3-((4-iodophenyl)amino)-1-methylquinoxalin-2(1H)-one | 857089-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-((4-iodophenyl)amino)-1-methylquinoxalin-2(1H)-one
• 英文别名: 3-(4-Iodoanilino)-1-methylquinoxalin-2-one
• CAS: 857089-92-0
• 化学式: C₁₅H₁₂IN₃O
• 分子量: 377.184
• InChiKey: OZXWWZWLHHTLQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-((4-iodophenyl)amino)-1-methylquinoxalin-2(1H)-one 、 2-吡咯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 生成 1-Methyl-3-[4-(1H-pyrrol-2-yl)-phenylamino]-1H-quinoxalin-2-one
  参考文献：
  名称：

  Synthesis and evaluation of 3-anilino-quinoxalinones as glycogen phosphorylase inhibitors

  摘要：

  A series of 3-anilino-quinoxalinones has been identified as a new class of glycogen phosphorylase inhibitors. The lead compound I was identified through high throughput screening as well as through pharmacophore-based electronic screening. Modifications were made to the scaffold of 1 to produce novel analogues, some of which are 25 times more potent than the lead compound. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.021
• 作为产物：
  描述：

  N-甲基-1,2-苯二胺 在 三乙胺 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 生成 3-((4-iodophenyl)amino)-1-methylquinoxalin-2(1H)-one
  参考文献：
  名称：

  Synthesis and evaluation of 3-anilino-quinoxalinones as glycogen phosphorylase inhibitors

  摘要：

  A series of 3-anilino-quinoxalinones has been identified as a new class of glycogen phosphorylase inhibitors. The lead compound I was identified through high throughput screening as well as through pharmacophore-based electronic screening. Modifications were made to the scaffold of 1 to produce novel analogues, some of which are 25 times more potent than the lead compound. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.021

文献信息

• Quinoxalinones
  申请人：Beavers Pat Mary

  公开号：US20050148586A1

  公开（公告）日：2005-07-07

  The invention features quinoxalinones, pharmaceutical compositions containing them and methods of using them to treat, for example, diabetes.

  这项发明涉及喹喔啉酮，包含它们的药物组合物以及使用它们治疗糖尿病等疾病的方法。
• Ionic liquid-catalysed regioselective oxygenation of quinoxalin-2(1<i>H</i>)-ones under visible-light conditions
  作者：Gaurav Badhani、Valvi Mangesh Biramya、Subbarayappa Adimurthy

  DOI：10.1039/d3nj04496c

  日期：——

  liquid-catalysed oxygenation of quinoxalin-2(1H)-one utilizing aerobic oxygen as a green oxidant under visible light conditions at room temperature has been described. Various N-1-alkyl and aryl-substituted quinoxalin-2(1H)-ones provided good yields of the desired products. The ionic-liquid tetramethylammonium hydroxide (TMAH) employed is readily available and promotes the oxygenation under additive

  描述了在室温可见光条件下利用有氧氧作为绿色氧化剂的离子液体催化的喹喔啉-2(1H)-酮氧化反应。各种N -1 -烷基和芳基取代的喹喔啉-2(1 H )-酮提供了良好收率的所需产物。所用的离子液体四甲基氢氧化铵（TMAH）很容易获得，并且在无添加剂和无碱条件下促进氧化。本程序说明了克级反应的适用性，并展示了目标产物随后转化为糖原磷酸化酶抑制剂。
• Lewis Acid-Mediated Isothiocyanation and Chlorination of Quinoxalin-2(1H)-ones under Visible Light Conditions
  作者：Gaurav Badhani、Shubham、Valvi Mangesh Biramya、Subbarayappa Adimurthy

  DOI：10.1021/acs.joc.4c00995

  日期：2024.8.2

  Lewis acid-mediated selective C3-isothiocyanation of quinoxalin-2(1H)-ones using N-thiocyanatosaccharin as an isothiocyanate source under visible light conditions at room temperature is described. Under similar conditions with N-chlorosaccharin, the C3-chlorination of quinoxalin-2(1H)-ones achieved a 2 h time frame. Good to an excellent yield of products was obtained in both cases with broad functional

  描述了在室温可见光条件下使用N-硫氰酸糖精作为异硫氰酸酯源对喹喔啉-2(1 H )-酮进行路易斯酸介导的选择性 C3-异硫氰化反应。在与N-氯糖精相似的条件下，喹喔啉-2(1 H )-酮的 C3 氯化达到了 2 小时的时间范围。在这两种情况下均获得了良好至优异的产物收率，且具有广泛的官能团耐受性。对照实验表明该反应通过自由基机制进行。本程序证明了其在克级反应中的适用性，并强调了异硫氰酸酯随后转化为代表性的硫脲衍生物，以及一种氯代衍生物转化为糖原磷酸化酶抑制剂。
• (3-OXO-3,4-DIHYDRO-QUINOXALIN-2-YL-AMINO)-BENZAMIDE DERIVATIVES AND RELATED COMPOUNDS AS GLYCOGEN PHOSPHORYLASE INHIBITORS FOR THE TREATMENT OF DIABETES AND OBESITY
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP1711184A1

  公开（公告）日：2006-10-18
• [EN] (3-OXO-3, 4-DIHYDRO-QUINOXALIN-2-YL-AMINO) -BENZAMIDE DERIVATIVES AND RELATED COMPOUND AS GLYCOGEN PHOSPHORYLASE INHIBITORS FOR THE TREATMENT OF DIABETES AND OBESITY<br/>[FR] DERIVES DE (3-OXO-3, 4-DIHYDRO-QUINOXALIN-2-YL-AMINO)-BENZAMIDE ET COMPOSES AFFERENTS COMME INHIBITEURS DE LA GLYCOGENE PHOSPHORYLASE DANS LE TRAITEMENT DU DIABETE ET DE L'OBESITE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005067932A1

  公开（公告）日：2005-07-28

  The invention features pharmaceutically active quinoxalinones of formula (1), compositions containing them, and methods of making and using theme: Formula (I) wherein R1 is H, C 1-6 alkyl, or halo; R2 is H or halo; R3 is H, C 1-6 alkyl, X is N or CH; Y is a covalent bond, -NHCO- or -CONH-; Z is phenyl or a 5 or 6-membered heterocyclyl with between l and 2 heteroatoms independently selected from N, O, and S; and n is 0, 1 or 2; or a pharmaceutically acceptable salt, ester, amide, hydrate, or solvate thereof; as well as their use as glycogen phosphorylase inhibitors for the treatment of i diabetes and obesity.