N-(3,5-di-tert-butyl-4-hydroxybenzyl)piperazine | 13790-75-5

• 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-(3,5-di-tert-butyl-4-hydroxybenzyl)piperazine
• 英文别名: 2,6-di-tert-butyl-4-piperazin-1-ylmethyl-phenol；1-(3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)methylpiperazine；2,6-Di-tert-butyl-4-[(piperazin-1-yl)methyl]phenol；2,6-ditert-butyl-4-(piperazin-1-ylmethyl)phenol
• CAS: 13790-75-5
• 化学式: C₁₉H₃₂N₂O
• 分子量: 304.476
• InChiKey: NSHPHKYHPUUZGS-UHFFFAOYSA-N

物化性质

• 熔点：
  197-199 °C
• 沸点：
  375.2±37.0 °C(Predicted)
• 密度：
  1.002±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  35.5
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6,6-双(4-氟苯基)-正己酸 、 N-(3,5-di-tert-butyl-4-hydroxybenzyl)piperazine 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-[4-[(3,5-Ditert-butyl-4-hydroxyphenyl)methyl]piperazin-1-yl]-6,6-bis(4-fluorophenyl)hexan-1-one
  参考文献：
  名称：

  Structure–activity relationships of trimethoxybenzyl piperazine N-type calcium channel inhibitors

  摘要：

  We previously reported the small organic N-type calcium channel blocker NP078585 that while efficacious in animal models for pain, exhibited modest L-type calcium channel selectivity and substantial off-target inhibition against the hERG potassium channel. Structure-activity studies to optimize NP078585 preclinical properties resulted in compound 16, which maintained high potency for N-type calcium channel blockade, and possessed excellent selectivity over the hERG (similar to 120-fold) and L-type (similar to 3600-fold) channels. Compound 16 shows significant anti-hyperalgesic activity in the spinal nerve ligation model of neuropathic pain and is also efficacious in the rat formalin model of inflammatory pain. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.054
• 作为产物：
  描述：

  3,5-二叔丁基-4-羟基苯甲酸 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-(3,5-di-tert-butyl-4-hydroxybenzyl)piperazine
  参考文献：
  名称：

  Structure–activity relationships of trimethoxybenzyl piperazine N-type calcium channel inhibitors

  摘要：

  We previously reported the small organic N-type calcium channel blocker NP078585 that while efficacious in animal models for pain, exhibited modest L-type calcium channel selectivity and substantial off-target inhibition against the hERG potassium channel. Structure-activity studies to optimize NP078585 preclinical properties resulted in compound 16, which maintained high potency for N-type calcium channel blockade, and possessed excellent selectivity over the hERG (similar to 120-fold) and L-type (similar to 3600-fold) channels. Compound 16 shows significant anti-hyperalgesic activity in the spinal nerve ligation model of neuropathic pain and is also efficacious in the rat formalin model of inflammatory pain. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.054

文献信息

• Arylalkylpiperazine compounds as antioxidants
  申请人：Monash University

  公开号：US06232314B1

  公开（公告）日：2001-05-15

  Arylalkylpiperazine compounds (1) wherein B is aryl or optionally substituted aryl; R1 is hydroxy; R2 and R3 are the same or different and are independently selected from hydrogen or C1-3 alkyl; m is 0, 1 or 2; D is a linking chain of atoms which may be optionally substituted and which contains from 1 to 8 atoms in the chain; E is a phenolic antioxidant group or a corresponding amino derivative thereof wherein the phenolic hydroxyl is replaced by amino, are disclosed. The compounds have both free radical scavenging activity and block excitatory amino acid activity. Some compounds of the present invention also display an affinity for voltage-sensitive sodium channels.

  本发明揭示了芳基烷基哌嗪化合物（1），其中B是芳基或可选取代芳基；R1是羟基；R2和R3相同或不同，且独立地选自氢或C1-3烷基；m为0、1或2；D为原子连接链，可以选择性地取代，且链中含有1至8个原子；E为酚类抗氧化剂基团或相应的氨基衍生物，其中酚羟基被氨基取代。这些化合物既具有自由基清除活性，又具有抑制兴奋性氨基酸活性的作用。本发明的某些化合物还显示出与电压敏感型钠通道的亲和力。
• [EN] ARYLALKYLPIPERAZINE COMPOUNDS AS ANTIOXIDANTS<br/>[FR] COMPOSES ANTIOXYDANTS D'ARYLALKYLPIPERAZINE
  申请人：MONASH UNIVERSITY

  公开号：WO1997043259A1

  公开（公告）日：1997-11-20

  (EN) Arylalkylpiperazine compounds (1) wherein B is aryl or optionally substituted aryl; R1 is hydroxy; R2 and R3 are the same or different and are independently selected from hydrogen or C1-3 alkyl; m is 0, 1 or 2; D is a linking chain of atoms which may be optionally substituted and which contains from 1 to 8 atoms in the chain; E is a phenolic antioxidant group or a corresponding amino derivative thereof wherein the phenolic hydroxyl is replaced by amino, are disclosed. The compounds have both free radical scavenging activity and block excitatory amino acid activity. Some compounds of the present invention also display an affinity for voltage-sensitive sodium channels.(FR) L'invention porte sur des composés d'arylalkylpipérazine de formule (1) dans laquelle: B est aryle ou aryle facultativement substitué; R1 est hydroxy; R2 et R3 sont identiques ou différents et choisis indépendamment parmi H ou alkyle C1-3; m est 0, 1 ou 2; D est une chaîne d'atomes de liaison éventuellement facultativement substituée et qui contient de un à huit atomes; E est un groupe phénolique antioxydant ou l'un de ses dérivés amino correspondants dans lequel l'hydroxyle phénolique est remplacé par amino. Ces composés présentent à la fois une activité d'absorption de radicaux libres, et de blocage de l'activité des acides aminés excitateurs. Certains de ces composés présentent également une affinité pour les canaux sodiques sensibles aux tensions électriques.

  Arylalkylpiperazine化合物（1），其中B是芳基或可选择取代的芳基；R1是羟基；R2和R3相同或不同，并且独立地选择氢或C1-3烷基；m为0、1或2；D是原子链的连接链，可以选择取代，并且链中包含1至8个原子；E是酚类抗氧化剂基团或相应的氨基衍生物，其中酚羟基被氨基取代。这些化合物具有自由基清除活性和阻断兴奋性氨基酸活性。本发明的一些化合物还显示了对电压敏感的钠通道的亲和力。
• EP0901469A4
  申请人：——

  公开号：EP0901469A4

  公开（公告）日：2000-11-15
• ARYLALKYLPIPERAZINE COMPOUNDS AS ANTIOXIDANTS
  申请人：MONASH UNIVERSITY

  公开号：EP0901469A1

  公开（公告）日：1999-03-17
• US6232314B1
  申请人：——

  公开号：US6232314B1

  公开（公告）日：2001-05-15