(E)-1-(2-乙氧基苯基)-N-羟基甲亚胺 | 352220-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (E)-1-(2-乙氧基苯基)-N-羟基甲亚胺
• 英文名称: 2-ethoxybenzaldehyde oxime
• 英文别名: Benzaldehyde, 2-ethoxy-, oxime；N-[(2-ethoxyphenyl)methylidene]hydroxylamine
• CAS: 352220-16-7
• 化学式: C₉H₁₁NO₂
• mdl: MFCD03931940
• 分子量: 165.192
• InChiKey: WZRKOXBTHOWETA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-乙氧基苯基)-N-羟基甲亚胺 在 三氯异氰尿酸 、 盐酸羟胺 、 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 3-(2-ethoxyphenyl)-N-hydroxy-4,5-dihydroisoxazole-5-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Hydroxamic Acid Derivatives as Promising Agents for the Management of Chagas Disease

  摘要：

  Today, there are approximately 8 million cases of Chagas disease in the southern cone of South America alone, and about 100 million people are living with the risk of becoming infected. The present pharmacotherapy is sometimes ineffective and has serious side effects. Here, we report a series of 4,5 ''. -dihydroisoxazoles incorporating hydroxamate moieties, which act as effective inhibitors of the carbonic anhydrase (CA) from Trypanosoma cruzi (TcCA). One compound (5g)was evaluated in detail and shows promising features as an antitrypanosomal agent. Excellent values for the inhibition of growth for all three developmental forms of the parasite were observed at low concentrations of 5g (IC50 values from 7.0 to <1 mu M). The compound has a selectivity index (SI) of 6.7 and no cytotoxicity to macrophage cells. Preliminary in vivo data showed that 5g reduces bloodstream parasites and that all treated mice survived; it was also more effective than the standard drug benznidazole.

  DOI：

  10.1021/jm400902y
• 作为产物：
  描述：

  2-乙氧基苯甲醛 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-1-(2-乙氧基苯基)-N-羟基甲亚胺
  参考文献：
  名称：

  通过基于对接的虚拟筛选和结构修饰鉴定 3-芳基-5-甲基-异恶唑-4-甲酰胺衍生物和类似物作为新型 HIF-2α 激动剂

  摘要：

  缺氧诱导因子 2 (HIF-2) 是细胞对低氧水平反应的关键转录因子，特别是在调节促红细胞生成素 (EPO) 产生方面。对 HIF-2α 抑制剂晶体结构进行基于对接的虚拟筛选，意外地发现 3-苯基-5-甲基-异恶唑-4-甲酰胺衍生物是 HIF-2α 激动剂的热门药物。化合物的进一步结构优化导致一系列具有新型支架的 HIF-2α 激动剂的发现。最有前途的化合物 和 表现出有效的 HIF-2α 激动活性，EC 值分别为 2.29 μM 和 1.78 μM。分子动力学模拟揭示了它们变构增强 HIF-2 二聚化的能力，这揭示了它们的作用机制。此外，该化合物表现出良好的药代动力学 (PK) 特征，口服生物利用度高达 68.71%。这些发现强烈表明该化合物是治疗肾性贫血的有利先导化合物。

  DOI：

  10.1016/j.ejmech.2024.116227

文献信息

• Metal-free DBU promoted regioselective synthesis of isoxazoles and isoxazolines
  作者：Shabber Mohammed、Ram A. Vishwakarma、Sandip B. Bharate

  DOI：10.1039/c4ra14694h

  日期：——

  8-diazabicyclo[5.4.0]undec-7-ene (DBU) promoted regioselective synthesis of 3,5-disubstituted isoxazoles and isoxazolines from aldoximes has been described. This method allows the reaction to proceed efficiently on aldoximes containing unprotected phenolic hydroxyl groups. Furthermore, with the use of higher equivalents of N-chlorosuccinimide, chloro-substituted isoxazoles and isoxazolines were obtained as the

  已经描述了一种新的简单有效的无金属的1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）促进的由醛肟合成的3,5-二取代的异恶唑和异恶唑啉的区域选择性合成。该方法允许反应在含有未保护的酚羟基的醛肟上有效地进行。此外，通过使用较高当量的N-氯代琥珀酰亚胺，通过串联一锅的1，3-偶极环加成，然后进行区域选择性氯化，获得了氯取代的异恶唑和异恶唑啉作为唯一产物。
• 一种含二氢异噁唑的苯并咪唑类化合物及其 应用
  申请人：浙江工业大学

