3-(phenyl(pyridin-2-ylmethylamino)methyl)-2-hydroxy-1,4-naphthoquinone | 1256368-53-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 3-(phenyl(pyridin-2-ylmethylamino)methyl)-2-hydroxy-1,4-naphthoquinone
• 英文别名: 3-[N-(2-pyridylmethyl)aminobenzyl]-2-hydroxy-1,4-naphthoquinone
• CAS: 1256368-53-2
• 化学式: C₂₃H₁₈N₂O₃
• 分子量: 370.408
• InChiKey: UNWWZDNBXBCUFQ-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  79.29
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(phenyl(pyridin-2-ylmethylamino)methyl)-2-hydroxy-1,4-naphthoquinone 在 乙酰氯 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以100%的产率得到3-(phenyl(pyridin-2-ylmethylamino)methyl)-2-hydroxy-1,4-naphthoquinone hydrochloride
  参考文献：
  名称：

  New insights into 3-(aminomethyl)naphthoquinones: Evaluation of cytotoxicity, electrochemical behavior and search for structure–activity correlation

  摘要：

  Herein we describe the structure-activity relationship of a large library of Mannich bases (MBs) synthesized from 2-hydroxy-1,4-naphthoquinone. In general, the compounds have shown high to moderate activity against the HL-60 (promyelocytic leukaemia) cell line with IC50 = 1.1-19.2 mu M. Our results suggest that the nature of the aryl moiety introduced in the structure of MBs by the aldehyde component is crucial to the cytotoxicity, and although the group originated from the primary amine has a lesser influence, aromatic ones were found to suppress the activity. Thus, MBs derived from salicylaldehydes or 2-pyridinecarboxaldehyde and aliphatic amines are the most active compounds. A satisfactory correlation of the E-pIIc versus IC50 (mu M) in dimethylsulfoxide was observed. The most cytotoxic MBs (Series a-c, derived from salicylaldehydes) showed the least negative E-pIIc values. Noteworthy, however, Series d (derived from 2-pyridinecarboxaldehyde) did not follow this correlation. They exhibited both the lowest IC50 and the most negative E-pIIc values, thus suggesting that other factors also influence the cytotoxicity of the MBs, such as lipophilicity, electronic distribution and hydrogen bonding. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.06.027
• 作为产物：
  描述：

  吡啶-2-甲醛 、 2-羟基-1,4-萘醌 、 苯甲醛 以 乙醇 为溶剂， 反应 12.0h， 生成 3-(phenyl(pyridin-2-ylmethylamino)methyl)-2-hydroxy-1,4-naphthoquinone
  参考文献：
  名称：

  New insights into 3-(aminomethyl)naphthoquinones: Evaluation of cytotoxicity, electrochemical behavior and search for structure–activity correlation

  摘要：

  Herein we describe the structure-activity relationship of a large library of Mannich bases (MBs) synthesized from 2-hydroxy-1,4-naphthoquinone. In general, the compounds have shown high to moderate activity against the HL-60 (promyelocytic leukaemia) cell line with IC50 = 1.1-19.2 mu M. Our results suggest that the nature of the aryl moiety introduced in the structure of MBs by the aldehyde component is crucial to the cytotoxicity, and although the group originated from the primary amine has a lesser influence, aromatic ones were found to suppress the activity. Thus, MBs derived from salicylaldehydes or 2-pyridinecarboxaldehyde and aliphatic amines are the most active compounds. A satisfactory correlation of the E-pIIc versus IC50 (mu M) in dimethylsulfoxide was observed. The most cytotoxic MBs (Series a-c, derived from salicylaldehydes) showed the least negative E-pIIc values. Noteworthy, however, Series d (derived from 2-pyridinecarboxaldehyde) did not follow this correlation. They exhibited both the lowest IC50 and the most negative E-pIIc values, thus suggesting that other factors also influence the cytotoxicity of the MBs, such as lipophilicity, electronic distribution and hydrogen bonding. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.06.027

文献信息

• Dinuclear copper(II) complexes of a novel 3-(aminomethyl)naphthoquinone Mannich base: Synthesis, structural, magnetic and electrochemical studies
  作者：Amanda P. Neves、Kelly C.B. Maia、Maria D. Vargas、Lorenzo C. Visentin、Annelise Casellato、Miguel A. Novak、Antônio S. Mangrich

  DOI：10.1016/j.poly.2010.07.011

  日期：2010.10

  magnetic susceptibility measurements of complex 1b showed weak antiferromagnetic intramolecular coupling between the copper(II) centers, with J = −5.7 cm−1, and evidenced for complex 2 strong antiferromagnetic coupling, with J ∼ −120 cm−1. Furthermore, the magnetic behaviour of compound 1a suggested an infinite 1D coordination polymeric structure in which the copper(II) centers are connected by Cl–Cu–Cl

  从2-羟基-1的曼尼希反应中获得了一种新型的多功能三齿3-（氨基甲基）萘醌配体3- [ N-（2-吡啶基甲基）氨基苄基] -2-羟基-1,4-萘醌（HL）。 ，4-萘醌（Lawsone）与2-氨基甲基吡啶（amp）和苯甲醛。HL与CuCl 2 ·2H 2 O的反应产生了两种新型的双核铜（II）配合物，[Cu（L）（H 2 O）（μ-Cl）Cu（L）Cl]（1b），[CuCl（L）（μ-Cl）Cu（amp）Cl]（2）和高分子化合物[Cu（L ClCl）] n（1a），其相对产量对温度，试剂浓度和碱的存在敏感。1b和2的晶体结构通过X射线衍射研究确定。络合物1b中的两个铜原子通过一个单氯桥连接，其Cu 4.1Cu间距为4.1342（8）Å，Cu（1）-Cl（1）-Cu（2）角为109.31（4）°。在络合物2中，两个铜原子通过氯和萘-2-油酸酯桥[Cu（1）–Cl（2）–Cu（2）和Cu（1