——