2-(2,6-difluorophenoxy)ethylamine | 13697-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2,6-difluorophenoxy)ethylamine
• 英文别名: 2-(2,6-difluorophenoxy)ethan-1-amine；2,6-Difluor-1-(2-aminoethoxy)-benzol；2-(2,6-Difluorphenoxy)ethylamin；2-<2.6-Difluor-phenoxy>-ethylamin；2-(2,6-difluorophenoxy)ethanamine
• CAS: 13697-90-0
• 化学式: C₈H₉F₂NO
• 分子量: 173.162
• InChiKey: KVZOWNYWTLIPIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,6-difluorophenoxy)ethylamine 、 (2R)-2-(iodomethyl)-1,4-benzodioxane 以 异丙醇 为溶剂， 反应 18.0h， 以42%的产率得到(S)-2-[((2-(2,6-difluorophenoxy)ethyl)amino)methyl]-1,4-benzodioxane
  参考文献：
  名称：

  QSAR study for a novel series of ortho disubstituted phenoxy analogues of α1-adrenoceptor antagonist WB4101

  摘要：

  On the basis of the affinities at the alpha(1a)-, alpha(1b)- and alpha(1d)-adrenoceptors and the 5-HT1A receptor of a previous series of sixteen 2-[(2-phenoxyethyl)aminomethyl]-1,4-benzodioxanes ortho monosubstituted at the phenoxy moiety, a number of ortho disubstituted analogues were designed, synthesized in both the enantiomeric forms and tested in binding assays on the same receptors. The affinity values of the new compounds 1-11 were compared with those of the enantiomers of the 2,6-dimethoxyphenoxy analogue, the well-known alpha 1 antagonist WB4101, and of the ortho monosubstituted derivatives, suggesting some distinctive aspects of the interaction of the phenoxy moiety, in particular with the alpha 1a-AR and the 5-HT1A receptor, of the monosubstituted and the disubstituted compounds. A classical quantitative structure-activity relationship (Hansch) analysis was applied to the whole set of the S enantiomers of the ortho mono- and disubstituted WB4101 analogues (26 compounds), finding a very good correlation for the a,, affinity. For this latter, a significant parabolic relationship was also found with the volume of the two ortho substituents. Diametrically opposite, the same relationships for the 5-HT1A exhibit low or insignificant correlation coefficients. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.04.004
• 作为产物：
  描述：

  2,6-二氟苯酚 在 吡啶 、 sodium azide 、 potassium carbonate 、 一水合肼 、 1,3-丙二醇 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 31.0h， 生成 2-(2,6-difluorophenoxy)ethylamine
  参考文献：
  名称：

  QSAR study for a novel series of ortho disubstituted phenoxy analogues of α1-adrenoceptor antagonist WB4101

  摘要：

  On the basis of the affinities at the alpha(1a)-, alpha(1b)- and alpha(1d)-adrenoceptors and the 5-HT1A receptor of a previous series of sixteen 2-[(2-phenoxyethyl)aminomethyl]-1,4-benzodioxanes ortho monosubstituted at the phenoxy moiety, a number of ortho disubstituted analogues were designed, synthesized in both the enantiomeric forms and tested in binding assays on the same receptors. The affinity values of the new compounds 1-11 were compared with those of the enantiomers of the 2,6-dimethoxyphenoxy analogue, the well-known alpha 1 antagonist WB4101, and of the ortho monosubstituted derivatives, suggesting some distinctive aspects of the interaction of the phenoxy moiety, in particular with the alpha 1a-AR and the 5-HT1A receptor, of the monosubstituted and the disubstituted compounds. A classical quantitative structure-activity relationship (Hansch) analysis was applied to the whole set of the S enantiomers of the ortho mono- and disubstituted WB4101 analogues (26 compounds), finding a very good correlation for the a,, affinity. For this latter, a significant parabolic relationship was also found with the volume of the two ortho substituents. Diametrically opposite, the same relationships for the 5-HT1A exhibit low or insignificant correlation coefficients. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.04.004

文献信息

• [EN] ASPARAGINE DERIVATIVES AND METHODS OF USING SAME<br/>[FR] DÉRIVÉS D'ASPARAGINE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SENDA BIOSCIENCES INC

  公开号：WO2021252640A1

  公开（公告）日：2021-12-16

  The present disclosure relates to compounds of formulas (A) and (I), pharmaceutically acceptable salts thereof, and solvates of any of the foregoing, pharmaceutical compositions comprising the same, methods of preparing the same, intermediate compounds useful for preparing the same, and methods for treating or prophylaxis of diseases, in particular cancer, such as colorectal cancer, using the same.

