2-(4-fluoro-2-methoxyphenoxy)ethylamine | 125960-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-fluoro-2-methoxyphenoxy)ethylamine
• 英文别名: 2-(4-fluoro-2-methoxyphenoxy)ethan-1-amine；2-(4-fluoro-2-methoxyphenoxy)ethanamine
• CAS: 125960-68-1
• 化学式: C₉H₁₂FNO₂
• 分子量: 185.198
• InChiKey: UWXIVZINHGDVOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  262.0±30.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-fluoro-2-methoxyphenoxy)ethylamine 、 5-丙酮基-2-甲氧基苯磺酰胺 以 甲醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Novel Phenoxyalkylamine Derivatives. VII. Synthesis and Pharmacological Activities of 2-Alkoxy-5-((phenoxyalkylamino)alkyl)benzenesulfonamide Derivatives.

  摘要：

  为了找到一种对多巴胺D2受体亲和力具有高选择性的新的α-拮抗剂，我们对2-烷氧基-5-[(苯氧烷基氨基)烷基]苯磺酰胺衍生物的烷基链及两个苯环上的取代基进行了结构改造。发现位于分子中心的氨基部分与苯环（环A）之间的烷基链的改造是最显著的。具备1-甲基乙基作为烷基链的5-[2-[[2-(5-氟-2-甲氧基苯氧基)乙基]氨基]丙基]-2-甲氧基苯磺酰胺（II-4）表现出高α-拮抗选择性以及强效的α-拮抗活性。

  DOI：

  10.1248/cpb.40.1443
• 作为产物：
  描述：

  4-氟-2-甲氧基苯酚 在 dimethyl sulfide borane 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 丁酮 为溶剂， 反应 64.0h， 生成 2-(4-fluoro-2-methoxyphenoxy)ethylamine
  参考文献：
  名称：

  New Serotonin 5-HT_1A Receptor Agonists Endowed with Antinociceptive Activity in Vivo

  摘要：

  We report the synthesis of new compounds 4-35 based on two different openings (A and B) of the chromane ring present in the previously identified 5-HT1A receptor (5-HT1AR) ligand 3. The synthesized compounds were assessed for binding affinity, selectivity, and functional activity at the 5-HT1AR Selected candidates resulting from B opening were also evaluated for their potential antinociceptive effect in vivo and pharmacokinetic properties in vitro. Analogue 19 [2-(4-{[2-(2-ethoxyphenoxy)ethyl]amino}butyl)tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione] has been characterized as a high-affinity and potent 5-HT1AR agonist (K-i = 2.3 nM; EC50 = 19 nM). Pharmacokinetic studies indicated that compound 19 displays a good metabolic stability in human liver microsomes (t(1/2) similar to 3 h and CLint = 3.5 mL/min/kg, at 5 mu M), and a low level of protein binding (25%, at 5 mu M). Interestingly, 19 (3 mg/kg, ip, and 30 mg/kg, po) caused significant attenuation of formalin-induced behavior in early and late phases of the mouse intradermal formalin test of pain, and this in vivo effect was reversed by the selective 5-HT1AR antagonist WAY-100635. Thus, the new 5-HT1AR agonist identified in this work, 19, exhibits oral analgesic activity, and the results herein represent a step toward identifying new therapeutics for the control of pain.

  DOI：

  10.1021/jm400766k

文献信息

• N-aryloxyethylamine derivatives for the treatment of depression
  申请人：American Home Products Corp.

  公开号：US06110956A1

  公开（公告）日：2000-08-29

  Compounds effective in treating disorders of the serotonin-affected neurological systems are provided, such compounds having the following formula: ##STR1## wherein: R.sub.1 and R.sub.2 are each, independently, hydrogen, halogen, CF.sub.3, lower alkyl, lower alkoxy, MeSO.sub.2, or together can form a 5-7 membered carbocyclic or heterocyclic ring; R.sub.3 is alkoxy, halogen, hydrogen or carbamoyl; R.sub.4 is hydrogen, hydroxy, lower alkyl, or lower alkoxy; R.sub.5 is hydrogen, lower alkyl, or halogen; R.sub.6 is hydrogen, lower alkyl, or phenyl; R.sub.7 is hydrogen, lower alkyl, lower alkoxy, halogen, CN, CF.sub.3, or hydroxy; and X is (CH.sub.2).sub.n, wherein n is 0 to 3; or pharmaceutically acceptable salts thereof.

