5-([(1E)-(2-hydroxyphenyl)methylene]amino)-2-hydroxybenzoic acid | 151391-75-2

• 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: 5-([(1E)-(2-hydroxyphenyl)methylene]amino)-2-hydroxybenzoic acid
• 英文别名: 5-{[(1E)-(2-hydroxyphenyl)methylene]amino}-2-hydroxybenzoic acid
• CAS: 151391-75-2
• 化学式: C₁₄H₁₁NO₄
• 分子量: 257.246
• InChiKey: BICCUOGEUODANY-OVCLIPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.12
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-([(1E)-(2-hydroxyphenyl)methylene]amino)-2-hydroxybenzoic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 2-Hydroxy-5-(2-hydroxy-benzylamino)-benzoic acid
  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
• 作为产物：
  描述：

  5-氨基水杨酸 、 水杨醛 以 乙醇 为溶剂， 反应 2.0h， 生成 5-([(1E)-(2-hydroxyphenyl)methylene]amino)-2-hydroxybenzoic acid
  参考文献：
  名称：

  异双金属拓扑异构酶I和II抑制剂复合物的设计和合成：体外DNA结合，与5'-GMP和5'-TMP的相互作用以及裂解研究。

  摘要：

  设计并制备了新的潜在的癌症化学治疗复合物Cu-Sn（2）/ Zn-Sn（2）3和4作为拓扑异构酶抑制剂。他们进行了体外DNA结合研究，除其他结合方式外，还通过DNA螺旋的磷酸盐骨架显示出强大的静电结合。协调共价和部分插入。为了深入了解目标位点的分子结合事件，用（1）的（3）和（4）情况下的目标单核苷酸，即5'-GMP和5'-TMP进行了UV-vis滴定。 1 H和（31）P NMR。使用凝胶电泳的裂解研究表明，复合物3和4都是有效的裂解剂，并且是特定的凹槽结合剂（复合物3结合到主要和次要凹槽，而复合物4仅是具体的次要凹槽结合剂）。此外，该复合物显示出对拓扑异构酶I和II的高抑制活性。然而，复合物4在约2.5μM的非常低的浓度下对Topo I活性显示出显着的抑制作用。

  DOI：

  10.1016/j.jphotobiol.2010.06.009

文献信息

• Late metal salicylaldimine complexes derived from 5-aminosalicylic acid — Molecular structure of a zwitterionic mono Schiff base zinc complex
  作者：Tara A Bourque、Megan E Nelles、Teri J Gullon、Christian N Garon、Melissa K Ringer、Lisa J Leger、Jamie W Mason、Susan L Wheaton、Felix J Baerlocher、Christopher M Vogels、Andreas Decken、Stephen A Westcott

  DOI：10.1139/v05-091

  日期：2005.8.1

  Condensation of salicylaldehyde (2-HOC₆H₄C(O)H) with 5-aminosalicylic acid (5-H₂NC₆H₃-2-(OH)-CO₂H) afforded the Schiff base 2-HOC₆H₄C(H)=NC₆H₃-2-(OH)-5-CO₂H (a). Similar reactivity with 5-bromosalicylaldehyde was also observed to give 5-Br-2-HOC₆H₃C(H)=NC₆H₃-2-(OH)-5-CO₂H (b). Reaction of these salicylaldehydes with Pd(II), Cu(II), and Zn(II) salts gave the corresponding bis(N-arylsalicylaldiminato)metal complexes (M = Pd (1), Cu (2), Zn (3)). The molecular structure of the Schiff base compound a has been confirmed by an X-ray diffraction study. Crystals of a were monoclinic, space group P2(1)/c, a = 7.0164(7) Å, b = 11.0088(11) Å, c = 14.8980(15) Å, β = 102.917(2)°, Z = 4. The molecular structure of a novel zwitterionic conformer of 3a was also characterized by an X-ray diffraction study. Crystals of 4 were monoclinic, space group P2(1)/c, a = 9.5284(5) Å, b = 19.5335(11) Å, c = 8.6508(5) Å, β = 90.596(1)°, Z = 4. All new compounds have been tested for their antifungal activity against Aspergillus niger and Aspergillus flavus. Key words: 5-aminosalicylic acid (5-ASA), antifungal, copper, palladium, salicylaldimines, Schiff base, zinc.

