N-(2-acetyl-phenyl)-4-chloro-benzamide | 1640-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-acetyl-phenyl)-4-chloro-benzamide
• 英文别名: N-(2-acetylphenyl)-4-chlorobenzamide；N-(p-Chlorbenzoyl)-o-aminoacetophenon；Benzamide, N-(2-acetylphenyl)-4-chloro-
• CAS: 1640-44-4
• 化学式: C₁₅H₁₂ClNO₂
• mdl: MFCD04068492
• 分子量: 273.719
• InChiKey: ZFZMSNPPLMFOCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 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-acetyl-phenyl)-4-chloro-benzamide 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以90%的产率得到2-(4-chlorophenyl)quinolin-4(1H)-one
  参考文献：
  名称：

  通过使用二芳基碘鎓盐直接形成C sp 2 O键温和，快速，有效地无金属合成2-芳基-4-芳氧基氧基喹啉

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2016.11.093
• 作为产物：
  描述：

  1-(2-(4-chlorobenzylamino)phenyl)ethanone 在 copper(I) bromide 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以52%的产率得到N-(2-acetyl-phenyl)-4-chloro-benzamide
  参考文献：
  名称：

  Copper-Mediated Selective C–H Activation and Cross-Dehydrogenative C–N Coupling of 2′-Aminoacetophenones

  摘要：

  Isatins were obtained by cross-dehydrogenative C-N annulation and dealkylative C-N annulation of 2'-N-aryl/alkylaminoacetophenones and 2'-N,N-dialkylaminoacetophenones respectively in the presence of Cu(OAc)(2)center dot H2O/NaOAc/air. However, on reaction with CuBr, 2'-N-benzylaminoacetophenones underwent selective oxidation of an a-methylene group of amine rather than the 2-acetyl group to provide corresponding benzamides exclusively. Base played an important role in selective oxidation by lowering the temperature and time.

  DOI：

  10.1021/ol402750r

文献信息

• Tautomeric 2-arylquinolin-4(1H)-one derivatives- spectroscopic, X-ray and quantum chemical structural studies
  作者：Malose J Mphahlele、Ahmed M El-Nahas

  DOI：10.1016/j.molstruc.2003.10.003

  日期：2004.1

  Abstract A convenient method for the synthesis of 2-aryl-1-methylquinolin-4(1 H )-ones is described. Spectroscopic and X-ray crystallographic techniques as well as quantum chemical calculations have been used to probe the structure of potentially tautomeric 2-arylquinolin-4(1 H )-ones in solution phase, gas phase and solid state. The exclusive NH-4-oxo nature of the title compounds in solution phase

  摘要 描述了一种合成 2-芳基-1-甲基喹啉-4(1 H)-酮的简便方法。光谱和 X 射线晶体学技术以及量子化学计算已被用于探测溶液相、气相和固态中潜在互变异构的 2-芳基喹啉-4(1 H)-酮的结构。通过将它们的光谱数据与相应的 2-芳基-1-甲基喹啉- 4(1 H)-酮和2-芳基-4-甲氧基喹啉衍生物。质谱分析的结果证实了气相中 4-喹啉酮和 4-羟基喹啉异构体的共存，这得到了量子化学计算的支持。
• Synthesis, in vitro and in silico enzyme (COX-1/2 & LOX-5), free radical scavenging and cytotoxicity profiling of the 2,4-dicarbo substituted quinazoline 3-oxides
  作者：Malose J. Mphahlele、Eugene E. Onwu、Emmanuel N. Agbo、Marole M. Maluleka、Garland K. More、Yee Siew Choong

  DOI：10.1007/s00044-021-02811-9

  日期：2022.1

  enzymatic assays in vitro and in silico for potential inhibitory effect against cyclooxygenase-1/2 (COX-1/2) and lipoxygenase-5 activities as well as for free radical scavenging potential and cytotoxicity. The 6-bromo (3k) and 6-iodo substituted 2-(4-chlorophenyl)-4-methylquinazoline 3-oxide (3q) exhibited significant inhibitory effect against both COX-1 (IC50 = 13.9 ± 3.21 µM and 9.7 ± 0.09 µM, respectively)

  一系列 3-甲基喹唑啉 3-氧化物衍生物通过体外和计算机上的酶促测定对环氧合酶-1/2 (COX-1/2 )和脂加氧酶-5 活性的潜在抑制作用以及自由基清除能力进行了评估和细胞毒性。6-溴 ( 3k ) 和 6-碘取代的 2-(4-氯苯基)-4-甲基喹唑啉 3-氧化物 ( 3q ) 对 COX-1 均表现出显着的抑制作用 (IC 50  = 13.9 ± 3.21 µM 和 9.7 ± 0.09 µM，分别）和 COX-2（IC 50  = 6.4 ± 0.74 µM 和 4.6 ± 1.45 µM，分别）与槲皮素（IC 50 = 13.84 ± 1.57 µM 和 5.06 ± 2.60 µM，分别）。然而，与选择性 COX-2 抑制剂塞来昔布相比，它们的活性适中，对 COX-1 和 COX-2 的IC 50值分别为 7.35 ± 0.88 µM 和 0.62 ± 0.74 µM。这两种化合物对
• 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。
• E-N-(2-acetyl-phenyl)-3-phenyl-acrylamide targets abrin and ricin toxicity: Hitting two toxins with one stone
  作者：Pooja Phatak、Vinita Chauhan、Ram Kumar Dhaked、Uma Pathak、Nandita Saxena

  DOI：10.1016/j.biopha.2021.112134

  日期：2021.11
• 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.