3-hydroxy-5-(hydroxymethyl)-4-(((2-hydroxyphenyl)imino)methyl)-2-methylpyridine | 166542-02-5

• 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: 3-hydroxy-5-(hydroxymethyl)-4-(((2-hydroxyphenyl)imino)methyl)-2-methylpyridine
• 英文别名: 5-(hydroxymethyl)-4-[(2-hydroxyphenyl)iminomethyl]-2-methylpyridin-3-ol
• CAS: 166542-02-5
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: VVOPIXHQVKBUMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  85.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxy-5-(hydroxymethyl)-4-(((2-hydroxyphenyl)imino)methyl)-2-methylpyridine 在 sodium tetrahydroborate 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以40%的产率得到5-(hydroxymethyl)-4-(((2-hydroxyphenyl)amino)methyl)-2-methylpyridin-3-ol
  参考文献：
  名称：

  Exploring the therapeutic potential of Cu(II)-complexes with ligands derived from pyridoxal

  摘要：

  Three new copper(II) complexes formulated as [Cu(L)(X)], where X = H2O or Cl and H2L is a Schiff base (H2L1,2) or its reduced version ((H3LCl)-Cl-3) derived from pyridoxal, are prepared, as well as two ternary complexes [Cu(L) (phen)] also containing 1,10-phenanthroline. All compounds are characterized by the usual techniques: elemental analyses, ESI mass spectrometry, UV-Vis absorption, FTIR and EPR spectroscopies. The ligands co-ordinate the Cu(II) center forming complexes with square-planar based geometries. Their antioxidant properties are evaluated with a radical scavenging activity assay, with one of the ligand precursors showing activity higher than the positive control, ascorbic acid. The antiproliferative activity of all compounds is evaluated against two cancer cell lines: ovarian (A2780) and breast (MCF7). All complexes show moderate to excellent activity with the ternary Cu-complexes showing IC50 values between 0.7 and 9.3 mu M after 24 h of incubation, values much lower than those reported for cisplatin, the reference drug. The hydrolytic stability of the complexes and their ability to bind albumin and DNA are evaluated by spectroscopic techniques, showing that the compounds bind bovine serum albumin. The [Cu(L)(phen)] complexes show ability to target DNA via intercalation.

  DOI：

  10.1016/j.ica.2020.119558
• 作为产物：
  描述：

  、 2-氨基苯酚 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 3-hydroxy-5-(hydroxymethyl)-4-(((2-hydroxyphenyl)imino)methyl)-2-methylpyridine
  参考文献：
  名称：

  Bioactive Penta-Coordinated Diorganotin(Iv) Complexes of Pyridoxalimine Schiff Bases

  摘要：

  Diorganotin(IV) complexes of an extended system derived from the condensation of pyridoxal hydrochloride with 2-amino phenol (H2L1), 2-amino-4-methyl phenol (H2L2), 2-amino-4-chloro phenol (H2L3), 2-amino-4-nitro phenol (H2L4), 1-amino-2-naphthol hydrochloride (H2L5) have been synthesized by the reaction of dichlorodiorganotin(IV) in a 1:1 molar ratio with these ligands. Spectral studies (IR, H-1, C-13, Sn-119 NMR) along with physical data evidenced the formation of penta-coordinated species with the ligands acting as tridentate (ONO) with oxygen occupying the axial positions, and nitrogen at one of the equatorial positions. The ligands and their organotin complexes have been evaluated for antimicrobial activity against phytopathogenic fungi Candida albicans and Aspergillus niger at 25 +/- 1 degrees C and bacteria Bacillus subtilis, Escherichia coli, and Staphylococcus aureus at 37 +/- 1 degrees C. The activities of the ligands have been enhanced on complexation and the results indicate that they exhibit significant antimicrobial properties.

