2-(3-氧代-1,4-苯并恶嗪-4-基)乙酸乙酯 | 26673-71-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-(3-氧代-1,4-苯并恶嗪-4-基)乙酸乙酯
• 中文别名: (3-氧代-2,3-二氢-苯并[1,4]咯嗪-4-基)-乙酸乙酯
• 英文名称: ethyl 2-(3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)acetate
• 英文别名: ethyl 2-(3-oxo-2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)acetate；Ethyl (3-Oxo-2,3-Dihydro-4h-1,4-Benzoxazin-4-Yl)acetate；ethyl 2-(3-oxo-1,4-benzoxazin-4-yl)acetate
• CAS: 26673-71-2
• 化学式: C₁₂H₁₃NO₄
• mdl: MFCD00268750
• 分子量: 235.24
• InChiKey: PNKJMWWGWBCNQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-氧代-1,4-苯并恶嗪-4-基)乙酸乙酯 在 一水合肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 34.0h， 生成 4-(5-phenyl-[1,3,4]-oxadiazol-2-ylmethyl)-4H-benzo[1,4]oxazin-3-one
  参考文献：
  名称：

  Synthesis of new 1,3,4-oxadiazole-1,4-benzoxazinone hybrids as tubulin polymerization inhibiting anticancer agents and their in silico studies

  摘要：

  DOI：

  10.1016/j.tet.2022.132979
• 作为产物：
  描述：

  2-bromo-N-(2-hydroxyphenyl)acetamide 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-(3-氧代-1,4-苯并恶嗪-4-基)乙酸乙酯
  参考文献：
  名称：

  Synthesis, biological activity and conformational study of 1,4-benzoxazine derivatives as potassium channel modulators

  摘要：

  With the aim of discovering new molecules with K+-channel activating properties, we have synthesized derivatives of cromakalim (CRK), an important molecule which shows specific affinity towards K+ channels, by replacing the benzopyrane ring of this reference compound with a 1,4-benzoxazine moiety. A different number of substituents showing a good discrimination between hydrophobic and electronic properties have been inserted at the 6-position of the 1,4-benzoxazine ring. We describe here the synthesis and discuss the solid state conformation of these new molecules. When tested on rat aorta ring precontracted with phenylephrine, two compounds (2c and 2d) showed a concentration-dependent relaxation similar to that measured for cromakalim but less potent than this reference drug. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80020-8

文献信息

• 2,4-Pyrimidinediamine Compounds and Their Uses
  申请人：Singh Rajinder

  公开号：US20150266828A1

  公开（公告）日：2015-09-24

  The present invention provides 2,4-pyrimidinediamine compounds that inhibit the IgE and/or IgG receptor signaling cascades that lead to the release of chemical mediators, intermediates and methods of synthesizing the compounds and methods of using the compounds in a variety of contexts, including in the treatment and prevention of diseases characterized by, caused by or associated with the release of chemical mediators via degranulation and other processes effected by activation of the IgE and/or IgG receptor signaling cascades.

  本发明提供了抑制IgE和/或IgG受体信号级联反应的2,4-嘧啶二胺化合物，该级联反应导致化学介质的释放，以及合成这些化合物的中介体和方法，以及在多种情况下使用这些化合物的方法，包括在治疗和预防由脱粒和其他由IgE和/或IgG受体信号级联反应激活引起的化学介质释放所表征、引起或相关的疾病。
• Methods of Treating Cell Proliferative Disorders
  申请人：Hitoshi Yasumichi

  公开号：US20090012045A1

  公开（公告）日：2009-01-08

  The present disclosure provides methods for the treatment of cell proliferative disorders by administration of a RET kinase inhibitor. Cell proliferative disorders treatable by the methods include, thyroid tumors.

  本公开提供了一种通过给予RET激酶抑制剂治疗细胞增殖性疾病的方法。这些方法可用于治疗的细胞增殖性疾病包括甲状腺肿瘤。
• Synthesis and Structure–Activity Relationship Studies of Benzo[ <i>b</i> ][1,4]oxazin‐3(4 <i>H</i> )‐one Analogues as Inhibitors of Mycobacterial Thymidylate Synthase X
  作者：Jakub Modranka、Jiahong Li、Anastasia Parchina、Michiel Vanmeert、Shrinivas Dumbre、Mayla Salman、Hannu Myllykallio、Hubert F. Becker、Roeland Vanhoutte、Lia Margamuljana、Hoai Nguyen、Rania Abu El‐Asrar、Jef Rozenski、Piet Herdewijn、Steven De Jonghe、Eveline Lescrinier

  DOI：10.1002/cmdc.201800739

  日期：2019.3.22

  report herein an optimization campaign of a novel series of inhibitors with a unique inhibition profile. The inhibitors display competitive inhibition toward the methylene tetrahydrofolate cofactor of ThyX, enabling us to generate a model of the compounds bound to their target, thus offering insight into their structure-activity relationships.

