3-乙基喹唑啉-4-酮 | 3476-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-乙基喹唑啉-4-酮
• 英文名称: 3-ethylquinazolin-4(3H)-one
• 英文别名: 3-ethylquinazolin-4-one；3-Ethyl-3,4-dihydro-chinazol-4-on；4(3H)-Quinazolinone, 3-ethyl-
• CAS: 3476-65-1
• 化学式: C₁₀H₁₀N₂O
• mdl: MFCD01686075
• 分子量: 174.202
• InChiKey: BMFONNKQZRYQSO-UHFFFAOYSA-N

物化性质

• 熔点：
  102 °C
• 沸点：
  182 °C(Press: 15 Torr)
• 密度：
  1.17±0.1 g/cm3(Predicted)
• 保留指数：
  1664;1664

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-乙基喹唑啉-4-酮 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.67h， 生成 3-Ethyl-1-methyl-2-sulfanylidenequinazolin-4-one
  参考文献：
  名称：

  A New Mixed Amino–Amido N-Heterocyclic Carbene Based on Anthranilic Acid

  摘要：

  The synthesis of a new mixed amino-amido N-heterocyclic carbene (type A) starting from anthranilic acid is presented. A new straightforward synthetic approach to related diaminocarbenes of type B is also described. Both NHCs react with group 6 elements to form heteroureas and coordinate to L2CIM fragments (M = Rh, Ir; L-2 = COD, (CO)(2)). IR spectroscopic analysis of the carbonyl complexes reveals that the diamino-NHC is a better donor ligand (TEP: 2054 cm(-1)) compared to the amino-amido NHC (TEP: 2060 cm(-1)). In line with this behavior, a carbene dimerization to give the corresponding olefin is observed only for derivatives of type A. X-ray structure determinations are reported for two Rh complexes of ligand A and its cationic precursor.

  DOI：

  10.1021/om301152n
• 作为产物：
  描述：

  邻氨基苯甲酸 在 potassium hydroxide 作用下， 以 乙腈 为溶剂， 反应 7.25h， 生成 3-乙基喹唑啉-4-酮
  参考文献：
  名称：

  A New Mixed Amino–Amido N-Heterocyclic Carbene Based on Anthranilic Acid

  摘要：

  The synthesis of a new mixed amino-amido N-heterocyclic carbene (type A) starting from anthranilic acid is presented. A new straightforward synthetic approach to related diaminocarbenes of type B is also described. Both NHCs react with group 6 elements to form heteroureas and coordinate to L2CIM fragments (M = Rh, Ir; L-2 = COD, (CO)(2)). IR spectroscopic analysis of the carbonyl complexes reveals that the diamino-NHC is a better donor ligand (TEP: 2054 cm(-1)) compared to the amino-amido NHC (TEP: 2060 cm(-1)). In line with this behavior, a carbene dimerization to give the corresponding olefin is observed only for derivatives of type A. X-ray structure determinations are reported for two Rh complexes of ligand A and its cationic precursor.

  DOI：

  10.1021/om301152n

文献信息

• BRM TARGETING COMPOUNDS AND ASSOCIATED METHODS OF USE
  申请人：Arvinas Operations, Inc.

  公开号：US20190300521A1

  公开（公告）日：2019-10-03

  The present disclosure relates to bifunctional compounds, which find utility as modulators of SMARCA2 or BRM (target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a ligand that binds to the Von Hippel-Lindau E3 ubiquitin ligase, and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.

  本公开涉及双功能化合物，其作为SMARCA2或BRM（靶蛋白）的调节剂具有实用性。具体而言，本公开涉及包含一端结合Von Hippel-Lindau E3泛素连接酶的配体，另一端结合靶蛋白的双功能化合物，使得靶蛋白与泛素连接酶靠近以实现靶蛋白的降解（和抑制）。本公开展示了与靶蛋白降解/抑制相关的广泛药理活性。本公开的化合物和组合物用于治疗或预防由靶蛋白聚集或积累导致的疾病或紊乱。
• Copper(I)/Bpy-Catalyzed C-2-H Benzylation of Quinazolin-4(3<i>H</i> )-ones with <i>N</i> -Tosylhydrazones
  作者：Fei Li、Xiao-Juan Gu、Chang-E. Zeng、Xia Li、Bo Liu、Guo-Li Huang

  DOI：10.1002/ejoc.202000244

  日期：2020.5.22

  Regioselective C‐2‐H benzylation of quinazolin‐4(3H)‐ones with N‐tosylhydrazones in a ligand dependent copper system was studied. An array of substituted quinazolin‐4(3H)‐ones were coupled effectively with a wide variety of N‐tosylhydrazones derived from aryl ketones to afford the alkylated products in moderate to good yields. This is a useful, time‐efficient, and scalable procedure for the construction

