4-acetyl-N-ethyl-N-methylbenzenesulfonamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetyl-N-ethyl-N-methylbenzenesulfonamide
• 英文别名: 1-(4-(N-ethyl-N-methylsulfonyl)phenyl)ethanone
• 化学式: C₁₁H₁₅NO₃S
• 分子量: 241.311
• InChiKey: JKEUDUNHEYUJSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-acetyl-N-ethyl-N-methylbenzenesulfonamide 在 溴 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 以87%的产率得到4-(2-bromoacetyl)-N-ethyl-N-methylbenzenesulfonamide
  参考文献：
  名称：

  N-乙基-N-甲基苯磺酰胺衍生物作为有效抗菌和抗增殖剂的设计、合成、分子对接和生物筛选

  摘要：

  摘要 磺胺类药物是最著名的药物，已被用于制备有效的抗增殖剂。因此，本文描述了具有各种生物活性部分的新系列 N-乙基-N-甲基苯磺酰胺衍生物的合成，例如噻唑 3、4、11、12、14、15、21、1,3,4-噻二嗪 6 , 咪唑 [2,1-b] 噻唑 8、2-氧代-2H-色烯 17 和 3-氧代-3H-苯并[f] 色烯 19，以 4-(2-溴乙酰基)-N-乙基-N 开始-甲基苯磺酰胺 (2)，由 4-乙酰基-N-乙基-N-甲基苯磺酰胺 (1) 与溴在二恶烷/二乙醚混合物中搅拌下相互作用合成。通过元素分析和光谱数据证明了新结构。然而，他们还筛选了它们对两种不同人类细胞系的细胞毒活性，肺泡腺癌（肺）（A-549）和肝癌（HepG2）和抗菌素。具有咪唑并[2,1-b]噻唑部分的化合物8对(A-549)细胞系(SI；30.77)表现出最有效的细胞毒活性。同时，具有 2-氰基甲基噻唑部分的化合物 11

  DOI：

  10.1016/j.molstruc.2019.04.048

文献信息

• Study of reactivity of cyanoacetohydrazonoethyl-<i>N</i>-ethyl-<i>N</i>-methyl benzenesulfonamide: preparation of novel anticancer and antimicrobial active heterocyclic benzenesulfonamide derivatives and their molecular docking against dihydrofolate reductase
  作者：Khaled F. Debbabi、Sami A. Al-Harbi、Hamed M. Al-Saidi、Enas H. Aljuhani、Shimaa M. Abd El-Gilil、Mahmoud S. Bashandy

  DOI：10.1080/14756366.2016.1217851

  日期：2016.11.4

  compounds were confirmed by elemental analysis, IR, 1H NMR, 13C NMR, 19F NMR and MS spectral data. All the newly synthesized heterocyclic sulfonamides were evaluated as in-vitro anti-breast cancer cell line (MCF7) and as in-vitro antimicrobial agents. Compounds 8, 5 and 11 were more active than MTX reference drug and compounds 12, 7, 4, 14, 5 and 8 were highly potent against Klebsiella pneumonia. Molecular

  本文介绍了一些具有生物活性噻吩3、4、5、6，香豆素8，苯并香豆素9，噻唑7，哌啶10，吡咯烷11，吡唑14和吡啶12、13的新型杂环磺酰胺的合成。从4-（ 1-（2-（2-氰基乙酰基）肼基）乙基）-N-乙基-N-甲基苯磺酰胺（2），其是通过将苯乙酮衍生物1与2-氰基乙酰肼缩合而制备的。通过元素分析，IR，1 H NMR，13 C NMR，19 F NMR和MS光谱数据确认了新合成的化合物的结构。所有新合成的杂环磺酰胺均被评估为体外抗乳腺癌细胞系（MCF7）和体外抗微生物剂。化合物8、5和11比MTX参比药物更具活性，化合物12、7、4、14、5和8对肺炎克雷伯菌具有很强的抵抗力。分子操作环境使用合成化合物的分子对接研究进行了虚拟筛选。结果表明，所制备的某些化合物是适合的二氢叶酸还原酶（DHFR）酶（PDBSD：4DFR）的抑制剂，并进行了进一步修饰。
• Synthesis and molecular docking against dihydrofolate reductase of novel pyridin-N-ethyl-N-methylbenzenesulfonamides as efficient anticancer and antimicrobial agents
  作者：Khaled F. Debbabi、Mahmoud S. Bashandy、Sami A. Al-Harbi、Enas H. Aljuhani、Hamed M. Al-Saidi

