Hpyramol | 473969-47-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Hpyramol
• 英文别名: 4-methyl-2-N-(2-pyridylmethyl)aminophenol；4-Methyl-2-{[(pyridin-2-yl)methyl]amino}phenol；4-methyl-2-(pyridin-2-ylmethylamino)phenol
• CAS: 473969-47-0
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: JPOJKXKACUOZJP-UHFFFAOYSA-N

物化性质

• 沸点：
  367.1±37.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Hpyramol 在 air 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 [Pt(9-ethylguanosine-N7)(pyrimol)]Cl
  参考文献：
  名称：

  4-甲基-2-N-（2-吡啶基甲基）氨基苯酚衍生的铂（II）和铜（II）化合物的DNA裂解和抗肿瘤活性：光谱，电化学和生物学研究。

  摘要：

  氧化还原活性配体Hpyramol（4-甲基-2-N-（2-吡啶基甲基）氨基苯酚）与K（2）PtCl（4）的反应产生单官能正方形[Pt（pyrimol）Cl]，PtL- Cl，其通过单晶X射线衍射和NMR光谱表征。在生理条件下，该化合物意外地以非特异性方式化学计量和氧化方式切割了超螺旋双链DNA，而未添加任何外部还原剂。与类似物CuL-Cl作为参考化合物相比，对PtL-Cl进行了光谱电化学研究。结果支持酚盐氧化，产生苯氧基自由基，该苯氧基自由基负责标题化合物的基于配体的DNA切割特性。PtL-Cl和CuL-Cl在各种癌细胞系中均进行了时间依赖性体外细胞毒性测定。化合物CuL-Cl克服了卵巢癌和小鼠白血病细胞系对顺铂的耐药性，并在其他一些细胞中具有额外的活性。铂类似物PtL-Cl也可以选择性抑制细胞增殖。此外，在卵巢癌细胞系中对这两种化合物进行的细胞摄取研究表明，A2780和A2780R癌细胞

  DOI：

  10.1039/b911542k

文献信息

• New Chloro, μ-Oxo, and Alkyl Derivatives of Dioxomolybdenum(VI) and -Tungsten(VI) Complexes Chelated with N₂O Tridentate Ligands:  Synthesis and Catalytic Activities toward Olefin Epoxidation
  作者：Yee-Lok Wong、Dennis K. P. Ng、Hung Kay Lee

  DOI：10.1021/ic020173k

  日期：2002.10.1

  tungsten derivatives WO(2)(L(n))Cl (n = 6, 7) and [WO(2)(L(n))](2)O (n = 1, 4, 6, 7) were prepared by the reaction of WO(2)Cl(2)(DME) with HL(n) in the presence of triethylamine. Similar to their molybdenum analogues, the tungsten alkyl complexes WO(2)(L(n))(R) (n = 6, 7; R = Me, Et, CH(2)SiMe(3), C(6)H(4)(t)Bu-4) were synthesized by treating WO(2)(L(n))Cl or [WO(2)(L(n))](2)O (n = 6, 7) with the appropriate

  通过MoO（2）Cl（2）（DME）（DME = 1）反应制备了一系列新的顺式-二氧钼钼（VI）复合物MoO（2）（L（n））Cl（n = 1-5）在三乙胺存在下，用2-N-（2-吡啶基甲基）氨基苯酚（HL（1））或它的N-烷基衍生物（HL（n））（n = 2-5）与（2-二甲氧基乙烷）。还通过用MoO（2）处理相应的配体HL（n）来制备新的mu-oxo二钼化合物[MoO（2）（L（n））]（2）O（n = 1，4，5，7） ）（acac）（2）（acac =乙酰丙酮酸）在温热的甲醇溶液中或在稀HCl的存在下（NH（4））（6）[Mo（7）O（24）]。4H（2）O。用格氏试剂Me（3）SiCH（2）MgCl处理MoO（2）（L（1））Cl或[MoO（2）（L（1））]（2）O得到烷基化合物MoO（2 ）（L（1））（CH（2）SiMe（3）），代表由N（2）O型辅助配体支撑的二氧钼（VI
• Solution-stable trinuclear zinc(<scp>ii</scp>) cluster from 4-methyl-2-N-(2-pyridylmethylene)aminophenol (HPyrimol)
  作者：Paul de Hoog、Laura Durán Pachón、Patrick Gamez、Martin Lutz、Anthony L. Spek、Jan Reedijk

  DOI：10.1039/b407637k

  日期：——

  The reaction of zincII acetate with 4-methyl-2-N-(2-pyridylmethyl)aminophenol (HPyramol) in methanol leads to a solution stable linear trinuclear zinc cluster with intramolecular ligand oxidation.