  使用5-氨基水杨酸（5-ASA）与水杨醛（2-HOC6H4C（O）H）的缩合反应制备了席夫碱2-HOC6H4C（H）=NC6H3-2-（OH）-5-CO2H（a）。观察到与5-溴水杨醛的类似反应也产生了5-Br-2-HOC6H3C（H）=NC6H3-2-（OH）-5-CO2H（b）。这些水杨醛与Pd（II）、Cu（II）和Zn（II）盐的反应产生了相应的双（N-芳基水杨醛亚胺）金属配合物（M = Pd（1）、Cu（2）、Zn（3））。席夫碱化合物a的分子结构已通过X射线衍射研究得到证实。化合物a的晶体为单斜晶系，空间群P2（1）/c，a = 7.0164（7）Å，b = 11.0088（11）Å，c = 14.8980（15）Å，β = 102.917（2）°，Z = 4。还通过X射线衍射研究表征了3a的一种新型带电离子构象的分子结构。化合物4的晶体为单斜晶系，空间群P2（1）/c，a = 9.5284（5）Å，b = 19.5335（11）Å，c = 8.6508（5）Å，β = 90.596（1）°，Z = 4。所有新化合物均已针对曲霉和黄曲霉的抗真菌活性进行了测试。
• Jaysekhar; Rao; Santhakumari, Bollettino Chimico Farmaceutico, 2004, vol. 143, # 8, p. 309 - 313
  作者：Jaysekhar、Rao、Santhakumari

  DOI：——

  日期：——
• Synthesis and structure-activity studies of a series of [(hydroxybenzyl)amino]salicylates as inhibitors of EGF receptor-associated tyrosine kinase activity
  作者：Huixiong Chen、Janine Boiziau、Fabienne Parker、Rachid Maroun、Bruno Tocque、Bernard P. Roques、Christiane Garbay-Jaureguiberry

  DOI：10.1021/jm00077a014

  日期：1993.12

  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.
• Design and synthesis of heterobimetallic topoisomerase I and II inhibitor complexes: In vitro DNA binding, interaction with 5′-GMP and 5′-TMP and cleavage studies
  作者：Farukh Arjmand、Mohd. Muddassir

  DOI：10.1016/j.jphotobiol.2010.06.009

  日期：2010.10

  studies employing gel electrophoresis demonstrate both the complexes 3 and 4 are efficient cleavage agents and are specific groove binders (complex 3 binds to both major and minor groove while complex 4 is specifically minor groove binder only). In addition, the complexes show high inhibition activity against topoisomerase I and II. However, complex 4 exhibits significant inhibitory effects on the Topo

  设计并制备了新的潜在的癌症化学治疗复合物Cu-Sn（2）/ Zn-Sn（2）3和4作为拓扑异构酶抑制剂。他们进行了体外DNA结合研究，除其他结合方式外，还通过DNA螺旋的磷酸盐骨架显示出强大的静电结合。协调共价和部分插入。为了深入了解目标位点的分子结合事件，用（1）的（3）和（4）情况下的目标单核苷酸，即5'-GMP和5'-TMP进行了UV-vis滴定。 1 H和（31）P NMR。使用凝胶电泳的裂解研究表明，复合物3和4都是有效的裂解剂，并且是特定的凹槽结合剂（复合物3结合到主要和次要凹槽，而复合物4仅是具体的次要凹槽结合剂）。此外，该复合物显示出对拓扑异构酶I和II的高抑制活性。然而，复合物4在约2.5μM的非常低的浓度下对Topo I活性显示出显着的抑制作用。