N-[2-(4-aminophenyl)ethyl]-3,5-di-tert-butyl-4-hydroxybenzamide | 214124-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2-(4-aminophenyl)ethyl]-3,5-di-tert-butyl-4-hydroxybenzamide
• 英文别名: 3,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-[2-(4-aminophenyl)ethyl]-benzamide；N-[2-(4-aminophenyl)ethyl]-3,5-ditert-butyl-4-hydroxybenzamide
• CAS: 214124-43-3
• 化学式: C₂₃H₃₂N₂O₂
• 分子量: 368.519
• InChiKey: ZVGSJHDXNLJHEL-UHFFFAOYSA-N

物化性质

• 沸点：
  492.3±45.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-(4-aminophenyl)ethyl]-3,5-di-tert-butyl-4-hydroxybenzamide 、 6-氯嘌呤核苷 在 N,N-二异丙基乙胺 作用下， 以 叔丁醇 为溶剂， 反应 45.0h， 以76%的产率得到N⁶-[4-[2-[3,5-di-tert-butyl-4-hydroxybenzamido]ethyl]phenyl]adenosine
  参考文献：
  名称：

  Dual acting antioxidant A1 adenosine receptor agonists

  摘要：

  Herein we report the synthesis and biological evaluation of some potent and selective A, adenosine receptor agonists, which incorporate a functionalised linker attached to an antioxidant moiety. N-6-(2,2,5,5-Tetramethylpyrrolidin-1-yloxyl-3-ylmethyl)-adenosine (VCP28, 2e) proved to be an agonist with high affinity (K-i = 50 nM) and good selectivity (A(3)/A(1) >= 400) for the A, adenosine receptor. N-6-[4-[2-[1,1,3,3-Tetramethylisoindolin-2-yloxyl-5-amido]ethyl]phenyl]adenosine (VCP102, 5a) has higher binding affinity (Ki = 7 nM), but lower selectivity (A(3)/A(1) = similar to 3). All compounds bind weakly (K-i > 1 mu M) to A(2A) and A(2B) receptors. The combination of-A, agonist activity and antioxidant activity has the potential to produce cardioprotective effects. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.035
• 作为产物：
  描述：

  3,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-[2-(4-nitrophenyl)ethyl]-benzamide 以76%的产率得到N-[2-(4-aminophenyl)ethyl]-3,5-di-tert-butyl-4-hydroxybenzamide
  参考文献：
  名称：

  Derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them

  摘要：

  从以下化合物组中选择的一种化合物，其化学式为 其中A是从以下组中选择的 其他取代基在规范中定义，具有抑制NO合酶产生一氧化氮的活性和/或捕获活性氧化物种的活性。

  公开号：

  US06335445B1

文献信息

• New derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them
  申请人：——

  公开号：US20030078420A1

  公开（公告）日：2003-04-24

  The invention relates to new derivatives of 2-(iminomethyl)amino-phenyl which are NO synthase inhibitors and can trap reactive oxygen species. These compounds can notably be used for the treatment of stroke, of neurodegenerative diseases and of ischemic or hemorragic cardiac or cerebral infarctions. These compounds include: N-{4-[({[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}amino)methyl]phenyl}thiophene-2-carboximidamide; N-{3-[({[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}amino)methyl]phenyl}thiophene-2-carboximidamide; N-(4-{[{[4-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl}(methyl)amino]methyl}phenyl)thiophene-2-carboximidamide; N-[3-({[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-(3-{[(3,5-di-tert-butyl-4-hydroxybenzyl)amino]methyl}phenyl) thiophene-2-carboximidamide; N-[3-({[2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-[3-({[3-(4-hydroxy-3,5-diisopropylphenyl)propyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-(3-{[(4-hydroxy-3,5-diisopropylbenzyl)amino]methyl}phenyl) thiophene-2-carboximidamide; N-[3-({[2-(4-hydroxy-3,5-diisopropylphenyl)ethyl]amino}methyl) phenyl]thiophene-2-carboximidamide; N-2-(3,5-di-tert-butyl-4-hydroxybenzoyl)-N-1-(4-{[imino(thien-2-yl)methyl]amino}phenyl)-L-leucinamide; and pharmaceutically acceptable salts thereof.

