2-(5-bromo-1-naphthalenyl)-1,6-dihydro-4-[(1-naphthalenyl)methyl]-6-oxo-5-pyrimidinecarbonitrile | 119491-97-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(5-bromo-1-naphthalenyl)-1,6-dihydro-4-[(1-naphthalenyl)methyl]-6-oxo-5-pyrimidinecarbonitrile
• 英文别名: 2-(5-Bromo-1-naphthalenyl)-1,6-dihydro-4-[(1-naphthalenyl)methyl]-6-oxo-5-pyrimidinecarbonitrile；2-(5-bromonaphthalen-1-yl)-4-(naphthalen-1-ylmethyl)-6-oxo-1H-pyrimidine-5-carbonitrile
• CAS: 119491-97-3
• 化学式: C₂₆H₁₆BrN₃O
• 分子量: 466.337
• InChiKey: SAUMGGUMZHKXGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-bromo-1-naphthalenyl)-1,6-dihydro-4-[(1-naphthalenyl)methyl]-6-oxo-5-pyrimidinecarbonitrile 、 alkaline earth salt of/the/ methylsulfuric acid 生成 [2-(5-Bromo-naphthalen-1-yl)-5-cyano-4-naphthalen-1-ylmethyl-6-oxo-6H-pyrimidin-1-yl]-acetic 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
• 作为产物：
  描述：

  methyl-N-(5-bromo-1-naphthoyl)-2-(1-naphthalenyl)acetimidate 、 氰乙酰胺 在 sodium methylate 、 sodium 作用下， 以 甲醇 为溶剂， 以71%的产率得到2-(5-bromo-1-naphthalenyl)-1,6-dihydro-4-[(1-naphthalenyl)methyl]-6-oxo-5-pyrimidinecarbonitrile
  参考文献：
  名称：

  2,6-disubstituted-5-cyano-4-pyrimidinyloxyacetic acid aldose reductase

  摘要：

  本文披露了2,6-二取代-5-氰基-4-嘧啶氧乙酸及其药用盐以及其制备方法。这些化合物是新型醛糖还原酶抑制剂，可用于治疗或预防糖尿病并发症。

  公开号：

  US04786640A1

文献信息

• ELLINGBOE, JOHN;ALESSI, THOMAS;MILLEN, JANE;SREDY, JANET;KING, ANDREW;PRU+, J. MED. CHEM., 3,(1990) N0, C. 2892-2899
  作者：ELLINGBOE, JOHN、ALESSI, THOMAS、MILLEN, JANE、SREDY, JANET、KING, ANDREW、PRU+

  DOI：——

  日期：——
• US4786640A
  申请人：——

  公开号：US4786640A

  公开（公告）日：1988-11-22
• US4906753A
  申请人：——

  公开号：US4906753A

  公开（公告）日：1990-03-06