2-(5-fluoro-2-methoxy-phenoxy)ethylamine | 120352-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(5-fluoro-2-methoxy-phenoxy)ethylamine
• 英文别名: 2-(5-fluoro-2-methoxyphenoxy)ethanamine
• CAS: 120352-00-3
• 化学式: C₉H₁₂FNO₂
• 分子量: 185.198
• InChiKey: IJBZWNMACGOPAI-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-(5-fluoro-2-methoxy-phenoxy)ethylamine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 5-[2-[2-(5-Fluoro-2-methoxyphenoxy)ethylamino]propyl]-2-n-propoxybenzenesulfonamide
  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：

  2-(5-fluoro-2-methoxy-phenoxy)ethylchloride 在 sodium azide 、 水 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 2-(5-fluoro-2-methoxy-phenoxy)ethylamine
  参考文献：
  名称：

  Studies toward the Discovery of the Next Generation of Antidepressants. 3. Dual 5-HT_1A and Serotonin Transporter Affinity within a Class of N-Aryloxyethylindolylalkylamines

  摘要：

  N-Aryloxylethylindolealkylamines (5) having dual 5-HT transporter and 5-HT1A affinity are described. These compounds represent truncated analogues of our previously reported piperidinyl derivatives (3). Compounds in this investigation were found to have more similar affinities and functional activities for the 5-HT1A receptor and 5-HT transporter. Though 5-HT1A antagonism is not consistently observed throughout series 5, several molecular features were found to be essential to obtain high and balanced activities. The proper placement of a heteroatom in the aryl ring and the length of the linkage used to tether the indole moiety had significant influence on 5-HT1A and 5-HT transporter affinities. Introduction of a halogen into the aryl ring usually lowered intrinsic activity and in some cases led to full 5-HT1A antagonists. Compounds 33 and 34 were observed to be full 5-HT1A antagonists with K-i values of approximately 30 nM for the 5-HT1A receptor and K-i values of 5 and 0.5 nM for the 5-HT transporter, respectively. Unfortunately, similar to our previous series (3), compounds in this report also had high affinity for the alpha(1) receptor.

  DOI：

  10.1021/jm0304010

文献信息

• N-aryloxyethyl-indoly-alkylamines for the treatment of depression
  申请人：American Home Products Corp.

  公开号：US06121307A1

  公开（公告）日：2000-09-19

  Compounds useful for alleviating symptoms of depression are provided which have the following formula: wherein: R.sub.1 is hydrogen, lower alkyl or aryl; R.sub.2 is hydrogen, lower alkyl, phenyl or substituted phenyl; X and Y are each, independently, hydrogen, lower alkyl, lower alkoxy, or halogen, or together combine with the carbon atoms to which they are attached to complete a pyranyl, dihydrofuranyl, furanyl, or dioxanyl, group; Z is hydrogen, halogen or lower alkoxy; with the proviso that when X, Y or Z represent lower alkoxy, they are not present at the ortho position; W is hydrogen, halogen, lower alkyl, cyano or a trifluoromethyl group; and n is 2-5; or pharmaceutically acceptable salts thereof.

  提供了用于缓解抑郁症症状的化合物，其具有以下结构式：其中：R.sub.1为氢、低碳基或芳基；R.sub.2为氢、低碳基、苯基或取代苯基；X和Y分别独立地为氢、低碳基、低烷氧基或卤素，或者与它们连接的碳原子结合在一起形成吡喃基、二氢呋喃基、呋喃基或二氧杂环基；Z为氢、卤素或低烷氧基；但当X、Y或Z代表低烷氧基时，它们不位于邻位；W为氢、卤素、低碳基、氰基或三氟甲基基团；n为2-5；或其药用盐。
• Novel phenoxyalkylamine derivatives. V. Synthesis, .ALPHA.-blocking activity and quantitative structure-activity analysis of .ALPHA.-((phenoxyethylamino)propyl)-.ALPHA.-phenylacetonitrile derivatives.
  作者：KAZUYA MITANI、SHUNICHIRO SAKURAI、TOSHIHIRO SUZUKI、KOJI MORIKAWA、EIICHI KOSHINAKA、HIDEO KATO、YASUO ITO、TOSHIO FUJITA