  醋酸锌 II 与 4-甲基-2-N-（2-吡啶基甲基）氨基苯酚（Hpyramol）在甲醇中发生反应，生成分子内配体氧化的溶液稳定线性三核锌簇。
• Synthesis, crystal structure and biological studies of the highly anticancer active compound trans-dichloridobis(4-methyl-2-N-(2-pyridylmethylene)-aminophenol)ruthenium(II)
  作者：Sudeshna Roy、Palanisamy Uma Maheswari、Amalija Golobič、Bojan Kozlevčar、Jan Reedijk

  DOI：10.1016/j.ica.2012.07.023

  日期：2012.12

  A new Ru(II) compound of formula, trans-[Ru-II(Hpyrimol)(2)Cl-2] (Hpyrimol = 4-methyl-2-N-(2-pyridylmethylene) aminophenol) has been synthesised, starting from Ru(III) chloride and the redox-active ligand Hpyramol. Ligand dehydrogenation takes place to form the coordinated neutral ligand Hpyrimol. This mononuclear compound contains two relatively labile coordinated chloride ligands at trans axial positions. Although the ligand is potentially tridentate and anionic, as found in all previously reported compounds with this ligand so far, the coordination motif of Hpyrimol in the title compound is only bidentate, as a N, N-donor and a non-coordinated neutral phenol group. The neutral phenol groups instead form stable intramolecular hydrogen bonds with the coordinated chloride anions. The compound has been fully structurally characterised by spectroscopy and X-ray diffraction and has also been evaluated for its biological activities. Combined effects of coordinative binding and partial intercalation to DNA are evident from spectroscopic studies. The title compound has also been studied for DNA interaction by using an electrophoretic mobility assay and UV-Vis spectroscopy, and information on the difference of DNA-metal complex interactions guided by metal centres, hydrogen bonds and ligand binding modes was obtained. The in vitro cytotoxic activity makes this compound interesting as a starting point for research on a new class of Ru(II) antitumour compounds. (C) 2012 Elsevier B. V. All rights reserved.
• Intramolecular oxidation of the ligand 4-methyl-2-N-(2-pyridylmethyl)aminophenol (Hpyramol) upon coordination with iron(II) chloride and manganese(II) perchlorate
  作者：Laura Durán Pachón、Amalija Golobič、Bojan Kozlevčar、Patrick Gamez、Huub Kooijman、Anthony L. Spek、Jan Reedijk

  DOI：10.1016/j.ica.2004.04.019

  日期：2004.9

  The ligand Hpyramol (Hpyramol = 4-methyl-2-N-(2-pyridylmethyl)aminophenol) is found to undergo an oxidative dehydrogenation of its amine function to an imine group upon coordination with iron(II) chloride and manganese(II) perchlorate. X-ray diffraction analyses for both complexes shows differences in the coordination geometry of the complexes most likely because of the two different counter-ions namely the strong coordinating chloride anions and the weak coordinating perchlorate anions. The coordination sphere of the iron(III) complex in [FeCl2(pyrimol)(MeOH)](MeOH) is best described as a distorted octahedral FeN2O2Cl2 chromophore, while the manganese(II) ions in [Mn(ClO4)(pyrimol)(Hpyrimol)](2) are in a distorted octahedral MnN4O2 environment with a 2:1 ligand to metal ratio instead of 1:1. (C) 2004 Elsevier B.V. All rights reserved.
• DNA cleavage and antitumour activity of platinum(II) and copper(II) compounds derived from 4-methyl-2-N-(2-pyridylmethyl)aminophenol: spectroscopic, electrochemical and biological investigation
  作者：Sudeshna Roy、Palanisamy Uma Maheswari、Martin Lutz、Anthony L. Spek、Hans den Dulk、Sharief Barends、Gilles P. van Wezel、František Hartl、Jan Reedijk

  DOI：10.1039/b911542k

  日期：——

  The platinum analogue, PtL-Cl also inhibits cell-proliferation selectively. Additionally, cellular-uptake studies performed for both compounds in ovarian carcinoma cell lines showed that significant amounts of Pt and Cu were accumulated in the A2780 and A2780R cancer cells. The conformational and structural changes induced by PtL-Cl and CuL-Cl on calf thymus DNA and phiX174 supercoiled phage DNA at

  氧化还原活性配体Hpyramol（4-甲基-2-N-（2-吡啶基甲基）氨基苯酚）与K（2）PtCl（4）的反应产生单官能正方形[Pt（pyrimol）Cl]，PtL- Cl，其通过单晶X射线衍射和NMR光谱表征。在生理条件下，该化合物意外地以非特异性方式化学计量和氧化方式切割了超螺旋双链DNA，而未添加任何外部还原剂。与类似物CuL-Cl作为参考化合物相比，对PtL-Cl进行了光谱电化学研究。结果支持酚盐氧化，产生苯氧基自由基，该苯氧基自由基负责标题化合物的基于配体的DNA切割特性。PtL-Cl和CuL-Cl在各种癌细胞系中均进行了时间依赖性体外细胞毒性测定。化合物CuL-Cl克服了卵巢癌和小鼠白血病细胞系对顺铂的耐药性，并在其他一些细胞中具有额外的活性。铂类似物PtL-Cl也可以选择性抑制细胞增殖。此外，在卵巢癌细胞系中对这两种化合物进行的细胞摄取研究表明，A2780和A2780R癌细胞