2-(4-phenyl-5,6-dihydropyridin-1(2H)-yl)ethanamine | 39793-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(4-phenyl-5,6-dihydropyridin-1(2H)-yl)ethanamine
• 英文别名: 2-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-ethylamine；1-(2-aminoethyl)-4-phenyl-1,2,3,6-tetrahydropyridine；3,6-dihydro-4-phenyl-1(2H)-pyridineethanamine；1-(2-Amino-ethyl)-4-phenyl-1,2,3,6-tetrahydro-pyridin；2-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)ethanamine
• CAS: 39793-35-6
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: HWSMPYJWEGDUGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-phenyl-5,6-dihydropyridin-1(2H)-yl)ethanamine 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-((3-isopropylisoxazol-5-yl)methyl)-2-(4-phenyl-5,6-dihydropyridin-1(2H)-yl)ethanamine
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-(isoxazol-5-ylmethylaminoethyl)-4-phenyl tetrahydropyridine and piperidine derivatives as potent T-type calcium channel blockers with antinociceptive effect in a neuropathic pain model

  摘要：

  New tetrahydropyridinyl and piperidinyl ethylamine derivatives were designed with hypothetical mapping on pharmacophore model generated from ligand-based virtual screening. The designed compounds were synthesized, and their inhibitory activities on T-type calcium channel were assayed using FDSS and patch-clamp assay. Among them, compounds 7b and 10b showed potent T-type calcium current blocking activity against Ca(v)3.1 (alpha(1G)) and Ca(v)3.2 (alpha(1H)) channel simultaneously. With hERG and pharmacokinetics studies, compounds 7b and 10b were evaluated for the antinociceptive effect on rat model of neuropathic pain. They were significantly effective in decreasing the pain responses to mechanical and cold allodynia induced by spinal nerve ligation. These results suggest that modulation of alpha(1G) and am subtype T-type calcium channels may provide a promising approach for the treatment of neuropathic pain. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.056
• 作为产物：
  描述：

  4-苯基-3,6-二氢-2H-吡啶-1-羧酸叔丁酯 在 potassium carbonate 、 一水合肼 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 2-(4-phenyl-5,6-dihydropyridin-1(2H)-yl)ethanamine
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-(isoxazol-5-ylmethylaminoethyl)-4-phenyl tetrahydropyridine and piperidine derivatives as potent T-type calcium channel blockers with antinociceptive effect in a neuropathic pain model

  摘要：

  New tetrahydropyridinyl and piperidinyl ethylamine derivatives were designed with hypothetical mapping on pharmacophore model generated from ligand-based virtual screening. The designed compounds were synthesized, and their inhibitory activities on T-type calcium channel were assayed using FDSS and patch-clamp assay. Among them, compounds 7b and 10b showed potent T-type calcium current blocking activity against Ca(v)3.1 (alpha(1G)) and Ca(v)3.2 (alpha(1H)) channel simultaneously. With hERG and pharmacokinetics studies, compounds 7b and 10b were evaluated for the antinociceptive effect on rat model of neuropathic pain. They were significantly effective in decreasing the pain responses to mechanical and cold allodynia induced by spinal nerve ligation. These results suggest that modulation of alpha(1G) and am subtype T-type calcium channels may provide a promising approach for the treatment of neuropathic pain. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.056

文献信息

• Chemical Modifications on 4-Arylpiperazine-Ethyl Carboxamide Derivatives Differentially Modulate Affinity for 5-HT1A, D4.2, and α2A Receptors: Synthesis and In Vitro Radioligand Binding Studies
  作者：Amaury Graulich、Marc Léonard、Mélissa Résimont、Xi-Ping Huang、Bryan L. Roth、Jean-François Liégeois

  DOI：10.1071/ch09353

  日期：——

  A series of substituted 4-aryl-piperazine-ethyl heteroarylcarboxamides were prepared and tested in in vitro radioligand binding studies. The presence of a quinoxaline has a favourable impact in terms of serotonin 5-HT1A versus dopamine D4.2 receptor selectivity. Compounds with a 3-CF3 group at the distal phenyl ring are the most effective in terms of affinity and selectivity for 5-HT1A versus D4.2 receptors. A 4-phenyl-1,2,3,6-tetrahydropyridine in place of the corresponding 4-phenyl-piperazine side chain is also favourable not only for the affinity for 5-HT1A and D4.2 receptors but also in some cases for α 2A-adrenoceptors.

  我们制备了一系列取代的 4-芳基哌嗪-乙基杂芳基羧酰胺，并在体外放射性配体结合研究中进行了测试。喹喔啉的存在对血清素 5-HT1A 与多巴胺 D4.2 受体的选择性具有有利影响。就对 5-HT1A 受体和 D4.2 受体的亲和力和选择性而言，远端苯环上带有 3-CF3 基团的化合物最为有效。用 4-苯基-1,2,3,6-四氢吡啶取代相应的 4-苯基-哌嗪侧链也不仅有利于提高对 5-HT1A 和 D4.2 受体的亲和力，而且在某些情况下还有利于提高对 α 2A 肾上腺素受体的亲和力。
• 3-(Arylcycloiminoalkyl)benzisothiazole 1,1-dioxides
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04104387A1

  公开（公告）日：1978-08-01

  3-(Arylcycloiminoalkyl)benzisothiazole 1,1-dioxides are provided having the structure ##STR1## wherein R is hydrogen, halogen, lower alkyl, lower alkoxy or nitro; R.sup.1 is hydrogen, lower alkoxy or halogen with the proviso that R.sup.1 can be lower alkoxy or halogen only when R is lower alkoxy or halogen, respectively; A is O or NH; X is hydrogen, halogen lower alkyl, lower alkoxy, or trifluoromethyl; Y is C or N, where Y is C, is a double bond, and when Y is N, represents a single bond, B is an alkylene group containing 2 to 5 carbons in the normal chain; Q is a single bond or an alkylene group containing 1 to 3 carbons in the normal chain; and physiologically acceptable acid-addition salts thereof. These compounds are useful as antiinflammatory agents.

