(+)-3'-Methylspiro-2,2',5(3'H)-trione | 107656-71-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (+)-3'-Methylspiro-2,2',5(3'H)-trione
• 英文别名: (4R)-3-methylspiro[1H-quinazoline-4,5'-imidazolidine]-2,2',4'-trione
• CAS: 107656-71-3
• 化学式: C₁₁H₁₀N₄O₃
• 分子量: 246.225
• InChiKey: WTRHXNHBRZONAP-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  18
• 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：

  (+)-3'-Methylspiro-2,2',5(3'H)-trione 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以97%的产率得到3-methyl-spiro<1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine>-2,2',5'-trione
  参考文献：
  名称：

  Preparation of optically pure 3'-methylspiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-trione by combination of optical resolution and racemization

  摘要：

  Optically pure 3'-methylspiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-trione was prepared by optical resolution using brucine as a resolving agent. The resulting optically pure spirohydantoin was racemized by refluxing in 1,2-dichlorobenzene for 17 h, or more effectively upon heating in 10% HCl at 90-degrees-C for 2 h. In the acid-catalyzed racemization, the introduction of difluoromethyl group at the 3-nitrogen of hydantoin ring increased the racemization rate, while the introduction of methyl group at the 3-nitrogen reduced it. These results suggest that the acid-catalyzed racemization proceeds via the N-acyliminium ion generated by the cleavage of the N3-C4 bond of the spirohydantoin ring.

  DOI：

  10.1021/jo00031a043
• 作为产物：
  描述：

  (5aS,8aS,13aR)-10,11-dimethoxy-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinolin-14-one;(4R)-3-methylspiro[1H-quinazoline-4,5'-imidazolidine]-2,2',4'-trione 、 盐酸 生成 (+)-3'-Methylspiro-2,2',5(3'H)-trione
  参考文献：
  名称：

  YAMADA, YOSHIHISA;MATSUOKA, YUZO;MATSUMOTO, MAMORU

  摘要：

  DOI：

文献信息

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

  DOI：——

  日期：——
• Preparation of optically pure 3'-methylspiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-trione by combination of optical resolution and racemization
  作者：Masafumi Yamagishi、Yoshihisa Yamada、Kenichi Ozaki、Tadamasa Date、Kimio Okamura、Mamoru Suzuki、Kazuo Matsumoto

  DOI：10.1021/jo00031a043

  日期：1992.2

  Optically pure 3'-methylspiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-trione was prepared by optical resolution using brucine as a resolving agent. The resulting optically pure spirohydantoin was racemized by refluxing in 1,2-dichlorobenzene for 17 h, or more effectively upon heating in 10% HCl at 90-degrees-C for 2 h. In the acid-catalyzed racemization, the introduction of difluoromethyl group at the 3-nitrogen of hydantoin ring increased the racemization rate, while the introduction of methyl group at the 3-nitrogen reduced it. These results suggest that the acid-catalyzed racemization proceeds via the N-acyliminium ion generated by the cleavage of the N3-C4 bond of the spirohydantoin ring.