3',4'-methylenedioxy-2-hydroxyiminoacetanilide | 154869-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3',4'-methylenedioxy-2-hydroxyiminoacetanilide
• 英文别名: methylenedioxyisonitrosoacetanilide；N-1,3-Benzodioxol-5-yl-2-(hydroxyimino)acetamide；N-(1,3-benzodioxol-5-yl)-2-hydroxyiminoacetamide
• CAS: 154869-11-1
• 化学式: C₉H₈N₂O₄
• 分子量: 208.174
• InChiKey: LVYDLZFUOFOSLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  80.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3',4'-methylenedioxy-2-hydroxyiminoacetanilide 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 N-methyl-6,7-dioxo-[1,3]dioxolo[4,5-f]indole-5-carboxamide
  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：

  3,4-亚甲二氧基苯胺 、 三氯乙醛 在 盐酸 、 盐酸羟胺 、 sodium sulfate 作用下， 以 水 为溶剂， 反应 0.33h， 以86%的产率得到3',4'-methylenedioxy-2-hydroxyiminoacetanilide
  参考文献：
  名称：

  Synthesis of Substituted Quinoline-4-carboxylic Acids

  摘要：

  利用改良的Pfitzinger方法，在水酸性条件下，通过酮与靛红衍生物的缩合，成功实现了一系列喹啉-4-羧酸的高产率合成。此外，还描述了便捷合成替代靛红前体的方法。

  DOI：

  10.1055/s-1993-25987

文献信息

• Lead optimization study on indoline-2,3-dione derivatives as potential fatty acid amide hydrolase inhibitors
  作者：Shivani Jaiswal、Senthil Raja Ayyannan

  DOI：10.1080/07391102.2022.2145372

  日期：——

  isatin-based fatty acid amide hydrolase (FAAH) inhibitor BSS-7, we designed and synthesized two small sets (6–13 and 17–20) of N-1 and C-3 substituted isatin derivatives and evaluated them for their in vitro FAAH inhibition properties. The lead simplification by modification of bulky aryl moiety at N-1 with a flexible allyl group produced a nanomolar (IC50 = 6.7 nM, Ki = 5 nM) inhibitor 11 (Z)-3-((1H-benzo[

  摘要 基于已知的基于靛红的脂肪酸酰胺水解酶（FAAH）抑制剂BSS-7，我们设计并合成了两小组（6-13和17-20）N-1和C-3取代的靛红衍生物，并对其进行了评估它们的体外FAAH 抑制特性。通过用柔性烯丙基修饰 N-1 处的大芳基部分进行先导简化，产生纳摩尔 (IC 50 = 6.7 nM，K i = 5 nM) 抑制剂11 (Z)-3-((1H-苯并[d]) imidazol-2-yl)imino)-1-allylindolin-2-one 表现出可逆和竞争性的 FAAH 抑制作用，其效力是BSS-7 的1500 倍(1.49 ± 0.03 µM)。先导化合物11还表现出高血脑渗透性和显着的抗氧化特性，且无神经毒性。对接结果表明抑制剂分子占据了 FAAH 的活性位点并提供了最佳的结合相互作用。分子动力学模拟研究确定了先导抑制剂11 -FAAH 复合物的稳定性。计算机ADMET 分析
• 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.
• Synthesis of Substituted Quinoline-4-carboxylic Acids
  作者：Karen Lackey、Daniel D. Sternbach

  DOI：10.1055/s-1993-25987

  日期：——

  A high yielding synthesis of a variety of quinoline-4-carboxylic acids has been accomplished using a modified Pfitzinger approach involving the condensation of a ketone with an isatin derivative employing aqueous acid conditions. A convenient synthesis of the substituted isatin precursor is also described.

  利用改良的Pfitzinger方法，在水酸性条件下，通过酮与靛红衍生物的缩合，成功实现了一系列喹啉-4-羧酸的高产率合成。此外，还描述了便捷合成替代靛红前体的方法。