1-(3'-methyl-2'-butenyl)isatoic anhydride | 223668-31-3

• 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-(3'-methyl-2'-butenyl)isatoic anhydride
• 英文别名: N-isoprenyl isatoic anhydride；N-isoprenylisatoic anhydride；1-(3-methyl-but-2-enyl)-1H-benzo[d][1,3]oxazine-2,4-dione；1-(3-Methylbut-2-enyl)-3,1-benzoxazine-2,4-dione
• CAS: 223668-31-3
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: UKBMGSIDMWAQMV-UHFFFAOYSA-N

物化性质

• 熔点：
  119 °C
• 沸点：
  354.3±35.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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-(3'-methyl-2'-butenyl)isatoic anhydride 在 sodium hydride 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 1-(3'-methyl-2'-butenyl)-3-diazoquinoline-2,4-dione
  参考文献：
  名称：

  Rhodium-Mediated Dipolar Cycloaddition of Diazoquinolinediones

  摘要：

  As an entry to furoquinoline structures of natural origin, the rhodium-mediated dipolar cycloaddition of diazoquinolinediones with alkenes and alkynes has been examined. Because of the unsymmetrical nature of the diazo compounds, both linear and angular furoquinoline products are possible. For the most part, a mixture of regioisomers is generated in moderate to good yields, though in a few cases dominant products are obtained in high yields. The products can be further converted to naturally occurring alkaloids such as isodictamnine. A novel observation in this work is that catalytic quantities of acid enhance the yield and regiochemical control in the cycloaddition.

  DOI：

  10.1021/jo982503h
• 作为产物：
  描述：

  靛红酸酐 、 1-溴-3-甲基-2-丁烯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(3'-methyl-2'-butenyl)isatoic anhydride
  参考文献：
  名称：

  抗生素天然产物 hunanamycin A：抗沙门氏菌药物的先导鉴定

  摘要：

  本文公开了抗生素天然产物 hunanamycin A 支架周围化合物库的设计和合成及其生物学评价。这些努力导致了先导化合物36的鉴定，它是原始 hunanamycin A 的结构简化类似物，具有令人印象深刻的抗肠沙门氏菌活性，并具有其他可成药特性。此外，在瑞士白化病小鼠中未观察到化合物36的急性经口毒性，剂量高达 2 g/kg。它有可能被开发用于治疗由沙门氏菌引起的食物感染。

  DOI：

  10.1016/j.ejmech.2022.114245

文献信息

• Heterocyclic GSK-3 Allosteric Modulators
  申请人：Consejo Superior de Investigaciones Cientificas (CSIC)

  公开号：US20150057311A1

  公开（公告）日：2015-02-26

  The present invention relates to heterocyclic substituted quinoline derivatives as allosteric inhibitors of the glycogen synthase kinase-3 (GSK-3) enzyme. Therefore, these compounds are useful for the manufacturing of a medicament designed for the treatment and/or prevention of diseases wherein GSK-3 is involved, such as neurodegenerative diseases, inflammatory diseases, cancer, diabetes, and to promote various regenerative processes.

  本发明涉及杂环取代喹啉衍生物作为糖原合成酶激酶-3 (GSK-3) 酶的变构抑制剂。因此，这些化合物可用于制造用于治疗和/或预防 GSK-3 参与的疾病的药物，例如神经退行性疾病、炎症性疾病、癌症、糖尿病，以及促进各种再生过程。
• [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。
• Novel anti-infectives
  申请人：——

  公开号：US20040147739A1

  公开（公告）日：2004-07-29

  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.

  本文披露了具有以下公式的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，还披露了制备和使用这些化合物的方法。
• 3-(1,1-Dioxo-2<i>H</i>-(1,2,4)-benzothiadiazin-3-yl)-4-hydroxy-2(1<i>H</i>)-quinolinones, Potent Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase
  作者：Rosanna Tedesco、Antony N. Shaw、Ramesh Bambal、Deping Chai、Nestor O. Concha、Michael G. Darcy、Dashyant Dhanak、Duke M. Fitch、Adam Gates、Warren G. Gerhardt、Dina L. Halegoua、Chao Han、Glenn A. Hofmann、Victor K. Johnston、Arun C. Kaura、Nannan Liu、Richard M. Keenan、Juili Lin-Goerke、Robert T. Sarisky、Kenneth J. Wiggall、Michael N. Zimmerman、Kevin J. Duffy

  DOI：10.1021/jm050855s

  日期：2006.2.1

  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.
• Subtly Modulating Glycogen Synthase Kinase 3 β: Allosteric Inhibitor Development and Their Potential for the Treatment of Chronic Diseases
  作者：Valle Palomo、Daniel I. Perez、Carlos Roca、Cara Anderson、Natalia Rodríguez-Muela、Concepción Perez、Jose A. Morales-Garcia、Julio A. Reyes、Nuria E. Campillo、Ana M. Perez-Castillo、Lee L. Rubin、Lubov Timchenko、Carmen Gil、Ana Martinez

  DOI：10.1021/acs.jmedchem.7b00395

  日期：2017.6.22

  Glycogen synthase kinase 3 beta (GSK-3 beta) is a central target in several unmet diseases. To increase the specificity of GSK-3 beta inhibitors in chronic treatments, we developed small molecules allowing subtle modulation of GSK-3 beta activity. Design synthesis, structure activity relationships, and binding mode of quinoline-3-carbohydrazide derivatives as allosteric modulators of GSK-3 beta are presented here. Furthermore, we show how allosteric binders may overcome the beta-catenin side effects associated with strong GSK-3 beta inhibition. The therapeutic potential of some of these modulators has been tested in human samples from patients with congenital myotonic dystrophy type 1 (CDM1) and spinal it atrophy (SMA) patients. We found that compound 53 improves delayed myogenesis in CDM1 myoblasts, while compounds 1 and 53 have neuroprotective properties in SMA-derived cells. These findings suggest that the allosteric modulators of GSK-3 beta may be used for future development of drugs for DM1, SMA, and other chronic diseases where GSK-3 beta inhibition exhibits therapeutic effects.