(Z)-α-(2'-bromo-5'-hydroxy-4'-methoxyphenyl)-N-tert-butylnitrone | 1271303-77-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (Z)-α-(2'-bromo-5'-hydroxy-4'-methoxyphenyl)-N-tert-butylnitrone
• 英文别名: 1-(2-bromo-5-hydroxy-4-methoxyphenyl)-N-tert-butylmethanimine oxide
• CAS: 1271303-77-5
• 化学式: C₁₂H₁₆BrNO₃
• 分子量: 302.168
• InChiKey: REZROVMMZGHASO-AUWJEWJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-5-羟基-4-甲氧基苯甲醛 、 N-叔丁基羟胺盐酸盐 在 sodium sulfate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以65%的产率得到(Z)-α-(2'-bromo-5'-hydroxy-4'-methoxyphenyl)-N-tert-butylnitrone
  参考文献：
  名称：

  Synthesis, structure, theoretical and experimental in vitro antioxidant/pharmacological properties of α-aryl, N-alkyl nitrones, as potential agents for the treatment of cerebral ischemia

  摘要：

  The synthesis, structure, theoretical and experimental in vitro antioxidant properties using the DPPH, ORAC, and benzoic acid, as well as preliminary in vitro pharmacological activities of (Z)-alpha-aryl and heteroaryl N-alkyl-nitrones 6-15, 18, 19, 21, and 23, is reported. In the in vitro antioxidant activity, for the DPPH radical test, only nitrones bearing free phenol groups gave the best RSA (%) values, nitrones 13 and 14 showing the highest values in this assay. In the ORAC analysis, the most potent radical scavenger was nitrone indole 21, followed by the N-benzyl benzene-type nitrones 10 and 15. Interestingly enough, the archetypal nitrone 7 (PBN) gave a low RSA value (1.4%) in the DPPH test, or was inactive in the ORAC assay. Concerning the ability to scavenge the hydroxyl radical, all the nitrones studied proved active in this experiment, showing high values in the 94-97% range, the most potent being nitrone 14. The theoretical calculations for the prediction of the antioxidant power, and the potential of ionization confirm that nitrones 9 and 10 are among the best compounds in electron transfer processes, a result that is also in good agreement with the experimental values in the DPPH assay. The calculated energy values for the reaction of ROS (hydroxyl, peroxyl) with the nitrones predict that the most favourable adduct-spin will take place between nitrones 9, 10, and 21, a fact that would be in agreement with their experimentally observed scavenger ability. The in vitro pharmacological analysis showed that the neuroprotective profile of the target molecules was in general low, with values ranging from 0% to 18.7%, in human neuroblastoma cells stressed with a mixture of rotenone/oligomycin-A, being nitrones 18, and 6-8 the most potent, as they show values in the range 24-18.4%. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.053

文献信息

• STEROIDAL NITRONES FOR THE TREATMENT AND PREVENTION OF A CEREBRAL STROKE OR ISCHAEMIA, ALZHEIMER AND PARKINSON DISEASE AND AMYOTROPHIC LATERAL SCLEROSIS
  申请人：FUNDACIÓN PARA LA INVESTIGACIÓN BIOMÉDICA DEL HOSPITAL UNIVERSITARIO RAMÓN Y CAJAL

  公开号：US20160089382A1

  公开（公告）日：2016-03-31

  The invention relates to neuroprotective, antioxidant steroidal nitrones to which the blood-brain barrier is highly permeable, as potential drugs for the treatment of a cerebral stroke or ischaemia, Alzheimer and Parkinson disease and amyotrophic lateral sclerosis.

  这项发明涉及神经保护、抗氧化的类固醇亚硝酮，其对血脑屏障有很高的渗透性，作为治疗脑卒中或缺血、阿尔茨海默病、帕金森病和肌萎缩侧索硬化症的潜在药物。
• Steroidal nitrones for the treatment and prevention of a cerebral stroke or ischaemia, alzheimer and parkinson disease and amyotrophic lateral sclerosis
  申请人：FUNDACIÓN PARA LA INVESTIGACIÓN BIOMÉDICA DEL HOSPITAL UNIVERSITARIO RAMÓN Y CAJAL

  公开号：US10071106B2

  公开（公告）日：2018-09-11

  The invention relates to neuroprotective, antioxidant steroidal nitrones to which the blood-brain barrier is highly permeable, as potential drugs for the treatment of a cerebral stroke or ischaemia, Alzheimer and Parkinson disease and amyotrophic lateral sclerosis.

  本发明涉及具有神经保护作用的抗氧化甾体硝基化合物，血脑屏障对其具有高渗透性，可作为治疗脑中风或脑缺血、阿尔茨海默病、帕金森病和肌萎缩性脊髓侧索硬化症的潜在药物。
• Synthesis, structure, theoretical and experimental in vitro antioxidant/pharmacological properties of α-aryl, N-alkyl nitrones, as potential agents for the treatment of cerebral ischemia
  作者：Abdelouahid Samadi、Elena Soriano、Julia Revuelta、Carolina Valderas、Mourad Chioua、Ignacio Garrido、Begoña Bartolomé、Isabelle Tomassolli、Lhassane Ismaili、Laura González-Lafuente、Mercedes Villarroya、Antonio G. García、María J. Oset-Gasque、José Marco-Contelles

  DOI：10.1016/j.bmc.2010.11.053

  日期：2011.1

  The synthesis, structure, theoretical and experimental in vitro antioxidant properties using the DPPH, ORAC, and benzoic acid, as well as preliminary in vitro pharmacological activities of (Z)-alpha-aryl and heteroaryl N-alkyl-nitrones 6-15, 18, 19, 21, and 23, is reported. In the in vitro antioxidant activity, for the DPPH radical test, only nitrones bearing free phenol groups gave the best RSA (%) values, nitrones 13 and 14 showing the highest values in this assay. In the ORAC analysis, the most potent radical scavenger was nitrone indole 21, followed by the N-benzyl benzene-type nitrones 10 and 15. Interestingly enough, the archetypal nitrone 7 (PBN) gave a low RSA value (1.4%) in the DPPH test, or was inactive in the ORAC assay. Concerning the ability to scavenge the hydroxyl radical, all the nitrones studied proved active in this experiment, showing high values in the 94-97% range, the most potent being nitrone 14. The theoretical calculations for the prediction of the antioxidant power, and the potential of ionization confirm that nitrones 9 and 10 are among the best compounds in electron transfer processes, a result that is also in good agreement with the experimental values in the DPPH assay. The calculated energy values for the reaction of ROS (hydroxyl, peroxyl) with the nitrones predict that the most favourable adduct-spin will take place between nitrones 9, 10, and 21, a fact that would be in agreement with their experimentally observed scavenger ability. The in vitro pharmacological analysis showed that the neuroprotective profile of the target molecules was in general low, with values ranging from 0% to 18.7%, in human neuroblastoma cells stressed with a mixture of rotenone/oligomycin-A, being nitrones 18, and 6-8 the most potent, as they show values in the range 24-18.4%. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.