C-(3,4-二氢-2H-苯并[1,4]嗪-3-基)-甲胺 | 54252-56-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: C-(3,4-二氢-2H-苯并[1,4]嗪-3-基)-甲胺
• 中文别名: (3,4-二氢-2H-苯并[1,4]噁嗪-3-基)甲胺
• 英文名称: C-(3,4-dihydro-2H-benzo[1,4]oxazin-1-yl)methanamine
• 英文别名: C-(3,4-dihydro-2H-benzo[1,4]oxazin-3-yl)-methylamine；2H-3,4-dihydro-3-aminomethyl[1,4]benzoxazine；3-aminomethyl-3,4-dihydro-2H-1,4-benzoxazine；3-Aminomethyl-1,4-benzoxazin；(3,4-Dihydro-2H-benzo[b][1,4]oxazin-3-yl)methanamine；3,4-dihydro-2H-1,4-benzoxazin-3-ylmethanamine
• CAS: 54252-56-1
• 化学式: C₉H₁₂N₂O
• mdl: MFCD05664019
• 分子量: 164.207
• InChiKey: UOBUMUKUDJXGKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  47.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  C-(3,4-二氢-2H-苯并[1,4]嗪-3-基)-甲胺 在 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 144.0h， 生成 benzyl 1,2,3,4,4a,5-hexahydro-1H-pyrazino[2,1-c][1,4]benzoxazine-1-one-3-carboxylate
  参考文献：
  名称：

  New Pyrimido[5,4-b]indoles as Ligands for α₁-Adrenoceptor Subtypes

  摘要：

  A new series of compounds were designed as structural analogues of the alpha(1)-AR ligand RN5 (4), characterized by a tricyclic 5H-pyrimido[5,4-b]indole-(1H,3H)2,4-dione system connected through an alkyl. chain to a phenylpiperazine (PP) moiety. These compounds were synthesized and tested in binding assays on human alpha(1A)-AR, alpha(1B)-AR, and alpha(1D)-AR subtypes expressed in HEK293 cells. Several structural modifications were performed on the PP moiety, the tricyclic system, and the connecting alkyl chain. Many of the new molecules showed a preferential affinity for the alpha(1D)-AR subtype. Some compounds, including 39 and 40, displayed substantial alpha(1D)-AR selectivity with respect to alpha(1A)-AR, alpha(1B)-AR, serotonergic 5-HT1A, 5-HT1B, 5-HT2A, and dopaminergic D-1 and D-2 receptors. Two conformationally rigid analogues of 4, useful for studying the architecture of the receptor/ligand complex, were also prepared and tested. A subset of the new compounds was then used to evolve a preliminary pharmacophore model for alpha(1D)-AR antagonists, based on a more generalized model we had developed for alpha(1)-AR antagonists. This new model rationalized the relationships between structural properties and biological data of the pyrimido[5,4-b]indole compounds, as well as other compounds.

  DOI：

  10.1021/jm0307741
• 作为产物：
  描述：

  1,2-环氧-3-(2-硝基苯氧基)丙烷 在 palladium on activated charcoal 吡啶 、 chromium(VI) oxide 、 氢气 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 、 正丁醇 为溶剂， 反应 2.0h， 生成 C-(3,4-二氢-2H-苯并[1,4]嗪-3-基)-甲胺
  参考文献：
  名称：

  Hindered rotation congeners of mazapertine: High affinity ligands for the 5-HT1A receptor

  摘要：

  Hindered rotation analogs of the antipsychotic mazapertine (1) were prepared. These compounds exhibited high affinity for the 5-HT1A receptor, but not for other serotonin or dopamine receptors. The related beta-carboline structures were also synthesized and were found to be potent 5-HT1A ligands. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00074-7

文献信息

• Derivatives of imidazo[5,1-<i>c</i>][1,4]benzoxazin-l-ones and related analogs. Part I
  作者：C. Banzatti、A. Della Torre、P. Melloni、D. Pieraccioli、P. Salvadori

  DOI：10.1002/jhet.5570200130

  日期：1983.1

  The bicyclic 2,3,3a,4-tetrahydro-1H-imidazo[5,1-c][1,4]benzoxazin-1-one system and the related 1,4-benzo-thiazine and 4,1]benzoxazepine analogs were synthesized. They were easily obtained by melting a suitable diamine derivative with urea. Some of them displayed very good reversible MAO-I activity selective for type A. The preparation of the intermediate amines is also given.

  双环2,3,3a，4-四氢-1 H-咪唑并[5,1-c] [1,4]苯并恶嗪-1-酮体系及相关的1,4-苯并噻嗪和4,1]苯并a氮平合成类似物。通过将合适的二胺衍生物与尿素熔融，可以轻松获得它们。它们中的一些显示出对A型具有选择性的非常好的可逆MAO-I活性。还给出了中间体胺的制备。
• Imidazo[5,1-c][1,4]benzoxazin-1-one
  申请人：Carlo Erba S. p. A.

