1-[2-hydroxy-4-(2-morpholinoethoxy)phenyl]-1-ethanone | 70744-30-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2-hydroxy-4-(2-morpholinoethoxy)phenyl]-1-ethanone
• 英文别名: 1-[2-hydroxy-4-(2-morpholin-4-yl-ethoxy)-phenyl]-ethanone；4-(2-Morpholino-aethoxy)-2-hydroxy-acetophenon；1-[2-Hydroxy-4-(2-morpholin-4-ylethoxy)phenyl]ethanone
• CAS: 70744-30-8
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: VKRLXEQXNWVQTR-UHFFFAOYSA-N

物化性质

• 沸点：
  446.5±45.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[2-hydroxy-4-(2-morpholinoethoxy)phenyl]-1-ethanone 在 盐酸 、 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 96.0h， 生成 2-(4-methoxyphenyl)-7-(2-morpholinoethoxy)-4-chromanone
  参考文献：
  名称：

  Homopterocarpanes as bridged triarylethylene analogues: synthesis and antagonistic effects in human MCF-7 breast cancer cells

  摘要：

  A series of new compounds structurally derived from 6a,12a-dihydro-6H,7H-[1]-benzopyran-[4,3-b]-benzopyran (homopterocarpane) was efficiently synthesized by reduction of the corresponding pyrilium salts obtained by treatment of selected flavanones and aldehydes with anhydrous HClO4. Cytotoxic effects on the human breast cancer cell line MCF-7 and antiestrogenic activity (only for compounds which resulted more active than tamoxifen (TAM)) on MCF-7 cells stimulated by 17beta-estradiol were evaluated. In vivo antiestrogenic activity and the relative binding affinity were also assessed. Some of the new compounds (4c, 4h, 4i and 4l) showed a biological activity in the micromolar range, and were more potent than TAM taken as the reference.

  DOI：

  10.1016/j.farmac.2004.09.006
• 作为产物：
  描述：

  1-(4-羟基-2-甲氧基苯基)乙酮 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 1-[2-hydroxy-4-(2-morpholinoethoxy)phenyl]-1-ethanone
  参考文献：
  名称：

  非瑟酮衍生物的设计、合成和生物活性评价作为潜在的抗 LPS 诱导的急性肺损伤的抗炎药

  摘要：

  急性肺损伤 (ALI) 是一种由炎症引起的常见且危及生命的疾病。然而，对于 ALI，有效的药物治疗很少见。天然产物被认为是药物发现的重要来源，这表明在天然产物中寻找新的抗炎药物是一种可行的方法。受非瑟酮各种生物活性的启发，我们报道了一系列非瑟酮衍生物的设计和合成，这些衍生物还评估了它们在 J774A.1 巨噬细胞中的抗炎活性。所得衍生物大部分在体外实验中均能有效抑制IL-6和TNF-α的释放，且无细胞毒性。最有希望的化合物5b在体内表现出显着LPS 诱导的小鼠 ALI 模型中的抗炎活性。总的来说，这项研究可以为治疗 ALI 提供新的候选者。

  DOI：

  10.1016/j.bmc.2021.116456

文献信息

• Substituted benzofuran, benzopyrrole, benzothiophene, and structurally related complement inhibitors
  申请人：BioCryst Pharmaceuticals, Inc.

  公开号：US11021458B2

  公开（公告）日：2021-06-01

  Disclosed are compounds of formulae I and II, and pharmaceutically acceptable salts and prodrugs thereof, which are inhibitors of the complement system. Also provided are pharmaceutical compositions comprising such a compound, and methods of using the compounds and compositions in the treatment or prevention of a disease or condition characterized by aberrant complement system activity.

  公开了式 I 和 II 的化合物及其药学上可接受的盐和原药，它们是补体系统的抑制剂。还提供了包含此类化合物的药物组合物，以及使用这些化合物和组合物治疗或预防以补体系统活性异常为特征的疾病或病症的方法。
• β-Phenoxyethylamines with Local Anesthetic and Antispasmodic Activity
  作者：Paolo. Da Re、Lucia. Verlicchi、Ivo. Setnikar

  DOI：10.1021/jm00314a036

  日期：1967.3
• Homopterocarpanes as bridged triarylethylene analogues: synthesis and antagonistic effects in human MCF-7 breast cancer cells
  作者：Angela Rampa、Alessandra Bisi、Federica Belluti、Silvia Gobbi、Lorna Piazzi、Piero Valenti、Antonella Zampiron、Anna Caputo、Katia Varani、Pier Andrea Borea、Maria Carrara

  DOI：10.1016/j.farmac.2004.09.006

  日期：2005.2

  A series of new compounds structurally derived from 6a,12a-dihydro-6H,7H-[1]-benzopyran-[4,3-b]-benzopyran (homopterocarpane) was efficiently synthesized by reduction of the corresponding pyrilium salts obtained by treatment of selected flavanones and aldehydes with anhydrous HClO4. Cytotoxic effects on the human breast cancer cell line MCF-7 and antiestrogenic activity (only for compounds which resulted more active than tamoxifen (TAM)) on MCF-7 cells stimulated by 17beta-estradiol were evaluated. In vivo antiestrogenic activity and the relative binding affinity were also assessed. Some of the new compounds (4c, 4h, 4i and 4l) showed a biological activity in the micromolar range, and were more potent than TAM taken as the reference.
• Design, synthesis and bioactivity evaluation of fisetin derivatives as potential anti-inflammatory agents against LPS-induced acute lung injury
  作者：Xiemin Wang、Jun Yang、Bingyu Ding、Pan Chen、Zhengwei Xu、Yunxi Zhao、Pengqin Chen、Nipon Chattipakorn、Guang Liang、Di Wu、Qidong Tang

  DOI：10.1016/j.bmc.2021.116456

  日期：2021.11

  various biological activities of fisetin, we reported the design and synthesis of a series of fisetin derivatives which were also evaluated for their anti-inflammatory activities in J774A.1 macrophages. Most of the obtain derivatives could effectively inhibit the release of IL-6 and TNF-α in vitro experiments without cytotoxicity. The most promising compound 5b exhibited significant in vivo anti-inflammatory

  急性肺损伤 (ALI) 是一种由炎症引起的常见且危及生命的疾病。然而，对于 ALI，有效的药物治疗很少见。天然产物被认为是药物发现的重要来源，这表明在天然产物中寻找新的抗炎药物是一种可行的方法。受非瑟酮各种生物活性的启发，我们报道了一系列非瑟酮衍生物的设计和合成，这些衍生物还评估了它们在 J774A.1 巨噬细胞中的抗炎活性。所得衍生物大部分在体外实验中均能有效抑制IL-6和TNF-α的释放，且无细胞毒性。最有希望的化合物5b在体内表现出显着LPS 诱导的小鼠 ALI 模型中的抗炎活性。总的来说，这项研究可以为治疗 ALI 提供新的候选者。