NSC 676538

• 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: NSC 676538
• 英文别名: 3-(2,5-Dihydroxy-benzylamino)-benzoic acid；3-[(2,5-dihydroxyphenyl)methylamino]benzoic acid
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: PCBHHKFQNAFXJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-氨基水杨酸 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 NSC 676538
  参考文献：
  名称：

  Synthesis and structure-activity studies of a series of [(hydroxybenzyl)amino]salicylates as inhibitors of EGF receptor-associated tyrosine kinase activity

  摘要：

  The synthesis and structure-activity relationships of a series of [(hydroxybenzylidene)amino] salicylates and a series of [(hydroxybenzyl)amino] salicylates as inhibitors of EGF receptor-associated tyrosine kinase activity are described. Their inhibitory potency was evaluated in vitro using ER 22 cell membranes (CCL 39 cells transfected with EGF receptor) as an enzyme source and the tridecapeptide RRSrc (RRLIEDAEYAARG) as substrate. Their cellular activity was measured by inhibition of the EGF-stimulated DNA synthesis of ER 22 cells. Chemical modifications were made to analyze the role of the different substituents. The amino series was found to be more active than the imino series. The hydroquinone moiety appears to be essential for tyrosine kinase inhibitory activity in the series of 5-[(2,5-dihydroxybenzyl)amino]salicylates. Comparison of the imino and amino series by molecular modeling techniques provides further evidence in support of the hypothesis that the important reduced linking chain, CH2NH, allows the correct positioning of the 2,5-dihydroxybenzyl ring, possibly in a cis-like conformational arrangement.

  DOI：

  10.1021/jm00077a014

文献信息

• Neuroprotective Compositions and Methods
  申请人：Lipton Stuart A.

  公开号：US20120296112A1

  公开（公告）日：2012-11-22

  Neurite outgrowth-promoting prostaglandins (NEPPs) and other electrophilic compounds bind to Keap1, a negative regulator of the transcription factor Nrf2, and prevent Keap1-mediated inactivation of Nrf2 and, thus, enhance Nrf2 translocation into the nucleus of neuronal cells. Therefore, neuroprotective compositions and related methods are provided that employ such neuroprotective compounds, and prodrugs of such compounds, to cause dissociation of Nrf2 from a Keap1/Nrf2 complex.

  神经突起促进前列腺素（NEPPs）和其他电子亲和力化合物结合到Keap1上，Keap1是转录因子Nrf2的负调节因子，防止Keap1介导的Nrf2失活，并增强Nrf2进入神经元细胞核的转位。因此，提供了使用这些神经保护化合物及其前药的神经保护组合物和相关方法，以使Nrf2与Keap1 / Nrf2复合物解离的方法。
• A Versatile Solid Phase Synthesis of Lavendustin A and Certain Biologically Active Analogs
  作者：Rajesh Devraj、Mark Cushman

  DOI：10.1021/jo961719l

  日期：1996.1.1

  Reaction of aminomethylated polystyrene resin (8) with succinic anhydride, followed by esterification of the free carboxylic acid of the product 9 with 2,5-dihydroxybenzaldehyde (4) afforded the resin-linked aldehyde intermediate 10. The key intermediate 10 was converted into the protein-tyrosine kinase inhibitor lavendustin A and certain analogs through reductive amination and reductive alkylation steps, followed by cleavage from the resin. This method enables the preparation of a wide variety of lavendustin A analogs using combinatorial chemistry and parallel synthesis techniques.
• AROMATIC COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：ZENECA LIMITED

  公开号：EP0847391A1

  公开（公告）日：1998-06-17
• Neuroprotective compositions and methods
  申请人：Lipton Stuart A.

  公开号：US20090042980A1

  公开（公告）日：2009-02-12

  Neurite outgrowth-promoting prostaglandins (NEPPs) and other electrophilic compounds bind to Keap1, a negative regulator of the transcription factor Nrf2, and prevent Keap1-mediated inactivation of Nrf2 and, thus, enhance Nrf2 translocation into the nucleus of neuronal cells. Therefore, neuroprotective compositions and related methods are provided that employ such neuroprotective compounds, and prodrugs of such compounds, to cause dissociation of Nrf2 from a Keap1/Nrf2 complex.
• US6100258A
  申请人：——

  公开号：US6100258A

  公开（公告）日：2000-08-08