  DOI：

  10.1080/10426507.2012.692129

文献信息

• Iron(III) Complexes of Vitamin B ₆ Schiff Base with Boron‐Dipyrromethene Pendants for Lysosome‐Selective Photocytotoxicity
  作者：Somarupa Sahoo、Santosh Podder、Aditya Garai、Shamik Majumdar、Nandini Mukherjee、Uttara Basu、Dipankar Nandi、Akhil R. Chakravarty

  DOI：10.1002/ejic.201701487

  日期：2018.4.9

  Iron(III) complexes of a vitamin B6 Schiff base and NNN‐donor ligands with pendant boron‐dipyrromethene (BODIPY) moieties; namely, [Fe(L1–3)(L4,5)](NO3) (1–4), where L1 is benzyl‐bis[(pyridin‐2‐yl)methyl]methanamine (bzdpa in 1), L2 is a noniodinated BODIPY‐appended dipicolylamine ligand (in 2, 3), L3 is the diiodinated BODIPY analogue in 4, L4 is a vitamin B6 Schiff base, namely 3‐hydroxy‐5(hydroxymethyl)

  维生素B 6 Schiff碱和NNN供体配体与侧基硼二吡咯亚甲基（BODIPY）部分形成的铁（III）配合物；即，[铁（L 1-3）（L 4,5）]（NO 3）（1 - 4），其中L 1是苄基双[（吡啶-2-基）甲基]甲胺（在bzdpa 1）中，L 2是一个noniodinated BODIPY-所附吡啶甲基胺配体（在2，3），L 3是在二碘化BODIPY类似物4，L 4是维生素B 6席夫碱，即3-羟基-5-（羟甲基）-4 - [（2-羟基苯基）亚氨基]甲基} -2-甲基吡啶（在1，3，和4），和L 5是2 - [（2-制备，表征了羟基苯基亚氨基）-甲基]苯酚（2）作为非吡ox醛席夫碱，并研究了它们在光照和黑暗条件下的细胞定位和细胞毒活性。二碘代-BODIPY复杂4个显示显着的细胞毒性光致在可见光（400-700纳米），用IC 50内0.11-0.25μ值米和大约200倍下的暗毒性。通过
• Schiff base Sn(IV) complexes as cytotoxic agents: Synthesis, structure, isosteric and bioisosteric replacement
  作者：José M. Galván-Hidalgo、Teresa Ramírez-Apan、Antonio Nieto-Camacho、Simón Hernández-Ortega、Elizabeth Gómez

  DOI：10.1016/j.jorganchem.2017.08.017

  日期：2017.10

  plane and the two oxygen atoms in the equatorial plane. Additionally, the in vitro cytotoxicity tests of the complexes towards six types of human cancerous cell lines U-251 (glioblastoma), K-562 (chronic myelogenous leukemia), HCT-15 (human colorectal), MCF-7 (human breast), MDA-MB-231(human breast) and SKLU-1 (non-small cell lung) showed the superior activity of the organotin complexes compared to the

  据报道，制备和表征了两个系列的有机锡（IV）配合物，每个系列在键合到锡原子（环己基或双（三甲基）甲硅烷基甲基）上的取代基的性质不同。等规和生物等规方法被用作分子设计的策略。配体是5-羟基甲基-4-[（2-羟基苯基）亚氨基甲基] -2-甲基吡啶-3-醇，在4位被甲基，卤代（F，Cl），甲氧基，硝基和叔丁基取代；取决于配体的性质，通过多组分策略以合理至高产率进行有机锡（IV）配合物的合成。所有新的配合物均通过IR，MS，X射线测定和NMR（1 H，13 C，119锡）。配合物的晶体学数据表明，金属锡中心周围采用的几何形状在2c的方形金字塔形和3b-3d的三角形双金字塔形之间变化，烷基在三角平面，两个氧原子在赤道平面。此外，该复合物对六种类型的人类癌细胞系U-251（胶质母细胞瘤），K-562（慢性粒细胞性白血病），HCT-15（人结肠直肠），MCF-7（人乳腺），与相应的顺铂用作阳性对照相比，
• Iron(III) Complexes of a Pyridoxal Schiff Base for Enhanced Cellular Uptake with Selectivity and Remarkable Photocytotoxicity
  作者：Uttara Basu、Ila Pant、Akhtar Hussain、Paturu Kondaiah、Akhil R. Chakravarty

