N-(2-乙酰基苯基)-4-甲基苯甲酰胺 | 710330-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-乙酰基苯基)-4-甲基苯甲酰胺
• 英文名称: N-(2-acetylphenyl)-4-methylbenzamide
• CAS: 710330-32-8
• 化学式: C₁₆H₁₅NO₂
• mdl: MFCD02670240
• 分子量: 253.301
• InChiKey: LSBKVRMPZJRVPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-乙酰基苯基)-4-甲基苯甲酰胺 在 碘 、 碳酸氢钠 、 叔丁基过氧化氢 作用下， 以 二甲基亚砜 、 正壬烷 为溶剂， 反应 3.03h， 以86%的产率得到2-(4-methylphenyl)-4H-3,1-benzoxazin-4-one
  参考文献：
  名称：

  未应变的C（sp 3）–C（sp 2）键的选择性氧化脱羰裂解：取代的苯并恶嗪酮的合成

  摘要：

  通过使用碘，碳酸氢钠和叔丁基过氧化氢在DMSO中对未应变的C（sp 3）-C（sp 2）键进行选择性氧化脱羰裂解，建立了与生物相关的苯并恶嗪酮的无过渡金属（TM）实用合成方法在95°C下。控制实验和密度泛函理论（DFT）计算表明，该反应涉及[1,5] H转变和CO气体挤出作为关键步骤。还使用PMA–PdCl 2建立了CO的挤出。

  DOI：

  10.1021/acs.orglett.6b02142
• 作为产物：
  描述：

  对甲基苯甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-(2-乙酰基苯基)-4-甲基苯甲酰胺
  参考文献：
  名称：

  使用全氟烷基亚磺酸钠对 4-喹诺酮进行区域选择性全氟烷基化

  摘要：

  在R f SO 2 Na 和(NH 4 ) 2 S 2 O 8存在下，通过自由基途径顺利获得了一系列C-3位全氟烷基化4-喹诺酮类化合物。该方案具有底物范围广、区域选择性高、不含过渡金属、易于获得的氟化试剂等特点，在获得生物活性化合物方面具有潜在的应用价值。

  DOI：

  10.1002/ejoc.202200842

文献信息

• Graveoline Analogs Exhibiting Selective Acetylcholinesterase Inhibitory Activity as Potential Lead Compounds for the Treatment of Alzheimer’s Disease
  作者：Zeng Li、Chaoyu Mu、Bin Wang、Juan Jin

  DOI：10.3390/molecules21020132

  日期：——

  synthesized a series of new graveoline analogs on the basis of the structural characteristics of acetylcholinesterase (AChE) dual-site inhibitors. The activity of these analogs was also evaluated. Results showed that the synthesized graveoline analogs displayed stronger inhibitory activity against AChE and higher selectivity than butyrylcholine esterase (BuChE) (Selectivity Index from 45 to 486). When

  本研究根据乙酰胆碱酯酶（AChE）双位点抑制剂的结构特点，设计并合成了一系列新的草甘膦类似物。还评估了这些类似物的活性。结果表明，合成的石蜡碱类似物对 AChE 显示出更强的抑制活性和比丁酰胆碱酯酶 (BuChE) 更高的选择性（选择性指数从 45 到 486）。当取代苯基和氨基末端的graveoline母环中的两个位点具有六个化学键（n = 3）且末端氨基为哌啶时，化合物5c显示出最佳活性。此外，通过酶动力学模拟、分子对接和基于硫黄素 T 的荧光测定法探索了作用机制和结合模式。
• Mild, rapid and efficient metal-free synthesis of 2-aryl-4-aryloxyquinolines via direct Csp2O bond formation by using diaryliodonium salts
  作者：Pradip D. Nahide、César R. Solorio-Alvarado

  DOI：10.1016/j.tetlet.2016.11.093

  日期：2017.1

  An efficient ligand- and transition metal-free procedure for the direct Csp2O bond formation for the arylation of 2-aryl-4-quinolones was developed. The synthesis of the starting quinolones was carried out under our optimized Cu-catalyzed CN bond formation conditions between 2′-bromoacetophenone and benzamide derivatives followed by cyclization. Easily prepared diaryliodonium salts were used as aryl

  开发了一种有效的无配体和过渡金属的方法，用于直接形成C sp 2 O键，用于2-芳基-4-喹诺酮的芳基化。起始喹诺酮类化合物的合成在我们优化的Cu催化的2'-溴苯乙酮和苯甲酰胺衍生物之间的C N键形成条件下进行，然后环化。容易制备的二芳基碘鎓盐用作芳基源。以温和且操作简单的方案获得了高度官能化的4-芳氧基喹啉，该方案涉及常规加热和较短时间。该方法显示出良好至极好的收率，对诸如氟或三氟甲基的官能团具有广泛的耐受性，这在药物化学中很重要。C sp 2本文所述的用于喹诺酮官能化的O键形成工艺提供了过渡金属催化的反应的极好的无毒替代物，其不仅可能潜在地污染最终化合物，而且还可能是环境污染物。
• Antiviral activity evaluation and action mechanism of myricetin derivatives containing thioether quinoline moiety
  作者：Qifan Wang、Li Xing、Yuanquan Zhang、Chenyu Gong、Yuanxiang Zhou、Nian Zhang、Bangcan He、Wei Xue

