1-Cyclohexylmethyl-1H-<3,1>benzoxazine-2,4-dione | 42239-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 1-Cyclohexylmethyl-1H-<3,1>benzoxazine-2,4-dione
• 英文别名: 1-cyclohexylmethyl-1H-benzo[d][1,3]oxazine-2,4-dione；N-cyclohexylmethylisatoic acid anhydride；1-(cyclohexylmethyl)-3,1-benzoxazine-2,4-dione
• CAS: 42239-95-2
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: KHFLPKVYPZLEKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Cyclohexylmethyl-1H-<3,1>benzoxazine-2,4-dione 、 3-( 1,1-二氧代-4H-苯并[1,2,4]噻二嗪)基乙酸乙酯 在 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以170 mg的产率得到1-Cyclohexylmethyl-3-(1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-4-hydroxy-1H-quinolin-2-one
  参考文献：
  名称：

  3-(1,1-Dioxo-2H-(1,2,4)-benzothiadiazin-3-yl)-4-hydroxy-2(1H)-quinolinones, Potent Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase

  摘要：

  Recently, we disclosed a new class of HCV polymerase inhibitors discovered through high-throughput screening (HTS) of the GlaxoSmithKline proprietary compound collection. This interesting class of 3-(1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-2(1H)-quinolinones potently inhibits HCV polymerase enzymatic activity and inhibits the ability of the subgenomic HCV replicon to replicate in Huh-7 cells. This report will focus on the structure-activity relationships (SAR) of substituents on the quinolinone ring, culminating in the discovery of 1-(2-cyclopropylethyl)-3-(1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxy-2(1H)-quinolinone (130), an inhibitor with excellent potency in biochemical and cellular assays possessing attractive molecular properties for advancement as a clinical candidate. The potential for development and safety assessment profile of compound 130 will also be discussed.

  DOI：

  10.1021/jm050855s
• 作为产物：
  描述：

  靛红酸酐 、 alkaline earth salt of/the/ methylsulfuric acid 生成 1-Cyclohexylmethyl-1H-<3,1>benzoxazine-2,4-dione
  参考文献：
  名称：

  2 H -3,1-苯并恶嗪-2,4（1 H）二酮（isatoic酐）的化学反应1. N-取代的2 H -3,1-苯并恶嗪-2,4（1 H）二酮的合成

  摘要：

  三种制备N-取代的2 H -3,1-苯并恶嗪-2,4（1 H）二酮（乙酸酐）的方法（1）使用2-氯-，2-硝基苯甲酸和N-未取代的等角酸酐作为制备方法描述了起始材料。

  DOI：

  10.1002/jhet.5570120325

文献信息

• One-Pot Total Synthesis of Evodiamine and Its Analogues through a Continuous Biscyclization Reaction
  作者：Zi-Xuan Wang、Jia-Chen Xiang、Miao Wang、Jin-Tian Ma、Yan-Dong Wu、An-Xin Wu

  DOI：10.1021/acs.orglett.8b02667

  日期：2018.10.19

  The one-pot total synthesis of evodiamine and its analogues is achieved using a three-component reaction. Through continuous biscyclization, various readily available substrates with good functional group tolerance were easily incorporated into biologically active quinazolinocarboline backbones. The use of triethoxymethane as a cosolvent was crucial for this quick and straightforward transformation

  使用三组分反应可实现一锅法合成乙二胺及其类似物。通过连续的双环化，容易将具有良好官能团耐受性的各种容易获得的底物掺入具有生物活性的喹唑啉代咔啉主链中。三乙氧基甲烷作为助溶剂的使用对于这种快速而直接的转化至关重要。
• Anthranyl amides and their use as medicaments
  申请人：——

  公开号：US20040029880A1

  公开（公告）日：2004-02-12

  Substituted anthranilamides and use thereof as pharmaceutical agents for treating diseases that are triggered by persistent angiogenesis as well as their intermediate products for the production of anthranilamides are described.

  描述了替代基苯甲酰胺及其用作治疗由持续血管生成引起的疾病的药物代理，以及用于生产基苯甲酰胺的中间产物。
• [4 + 2]-Annulation of Prop-2-ynylsulfonium Salts and Isatoic Anhydrides: Access to 3-Methylthio-4-quinolones
  作者：Qinfang Chen、Yihao Pan、Tingting Yue、Weiran Yang、Hua Liu、Jing Zheng

  DOI：10.1021/acs.orglett.0c02173

  日期：2020.8.7

  An unparalleled [4 + 2]-annulation of prop-2-ynylsulfonium salts with isatoic anhydrides was developed, affording a series of 4-quinolones with a alkylthio group in medium to good yields under mild conditions. In this reaction type, the prop-2-ynylsulfonium salt serves as a C2 synthon and sulfide does not act as a leaving group, providing facile access to organosulfur compounds. The resulting quinolone

  开发了无与伦比的[4 + 2]丙-2-炔基salts盐与isatoic酸酐，在温和条件下以中等至良好收率提供了一系列带有烷硫基的4-喹诺酮。在这种反应类型中，丙-2-炔基salt盐充当C2合成子，硫化物不充当离去基团，提供了轻松接触有机硫化合物的途径。所得的喹诺酮产物可以进一步转化为多种合成上有用的化合物。
• [EN] NOVEL ANTI-INFECTIVES<br/>[FR] NOUVEAUX ANTI-INFECTIEUX
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2002098424A1

  公开（公告）日：2002-12-12

  Compounds useful as HCV anti-infectives having the formula: wherein the formula variables are as defined herein, are disclosed. Also disclosed are methods of making and using the same.

  本发明揭示了具有以下式的HCV抗感染剂有用的化合物：其中，公式变量如本文所定义。同时还揭示了制备和使用该化合物的方法。
• Anthranilamides and their use as pharmaceutical agents
  申请人：Krueger Martin

  公开号：US20050261343A1

  公开（公告）日：2005-11-24

  Substituted anthranilamides and use thereof as pharmaceutical agents for treating diseases that are triggered by persistent angiogenesis as well as their intermediate products for the production of anthranilamides are described.

  本文描述了替代的蒽酰胺类化合物及其用作治疗由持续血管生成引起的疾病的药物代理，以及用于生产蒽酰胺类化合物的中间产物。