1,6-dihydro-4-methyl-2-(1-naphthalenyl)-6-oxo-5-pyrimidinecarbonitrile | 130168-83-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,6-dihydro-4-methyl-2-(1-naphthalenyl)-6-oxo-5-pyrimidinecarbonitrile
• 英文别名: 6-methyl-2-naphthalen-1-yl-4-oxo-1H-pyrimidine-5-carbonitrile
• CAS: 130168-83-1
• 化学式: C₁₆H₁₁N₃O
• 分子量: 261.283
• InChiKey: IDXPLVDZYZVTAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  69.54
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-萘甲酰氯 在 sodium ethanolate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 100.0h， 生成 1,6-dihydro-4-methyl-2-(1-naphthalenyl)-6-oxo-5-pyrimidinecarbonitrile
  参考文献：
  名称：

  (Pyrimidinyloxy)acetic acids and pyrimidineacetic acids as a novel class of aldose reductase inhibitors

  摘要：

  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.

  DOI：

  10.1021/jm00172a034