C-(3-hydroxyphenyl)-N-tert-butylnitrone | 104883-61-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: C-(3-hydroxyphenyl)-N-tert-butylnitrone
• 英文别名: N-tert-butyl-1-(3-hydroxyphenyl)methanimine oxide
• CAS: 104883-61-6
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: RWHHJPINUDSOJL-WQLSENKSSA-N

物化性质

• 沸点：
  351.6±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)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-叔丁基羟胺 、 间羟基苯甲醛 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以43%的产率得到C-(3-hydroxyphenyl)-N-tert-butylnitrone
  参考文献：
  名称：

  Synthesis and characterization of phenyl-substituted C-phenyl-N-tert-butylnitrones and some of their radical adducts

  摘要：

  Synthesis of C-phenyl-N-tert-butylnitrone (PBN) and several of its analogues with substituents in the 2-, 3-, or 4-position on the phenyl ring is described. While a one-pot reduction/condensation method proved suitable for most compounds, it was necessary to prepare some examples by direct condensation or through oxidation of the appropriate imine. The H-1 NMR data for the 3-X- and 4-X-PBN's can be correlated with the Hammett equation. For the 3-X series DELTA-delta for the alpha-proton correlates best with sigma(+) and has a correlation coefficient of 0.90. For the 4-X series a dual substituent parameter equation using sigma(R)0 gives the best correlation with r = 0.99. The hyperfine splitting constants (hfsc's) of the HO. and HOO. adducts of several substituted PBN's are also included and their correlation with the Hammett equation is discussed.

  DOI：

  10.1021/jo00035a020

文献信息

• 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。
• Synthesis, antioxidant and neuroprotective analysis of diversely functionalized α-aryl-N-alkyl nitrones as potential agents for ischemic stroke therapy
  作者：Alejandro Escobar-Peso、Emma Martínez-Alonso、Dimitra Hadjipavlou-Litina、Alberto Alcázar、José Marco-Contelles

  DOI：10.1016/j.ejmech.2024.116133

  日期：2024.2
• BUTYLNITRONE CONTAINING COMPOSITIONS FOR INHIBITION OF CANCER DEVELOPMENT
  申请人：Oklahoma Medical Research Foundation

  公开号：EP1267860A1

  公开（公告）日：2003-01-02
• ADJUVANT CHEMOTHERAPY FOR ANAPLASTIC GLIOMAS
  申请人：Oklahoma Medical Research Foundation

  公开号：EP1922075A2

  公开（公告）日：2008-05-21
• US5972977A
  申请人：——

  公开号：US5972977A

  公开（公告）日：1999-10-26