2-(2-溴-5-甲氧基苯基)乙胺 | 910381-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2-溴-5-甲氧基苯基)乙胺
• 英文名称: 2-(2-bromo-5-methoxyphenyl)ethylamine
• 英文别名: 2-(2-Bromo-5-methoxyphenyl)ethanamine
• CAS: 910381-02-1
• 化学式: C₉H₁₂BrNO
• 分子量: 230.104
• InChiKey: DKOJHGDTHVOSEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-(2-溴-5-甲氧基苯基)乙胺 在 硼烷四氢呋喃络合物 、 四磷十氧化物 、 palladium 10% on activated carbon 、 (1R,2S)-1-氨基-2-茚醇 、 氢气 、 potassium carbonate 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 157.0h， 生成 (1S)-8-methoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline hydrobromide
  参考文献：
  名称：

  Discovery of an 8-methoxytetrahydroisoquinoline derivative as an orally active N-type calcium channel blocker for neuropathic pain without CYP inhibition liability

  摘要：

  In lead optimization efforts starting from the tetrahydroisoquinoline (S)-1, we identified 2-{[(2R)-2-hydroxypropyl]amino}-1-[(1S)-8-methoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl]ethanone((1S)-8t) as a novel orally active small-molecule N-type calcium channel blocker without CYP inhibition liability. CYP3A4 inhibition profile was improved by reducing the lipophilicity of compound (S)-1. Moreover, introduction of a methoxy group to the C-8 position of tetrahydroisoquinoline led to identification of (1S)-8t, which eliminated CYP2D6 inhibition liability. Oral administration of (1S)-8t exerted efficacy in a rat spinal nerve ligation (SNL) model of neuropathic pain with an ED50 value of 2.8 mg/kg. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.05.053
• 作为产物：
  描述：

  N-Boc-N-[2-(2-bromo-5-methoxy-phenyl)ethyl]amine 在 三氟乙酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以1.1 g的产率得到2-(2-溴-5-甲氧基苯基)乙胺
  参考文献：
  名称：

  QSAR guided synthesis of simplified antiplasmodial analogs of naphthylisoquinoline alkaloids

  摘要：

  Naphthylisoquinoline alkaloids have attracted considerable interest because of their intriguing structure, their unique biosynthetic origin, and their biological activities against several pathogens causing tropical diseases. Their promising pharmacologic properties make them suitable lead structures for new agents, in particular against malaria. Since these natural products are not easy to isolate in sufficient quantities or to synthesize stereoselectively, quantitative structure activity relationship studies were accomplished to find new antiplasmodial analogs that are structurally related to the naturally occurring naphthylisoquinoline alkaloids, but more easily accessible, more active against Plasmodium falciparum, and, last but not least, less toxic. We report on the synthesis of several simplified compounds by a Suzuki coupling between the naphthalene and the isoquinoline moieties and on their activities against different pathogens causing infectious diseases. Some structures were found to exhibit excellent and selective activities against P. falciparum in vitro. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.062

文献信息

• One–Pot Phosphate-Mediated Synthesis of Novel 1,3,5-Trisubstituted Pyridinium Salts: A New Family of S. aureus Inhibitors
  作者：Thomas Pesnot、Markus C. Gershater、Martin Edwards、John M. Ward、Helen C. Hailes

  DOI：10.3390/molecules22040626

  日期：——

  provides conditions suitable for the use of less stable aldehydes and amines in this Chichibabin pyridine condensation. The evaluation of selected 1,3,5-trisubstituted pyridinium salts highlighted that they can inhibit the growth of S. aureus in the low μg/mL range. The synthetic accessibility of these compounds and preliminary growth inhibition data may pave the way towards the discovery of new anti-bacterials

  多取代吡啶盐是在许多生物活性分子中发现的有价值的药效团。它们的合成通常涉及使用多步程序或苛刻的反应条件。在这里，我们报告了水基磷酸盐介导的反应条件，这些条件促进芳基乙醛与胺缩合得到 1,3,5-吡啶鎓盐。该反应在 pH 6 下进行，提供了适合在这种 Chichibabin 吡啶缩合反应中使用稳定性较差的醛和胺的条件。对选定的 1,3,5-三取代吡啶盐的评估强调，它们可以在低 μg/mL 范围内抑制金黄色葡萄球菌的生长。这些化合物的合成可及性和初步的生长抑制数据可能为发现基于 1,3、
• [EN] PYRIDINIUM SALTS AND USES THEREOF<br/>[FR] SELS DE PYRIDINIUM ET LEURS UTILISATIONS
  申请人：UNIV LONDON