  提供具有以下结构的3-(芳基环亚胺烷基)苯并异噻唑-1,1-二氧化物：##STR1## 其中R为氢、卤素、低级烷基、低级烷氧基或硝基；R.sup.1为氢、低级烷氧基或卤素，但R.sup.1仅在R为低级烷氧基或卤素时可以为低级烷氧基或卤素；A为O或NH；X为氢、卤素、低级烷基、低级烷氧基或三氟甲基；Y为C或N，其中当Y为C时为双键，当Y为N时表示单键；B为含有2到5个碳原子的烷基链；Q为单键或含有1到3个碳原子的烷基链；以及其生理学上可接受的酸加成盐。这些化合物可用作抗炎剂。
• 2-Substituted benzisothiazol-3-ones
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04110449A1

  公开（公告）日：1978-08-29

  2-Substituted benzisothiazol-3-ones are provided having the structure ##STR1## wherein R is hydrogen, halogen, lower alkyl, lower alkoxy, or nitro; R.sup.1 is hydrogen, lower alkoxy or halogen, with the proviso that R.sup.1 can be lower alkoxy or halogen only when R is lower alkoxy or halogen, respectively; X is hydrogen, halogen, lower alkyl, lower alkoxy, or trifluoromethyl; Y is C or N, where Y is C, --------represents a single or double bond, and when Y is N, --------represents a single bond, p is 0 or 2, A is an alkylene group containing 2 to 5 carbons in the normal chain; and B is a single bond or an alkylene group containing from 1 to 3 carbons in the normal chain, and physiologically acceptable acid-addition salts thereof. These compounds have antiinflammatory activity, sedative and muscle relaxant activity. Pharmaceutical compositions containing such compounds and methods for using such compounds are also provided.

  提供了具有结构##STR1##的2-取代苯并异噻唑酮，其中R为氢、卤素、低烷基、低烷氧基或硝基；R.sup.1为氢、低烷氧基或卤素，但当R为低烷氧基或卤素时，R.sup.1只能为低烷氧基或卤素；X为氢、卤素、低烷基、低烷氧基或三氟甲基；Y为C或N，其中Y为C，--------表示单键或双键，当Y为N时，--------表示单键，p为0或2，A为含有2至5个碳的正常链烷基；B为单键或含有1至3个碳的正常链烷基，以及其生理上可接受的酸加合物盐。这些化合物具有抗炎活性、镇静和肌肉松弛活性。还提供了含有这些化合物的制药组合物和使用这些化合物的方法。
• Basic acyl amides of (5-amino-1,3-dialkylpyrazol-4-yl)(aryl)methanones, processes for their production, and pharmaceutical compositions containing such compounds
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0068806A2

  公开（公告）日：1983-01-05

  Basic acylamides of (5-amino-1,3-dialkylpyrazol-4-yl)-(aryl)methanones and their pharmaceutically acceptable salts are provided, which have the formula: where the radicals are as defined in the specification. These compounds are useful for treating psychoses. Also provided are processes for preparing the compounds of the invention, and pharmaceutical compositions containing these compounds.

  本发明提供了(5-氨基-1,3-二烷基吡唑-4-基)-(芳基)甲酮的碱性酰酰胺及其药学上可接受的盐，其式为： 其中基团如说明书中所定义。 这些化合物可用于治疗精神病。 还提供了制备本发明化合物的工艺和含有这些化合物的药物组合物。
• N-[(Amino)Alkyl]-1-pyrrolidine, 1-piperidine and 1-homopiperidinecarboxamides (and thiocarboxamides) with sulphur linked substitution in the 2, 3 or 4-position
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0160436A2

  公开（公告）日：1985-11-06

  Pyrrolidine, piperidine and homopiperidine- carboxamide and thiocarboxamide compounds of the formula: wherein X is -S-, -S(0)- or -S(0)2-; A is a loweralkalene chain and A1 and A2 are alkalene chains when p and d are one; R, R1 and R2 are hydrogen, loweralkyl, phenyl cycloalkyl or phenylalkyl and R1 and R2 may form a heterocyclic residue with the adjacent nitrogen atom; Q is a selected aromatic radical, and the pharmaceutically acceptable acid addition salts are useful as cardiac antiarrhythmia agents. Chemical intermediates, unsubstituted on pyrrolidine, piperidine and homopiperidine nitrogen but with the -(A2)p-X-(A2)d-Q side chain are also disclosed.

  式中的吡咯烷、哌啶和均哌啶-羧酰胺和硫代羧酰胺化合物： 其中，X 是-S-、-S(0)- 或-S(0)2-；A 是低级烯烃链，当 p 和 d 为 1 时，A1 和 A2 是烯烃链；R、R1 和 R2 是氢、低级烷基、苯基环烷基或苯基烷基，R1 和 R2 可与相邻的氮原子形成杂环残基；Q 是选定的芳香基，药学上可接受的酸加成盐可用作抗心律失常剂。 还公开了吡咯烷、哌啶和高哌啶氮上未取代但具有-(A2)p-X-(A2)d-Q 侧链的化学中间体。