  DOI：10.1248/cpb.36.4121

  日期：——

  α-[(Phenoxyethylamino) propyy]-α-phenylacetonitrile derivatives possessing various substituents on the benzene ring (A ring) at the phenylacetonitrile moiety, on the quaternary carbon atom and on the benzene ring (B ring) at the phenoxy moiety, and exhibiting various degrees of ablocking activity, were prepared. The variations in the activity were analyzed qualitatively as well as quantitatively by using physicochemical substituent parameters and a regression technique. The effect of substituents on the A ring was rationalized in terms of a parabolic function of their hydrophobic parameter. As regards substituents on the quaternary carbon atom, alkyl groups were desirable for high activity. The effects of substituents on the B ring were such that an optimum hydrophobic condition exists and that an alkoxy substituent at the o-position as well as smaller substituents at the m-and p-positions are favorable for high activity. The analysis for the combined series of analogs where substituents on the A and B rings are varied showed the existence of an optimum hydrophobicity for the whole molecule for the transport process of the molecule, besides above-mentioned various position-specific structural effects.

  合成了α-[(苯氧乙基氨基)丙基]-α-苯基乙腈衍生物，这些衍生物在苯乙腈部分的苯环（A环）上、在四面体碳原子上，以及在苯氧部分的苯环（B环）上，具有不同的取代基，并表现出各种程度的α-阻断活性。采用物理化学取代基参数及回归技术，对活性的变化进行了定性和定量分析。A环上取代基的影响根据其疏水参数的抛物线函数进行合理化。至于四面体碳原子上的取代基，烷基基团被认为是高活性的理想选择。B环上取代基的影响表明，存在一个最佳的疏水条件，并且在邻位的烷氧取代基以及在间位和对位的较小取代基有利于高活性。针对A环和B环取代基变化的综合系列类似物的分析显示，在分子的运输过程中，整个分子的最佳疏水性存在，此外也考虑了上述不同位置特异的结构效应。
• Phenoxyethylamine derivatives, for preparing the same and composition
  申请人：Hokuriku Pharmaceutical Co., Ltd.

  公开号：US04971990A1

  公开（公告）日：1990-11-20

  Phenoxyethylamine derivatives represented by the general formula (I): ##STR1## wherein R.sub.1 and R.sub.5 represent lower-alkyl, R.sub.2 and R.sub.3, which may be the same or different, each represents hydrogen or lower-alkyl, or ##STR2## represents a 5- or 6-membered ring system which may include nitrogen, oxygen or sulfur as a ring membered atom, R.sub.4 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 .alpha..sub.1 -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）表示的苯氧乙胺衍生物：其中R.sub.1和R.sub.5代表低碳烷基，R.sub.2和R.sub.3，可以相同也可以不同，每个代表氢或低碳烷基，或者##STR2##代表可能包含氮、氧或硫作为环成员原子的5-或6-成员环系统，R.sub.4代表氢或低碳烷基，n代表从1到3选择的整数，它们的光学异构体和药理学上可接受的酸盐加合物，表现出优异的α1-阻滞活性，公开了它们的制备方法、药物组合物以及通过给予这种化合物治疗患有高血压或尿路异物的受试者的方法。
• 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。
• N-arloxyethyl-alkylamines for the treatment of depression
  申请人：American Home Products Corp

  公开号：US06291683B1

  公开（公告）日：2001-09-18

  Compounds useful for alleviating symptoms of depression are provided which have the following formula: wherein: R1 is hydrogen, lower alkyl or aryl; R2 is hydrogen, lower alkyl, phenyl or substituted phenyl; X and Y are each, independently, hydrogen, lower alkyl, lower alkoxy, or halogen, or together combine with the carbon atoms to which they are attached to complete a cyclopentyl, cyclohexyl, phenyl, pyrrolyl, pyranyl, pyridinyl, dihydrofuranyl, furanyl, dioxanyl, oxazolyl or isoxazolyl group; Z is hydrogen, halogen or lower alkoxy; with the proviso that when X, Y or Z represent lower alkoxy, they are not present at the ortho position; W is hydrogen, halogen, lower alkyl, cyano or a trifluoromethyl group; and n is 2-5; or pharmaceutically acceptable salts thereof.

  提供了用于缓解抑郁症状的化合物，其具有以下结构式：其中：R1为氢、低级烷基或芳基；R2为氢、低级烷基、苯基或取代苯基；X和Y各自独立地为氢、低级烷基、低级烷氧基或卤素，或者结合它们所连接的碳原子以完成环戊基、环己基、苯基、吡咯基、吡喃基、吡啶基、二氢呋喃基、呋喃基、二氧杂环己基、噁唑基或异噁唑基；Z为氢、卤素或低级烷氧基；但当X、Y或Z表示低级烷氧基时，它们不出现在邻位；W为氢、卤素、低级烷基、氰基或三氟甲基基团；n为2-5；或其药学上可接受的盐。