  公开号：US04134974A1

  公开（公告）日：1979-01-16

  Cyclic derivatives of 1,4-benzoxazine and 1,4-benzothiazine are disclosd, such as, for instance, 1H,2,3,3a,4-tetrahydro-2-carbamoylmethyl-imidazo[5,1-c][1,4]benzoxazin-1-o ne and 1H,2,3,3a,4-tetrahydro-2-carbamoylmethyl-8-chloro-imidazo[5,1-c][1,4]benzo xazin-1-one. These compounds are active on the central nervous system, and function as antidepressant agents.

  公开了1,4-苯并噁嗪和1,4-苯并噻嗪的环状衍生物，例如，1H,2,3,3a,4-四氢-2-氨甲酰甲基-咪唑并[5,1-c][1,4]苯并噁嗪-1-酮和1H,2,3,3a,4-四氢-2-氨甲酰甲基-8-氯-咪唑并[5,1-c][1,4]苯并噁嗪-1-酮。这些化合物对中枢神经系统具有活性，并作为抗抑郁剂发挥作用。
• Use of certain 1,2-benzoisothiazol-3(2H)-1,1-dioxide derivatives in the treatment of depression and mania
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0492021A1

  公开（公告）日：1992-07-01

  This invention relates to the manufacture of certain aromatic 2-aminoalkyl-1,2-benzoisothiazol-3(2H)one-1,1-dioxide derivatives for their use as medicaments in the treatment of depression and mania.

  本发明涉及某些芳香族 2-氨基烷基-1,2-苯并异噻唑-3(2H)-1,1-二氧化物衍生物的生产，这些衍生物可用作治疗抑郁症和狂躁症的药物。
• [EN] 2- AND 3-AMINOMETHYL-6-ARYLCARBONYL-2,3-DIHYDROPYRROLO[1,2,3-de]-1,4-BENZOXAZINES
  申请人：STERLING DRUG INC.

  公开号：WO1990007505A1

  公开（公告）日：1990-07-12

  (EN) 2- and 3-aminomethyl-6-arylcarbonyl-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazines, useful as analgesic agents, are prepared either by reaction of a 2- or 3-aminomethyl-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine with an arylcarboxylic acid halide in the presence of a Lewis acid or by reaction of a 2- or 3-aminomethyl-4-amino-3,4-dihydro-2H-1,4-benzoxazine with a 1-lower-alkyl-3-aryl-1,3-diketone or with a $g(b)-aryl-$g(b)-ketopropionaldehyde under dehydrating conditions and heating the resulting hydrazone in an acid medium.(FR) 2- et 3-aminométhyl-6-arylcarbonyl-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazines, utiles en tant qu'agents analgésiques, sont préparés soit par réaction de 2- ou 3-aminométhyl-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazines avec un halogénure d'acide arylcarboxylique en présence d'un acide de Lewis soit par réaction de 2- ou 3-aminométhyl-4-amino-3,4-dihydro-2H-1,4-benzoxazines avec 1-alkyl inférieur-3-aryl-1,3-dicétone ou avec $g(b)-aryl-$g(b)-cétopropionaldéhyde dans des conditions de déshydratation et en chauffant l'hydrazone obtenu dans un milieu acide.

  2-和3-氨基乙基-6-甲基羰基-2,3-双氢吡咯-1,4-苯并环化合物（因其作为解痛剂的用途）可在以下两种方法中制备：第一种方法是将2-或3-氨基乙基-2,3-双氢吡咯-1,4-苯并环化合物与苯并环羰基的偏卤酐络合物在莱wis酸的存在下反应；第二种方法是将2-或3-氨基乙基-4-氨基-3,4-双氢-2H-1,4-苯并环化合物与1-下位-烷基-3-甲基-1,3- diketone或与$g(b)-甲基-甲基-乙烷-丙二醛酮在脱水条件下反应并加热反应所得的腙在酸性介质中。
• Hindered rotation congeners of mazapertine: High affinity ligands for the 5-HT1A receptor
  作者：Ellen W. Baxter、Allen B. Reitz

  DOI：10.1016/s0960-894x(97)00074-7

  日期：1997.1

  Hindered rotation analogs of the antipsychotic mazapertine (1) were prepared. These compounds exhibited high affinity for the 5-HT1A receptor, but not for other serotonin or dopamine receptors. The related beta-carboline structures were also synthesized and were found to be potent 5-HT1A ligands. (C) 1997 Elsevier Science Ltd.