N-(2,5-dihydroxybenzyl)-p-hydroxyaniline

• 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-(2,5-dihydroxybenzyl)-p-hydroxyaniline
• 英文别名: 2-[(4-Hydroxy-phenylamino)-methyl]-benzene-1,4-diol；2-[(4-hydroxyanilino)methyl]benzene-1,4-diol
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: AODCQEOEMRWMAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,5-二羟基苯甲醛 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 N-(2,5-dihydroxybenzyl)-p-hydroxyaniline
  参考文献：
  名称：

  Synthesis and biological activity of 5-[(2,5-dihydroxybenzyl)amino]salicylic acid analogs as inhibitors of EGF receptor-associated protein tyrosine kinase

  摘要：

  The synthesis and biological activity of a series of 5-[(2,5-dihydroxybenzyl)amino]salicylic acid derivatives (3-6) as analogs of the active partial structure (2) of the potent EGF-R tyrosine kinase inhibitor lavendustin A (1) are described. Analogs with an electron-withdrawing group in place of the carboxyl group of 2 showed activity. The N-hexylsalicylamide analog 6b (IC50 = 0.9 mu M) was about four times more potent than 2. (C) 1997, Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00014-0

文献信息

• NOUVEAUX DERIVES DE LA DIHYDROXYBENZYLAMINE, LEUR PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT
  申请人：RHONE-POULENC RORER S.A.

  公开号：EP0641311A1

  公开（公告）日：1995-03-08
• US4152452A
  申请人：——

  公开号：US4152452A

  公开（公告）日：1979-05-01
• [EN] NOVEL DIHYDROXYBENZYLAMINE DERIVATIVES, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME<br/>[FR] NOUVEAUX DERIVES DE LA DIHYDROXYBENZYLAMINE, LEUR PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT
  申请人：——

  公开号：WO1993023364A1

  公开（公告）日：1993-11-25

  [FR] Nouveaux dérivés de la 2,5-dihydroxybenzylamine de formule générale (I), leur préparation et les compositions pharmaceutiques qui les contiennent. Dans la formule générale (I), l'un des symboles R1 ou R2 représente un atome d'hydrogène ou d'halogène ou radical hydroxy, alcoxy, alcoylcarbonyloxy, arylcarbonyloxy, mercapto, alcoylthio, amino, formylamino, alcoylcarbonylamino, arylcarbonylamino et l'autre représente un radical alcoxy, alcoxyméthyle, acyle, arylcarbonyle, alcoyloxycarbonyle, aryloxycarbonyle, alcényloxycarbonyle, carbamoyle ou thiocarbamoyle dont l'atome d'azote est éventuellement substitué par un ou deux radicaux alcoyles ou phényles, les radicaux alcoyles, phényles et aryles étant éventuellement substitués. Les nouveaux produits de formule (I) manifestent une activité antitumorale remarquable.
  [EN] Novel 2,5 dihydroxybenzylamine derivatives of general formula (I), their preparation and pharmaceutical compositions containing same. In general formula (I), one of the symbols R1? or R2? denots a hydrogen or halo atom or a hydroxy, alkoxy, alkylcarbonyloxy arylcarbonyloxy, mercapto, alkylthio, amino, formylamino, alkylcarbonylamino, arylcarbonylamino radical and the other denotes an alkoxy, alkoxymethyl, acyl, arylcarbonyl, alkyloxycarbonyl, aryloxycarbonyl, alkenyloxycarbonyl, carbamoyl or thiocarbamoyl radical, the nitrogen atom being optionally substituted by one or two alkyl or phenyl radicals, the alkyl, phenyl and aryl radicals being optionally substituted. The novel products of formula (I) have outstanding tumour prevention activity.
• Synthesis and biological activity of 5-[(2,5-dihydroxybenzyl)amino]salicylic acid analogs as inhibitors of EGF receptor-associated protein tyrosine kinase
  作者：Tianming Liu、Ryuichi Shirai、Takashi Matsui、Kazuo Umezawa、Shigeo Iwasaki

  DOI：10.1016/s0960-894x(97)00014-0

  日期：1997.2

  The synthesis and biological activity of a series of 5-[(2,5-dihydroxybenzyl)amino]salicylic acid derivatives (3-6) as analogs of the active partial structure (2) of the potent EGF-R tyrosine kinase inhibitor lavendustin A (1) are described. Analogs with an electron-withdrawing group in place of the carboxyl group of 2 showed activity. The N-hexylsalicylamide analog 6b (IC50 = 0.9 mu M) was about four times more potent than 2. (C) 1997, Published by Elsevier Science Ltd.