  本公开涉及式（A）和（I）的化合物，其药学上可接受的盐，以及任何上述化合物的溶剂化合物，包括相同的药物组合物，制备相同的方法，用于制备相同的中间化合物，以及使用相同的方法治疗或预防疾病，特别是癌症，如结直肠癌。
• Discovery of novel selective phosphodiesterase‑1 inhibitors for the treatment of acute myelogenous leukemia
  作者：Mei-Ling Le、Yi-Yi Yang、Mei-Yan Jiang、Chuan Han、Zhi-Rong Guo、Run-Duo Liu、Zheng-Jiong Zhao、Qian Zhou、Shijun Wen、Yinuo Wu

  DOI：10.1016/j.bioorg.2024.107114

  日期：2024.3

  Acute myelogenous leukemia (AML) is the most common form of acute leukemia in adults. PDE1 (Phosphodiesterase 1) is a subfamily of the PDE super-enzyme families that can hydrolyze the second messengers cAMP and cGMP simultaneously. Previous research has shown that suppressing the gene expression of PDE1 can trigger apoptosis of human leukemia cells. However, no selective PDE1 inhibitors have been used

  急性髓性白血病（AML）是成人中最常见的急性白血病。 PDE1（磷酸二酯酶1）是PDE超级酶家族的一个亚家族，可以同时水解第二信使cAMP和cGMP。此前的研究表明，抑制PDE1基因表达可以引发人类白血病细胞凋亡。然而，尚未使用选择性 PDE1 抑制剂来探索 PDE1 是否是治疗 AML 的潜在靶点。基于我们之前报道的PDE9/PDE1双重抑制剂11a，本研究设计了一系列新型吡唑并嘧啶酮衍生物。先导化合物6c对 PDE1 的 IC 50为 7.5 nM，比其他 PDE 具有优异的选择性和良好的代谢稳定性。在AML细胞中，化合物6c显着抑制增殖并诱导细胞凋亡。进一步的实验表明， 6c诱导的细胞凋亡是通过线粒体依赖性途径，通过降低 Bcl-2/Bax 的比率并增加 caspase-3、7、9 和 PARP 的裂解来实现的。所有这些结果表明 PDE1 可能是 AML 的新靶点。
• 一种嘧啶酮类衍生物及其制备方法和应用
  申请人：中山大学

  公开号：CN115368367A

  公开（公告）日：2022-11-22

  本发明属于生物医药技术领域，具体涉及一种嘧啶酮类衍生物及其制备方法和应用。该嘧啶酮类衍生物对磷酸二酯酶一型(PDE1)表现出良好的抑制作用，可作为磷酸二酯酶一型抑制剂应用；并且根据现有技术对磷酸二酯酶一型相关疾病的研究，本发明嘧啶酮类衍生物还可以进一步应用于肺动脉高压、特发性肺纤维化等与磷酸二酯酶一型相关疾病的治疗中，可以提供更多的可选药物，具有重要的药用价值和临床应用前景。另外的，本发明嘧啶酮类衍生物结构新颖，制备方法简单，非常适用于大规模工业生产及应用。
• The synthesis and activity of some 2,6-difluorophenyl-substituted compounds
  作者：Anthony M. Roe、R. A. Burton、G. L. Willey、M. W. Baines、A. C. Rasmussen

  DOI：10.1021/jm00310a026

  日期：1968.7
• QSAR study for a novel series of ortho disubstituted phenoxy analogues of α1-adrenoceptor antagonist WB4101
  作者：M. Pallavicini、L. Fumagalli、M. Gobbi、C. Bolchi、S. Colleoni、B. Moroni、A. Pedretti、C. Rusconi、G. Vistoli、E. Valoti

  DOI：10.1016/j.ejmech.2006.04.004

  日期：2006.9

  On the basis of the affinities at the alpha(1a)-, alpha(1b)- and alpha(1d)-adrenoceptors and the 5-HT1A receptor of a previous series of sixteen 2-[(2-phenoxyethyl)aminomethyl]-1,4-benzodioxanes ortho monosubstituted at the phenoxy moiety, a number of ortho disubstituted analogues were designed, synthesized in both the enantiomeric forms and tested in binding assays on the same receptors. The affinity values of the new compounds 1-11 were compared with those of the enantiomers of the 2,6-dimethoxyphenoxy analogue, the well-known alpha 1 antagonist WB4101, and of the ortho monosubstituted derivatives, suggesting some distinctive aspects of the interaction of the phenoxy moiety, in particular with the alpha 1a-AR and the 5-HT1A receptor, of the monosubstituted and the disubstituted compounds. A classical quantitative structure-activity relationship (Hansch) analysis was applied to the whole set of the S enantiomers of the ortho mono- and disubstituted WB4101 analogues (26 compounds), finding a very good correlation for the a,, affinity. For this latter, a significant parabolic relationship was also found with the volume of the two ortho substituents. Diametrically opposite, the same relationships for the 5-HT1A exhibit low or insignificant correlation coefficients. (c) 2006 Elsevier SAS. All rights reserved.