  由于发现了人类中不存在的黄素依赖性胸苷酸合酶（ThyX或FDTS），但对于多种病原体中的DNA生物合成至关重要，该酶一直被用于开发针对结核分枝杆菌的新型抗菌剂。广泛的传染病结核病（TB）的病原体。为了响应对更有效的抗结核药物的日益增长的需求，我们在之前的筛选工作基础上，在此报告了一系列具有独特抑制谱的新型抑制剂的优化方案。抑制剂对ThyX的亚甲基四氢叶酸辅因子表现出竞争性抑制作用，使我们能够生成与目标结合的化合物模型，从而深入了解其结构与活性之间的关系。
• Ultrasound-assisted synthesis and antimicrobial evaluation of some novel benzoxanonyhyldrazone derivatives
  作者：Naouel CHETTIBI、Houria BENTOUMI、Messaoud LIACHA

  DOI：10.33224/rrch.2020.65.10.03

  日期：——

  Some new benzoxazinonylhydrazone analogs derived from substituted benzaldehydes and benzoxazin-3(4H)-one pharmacophore have been synthesized by simple and efficient methods, using ultrasound (US) irradiations as well as conventional thermal heating (CTH). The treatment of the benzoxazinonylhydrazide (3) with the corresponding aromatic aldehyde, resulted in the formation of benzoxazinonylhydrazones (4a–4f) in good yields and short reaction times. The proposed structures of the obtained hydrazone compounds were identified and elucidated on the basis of FT-IR and nuclear magnetic resonance (1H-NMR and 13C-NMR) spectroscopy. The synthesized compounds were screened in vitro for their antibacterial and antifungal activities against three types of bacteria (S. aureus, E. coli, P. aeruginosa) and one type of fungi (C. albicans), respectively, by disc diffusion method. All of these hydrazone compounds exhibited remarkable antifungal activity and very moderate antibacterial activity.

  一些新的苯并噁唑啉基腙类似物通过简单高效的方法，利用超声（US）辐照以及传统热加热（CTH）合成，这些类似物是由取代苯甲醛和苯并噁唑-3(4H)-酮药基衍生而来的。苯并噁唑基腙（3）与相应的芳香醛处理后，在良好的产率和短反应时间内形成了苯并噁唑基腙（4a-4f）。通过傅立叶变换红外光谱（FT-IR）和核磁共振（1H-NMR和13C-NMR）光谱鉴定和阐明了所得腙类化合物的结构。通过圆盘扩散法，对合成的化合物进行了体外抗菌和抗真菌活性筛选，针对三种细菌（金黄色葡萄球菌、大肠杆菌、铜绿假单胞菌）和一种真菌（白念珠菌）。所有这些腙类化合物表现出显著的抗真菌活性和非常适度的抗菌活性。
• Development of Small-Molecule<i>Trypanosoma brucei N</i>-Myristoyltransferase Inhibitors: Discovery and Optimisation of a Novel Binding Mode
  作者：Daniel Spinks、Victoria Smith、Stephen Thompson、David A. Robinson、Torsten Luksch、Alasdair Smith、Leah S. Torrie、Stuart McElroy、Laste Stojanovski、Suzanne Norval、Iain T. Collie、Irene Hallyburton、Bhavya Rao、Stephen Brand、Ruth Brenk、Julie A. Frearson、Kevin D. Read、Paul G. Wyatt、Ian H. Gilbert

  DOI：10.1002/cmdc.201500301

  日期：2015.11

  bound in the previously reported active site, utilising a novel binding mode. This provides potential for further optimisation. The benzomorpholinone was also found to bind in a similar region. Using an X‐ray crystallography/structure‐based design approach, the benzomorpholinone series was further optimised, increasing activity against T. brucei NMT by >1000‐fold. A series of trypanocidal compounds were

  来自布氏锥虫的N-肉豆蔻酰转移酶(NMT)已在化学和生物学上被证实是人类非洲锥虫病的潜在药物靶点。我们之前报道了一些基于吡唑磺酰胺系列的非常有效的化合物的开发，这些化合物源自高通量筛选。在此，我们描述了在屏幕中也发现的噻唑烷酮和苯并吗啉支架的工作。大利什曼原虫中噻唑烷酮的 X 射线晶体结构NMT 利用一种新的结合模式显示了该化合物结合在先前报道的活性位点中。这提供了进一步优化的潜力。苯并吗啉酮也被发现在类似的区域结合。使用基于 X 射线晶体学/结构的设计方法，进一步优化了苯并吗啉酮系列，将抗布氏锥虫NMT 的活性提高了 1000 倍以上。确定了一系列具有合适体外 DMPK 特性的杀锥虫化合物，包括用于进一步开发的 CNS 暴露。需要进一步的工作来提高对人类 NMT 同种型的选择性和对布氏锥虫的活性。