2-(2-nitrophenoxy)-1-phenylethan-1-one | 18065-01-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-nitrophenoxy)-1-phenylethan-1-one
• 英文别名: 2-(2-Nitrophenoxy)-1-phenylethanone
• CAS: 18065-01-5
• 化学式: C₁₄H₁₁NO₄
• mdl: MFCD05668759
• 分子量: 257.246
• InChiKey: NJPUIIJXFYTYRK-UHFFFAOYSA-N

物化性质

• 熔点：
  121 °C
• 沸点：
  445.5±25.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-nitrophenoxy)-1-phenylethan-1-one 在 palladium 10% on activated carbon 、 氢气 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 140.0 ℃ 、405.33 kPa 条件下， 反应 23.17h， 生成 3,7-dihydro-N-(3,5-dimethyladamant-1-yl)-7-oxo-3-phenyl-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide
  参考文献：
  名称：

  7-Oxo-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamides as Selective CB₂ Cannabinoid Receptor Ligands: Structural Investigations around a Novel Class of Full Agonists

  摘要：

  Cannabinoid receptor agonists have gained attention as potential therapeutic targets of inflammatory and neuropathic pain. Here, we report the identification and optimization of a series of 7-oxo-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide derivatives as a novel chemotype of selective cannabinoid CB2 receptor agonists. Structural modifications led to the identification of several compounds as potent and selective cannabinoid receptor agonists (20, hCB(2) K-i = 2.5 nM, SI = 166; 21, hCB(2) K-i = 0.81 nM, SI = 383; 38, hCB(2) K-i = 15.8 nM, SI > 633; 56, hCB(2) K-i = 8.12 nM, SI > 1231; (R)-58, hCB(2) K-i = 9.24 nM, SI > 1082). The effect of a chiral center on the biological activity was also investigated, and it was found that the (R)-enantiomers exhibited greater affinity at the CB2 receptor than the (S)-enantiomers. In 3,5-cyclic adenosine monophosphate assays, the novel series behaved as agonists, exhibiting functional activity at the human CB2 receptor.

  DOI：

  10.1021/jm300763w
• 作为产物：
  描述：

  2-[(2-phenyl-2-propenyl)oxy]-1-nitrobenzene 在 臭氧 、 二甲基硫 、 对甲苯磺酸 、 amberlyst-15 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 以98%的产率得到2-(2-nitrophenoxy)-1-phenylethan-1-one
  参考文献：
  名称：

  串联还原还原胺化反应制得二氢苯并恶嗪和四氢喹喔啉†

  摘要：

  串联还原-还原胺化反应已用于合成3,4-二氢-2 H -1,4-苯并恶嗪和1-乙酰基-1,2,3,4-四氢喹喔啉。苯并恶嗪环闭合所需要的硝基酮是通过（A）用烯丙基卤化物将2-硝基苯酚衍生的阴离子烷基化，或（B）在2-氟-1-硝基苯上进行烯丙基醇盐的亲核芳族取代，然后进行臭氧分解来制备的。喹喔啉的前体是通过将2-硝基乙酰苯胺的阴离子与烯丙基卤化物烷基化，然后进行臭氧分解来制备的。然后在甲醇中使用5％钯碳催化硝基酮的加氢反应，然后通过还原-还原胺化顺序得到目标杂环。该ñ通过在还原之前添加5-10当量的甲醛水溶液，可以轻松制备两个环系统的α-甲基衍生物。通过色谱法纯化后，高产率地分离出二氢苯并恶嗪。以相似的方式分离四氢喹喔啉，并在两个氮原子上具有不同的官能度。

  DOI：

  10.1002/jhet.5570400611

文献信息

• Searching for Novel Inhibitors of the<i>S. aureus</i>NorA Efflux Pump: Synthesis and Biological Evaluation of the 3-Phenyl-1,4-benzothiazine Analogues
  作者：Tommaso Felicetti、Rolando Cannalire、Maria Sole Burali、Serena Massari、Giuseppe Manfroni、Maria Letizia Barreca、Oriana Tabarrini、Bryan D. Schindler、Stefano Sabatini、Glenn W. Kaatz、Violetta Cecchetti