  DOI：10.1016/j.molstruc.2016.11.048

  日期：2017.3

  new prepared compounds were evaluated for their antitumor activities against the cell lines MCF-7 in comparison with the reference drug Doxorubicin using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) colorimetric assay. Compounds 25 , 21 , 23 with SI values of 9.72, 9.71, 8.81 respectively, exhibited better activity than doxorubicin (Dox) as a reference drug with SI value of

  摘要 本文描述了一些具有生物活性吡啶 21-28 的新型磺胺类药物的合成。以 4-(1-(2-(2-氰基乙酰基)腙)乙基)-N-乙基-N-甲基苯磺酰胺 (2) 开始，其由苯乙酮衍生物 1 与 2-氰基乙酰肼缩合制备。化合物 2 与不同的醛类即 4-氟苯甲醛、4-羟基苯甲醛和 4-N, N-二甲基苯甲醛相互作用，分别得到相应的腙-乙基-N-乙基-N-甲基苯磺酰胺 18-20，当与丙二腈和乙基反应时氰乙酸酯分别得到化合物 21-26。这些化合物 21-26 可以通过另一种反应路线通过化合物 2 与芳基丙二腈和芳基氰基乙酸乙酯在回流二恶烷中在三甲胺作为催化剂的存在下相互作用来制备。化合物 2 与丙二腈和氰基乙酸乙酯相互作用，分别得到氧代吡啶衍生物 27 和 28。与使用 3-(4,5-二甲基噻唑-2-基)-2,5-二苯基溴化四唑 (MTT) 的参考药物多柔比星相比，所有新制备的化合物都对 MCF-7
• Synthesis, Antimicrobial and Antihuman Liver Cancer Activities of Novel Sulfonamides Incorporating Benzofuran, Pyrazole, Pyrimidine, 1,4-Diazepine and Pyridine Moieties Prepared from (E)-4-(3-(Dimethylamino)acryloyl)-N-ethyl-N-methylbenzenesulfonamide
  作者：Mahmoud S. Bashandy、Sami A. Al-Harbi

  DOI：10.3987/com-15-13281

  日期：——

  Reaction of compound 1 with dimethylformamide dimethylacetal gave enaminone 2, which reacts with 1,4-benzoquinone and 4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one to afford 6 and 7, respectively. Treatment of 2 with hydroxylamine hydrochloride gave cyanoacetyl derivative 14. Enaminone 2 reacts with guanidine hydrochloride and phenylhydrazine to furnish 2-aminopyrimidine and pyrazole derivatives 15 and 16, respectively. Enaminone 2 also reacts with ethylenediamine and acetylacetone to afford the corresponding derivatives of 1,4-diazepine 18 and pyridine 20, respectively. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, H-1 NMR, C-13 NMR and MS spectral data. All the synthesized compounds were evaluated for antimicrobial activity. Compounds 6 and 20 were found to be highly active against the all microorganisms. In addition, all the compounds were tested in-vitro antihuman liver hepatocellular carcinoma cell line (HepG2). Compounds 14, 6, 18 and 16 with selectivity index (SI) values of 70.92, 55.56, 29.56 and 15.00, respectively, exhibited better activity than methotrexate (MTX) as a reference drug with SI value of 13.30. Virtual screening using molecular docking studies of the synthesized compounds was performed by Molecular Operating Environment (MOE). The results indicated that some synthesized compounds suitable inhibitor against dihydrofolate reductase (DHFR) enzyme (PDB ID: 4DFR) with further modification.