2-cyclohexyl-1,6-dihydro-4-(methylthio)-6-oxo-5-pyrimidinecarbonitrile | 119896-59-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-cyclohexyl-1,6-dihydro-4-(methylthio)-6-oxo-5-pyrimidinecarbonitrile
• 英文别名: 2-cyclohexyl-4-methylsulfanyl-6-oxo-1H-pyrimidine-5-carbonitrile
• CAS: 119896-59-2
• 化学式: C₁₂H₁₅N₃OS
• 分子量: 249.337
• InChiKey: PJQASSRZJSQVNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  90.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyclohexyl-1,6-dihydro-4-(methylthio)-6-oxo-5-pyrimidinecarbonitrile 、 溴乙酸甲酯 在 NaH 作用下， 以 乙二醇二甲醚 、 水 、 mineral oil 为溶剂， 以99%的产率得到methyl 5-cyano-2-cyclohexyl-1,6-dihydro-4-(methylthio)-6-oxo-1-pyrimidineacetate
  参考文献：
  名称：

  2,4-disubstituted-5-cyano-1,6-dihydro-6-oxo-1-pyrimidineacetic acid

  摘要：

  本文披露了2,4-二取代-5-氰基-1,6-二氢-6-氧-1-嘧啶乙酸及其药用盐，以及它们的制备方法。这些化合物是新的醛糖还原酶抑制剂，可用于治疗或预防糖尿病并发症。

  公开号：

  US04786638A1
• 作为产物：
  描述：

  环己基甲脒 、 2-氰-3,3-二(甲硫基)丙烯酸甲酯 生成 2-cyclohexyl-1,6-dihydro-4-(methylthio)-6-oxo-5-pyrimidinecarbonitrile
  参考文献：
  名称：

  BAGLI, JEHAN F.;ELLINGBOE, JOHN W.;ALESSI, THOMAS R.

  摘要：

  DOI：

文献信息

• (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.
• BAGLI, JEHAN F.;ELLINGBOE, JOHN W.;ALESSI, THOMAS R.
  作者：BAGLI, JEHAN F.、ELLINGBOE, JOHN W.、ALESSI, THOMAS R.

  DOI：——

  日期：——
• BAGLI, JEHAN F.;ELLINGBOE, JOHN W.;ALLESI, THOMAS R.
  作者：BAGLI, JEHAN F.、ELLINGBOE, JOHN W.、ALLESI, THOMAS R.

  DOI：——

  日期：——
• US4786638A
  申请人：——

  公开号：US4786638A

  公开（公告）日：1988-11-22
• US4900829A
  申请人：——

  公开号：US4900829A

  公开（公告）日：1990-02-13