  研究了在依赖配体的铜体系中，喹唑啉-4（3 H）-酮与N-甲苯磺酰hydr的区域选择性C-2-H苄基化。将一系列取代的喹唑啉-4（3 H）-酮与衍生自芳基酮的各种N-甲苯磺酰hydr有效地偶联，以中等至良好的产率提供烷基化产物。这是构造C（sp 2）–C（sp 3）键的有用，省时且可扩展的过程。
• Cell-Active Small Molecule Inhibitors of the DNA-Damage Repair Enzyme Poly(ADP-ribose) Glycohydrolase (PARG): Discovery and Optimization of Orally Bioavailable Quinazolinedione Sulfonamides
  作者：Bohdan Waszkowycz、Kate M. Smith、Alison E. McGonagle、Allan M. Jordan、Ben Acton、Emma E. Fairweather、Louise A. Griffiths、Niall M. Hamilton、Nicola S. Hamilton、James R. Hitchin、Colin P. Hutton、Dominic I. James、Clifford D. Jones、Stuart Jones、Daniel P. Mould、Helen F. Small、Alexandra I. J. Stowell、Julie A. Tucker、Ian D. Waddell、Donald J. Ogilvie

  DOI：10.1021/acs.jmedchem.8b01407

  日期：2018.12.13

  DNA damage repair enzymes are promising targets in the development of new therapeutic agents for a wide range of cancers and potentially other diseases. The enzyme poly(ADP-ribose) glycohydrolase (PARG) plays a pivotal role in the regulation of DNA repair mechanisms; however, the lack of potent drug-like inhibitors for use in cellular and in vivo models has limited the investigation of its potential

  DNA损伤修复酶是开发用于多种癌症和其他潜在疾病的新型治疗剂的有希望的目标。聚（ADP-核糖）糖水解酶（PARG）在调节DNA修复机制中起着关键作用。然而，由于缺乏用于细胞和体内模型的有效药物样抑制剂，限制了其作为新型治疗靶标的潜力的研究。通过将人类PARG的晶体结构与弱活性和具有细胞毒性的蒽醌8a配合使用，已通过基于结构的虚拟筛选和库设计方法鉴定了新型喹唑啉二酮磺酰胺类PARG抑制剂。1-氧杂-3-基甲基衍生物33d和35d选择用于体内的初步研究。X射线晶体结构有助于合理化所观察到的这些新型抑制剂的构效关系。
• Building Heterocyclic Systems with RC(OR)2+ Carbocations in Recyclable Brønsted Acidic Ionic Liquids: Facile Synthesis of 1-Substituted 1H-1,2,3,4-Tetrazoles, Benzazoles and Other Ring Systems with CH(OEt)3 and EtC(OEt)3 in [EtNH3][NO3] and [PMIM(SO3H)][O
  作者：Gopalakrishnan Aridoss、Kenneth K. Laali

  DOI：10.1002/ejoc.201100128

  日期：2011.5

  IL-1/CH(OEt) 3 . The latter was also formed from 2-aminobenzoic acid in IL-1/CH(OEt) 3 . Mechanistic implications are addressed. The reported protocols enable rapid assembly of a host of heterocyclic systems in high yields with the added advantage of recycling and reuse of the ILs.

  1-芳基/烷基-1H-1,2,3,4-四唑可以通过与TMSN 3 和CH(OEt) 3 反应，使用容易获得的、可回收的、布朗斯台德酸性从相应的胺在一锅反应中方便地合成离子液体 [EtNH 3] -[NO 3 ] IL-1 和 [PMIM(SO 3 H)][OTf] IL-2 在温和条件下以高收率。基于对比反应，虽然两种 IL 都是极好的促进剂，但使用 IL-2 可以在更短的反应时间和更高的产率下完成反应。在提供的 24 个实施例中，除了 2-氨基苯甲酸与 IL-2 形成四唑和 IL-1 形成 2-乙基喹唑啉-4(3H)-one 外，通过两种 IL 获得了相同的产物。通过从反应中排除 TMS-N 3，原位形成的 CH(OEt) 2 + 和 Et-C(OEt) 2 +（通过它们相应的原酸酯）在超声处理下与带有各种取代基的邻苯二胺、邻氨基苯硫酚和邻氨基苯酚反应，形成一系列广泛的苯并咪唑（苯并咪唑
• Copper-Catalyzed Oxidative Cyclization of 2-Aminobenzamide Derivatives: Efficient Syntheses of Quinazolinones and Indazolones
  作者：Wei-Yu Lin、Karthick Govindan、Tamilselvan Duraisamy、Alageswaran Jayaram、Gopal Chandru Senadi

  DOI：10.1055/a-1667-3977

  日期：2022.2

  transformations are based on the fact that DMF can serve as a reaction solvent and one carbon synthon for the construction of heterocyclic rings. Moreover, this protocol features base-free and Brønsted acid free environmentally benign conditions with broad synthetic scope. A good scalability is demonstrated.

  报道了一种简单的铜催化组装，以单一协议方式配制喹唑啉酮和吲唑酮衍生物。这些转化是基于 DMF 可以作为反应溶剂和一个碳合成子来构建杂环的事实。此外，该协议具有无碱和无布朗斯台德酸的环境良性条件，具有广泛的合成范围。展示了良好的可扩展性。