  这项发明涉及新的2-(亚甲基亚胺)氨基苯基衍生物，它们是一氧化氮合酶抑制剂，可以捕获活性氧物质。这些化合物可以显著用于中风、神经退行性疾病、缺血性或出血性心脏或脑梗死的治疗。 这些化合物包括： N-4-[(4-(3,5-二叔丁基-4-羟基苯基)-1,3-噻唑-2-基}甲基)氨基]苯基}噻吩-2-甲酰亚胺； N-3-[(4-(3,5-二叔丁基-4-羟基苯基)-1,3-噻唑-2-基}甲基)氨基]苯基}噻吩-2-甲酰亚胺； N-(4-[4-(3,5-二叔丁基-4-羟基苯基)-1,3-噻唑-2-基}甲基(甲基)氨基]甲基}苯基)噻吩-2-甲酰亚胺； N-[3-([3-(3,5-二叔丁基-4-羟基苯基)丙基]氨基}甲基)苯基]噻吩-2-甲酰亚胺； N-(3-[(3,5-二叔丁基-4-羟基苯基)甲基]氨基}苯基)噻吩-2-甲酰亚胺； N-[3-([2-(3,5-二叔丁基-4-羟基苯基)乙基]氨基}甲基)苯基]噻吩-2-甲酰亚胺； N-[3-([3-(4-羟基-3,5-二异丙基苯基)丙基]氨基}甲基)苯基]噻吩-2-甲酰亚胺； N-(3-[(4-羟基-3,5-二异丙基苯基)甲基]氨基}苯基)噻吩-2-甲酰亚胺； N-[3-([2-(4-羟基-3,5-二异丙基苯基)乙基]氨基}甲基)苯基]噻吩-2-甲酰亚胺； N-2-(3,5-二叔丁基-4-羟基苯甲酰)-N-1-4-[imino(噻唑-2-基)甲基]氨基}苯基-L-亮氨酰； 及其药学上可接受的盐。
• 2-(iminomethyl) amino-phenyl derivatives, preparation, application as medicines and pharmaceutical compositions containing same
  申请人：Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)

  公开号：US06340700B1

  公开（公告）日：2002-01-22

  A compound of the formula wherein the substituents are defined as in the specification and their pharmaceutically acceptable salts having NOS and ROS activity.

  该化合物的分子式如下，其中取代基的定义如规范中所述，以及其具有NOS和ROS活性的药用可接受盐。
• Synthesis and evaluation of new N6-substituted adenosine-5′-N-methylcarboxamides as A3 adenosine receptor agonists
  作者：Shane M. Devine、Alison Gregg、Heidi Figler、Kate McIntosh、Vijay Urmaliya、Joel Linden、Colin W. Pouton、Paul J. White、Steven E. Bottle、Peter J. Scammells

  DOI：10.1016/j.bmc.2010.03.047

  日期：2010.5

  A number of N6-substituted adenosine-5′-N-methylcarboxamides were synthesised and their pharmacology, in terms of their receptor affinity, selectivity and cardioprotective effects, were explored. The first series of compounds, 4a–4f and 5a–5f, showed modest receptor affinity for the A3AR with Ki values in the low to mid μM range. However, the incorporation of a 4-(2-aminoethyl)-2,6-di-tert-butylphenol

  合成了许多N 6-取代的腺苷-5'- N-甲基羧酰胺，并就其受体亲和力，选择性和心脏保护作用探讨了其药理作用。第一系列的化合物，4A - 4F和5A - 5F显示出适度的受体的亲和力的A 3 AR与ķ我在低位μM中间范围的值。但是，在N 6位（在化合物4g和5g中）引入4-（2-氨基乙基）-2,6-二叔丁基苯酚基团可以显着改善与K i值分别为30和9 nM。当引入功能化的接头时，亲和力和选择性都得到了改善。所述Ñ 6 -苯基系列，化合物7A - 7D，表明低到中纳摩尔亲和力受体（ķ我 = 2.3-45.0纳米），与图7B显示用于A 109倍的选择性3 AR（Vs的1）。所述Ñ 6 -苄基系列图9a - 9c中也被证明是有效的和选择性阿3 AR激动剂和较长链长的接头13在A是不能容忍的3 AR，无需取消亲和力或选择性。通过模拟的局部缺血细胞培养测定法证明了心脏保护作用，其中7b，7c，9a，9b和9c均在100
• [EN] NOVEL 2-(IMINOMETHYL)AMINO-PHENYL DERIVATIVES, PREPARATION, APPLICATION AS MEDICINES AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME<br/>[FR] NOUVEAUX DERIVES DU 2-(IMINOMETHYL)AMINO-PHENYLE, LEUR PREPARATION, LEUR APPLICATION A TITRE DE MEDICAMENTS ET LES COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.)

  公开号：WO1998042696A1

  公开（公告）日：1998-10-01

  (EN) The invention concerns novel 2-(iminomethyl)amino-phenyl derivatives, their preparation, their application as medicines and pharmaceutical compositions containing them.(FR) L'invention a pour objet des nouveaux dérivés du 2-(iminométhyl)amino-phényle, leur préparation, leur application à titre de médicaments et les compositions pharmaceutiques les contenant.

  这项发明涉及新的2-(亚胺甲基)氨基苯基衍生物，它们的制备，它们作为药物的应用，以及含有它们的药物组合物。
• New derivatives of 2-(iminomethyl) amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them
  申请人：SOCIETE DE CONSEILS DE RECHERCHES ET D' APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.)

  公开号：US20020007062A1

  公开（公告）日：2002-01-17

  A method for treating neurodegenerative diseases in a warm-blooded animal comprising administering to a warm-blooded animal in need thereof an amount of a compound of the formula 1 wherein A selected from the group consisting of hydrogen and 2 wherein the substituents are defined as set forth in the specification.

  一种治疗恒温动物神经退行性疾病的方法，包括向需要治疗的恒温动物中给予化合物1的量，其中A选自氢和2，其中取代基的定义如规范中所述。