  公开号：WO2018189199A1

  公开（公告）日：2018-10-18

  A 1,3,5-trisubstituted pyridinium salt of general formula I (I) wherein Xn- is a counterion in which n is an integer from 1 to 4; wherein R2 and R3 are each independently a substituent group comprising Ar, wherein Ar is an aryl or heteroaryl group, which is substituted or unsubstituted; wherein R1 is a substituent group linked to the quarternary nitrogen of the pyridinium ring by an aliphatic carbon; and wherein, when R1 is benzyl, R2 and R3 are not both phenyl, 3-MeO phenyl, 4-Br phenyl, 3-CF3 phenyl, 2-Me phenyl or 4-(4-tert BuPh) phenyl; when R1 is 3-MeO phenethyl, R2 and R3 are not both 3-MeO phenyl; and when R1 is dimethoxyphenethyl, R2 and R3 are not both phenyl.

  通式I（I）的1,3,5-三取代吡啶盐，其中Xn-是一个计数离子，其中n是从1到4的整数；其中R2和R3分别是包含Ar的取代基团，其中Ar是取代或未取代的芳基或杂环基团；其中R1是通过脂肪碳与吡啶环的季铵氮连接的取代基团；当R1是苄基时，R2和R3不都是苯基、3-甲氧基苯基、4-溴苯基、3-三氟甲基苯基、2-甲基苯基或4-(4-叔丁基苄基)苯基；当R1是3-甲氧基苄基时，R2和R3不都是3-甲氧基苯基；当R1是二甲氧基苄基时，R2和R3不都是苯基。
• TETRAHYDROISOQUINOLINES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, AND THEIR USE IN THERAPY
  申请人：Amberg Wilhelm

  公开号：US20110105502A1

  公开（公告）日：2011-05-05

  The present invention relates to tetrahydroisoquinoline of the formula (I) or a physiologically tolerated salt thereof. The invention relates to pharmaceutical compositions comprising such tetrahydroisoquinolines, and the use of such tetrahydroisoquinolines for therapeutic purposes. The tetrahydroisoquinolines are GlyT1 inhibitors.

  本发明涉及式(I)的四氢异喹啉或其生理上可耐受的盐。本发明涉及包含这种四氢异喹啉的药物组合物，以及使用这种四氢异喹啉进行治疗目的的用途。这些四氢异喹啉是GlyT1抑制剂。
• Tetrahydroisoquinolines, pharmaceutical compositions containing them, and their use in therapy
  申请人：Amberg Wilhelm

  公开号：US20130203749A1

  公开（公告）日：2013-08-08

  The present invention relates to tetrahydroisoquinoline of the formula (I) or a physiologically tolerated salt thereof. The invention relates to pharmaceutical compositions comprising such tetrahydroisoquinolines, and the use of such tetrahydroisoquinolines for therapeutic purposes. The tetrahydroisoquinolines are GlyT1 inhibitors.

  本发明涉及公式（I）的四氢异喹啉或其生理上可容忍的盐。本发明涉及包含此类四氢异喹啉的制药组合物，以及使用此类四氢异喹啉进行治疗的用途。这些四氢异喹啉是GlyT1抑制剂。
• Heterocyclyl Derivatives and their use as Prostaglandin D2 Receptor Modulators
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：US20150252036A1

  公开（公告）日：2015-09-10

  The present invention relates to phenyl-substituted heterocyclyl derivatives of the formula (I), wherein Z, n, m, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are as described in the description and their use as prostaglandin receptor modulators, most particularly as prostaglandin D 2 receptor modulators, in the treatment of various prostaglandin-mediated diseases and disorders, to pharmaceutical compositions containing these compounds and to processes for their preparation.

  本发明涉及公式（I）的苯基取代杂环基衍生物，其中Z，n，m，R1，R2，R3，R4，R5，R6，R7和R8如描述中所述，并且它们作为前列腺素受体调节剂的用途，特别是作为前列腺素D2受体调节剂，在治疗各种前列腺素介导的疾病和疾患中使用，以及包含这些化合物的制药组合物和它们的制备过程。