2-hydroxy-3-[(n-heptylamino)(pyridin-2-yl)methyl]-1,4-naphthoquinone | 1258440-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-3-[(n-heptylamino)(pyridin-2-yl)methyl]-1,4-naphthoquinone
• 英文别名: 3-[(heptylamino)(pyridin-2-yl)methyl]-2-hydroxy-1,4-naphthoquinone
• CAS: 1258440-35-5
• 化学式: C₂₃H₂₆N₂O₃
• 分子量: 378.471
• InChiKey: XLIDYKIFFYGVPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  cis-dichlorobis(dimethylsulfoxide)platinum(II) 、 2-hydroxy-3-[(n-heptylamino)(pyridin-2-yl)methyl]-1,4-naphthoquinone 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Novel 3-(Aminomethyl)naphthoquinone Mannich Base-Platinum(IV) Complexes: Synthesis, Characterization, Electrochemical and Cytotoxic Studies

  摘要：

  DOI：

  10.5935/0103-5053.20130087
• 作为产物：
  描述：

  吡啶-2-甲醛 、 2-羟基-1,4-萘醌 、 庚胺 以 乙醇 为溶剂， 反应 5.0h， 以85%的产率得到2-hydroxy-3-[(n-heptylamino)(pyridin-2-yl)methyl]-1,4-naphthoquinone
  参考文献：
  名称：

  3-（氨基甲基）萘醌曼尼希碱的 新型铂（ii）配合物：合成，晶体结构和细胞毒性活性†

  摘要：

  第一个例子 铂金（II） 的复合体 3-（氨基甲基）萘醌已经合成了曼尼希碱，并描述了其晶体结构。已获得中性和带电复合物，对其进行了充分表征，还研究了它们的细胞毒性活性。3-[（R 1-氨基）（吡啶-2-基）甲基] -2-羟基-1,4-萘醌（R 1 =正丁基，HL1 ;n，HL2 ; 糠基，HL3 ;正庚基，HL4和正癸基，HL5）协调到铂金（II）通过两个氮原子。中性复合物顺式-[Pt（HL）Cl 2 ] 1a-5a与顺铂与双齿配体HL和两个氯原子占据顺式位置。在电荷的复合物的顺式- [铂（大号- ）（NH 3）2 ] NO 3 1B-5B的去质子化的配体的形式大号-也坐标经由氮原子，和周围的其它两个位置铂金（II）离子用NH 3配体完成。已测试了所有化合物对六种不同癌细胞系的细胞毒活性：MDA-MB-435（黑色素瘤），HL-60（早幼粒细胞白血病），HCT-8 （冒号）， SF-295

  DOI：

  10.1039/c0dt00572j

文献信息

• Novel platinum(ii) complexes of 3-(aminomethyl)naphthoquinone Mannich bases: synthesis, crystal structure and cytotoxic activities
  作者：Amanda P. Neves、Gustavo B. da Silva、Maria D. Vargas、Carlos B. Pinheiro、Lorenzo do C. Visentin、José D. B. M. Filho、Ana J. Araújo、Letícia V. Costa-Lotufo、Cláudia Pessoa、Manoel O. de Moraes

  DOI：10.1039/c0dt00572j

  日期：——

  chlorido complexes 1a–5a have shown high to moderate cytotoxic activities, complex 4a (R1 = n-heptyl) being more active than proligand HL4 against melanoma (IC50 = 6.4 and > 40 μmol L−1, respectively) and more active than cisplatin against all tested cell lines. Among the amine charged complexes only 4b and 5b have exhibited significant cytotoxic activity against the tested cell lines, although they were

  第一个例子 铂金（II） 的复合体 3-（氨基甲基）萘醌已经合成了曼尼希碱，并描述了其晶体结构。已获得中性和带电复合物，对其进行了充分表征，还研究了它们的细胞毒性活性。3-[（R 1-氨基）（吡啶-2-基）甲基] -2-羟基-1,4-萘醌（R 1 =正丁基，HL1 ;n，HL2 ; 糠基，HL3 ;正庚基，HL4和正癸基，HL5）协调到铂金（II）通过两个氮原子。中性复合物顺式-[Pt（HL）Cl 2 ] 1a-5a与顺铂与双齿配体HL和两个氯原子占据顺式位置。在电荷的复合物的顺式- [铂（大号- ）（NH 3）2 ] NO 3 1B-5B的去质子化的配体的形式大号-也坐标经由氮原子，和周围的其它两个位置铂金（II）离子用NH 3配体完成。已测试了所有化合物对六种不同癌细胞系的细胞毒活性：MDA-MB-435（黑色素瘤），HL-60（早幼粒细胞白血病），HCT-8 （冒号）， SF-295
• New insights into 3-(aminomethyl)naphthoquinones: Evaluation of cytotoxicity, electrochemical behavior and search for structure–activity correlation
  作者：Gustavo B. da Silva、Amanda P. Neves、Maria D. Vargas、José D.B. Marinho-Filho、Letícia V. Costa-Lotufo

  DOI：10.1016/j.bmcl.2016.06.027

  日期：2016.8

  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.
• Novel 3-(Aminomethyl)naphthoquinone Mannich Base-Platinum(IV) Complexes: Synthesis, Characterization, Electrochemical and Cytotoxic Studies
  作者：Gustavo B. da Silva、Amanda P. Neves、Maria D. Vargas、Wagner A. Alves、José D. B. Marinho-Filho、Cláudia Pessoa、Manoel O. Moraes、Letícia V. Costa-Lotufo

  DOI：10.5935/0103-5053.20130087

  日期：——