α-(2-hydroxyphenyl)-N-tert-butylnitrone | 104883-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: α-(2-hydroxyphenyl)-N-tert-butylnitrone
• 英文别名: (Z)-N-(2-hydroxybenzylidene)-2-methylpropan-2-amine oxide；α-(Z)-(2-hydroxyphenyl)-N-tert-butylnitrone；C-(2-hydroxyphenyl)-N-tert-butylnitrone
• CAS: 104883-60-5；130995-63-0
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: HGLLGCIZHHMQDE-WQLSENKSSA-N

物化性质

• 沸点：
  325.9±44.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  α-(2-hydroxyphenyl)-N-tert-butylnitrone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 N-o-hydroxybenzyl-N-tert-butylhydroxylamine
  参考文献：
  名称：

  Ali, Sk. Asrof; Hassan, Azfar; Wazeer, Mohammed I. M., Journal of the Chemical Society. Perkin transactions II, 1996, # 7, p. 1479 - 1484

  摘要：

  DOI：
• 作为产物：
  描述：

  N-叔丁基羟胺盐酸盐 、 水杨醛 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以90%的产率得到α-(2-hydroxyphenyl)-N-tert-butylnitrone
  参考文献：
  名称：

  Microwave-assisted synthesis of hydroxyphenyl nitrones with protective action against oxidative stress

  摘要：

  Oxidative stress plays an important role in neuronal death in neurodegenerative disorders such as Parkinson's disease (PD). Hydroxyphenyl nitrones, derivatives of the nitrone spin trap alpha-phenyl-N-tert-butylnitrone (PBN), were synthesized and their antioxidant, anti-inflammatory and neuroprotective activity in neural cells evaluated. These hydroxyphenyl nitrones 5-7 were synthesized by reaction of the corresponding hydroxybenzaldehyde with N-tert-butyl hydroxylamine under microwave irradiation. They showed good peroxyl free radical scavenger capacities, analyzed by oxygen radical absorbance capacity (ORAC). Also inhibited peroxynitrite-mediated tyrosine nitration of alpha-synuclein in vitro and protected human neuroblastoma (SH-SY5Y) cells against SIN-1 and 6-OHDA toxicity when micromolar concentrations were used. Besides, the hydroxyphenyl nitrones evaluated showed anti-inflammatory activity modulating nitrite production in primary neural cell cultures of astrocytes and microglia treated with lipopolysaccharide (LPS), a potent inflammatory agent. These experimental data suggest a potential therapeutic use of these hydroxyphenyl nitrones against oxygen and nitrogen reactive species involved in neurodegenerative pathology. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.044

文献信息

• NITRONE COMPOUNDS AND THEIR USE IN PERSONAL CARE
  申请人：Dow Global Technologies LLC

  公开号：US20150335546A1

  公开（公告）日：2015-11-26

  Provided are compounds and compositions thereof that are useful as antioxidants in personal care formulations. The compounds are of the formula I: wherein R, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined herein.

  提供了化合物及其组合物，可作为个人护理配方中的抗氧化剂。该化合物的化学式如下：其中R、R1、R2、R3、R4、R5和R6的定义如本文所述。
• Methods of treating, inhibiting and/or preventing an auditory impairment
  申请人：The Department of Veterans Affairs

  公开号：US10124062B2

  公开（公告）日：2018-11-13

  The present invention provides methods of treating an auditory impairment associated with outer hair cells of the cochlea in a subject. The method may comprise administering to said subject an effective amount of a composition comprising, as an active agent, an oligonucleotide sequence having a portion of a mammalian telomere sequence so as to reduce the auditory impairment thereby treating the auditory impairment in the subject.

  本发明提供了治疗与受试者耳蜗外毛细胞相关的听觉损伤的方法。该方法可包括向所述受试者施用有效量的组合物，该组合物作为活性剂包含具有哺乳动物端粒序列部分的寡核苷酸序列，以减少听觉损伤，从而治疗受试者的听觉损伤。
• Nitrone inhibition of oxidation of unsaturated fats
  申请人：Dow Global Technologies LLC

  公开号：US10130574B2

  公开（公告）日：2018-11-20

  Provided are compositions useful for inhibiting oxidation of unsaturated fats comprising an antioxidant compound of Formula I: wherein R, R1, R2, R3, R4, R5 and R6 are as defined herein.

  本发明提供了用于抑制不饱和脂肪氧化的组合物，其中包含式 I 的抗氧化剂化合物： 其中 R、R1、R2、R3、R4、R5 和 R6 如本文所定义。
• Nitrone inhibition of cancer development
  申请人：OKLAHOMA MEDICAL RESEARCH FOUNDATION

  公开号：US20020004531A1

  公开（公告）日：2002-01-10

  PBN (&agr;-phenyl-tert-butylnitrone), and its derivatives nitrone-based free radical traps, significantly reduce preneoplastic nodule development as well as inhibit hepatocellular carcinoma (HCC) formation at very low levels. The involvement of reactive oxygen species (ROS) in cancer development has been strongly implicated for many years. The involvement of ROS has been strongly implicated in cancer development is a model system where feeding a choline deficiency (CD) diet to rats leads to hepatocellular carcinoma (HCC) development. Administering PBN in the drinking water inhibits HCC formation. Preneoplastic nodule growth in the liver is significantly suppressed by administering PBN, or some ofits natural metabolites, in the diet. The effectiveness of PBN in preventing HCC development in the CD liver model is considered due to its prevention of tumor development after the target cells have already been initiated, i.e.genetically changed into tumor cells. Administration of PBN (or its potent derivatives) to humans that may already have microscopic tumor preneoplastic nodules should prevent the eventual frank tumor formation.

  PBN（&agr;-phenyl-tert-butylnitrone，苯基叔丁基硝酮）及其衍生物硝基自由基捕获剂可显著减少肿瘤前结节的发展，并在极低水平上抑制肝细胞癌（HCC）的形成。多年来，活性氧（ROS）与癌症发展的关系一直很密切。在一个模型系统中，给大鼠喂食胆碱缺乏（CD）饮食会导致肝细胞癌（HCC）的发生，ROS 与癌症的发生发展有着密切的关系。在饮用水中添加 PBN 可抑制 HCC 的形成。在饮食中添加 PBN 或其某些天然代谢物可显著抑制肝脏中肿瘤前结节的生长。在 CD 肝脏模型中，多肽萘能有效防止 HCC 的发展，这是因为多肽萘能在靶细胞已经开始生长（即基因改变为肿瘤细胞）后防止肿瘤的发展。对已经出现微小肿瘤前瘤结节的人体施用 PBN（或其强效衍生物），应能防止肿瘤最终形成。
• COMPOSITIONS COMPRISING A NITRONE COMPOUND FOR USE IN TREATING UVEITIS
  申请人：CENTAUR PHARMACEUTICALS, INC.

  公开号：EP0910370B1

  公开（公告）日：2004-04-07