  提供了一些有效治疗受到血清素影响的神经系统疾病的化合物，这些化合物具有以下结构式：##STR1## 其中：R.sub.1和R.sub.2各自独立地是氢，卤素，CF.sub.3，较低的烷基，较低的烷氧基，MeSO.sub.2，或者一起可以形成一个5-7成员的碳环或杂环；R.sub.3是烷氧基，卤素，氢或者氨甲酰基；R.sub.4是氢，羟基，较低的烷基或较低的烷氧基；R.sub.5是氢，较低的烷基或卤素；R.sub.6是氢，较低的烷基或苯基；R.sub.7是氢，较低的烷基，较低的烷氧基，卤素，CN，CF.sub.3或羟基；X是(CH.sub.2).sub.n，其中n为0至3；或其药学上可接受的盐。
• Phenoxyethylamine derivatives, process for preparing the same, and composition for exhibiting excellent alpha-1-blocking activity containing the same
  申请人：Hokuriku Pharmaceutical Co.,Ltd

  公开号：EP0331943A1

  公开（公告）日：1989-09-13

  Phenoxyethylamine derivatives represented by the general formula (I): wherein R₁ and R₅ represent lower-alkyl, R₂ and R₃, which may be the same or different, each represents hydrogen or lower-alkyl, or represents a 5- or 6-membered ring system which may include nitrogen, oxygen or sulfur as a ring membered atom, R₄ represents hydrogen or lower-alkyl, and n represents an integer selected from 1 to 3, their optical isomers and pharmacologically-acceptable acid addition salts, which exhibit excellent α₁-blocking activity, a process for their preparation, pharmaceutical compositions thereof, and a method for the treatment of a subject afflicted with hypertension or dysuria by administrating such a compound, are all disclosed.

  通式(I)代表的苯氧基乙胺衍生物： 其中 R₁ 和 R₅ 代表低级烷基，R₂ 和 R₃ 可以相同或不同，各自代表氢或低级烷基，或 代表可包括氮、氧或硫作为环成员原子的 5 或 6 元环系统，R₄ 代表氢或低级烷基，n 代表选自 1 至 3 的整数，它们的光学异构体和药理学上可接受的酸加成盐、本发明公开了具有优异α₁阻断活性的光学异构体和药理学上可接受的酸加成盐、其制备工艺、药物组合物，以及通过施用这种化合物治疗高血压或排尿困难患者的方法。
• [EN] PYRIDIN-3-YL ACETIC ACID DERIVATIVES AS INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION<br/>[FR] DÉRIVÉS D'ACIDE PYRIDIN-3-YL-ACÉTIQUE EN TANT QU'INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'IMMUNODÉFICIENCE HUMAINE
  申请人：VIIV HEALTHCARE UK NO 5 LTD

  公开号：WO2019244066A3

  公开（公告）日：2020-03-05
• Novel Carvedilol Analogues That Suppress Store-Overload-Induced Ca²⁺ Release
  作者：Chris D. Smith、Aixia Wang、Kannan Vembaiyan、Jingqun Zhang、Cuihong Xie、Qiang Zhou、Guogen Wu、S. R. Wayne Chen、Thomas G. Back

  DOI：10.1021/jm401090a

  日期：2013.11.14

  Carvedilol is a uniquely effective drug for the treatment of cardiac arrhythmias in patients with heart failure. This activity is in part because of its ability to inhibit store-overload-induced calcium release (SOICR) through the RyR2 channel. We describe the synthesis, characterization, and bioassay of ca. 100 compounds based on the carvedilol motif to identify features that correlate with and optimize SOICR inhibition. A single-cell bioassay was employed on the basis of the RyR2-R4496C mutant HEK-293 cell line in which calcium release from the endoplasmic reticulum through the defective channel was measured. IC50 values for SOICR inhibition were thus obtained. The compounds investigated contained modifications to the three principal subunits of carvedilol, including the carbazole and catechol moieties, as well as the linker chain containing the beta-amino alcohol functionality. The SAR results indicate that significant alterations are tolerated in each of the three subunits.
• N-ARYLOXYETHYLAMINE DERIVATIVES FOR THE TREATMENT OF DEPRESSION
  申请人：Wyeth

  公开号：EP1068184B1

  公开（公告）日：2002-09-04