  DOI：10.1002/cmdc.201700286

  日期：2017.8.22

  overexpression of efflux pumps such as NorA of Staphylococcus aureus leads to a sub-lethal concentration of the antibacterial agent at the active site that in turn may predispose the organism to the development of high-level target-based resistance. With an aim to improve both the chemical stability and potency of our previously reported 3-phenyl-1,4-benzothiazine NorA inhibitors, we replaced the benzothiazine

  近年来，对抗菌剂的细菌耐药性已成为日益严重的健康问题。在可以实现抗药性的策略中，外排泵的过度表达（例如金黄色葡萄球菌的NorA）导致活性位点处的抗菌剂浓度达到亚致死浓度，进而可能使生物体易于形成高水平靶标抵抗。为了提高我们先前报道的3-苯基-1,4-苯并噻嗪NorA抑制剂的化学稳定性和效能，我们用不同的核取代了苯并噻嗪核心。新合成的化合物均未显示任何明显的固有抗菌活性，尤其是2-（3,4-二甲氧基苯基）喹啉（6 c）能够以浓度依赖性方式降低，
• Azacyclic compounds as inhibitors of sensory neurone specific channels
  申请人：Hamlyn John Richard

  公开号：US20070043024A1

  公开（公告）日：2007-02-22

  Compounds of the formula (I), and pharmaceutically acceptable salts thereof, are found to be antagonists of SNS sodium channels. They are therefore useful as analgesic and neuroprotective agents wherein: X is —N— or —CH—; n is from 0 to 3.

  公式（I）的化合物及其药学上可接受的盐被发现是SNS钠通道的拮抗剂。因此，它们可用作镇痛和神经保护剂，其中：X为—N—或—CH—; n为0至3。
• Rational Design, Synthesis, and Anti-Proliferative Evaluation of Novel 4-Aryl-3,4-Dihydro-2H-1,4-Benzoxazines
  作者：Xiaoming Fu、Daniel Wenholz、Daniel S. H. Chan、David StC. Black、Naresh Kumar

  DOI：10.3390/molecules29010166

  日期：——

  A synthetic pathway to a novel 4-aryl-3,4-dihydro-2H-1,4-benzoxazine scaffold was developed and a series of compounds based on the scaffold were synthesised as potential anticancer agents. The 4-aryl-substituted compounds were prepared via Buchwald–Hartwig cross-coupling between substituted bromobenzenes and various 1,4-benzoxazines, which in turn were generated from a cascade hydrogenation and reductive amination one-pot reaction. These analogues exhibited moderate to good potency against various cancer cell lines. Structure–activity relationship analysis indicated that the inclusion of hydroxyl groups on ring A and ring B was beneficial to biological activity, while having a para-amino group on ring C significantly enhanced potency. Molecule 14f displayed the most potent anticancer activity (IC50 = 7.84–16.2 µM against PC-3, NHDF, MDA-MB-231, MIA PaCa-2, and U-87 MG cancer cell lines), indicating its potential as a lead compound for further structural optimisation. All the synthesised compounds were fully characterised with NMR, HMRS, and IR. The novel benzoxazine scaffold described in this study holds promise and deserves further in-depth studies.

  研究人员开发了一种新型 4-芳基-3,4-二氢-2H-1,4-苯并恶嗪支架的合成途径，并以该支架为基础合成了一系列潜在抗癌剂化合物。这些 4-芳基取代的化合物是通过取代的溴苯和各种 1,4-苯并噁嗪之间的 Buchwald-Hartwig 交叉偶联反应制备的，而 1,4-苯并噁嗪又是通过级联氢化和还原胺化一锅反应生成的。这些类似物对各种癌症细胞株具有中等至良好的药效。结构-活性关系分析表明，在环 A 和环 B 上加入羟基有利于提高生物活性，而在环 C 上加入对位氨基则能显著提高药效。分子 14f 的抗癌活性最强（对 PC-3、NHDF、MDA-MB-231、MIA PaCa-2 和 U-87 MG 癌细胞株的 IC50 = 7.84-16.2 µM），表明它有可能成为进一步优化结构的先导化合物。所有合成的化合物都通过核磁共振、高分辨红外光谱和红外光谱进行了全面表征。本研究中描述的新型苯并恶嗪支架前景广阔，值得进一步深入研究。
• WO2005/5392
  申请人：——

  公开号：——

  公开（公告）日：——
• Joseph; Jacob, Dominic E., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 2, p. 432 - 436
  作者：Joseph、Jacob, Dominic E.

  DOI：——

  日期：——