5-fluoro-1-methylcarbamoylisatin | 107582-86-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-fluoro-1-methylcarbamoylisatin
• 英文别名: 5-fluoro-N-methyl-2,3-dioxoindole-1-carboxamide
• CAS: 107582-86-5
• 化学式: C₁₀H₇FN₂O₃
• 分子量: 222.176
• InChiKey: NMYFQZMFXQYGON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-fluoro-1-methylcarbamoylisatin 在 盐酸 、 三乙胺 作用下， 反应 6.0h， 生成 (4R)-6-fluoro-3-methylspiro[1H-quinazoline-4,5'-imidazolidine]-2,2',4'-trione
  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
• 作为产物：
  描述：

  4-fluoroisonitrosoacetanilide 在 硫酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-fluoro-1-methylcarbamoylisatin
  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

• Quinazolinone copmpounds useful for the prophyloxis and treatment of
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US04762839A1

  公开（公告）日：1988-08-09

  Novel quinazolinone compounds of the formula: ##STR1## wherein R is hydrogen atom or a lower alkyl, R.sup.1 is a lower alkyl, a substituted or unsubstituted phenyl or an aralkyl, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same or different and are each hydrogen atom, a halogen atom, a lower alkyl, a lower alkoxy, a lower alkoxycarbonyl or a lower alkoxycarbonyl-lower alkenyl, or two adjacent groups of R.sup.2,R.sup.3, R.sup.4 and R.sup.5 when taken together form methylenedioxy and the other two are hydrogen atom, and a salt thereof, which are useful for the prophylaxis and treatment of various diabetic complications, and processes for the preparation thereof, and a pharmaceutical composition containing said compound as an active ingredient.

  新型喹唑啉酮化合物的化学式为：##STR1## 其中R为氢原子或较低的烷基，R.sup.1为较低的烷基，取代或未取代的苯基或芳基烷基，R.sup.2、R.sup.3、R.sup.4和R.sup.5相同或不同，分别为氢原子、卤原子、较低的烷基、较低的烷氧基、较低的烷氧羰基或较低的烷氧羰基-较低的烯基，或者当R.sup.2、R.sup.3、R.sup.4和R.sup.5中的两个相邻基团结合形成亚甲二氧基时，另外两个为氢原子，以及其盐。这些化合物对于预防和治疗各种糖尿病并发症非常有用，以及其制备方法，以及含有该化合物作为活性成分的药物组合物。
• Quinazolinone compounds and processes for the preparation thereof
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：EP0204534A2

  公开（公告）日：1986-12-10

  There are described novel quinazolinone compounds of the formula: wherein R is hydrogen atom or a lower alkyl, R1 is a lower alkyl, a substituted or unsubstituted phenyl or an aralkyl, and R2, R3, R4 and R5 are the same or different and are each hydrogen atom, a halogen atom, a lower alkyl, a lower alkoxy, a lower alkoxycarbonyl or a lower alkoxycarbonyl-lower alkenyl, ortwo adjacent groups of R2, R3, R4 and R5 when taken together form methylenedioxy and the other two are hydrogen atom, and salts thereof. The compounds are useful for the prophylaxis and treatment of various diabetic complications. There are also disclosed processes for the preparation of compound of formula I, and pharmaceutical compositions containing such compound as an active ingredient.

  描述了式中的新型喹唑啉酮化合物： 其中 R 是氢原子或低级烷基，R1 是低级烷基、取代或未取代的苯基或芳烷基，R2、R3、R4 和 R5 相同或不同，并且各自是氢原子、卤素原子、低级烷基、低级烷氧基、低级烷氧羰基或低级烷氧羰基-低级烯基，或者 R2、R3、R4 和 R5 的两个相邻基团在一起时形成亚甲基二氧基，另外两个是氢原子，以及它们的盐。这些化合物可用于预防和治疗各种糖尿病并发症。此外，还公开了制备式 I 化合物的工艺和含有此类化合物作为活性成分的药物组合物。
• YAMADA, YOSHIHISA;MATSUOKA, YUZO;MATSUMOTO, MAMORU
  作者：YAMADA, YOSHIHISA、MATSUOKA, YUZO、MATSUMOTO, MAMORU

  DOI：——

  日期：——
• US4762839A
  申请人：——

  公开号：US4762839A

  公开（公告）日：1988-08-09