4-[[(4-methylphenyl)sulfonyl]oxy]benzaldehyde oxime | 310873-47-3

• 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: 4-[[(4-methylphenyl)sulfonyl]oxy]benzaldehyde oxime
• 英文别名: [4-(Hydroxyiminomethyl)phenyl] 4-methylbenzenesulfonate
• CAS: 310873-47-3
• 化学式: C₁₄H₁₃NO₄S
• mdl: MFCD00820229
• 分子量: 291.328
• InChiKey: SWDMJPAJFORXTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  84.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[[(4-methylphenyl)sulfonyl]oxy]benzaldehyde oxime 在 sodium hypochlorite 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 5-(N,N-dimethylaminomethyl)-3-(4-(tosyloxy)phenyl)-4,5-dihydroisoxazole
  参考文献：
  名称：

  Synthesis and Biochemical Evaluation of Δ²-Isoxazoline Derivatives as DNA Methyltransferase 1 Inhibitors

  摘要：

  A series of Delta(2)-isoxazoline constrained analogues of procaine/procainamide (7a-k and 8a-k) were prepared and their inhibitory activity against DNA methyltransferase I (DNMT1) was tested. Among them, derivative 7b is far more potent in vitro (IC50 = 150 mu M) than other non-nucleoside inhibitors and also exhibits a strong and dose-dependent antiproliferative effect against HCT116 human colon carcinoma cells. The binding mode of 7b with the enzyme was also investigated by means of a simple competition assay as well as of docking simulations conducted using the recently published crystallographic structure of human DNMT1. On the basis of the findings, we assessed that the mode of inhibition of 7b is consistent with a competition with the cofactor and propose it as a novel lead compound for the development of non-nucleoside DNMT inhibitors.

  DOI：

  10.1021/jm2010404
• 作为产物：
  描述：

  4-tosyloxybenzaldehyde 在 盐酸羟胺 、 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成 4-[[(4-methylphenyl)sulfonyl]oxy]benzaldehyde oxime
  参考文献：
  名称：

  Synthesis and Biochemical Evaluation of Δ²-Isoxazoline Derivatives as DNA Methyltransferase 1 Inhibitors

  摘要：

  A series of Delta(2)-isoxazoline constrained analogues of procaine/procainamide (7a-k and 8a-k) were prepared and their inhibitory activity against DNA methyltransferase I (DNMT1) was tested. Among them, derivative 7b is far more potent in vitro (IC50 = 150 mu M) than other non-nucleoside inhibitors and also exhibits a strong and dose-dependent antiproliferative effect against HCT116 human colon carcinoma cells. The binding mode of 7b with the enzyme was also investigated by means of a simple competition assay as well as of docking simulations conducted using the recently published crystallographic structure of human DNMT1. On the basis of the findings, we assessed that the mode of inhibition of 7b is consistent with a competition with the cofactor and propose it as a novel lead compound for the development of non-nucleoside DNMT inhibitors.

  DOI：

  10.1021/jm2010404

文献信息

• A metal-free approach for in situ regioselective synthesis of isoxazoles via 1,3 dipolar cycloaddition reaction of nitrile oxide with propargyl bromide
  作者：Rajeshwar Reddy Aleti、Srinivasulu Cherukupalli、Sanjeev Dhawan、Vishal Kumar、Pankaj S. Girase、Sachin Mohite、Rajshekhar Karpoormath

  DOI：10.1007/s11696-021-02009-8

  日期：2022.5

  Herein, we report a multi-component reaction (MCRs) to synthesise a range of 3-phenyl-5-(bromomethyl)isoxazoles analogues using DMF/water mixture as solvent, providing desired products in good to excellent yields. The reaction efficiently involves the 1,3-dipolar cycloaddition reaction between propargyl bromide and in situ-generated α-chloro aldoximes. The protocol proceeded well under mild metal-free

  在此，我们报告了使用 DMF/水混合物作为溶剂合成一系列 3-苯基-5-(溴甲基)异恶唑类似物的多组分反应 (MCR)，以良好至优异的收率提供所需的产品。该反应有效地涉及炔丙基溴和原位生成的 α-氯醛肟之间的 1,3-偶极环加成反应。该协议在温和的无金属条件下进行得很好，并显示出对多种取代基的耐受性。 图形概要
• Synthesis and Biochemical Evaluation of Δ²-Isoxazoline Derivatives as DNA Methyltransferase 1 Inhibitors
  作者：Sabrina Castellano、Dirk Kuck、Monica Viviano、Jakyung Yoo、Fabian López-Vallejo、Paola Conti、Lucia Tamborini、Andrea Pinto、José L. Medina-Franco、Gianluca Sbardella

  DOI：10.1021/jm2010404

  日期：2011.11.10

  A series of Delta(2)-isoxazoline constrained analogues of procaine/procainamide (7a-k and 8a-k) were prepared and their inhibitory activity against DNA methyltransferase I (DNMT1) was tested. Among them, derivative 7b is far more potent in vitro (IC50 = 150 mu M) than other non-nucleoside inhibitors and also exhibits a strong and dose-dependent antiproliferative effect against HCT116 human colon carcinoma cells. The binding mode of 7b with the enzyme was also investigated by means of a simple competition assay as well as of docking simulations conducted using the recently published crystallographic structure of human DNMT1. On the basis of the findings, we assessed that the mode of inhibition of 7b is consistent with a competition with the cofactor and propose it as a novel lead compound for the development of non-nucleoside DNMT inhibitors.