  DOI：10.1007/s11030-023-10631-9

  日期：——

  A variety of myricetin derivatives containing thioether quinoline moiety were designed and synthesized. Their structures of title compounds were determined by 1H NMR, 13C NMR, 19F NMR, and HRMS. Single-crystal X-ray diffraction experiments were carried out with B4. Antiviral activity indicated that some of the target compounds exhibited remarkable anti-tobacco mosaic virus (TMV) activity. In particular, compound B6 possessed significant activity. The half maximal effective concentration (EC50) value of the curative activity of compound B6 was 169.0 μg/mL, which was superior to the control agent ningnanmycin (227.2 μg/mL). Meanwhile, the EC50 value of the protective activity of compound B6 was 86.5 μg/mL, which was better than ningnanmycin (179.2 μg/mL). Microscale thermophoresis (MST) indicated that compound B6 had a strong binding capability to the tobacco mosaic virus coat protein (TMV-CP) with a dissociation constant (Kd) value of 0.013 μmol/L, which was superior to that of myricitrin (61.447 μmol/L) and ningnanmycin (3.215 μmol/L). And the molecular docking studies were consistent with the experimental results. Therefore, these novel myricetin derivatives containing thioether quinoline moiety could become potential alternative templates for novel antiviral agents.

  设计并合成了多种含有硫醚喹啉分子的杨梅素衍生物。通过 1H NMR、13C NMR、19F NMR 和 HRMS 确定了标题化合物的结构。对 B4 进行了单晶 X 射线衍射实验。抗病毒活性表明，一些目标化合物具有显著的抗烟草花叶病毒（TMV）活性。其中，化合物 B6 具有显著的活性。化合物 B6 的半数最大有效浓度（EC50）值为 169.0 μg/mL，优于对照药剂宁南霉素（227.2 μg/mL）。同时，化合物 B6 的保护活性 EC50 值为 86.5 μg/mL，优于宁南霉素（179.2 μg/mL）。微尺度热泳（MST）表明，化合物B6与烟草花叶病毒衣壳蛋白（TMV-CP）的结合能力很强，其解离常数（Kd）值为0.013 μmol/L，优于myricitrin（61.447 μmol/L）和宁南霉素（3.215 μmol/L）。分子对接研究结果与实验结果一致。因此，这些含有硫醚喹啉分子的新型杨梅素衍生物可能成为新型抗病毒药物的潜在替代模板。
• Ruthenium(II) Catalyzed Regiospecific C–H/O–H Annulations of Directing Arenes via Weak Coordination
  作者：Arghya Banerjee、Sourav Kumar Santra、Prakash Ranjan Mohanta、Bhisma K. Patel

  DOI：10.1021/acs.orglett.5b02967

  日期：2015.11.20

  Ruthenium(II) catalyzed oxidative CH/OH annulations have been demonstrated using two different directing arenes viz. 2-arylquinolinone and 2-arylbenzoxazinone with internal alkynes. Regiospecific annulations have been observed for both directing arenes via the assistance of weaker carbonyl oxygen in the presence of a stronger nitrogen-directing site. In this substrate-controlled convergent protocol the weaker directing group dictates the annulation path.
• Evaluation of synthetic acridones and 4-quinolinones as potent inhibitors of cathepsins L and V
  作者：Emerson F. Marques、Mauro A. Bueno、Patrícia D. Duarte、Larissa R.S.P. Silva、Ariani M. Martinelli、Caio Y. dos Santos、Richele P. Severino、Dieter Brömme、Paulo C. Vieira、Arlene G. Corrêa

  DOI：10.1016/j.ejmech.2012.04.002

  日期：2012.8

  Cathepsins, also known as lysosomal cysteine peptidases, are members of the papain-like peptidase family, involved in different physiological processes. In addition, cathepsins are implicated in many pathological conditions. This report describes the synthesis and evaluation of a series of N-arylanthranilic acids, acridones, and 4-quinolinones as inhibitors of cathepsins V and L The kinetics revealed that compounds of the classes of acridones are reversible competitive inhibitors of the target enzyme with affinities in the low micromolar range. They represent promising lead candidates for the discovery of novel competitive cathepsin inhibitors with enhanced selectivity and potency. On the other hand, 4-quinolinones were noncompetitive inhibitors and N-arylanthranilic acids were uncompetitive inhibitors. (C) 2012 Elsevier Masson SAS. All rights reserved.