  公开号：CN104496976B

  公开（公告）日：2017-01-18

  本发明公开了一种含二氢异噁唑的苯并咪唑类化合物及其应用，所述含二氢异噁唑的苯并咪唑类化合物是式(Ⅰ)所示的1‑[3‑R‑二氢异噁唑‑5‑亚甲基]‑2‑三氟甲基‑1H‑苯并咪唑[d]，其中R取代基为取代苯基或2‑(3‑甲基噻吩)，取代苯基上的取代基为一个或多个，取代基各自独立选自下列之一：卤素、C1～C4的烷基、C1～C4的烷氧基、三氟甲基、氰基或二(C1～C2烷基)取代的氨基。所述的1‑[3‑R‑二氢异噁唑‑5‑亚甲基]‑2‑三氟甲基‑1H‑苯并咪唑[d]可应用于制备抗菌剂。本发明提供的1‑[3‑R‑二氢异噁唑‑5‑亚甲基]‑2‑三氟甲基‑1H‑苯并咪唑[d]对多种菌体菌(枯草芽孢杆菌、大肠杆菌、金黄色葡萄球菌、烟曲霉)有抑制作用，且合成工艺简单，易于产业化。
• 一种含异噁唑的苯并咪唑类化合物及其应用
  申请人：浙江工业大学

  公开号：CN104496975B

  公开（公告）日：2017-01-11

  本发明公开了一种含异噁唑的苯并咪唑类化合物及其应用，所述含异噁唑的苯并咪唑类化合物为式(Ⅰ)所示的1‑[3‑R‑异噁唑‑5‑亚甲基]‑2‑三氟甲基‑1H‑苯并咪唑[d]，其中R为取代苯基或2‑(3‑甲基噻吩)，取代苯基上的取代基为一个或多个，取代基各自独立选自卤素、C1～C4的烷基、C1～C4的烷氧基、三氟甲基或二(C1～C2烷基)取代的氨基。所述的1‑[3‑R‑异噁唑‑5‑亚甲基]‑2‑三氟甲基‑1H‑苯并咪唑[d]可用于制备抗菌剂。本发明提供的1‑[3‑R‑异噁唑‑5‑亚甲基]‑2‑三氟甲基‑1H‑苯并咪唑[d]对多种菌体菌(枯草芽孢杆菌、大肠杆菌、金黄色葡萄球菌、烟曲霉)有抑制作用，且合成工艺简单，易于产业化。
• Design, Synthesis, and Evaluation of Hydroxamic Acid Derivatives as Promising Agents for the Management of Chagas Disease
  作者：Giseli Capaci Rodrigues、Daniel Ferreira Feijó、Marcelo Torres Bozza、Peiwen Pan、Daniela Vullo、Seppo Parkkila、Claudiu T. Supuran、Clemente Capasso、Alcino Palermo Aguiar、Alane Beatriz Vermelho

  DOI：10.1021/jm400902y

  日期：2014.1.23

  Today, there are approximately 8 million cases of Chagas disease in the southern cone of South America alone, and about 100 million people are living with the risk of becoming infected. The present pharmacotherapy is sometimes ineffective and has serious side effects. Here, we report a series of 4,5 ''. -dihydroisoxazoles incorporating hydroxamate moieties, which act as effective inhibitors of the carbonic anhydrase (CA) from Trypanosoma cruzi (TcCA). One compound (5g)was evaluated in detail and shows promising features as an antitrypanosomal agent. Excellent values for the inhibition of growth for all three developmental forms of the parasite were observed at low concentrations of 5g (IC50 values from 7.0 to <1 mu M). The compound has a selectivity index (SI) of 6.7 and no cytotoxicity to macrophage cells. Preliminary in vivo data showed that 5g reduces bloodstream parasites and that all treated mice survived; it was also more effective than the standard drug benznidazole.
• Synthesis of 5-arylisoxazole-3-carboxylates derived from salicylaldehyde
  作者：S. K. Petkevich、E. A. Dikusar、V. I. Potkin、I. V. Mikhei

  DOI：10.1134/s1070428015010066

  日期：2015.1

  A procedure has been developed for the synthesis of 5-arylisoxazole-3-carboxylates on the basis of phenols and oximes derived from salicylaldehyde. Selective reduction of 4-(2-ethoxybenzylideneaminophenyl) 5-arylisoxazole-3-carboxylates afforded the corresponding amines.