5-hydroxymethyl-3-(4-nitrophenyl)-4,5-dihydroisoxazole | 605663-77-2

• 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: 5-hydroxymethyl-3-(4-nitrophenyl)-4,5-dihydroisoxazole
• 英文别名: (3-(4-Nnitrophenyl)-4,5-dihydroisoxazol-5-yl)methanol；[3-(4-Nitrophenyl)-4,5-dihydro-1,2-oxazol-5-yl]methanol
• CAS: 605663-77-2
• 化学式: C₁₀H₁₀N₂O₄
• 分子量: 222.2
• InChiKey: SUZOVVXVIZKQSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  87.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-hydroxymethyl-3-(4-nitrophenyl)-4,5-dihydroisoxazole 在 盐酸 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 13.17h， 生成 5-(N,N-dimethylaminomethyl)-3-(4-aminophenyl)-4,5-dihydroisoxazole hydrochloride
  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：

  1-(4-nitrophenyl)but-3-en-1-one oxime 在 2,2,2-三氟苯乙酮 、 双氧水 作用下， 以 水 、 乙腈 、 叔丁醇 为溶剂， 反应 18.0h， 以95%的产率得到5-hydroxymethyl-3-(4-nitrophenyl)-4,5-dihydroisoxazole
  参考文献：
  名称：

  一锅氧化烯丙基肟的绿色有机催化合成异恶唑啉

  摘要：

  从烯丙基肟开发了一种绿色，可持续，有机催化和高效的异恶唑啉合成方法。利用H 2 O 2作为绿色氧化剂，利用2,2,2-三氟苯乙酮催化的烯丙基肟的氧化反应，以引入廉价且环境友好的方法合成取代的异恶唑啉。芳香族和脂肪族部分的各种取代方式都具有良好的耐受性，从而导致异恶唑啉的产率中等至优异。

  DOI：

  10.1021/acs.orglett.6b03380

文献信息

• Synthesis and pharmacological evaluation of 1,3,4-oxadiazole bearing bis(heterocycle) derivatives as anti-inflammatory and analgesic agents
  作者：B. Jayashankar、K.M. Lokanath Rai、N. Baskaran、H.S. Sathish

  DOI：10.1016/j.ejmech.2009.04.006

  日期：2009.10

  oxide with allyl alcohol followed by intramolecular 1,3-diploar cycloaddition reaction of nitrile imine with carbonyl group. All the newly synthesized compounds were screened for their anti-inflammatory and analgesic activities. Among the list of compounds (7a–k) studied, 7d, 7g, 7j, and 7k exhibited excellent activity comparable to ibuprofen and aspirin at the similar dosages.

  通过一氧化氮与烯丙醇的[3 + 2]-环加成反应，然后与腈亚胺与羰基的分子内1,3-二齿环加成反应，合成了一系列新型的醚键联双（杂环）。筛选所有新合成的化合物的抗炎和镇痛活性。在研究的化合物列表（7a - k）中，在相似的剂量下7d，7g，7j和7k表现出与布洛芬和阿司匹林相当的出色活性。
• 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.
• Green Organocatalytic Synthesis of Isoxazolines via a One-Pot Oxidation of Allyloximes
  作者：Ierasia Triandafillidi、Christoforos G. Kokotos

  DOI：10.1021/acs.orglett.6b03380

  日期：2017.1.6

  A green, sustainable, organocatalytic, and efficient synthesis of isoxazolines from allyloximes was developed. A 2,2,2-trifluoroacetophenone-catalyzed oxidation of allyloximes, utilizing H2O2 as the green oxidant, was taken advantage of in order to introduce a cheap and environmentally friendly protocol for the synthesis of substituted isoxazolines. A variety of substitution patterns, both aromatic

  从烯丙基肟开发了一种绿色，可持续，有机催化和高效的异恶唑啉合成方法。利用H 2 O 2作为绿色氧化剂，利用2,2,2-三氟苯乙酮催化的烯丙基肟的氧化反应，以引入廉价且环境友好的方法合成取代的异恶唑啉。芳香族和脂肪族部分的各种取代方式都具有良好的耐受性，从而导致异恶唑啉的产率中等至优异。