L-半胱氨酰-L-脯氨酸乙酸酯(1:1) | 107583-21-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: L-半胱氨酰-L-脯氨酸乙酸酯(1:1)
• 中文别名: (4R)-6-氯-3-甲基螺[1H-喹唑啉-4,5'-咪唑烷]-2,2',4'-三酮
• 英文名称: (4R)-6'-chloro-3'-methylspiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5'(3'H)-trione
• 英文别名: Spiro-cimqat；(4R)-6-chloro-3-methylspiro[1H-quinazoline-4,5'-imidazolidine]-2,2',4'-trione
• CAS: 107583-21-1
• 化学式: C₁₁H₉ClN₄O₃
• 分子量: 280.67
• InChiKey: QBRYBUXHTFUNRQ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  90.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-半胱氨酰-L-脯氨酸乙酸酯(1:1) 、 sodium hydroxide 以84%的产率得到
  参考文献：
  名称：

  YAMADA, YOSHIHISA;MATSUOKA, YUZO;MATSUMOTO, MAMORU

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-3'-Methylspiro-2,2',5(3'H)-trione 在 磺酰氯 、 水 、 溶剂黄146 作用下， 生成 L-半胱氨酰-L-脯氨酸乙酸酯(1:1)
  参考文献：
  名称：

  Biological activities and quantitative structure-activity relationships of spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-triones as aldose reductase inhibitors

  摘要：

  A series of spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-triones were prepared and tested for aldose reductase inhibitory activity. The 6'-halogenated derivatives were found to be highly potent in vitro inhibitors of male rabbit lens aldose reductase and in vivo inhibitors of polyol accumulation in the sciatic nerves of galactosemic rats. Of these, (4R)-6'-chloro-3'-methylspiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-trione (67) showed the most potent in vitro and in vivo activities. An oral dose of 3 g/kg of compound 67 caused neither death nor behavioral abnormality in the preliminary acute toxicity study using mice and rats. Compound 67 was selected as a candidate for further evaluation. The quantitative structure-activity relationships in this series are also discussed.

  DOI：

  10.1021/jm00089a021

文献信息

• YAMADA, YOSHIHISA;MATSUOKA, YUZO;MATSUMOTO, MAMORU
  作者：YAMADA, YOSHIHISA、MATSUOKA, YUZO、MATSUMOTO, MAMORU

  DOI：——

  日期：——
• Biological activities and quantitative structure-activity relationships of spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-triones as aldose reductase inhibitors
  作者：Masafumi Yamagishi、Yoshihisa Yamada、Kenichi Ozaki、Masaaki Asao、Ryo Shimizu、Mamoru Suzuki、Mamoru Matsumoto、Yuzo Matsuoka、Kazuo Matsumoto

  DOI：10.1021/jm00089a021

  日期：1992.5

  A series of spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-triones were prepared and tested for aldose reductase inhibitory activity. The 6'-halogenated derivatives were found to be highly potent in vitro inhibitors of male rabbit lens aldose reductase and in vivo inhibitors of polyol accumulation in the sciatic nerves of galactosemic rats. Of these, (4R)-6'-chloro-3'-methylspiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-trione (67) showed the most potent in vitro and in vivo activities. An oral dose of 3 g/kg of compound 67 caused neither death nor behavioral abnormality in the preliminary acute toxicity study using mice and rats. Compound 67 was selected as a candidate for further evaluation. The quantitative structure-activity relationships in this series are also discussed.