1,6-Dihydro-2-(5-bromo-1-naphthalenyl)-6-oxo-4-phenyl-5-pyrimidinecarbonitrile | 119923-05-6

• 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: 1,6-Dihydro-2-(5-bromo-1-naphthalenyl)-6-oxo-4-phenyl-5-pyrimidinecarbonitrile
• 英文别名: 2-(5-bromonaphthalen-1-yl)-6-oxo-4-phenyl-1H-pyrimidine-5-carbonitrile
• CAS: 119923-05-6
• 化学式: C₂₁H₁₂BrN₃O
• 分子量: 402.25
• InChiKey: NUEOMHGQNLQJEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,6-Dihydro-2-(5-bromo-1-naphthalenyl)-6-oxo-4-phenyl-5-pyrimidinecarbonitrile 、 alkaline earth salt of/the/ methylsulfuric acid 生成 5-Cyano-1,6-dihydro-2-(5-bromo-1-naphthalenyl)-6-oxo-4-phenyl-1-pyrimidineacetic Acid
  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

文献信息

• 2,4-disubstituted-5-cyano-1,6-dihydro-6-oxo-1-pyrimidineacetic acid
  申请人：American Home Products Corporation

  公开号：US04786638A1

  公开（公告）日：1988-11-22

  Disclosed herein are 2,4-disubstituted-5-cyano-1,6-dihydro-6-oxo-1-pyrimidineacetic acids and pharmaceutically acceptable salts thereof and methods of their preparation. The compounds are new aldose reductase inhibitors useful for the treatment or prevention of diabetic complications.

  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。
• 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