[2-(1-萘氧基)乙基]胺盐酸盐 | 50882-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: [2-(1-萘氧基)乙基]胺盐酸盐
• 英文名称: 2-(1-naphthalenoxy)ethylamine
• 英文别名: 1-(2-aminoethoxy)naphthalene；2-(1-naphthyloxy)ethylamine；2-(naphthalen-1-yloxy)ethanamine；2-Amino-1-(naphthyl-(1)-oxy)-aethan；1-(2-Amino-aethoxy)-naphthalin；2-[1]Naphthyloxy-aethylamin；2-naphthalen-1-yloxyethanamine
• CAS: 50882-68-3
• 化学式: C₁₂H₁₃NO
• mdl: MFCD02598964
• 分子量: 187.241
• InChiKey: BRBZLKKWMHCRNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  344.0±25.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [2-(1-萘氧基)乙基]胺盐酸盐 在 盐酸 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  Structure–affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101

  摘要：

  A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the alpha(1a)-AR with respect to the other two alpha(1), subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific alpha(1a), affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high alpha(1a) affinity of (S)-1 and its alpha(1a) versus alpha(1b) selectivity slightly increasing the alpha(1a)/alpha(1d) and alpha(1a)/5HT(1A) affinity ratios. The SAR data were evaluated in the light of known alpha(1), subtype pharmacophores and of the alpha(1a)-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.040
• 作为产物：
  描述：

  2-(1-萘氧基)乙醇 在 偶氮二甲酸二异丙酯 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 16.5h， 生成 [2-(1-萘氧基)乙基]胺盐酸盐
  参考文献：
  名称：

  [EN] IRREVERSIBLE COVALENT INHIBITORS OF THE GTPASE K-RAS G12C
  [FR] INHIBITEURS COVALENTS IRRÉVERSIBLES DE LA GTPASE K-RAS G12C

  摘要：

  提供了包含G12C突变的K-Ras、H-Ras或N-ras蛋白的不可逆抑制剂。还公开了调节包含G12C突变的K-Ras、H-Ras或N-ras蛋白活性的方法，以及调节由K-Ras、H-Ras或N-ras G12C介导的疾病的方法。

  公开号：

  WO2014143659A1

文献信息

• Chiral Aryloxyalkylamines: Selective 5-HT1B/1D Activation and Analgesic Activity
  作者：Alessia Carocci、Giovanni Lentini、Alessia Catalano、Maria Maddalena Cavalluzzi、Claudio Bruno、Marilena Muraglia、Nicola Antonio Colabufo、Nicoletta Galeotti、Filomena Corbo、Rosanna Matucci、Carla Ghelardini、Carlo Franchini

  DOI：10.1002/cmdc.200900530

  日期：2010.5.3

  A series of chiral 2,3‐dichlorophenoxy and 1‐naphthyloxy alkylamines were synthesized, and their binding affinities towards 5‐HT1D and h5‐HT1B receptors were evaluated. In the naphthyloxy series, the (R)‐prolinol derivative was the most selective 5‐HT1D ligand, while (S)‐N‐methyl‐2‐(1‐naphthyloxy)propan‐1‐amine showed the highest selectivity for h5‐HT1B. Both compounds performed as 5‐HT1D agonists

  合成了一系列手性2,3-二氯苯氧基和1-萘氧基烷基胺，并评估了它们对5-HT 1D和h5-HT 1B受体的结合亲和力。在萘氧基系列中，（ R ）-脯氨醇衍生物是选择性最高的5-HT 1D配体，而（ S ） -N-甲基-2-（1-萘氧基）丙-1-胺对h5-的选择性最高HT 1B。两种化合物在分离的豚鼠试验中均作为5‐HT 1D激动剂发挥作用，并且显示出比舒马曲坦和非手性类似物20  b更高的镇痛活性。在鼠标热板测试中。两种配体都没有对小鼠脑膜中存在的烟碱型ACh受体表现出任何亲和力，因此表明它们的镇痛活性不会通过与这些受体的相互作用而产生。
• The Design of Novel <i>N</i>-4‘-Pyridinyl-α-methyl Proline Derivatives as Potent Catalysts for the Kinetic Resolution of Alcohols
  作者：Ghislaine Priem、Béatrice Pelotier、Simon J. F. Macdonald、Mike S. Anson、Ian B. Campbell

  DOI：10.1021/jo026485m

  日期：2003.5.1

  A novel family of chiral acylation catalysts based on a N-4'-pyridinyl-alpha-methyl proline structure has been studied. A set of 31 compounds has been easily prepared and screened in the kinetic resolution of racemic alcohol 33 resulting in high enantioselectivities in most cases. From results obtained, H-bonding interactions between the catalyst and the substrate would appear essential to afford high

  研究了基于N-4'-吡啶基-α-甲基脯氨酸结构的新型手性酰化催化剂。一组31种化合物很容易制备，并且在外消旋醇33的动力学拆分中进行了筛选，在大多数情况下会导致高对映选择性。从获得的结果来看，催化剂和底物之间的氢键相互作用对于在催化酰化过程中提供高对映选择性似乎是必不可少的。为了更好地确定机​​理，还进行了其他溶剂依赖性和酸酐研究。这项工作已进一步扩展到对许多结构不同的醇的研究。特别是乙醇胺衍生物在动力学分辨率上是高效的底物（最高S = 18.8）。
• Pyridinium derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd

  公开号：US04962113A1

  公开（公告）日：1990-10-09

  Novel pyridinium derivatives represented by the formula (I): ##STR1## wherein ##STR2## is an optionally substituted pyridinium ring; R.sup.1 is a lower alkyl group or aralkyl group; R.sup.7 and R.sup.10 are independently hydrogen, a lower alkyl group, aryl group or aralkyl group; l is 0 or 1; R.sup.5 is a phenylene group or an alkylene group which may be substituted; R.sup.11 is an alkyl group or aryl group; X is a group of the formula: --CH.sub.2 OCH.sub.2 -- or a group of the formula: ##STR3## wherein R.sup.6 is hydrogen, a lower alkyl or a lower alkoxy, and m is an integer of 0 to 3; U is a group of the formula: ##STR4## wherein R.sup.4 is hydrogen, a lower alkyl group, aryl group or aralkyl group; Y and Z are independently a divalent chain group consisting of one to six members which is selected from the class consisting of groups of the formulae: ##STR5## wherein R is hydrogen, a lower alkyl group, acyl group or aryl group and at least one of which is a group of the formula: ##STR6## with the proviso that R may be the same or different from each other, or may form a ring together when two or more groups of the formula: ##STR7## are present, that R may be bonded to R.sup.4 when Y contains a group of the formula: ##STR8## and that R may be bonded to R.sup.11 when Z contains a group of the formula: ##STR9## and W.sup..crclbar. is a counter anion; are useful as a platelet activating factor antagonist.

  新型吡啶盐衍生物的结构如下（I）：##STR1##其中##STR2##是一个可选择取代的吡啶环；R.sup.1是一个低碳烷基或芳基烷基；R.sup.7和R.sup.10独立地是氢、低碳烷基、芳基或芳基烷基；l为0或1；R.sup.5是一个苯基或可能被取代的烷基；R.sup.11是一个烷基或芳基；X是一个式子：--CH.sub.2 OCH.sub.2 --或一个式子：##STR3##其中R.sup.6是氢、低碳烷基或低烷氧基，m是0到3的整数；U是一个式子：##STR4##其中R.sup.4是氢、低碳烷基、芳基或芳基烷基；Y和Z独立地是由1到6个成员组成的二价链状基团，选自下列式：##STR5##其中R是氢、低碳烷基、酰基或芳基，至少有一个是下列式之一：##STR6##但要求R可以相同也可以不同，或者当存在两个或更多的下列式之一：##STR7##时，R可以一起形成环；当Y包含一个下列式之一：##STR8##时，R可以与R.sup.4结合；当Z包含一个下列式之一：##STR9##时，R可以与R.sup.11结合；W.sup..crclbar.是一个反离子；这些化合物可用作血小板活化因子拮抗剂。
• N-Acylated and N-Alkylated 2-Aminobenzothiazoles Are Novel Agents That Suppress the Generation of Prostaglandin E2
  作者：Maria A. Theodoropoulou、Anastasia Psarra、Martin Erhardt、Aikaterini Nikolaou、Anna-Dimitra D. Gerogiannopoulou、Dimitra Hadjipavlou-Litina、Daiki Hayashi、Edward A. Dennis、Andrea Huwiler、George Kokotos

  DOI：10.3390/biom12020267

  日期：——

  diseases. We synthesized a series of N-acylated and N-alkylated 2-aminobenzothiazoles and related heterocycles (benzoxazoles and benzimidazoles) and evaluated their ability to suppress the cytokine-stimulated generation of PGE2 in rat mesangial cells. 2-Aminobenzothiazoles, either acylated by the 3-(naphthalen-2-yl)propanoyl moiety (GK510) or N-alkylated by a chain carrying a naphthalene (GK543) or a phenyl

  寻求调节前列腺素 E2 (PGE2) 生成的新药物非常重要，因为这种类花生酸是炎症性疾病的关键因素。我们合成了一系列 N-酰化和 N-烷基化 2-氨基苯并噻唑和相关杂环（苯并恶唑和苯并咪唑），并评估了它们在大鼠系膜细胞中抑制细胞因子刺激的 PGE2 生成的能力。2-氨基苯并噻唑，或者被 3-(萘-2-基)丙酰基部分 (GK510) 酰化，或者被在三个碳原子距离处带有萘 (GK543) 或苯基部分 (GK562) 的链 N-烷基化，在抑制 PGE2 生成方面表现突出，EC50 值范围为 118 nM 至 177 nM。GK510 和 GK543 的体内抗炎活性均高于消炎痛。因此，
• AMINOETHYLATION PROCESS HAVING IMPROVED YIELD OF ARYLOXYALKYLENE AMINE COMPOUNDS AND REDUCED UREA BY-PRODUCTS
  申请人：McDougall Patrick J.

  公开号：US20140073814A1

  公开（公告）日：2014-03-13

  Disclosed is a process for preparing an aryloxyalkylene amine compound via an aminoethylation reaction comprising: a) reacting an aromatic hydroxyl compound in the presence of a basic catalyst with a 2-oxazolidinone compound of the formula II to form an intermediate reaction product; wherein R 3 is selected from the group consisting of hydrogen or lower alkyl having 1 to 6 carbon atoms, R 4 is selected from the group consisting of hydrogen, straight or branched chain alkyl having from one to six carbon atoms, phenyl, alkaryl, or arylalkyl; and b) reacting the intermediate product of step a) with a polyalkylene polyamine.

  揭示了一种通过氨基乙基化反应制备芳基氧基烷胺化合物的过程，包括：a)在碱性催化剂存在下，将芳香羟基化合物与式II的2-噁唑烷酮化合物反应，形成中间反应产物；其中R3选自氢或1至6个碳原子的较低烷基，R4选自氢、一元或分支链烷基（含1至6个碳原子）、苯基、烷基芳基或芳基烷基；b)将步骤a）中间产物与聚烷基聚胺反应。