  DOI：10.1021/ic5027625

  日期：2015.4.20

  near 520 and 420 nm from phenolate to the iron(III) center. The photophysical properties of the complexes are explained from the time dependent density functional theory calculations. The redox active complexes show a quasi-reversible Fe(III)/Fe(II) response near −0.3 V vs saturated calomel electrode. Complexes 2 and 3 exhibit remarkable photocytotoxicity in various cancer cells with IC50 values ranging

  铁（III）的吡哆醛复合物（维生素B6，维生素B6）或水杨醛席夫碱和改性dipicolylamines，即的[Fe（B）（L）]（NO 3）（1 - 5），其中B是苯基Ñ，Ñ双（（吡啶-2-基）甲基）甲胺（phbpa在1），（蒽-9-基） - ñ，ñ双（（吡啶-2-基）甲基）甲胺（anbpa在2，4）和（芘-1-基） - ñ，ñ -双（（吡啶-2-基）甲基）甲胺（pybpa在3，5）（H 2大号1为3-羟基-5-（羟甲基）-4 - （（（2-羟基苯基）亚氨基）甲基）-2-甲基吡啶（1 - 3）和H 2大号2是2 - [（2-羟基苯基-亚氨基）甲基制备]，并研究其在癌细胞中的摄取和光细胞毒性。制备具有非吡咯醛席夫碱的复合物4和5，以探测吡ido醛基团在肿瘤靶向和细胞摄取中的作用。配合物1的PF 6盐（1a）在结构上得到了表征。配合物具有扭曲的六坐标FeN 4 O 2核心，其中金属处于+3氧化
• Phosphorylation of pyridoxal azomethines. Synthesis of phosphorus containing azomethines and furopyridines
  作者：Michael A. Pudovik、Lyudmila Kibardina、Alexey Trifonov、Alexey Dobrynin、Sergei Katsyuba、Alexander Burilov

  DOI：10.1080/10426507.2018.1513516

  日期：2019.2.1

  O-phosphorylated pyridoxal derivatives have been synthesized through the reaction of azomethines with РV acid chlorides. 2-Chloro-2-thioxo-5,5-dimethyl-1,3,2-dioxaphosphinanes and diethylchlorothiophosphate have been employed as phosphorylating agents. Regardless of the nature of the phosphorylating agent, the reaction is regioselective at phenolic hydroxyl group. The structure of final products is determined

  摘要 通过偶氮甲碱与 РV 酰氯反应合成了新的 O-磷酸化吡哆醛衍生物。2-Chloro-2-thioxo-5,5-二甲基-1,3,2-dioxaphosphinanes 和二乙基氯硫代磷酸酯已被用作磷酸化剂。不管磷酸化剂的性质如何，该反应在酚羟基处是区域选择性的。最终产品的结构由氮原子上取代基的性质决定。如果R是烷基或环烷基，反应产物代表磷酸化吡哆醛亚胺，而在R是芳基取代基的情况下形成磷酸化呋喃吡啶。图形概要
• Targeted photodynamic therapy in visible light using BODIPY-appended copper(<scp>ii</scp>) complexes of a vitamin B₆Schiff base
  作者：Nandini Mukherjee、Santosh Podder、Koushambi Mitra、Shamik Majumdar、Dipankar Nandi、Akhil R. Chakravarty

  DOI：10.1039/c7dt03976j

  日期：——

  Copper(II) complexes [Cu(L1/L2/L3)(A)] (1–3), where H2A·HCl is a vitamin B6 Schiff base, viz. 3-hydroxy-5-(hydroxymethyl)-4-(((2-hydroxyphenyl)imino)methyl)-2-methylpyridin-1-ium chloride, L1 and L2 are 2-(2-pyridyl)benzimidazole based borondipyrromethene (BODIPY) ligands and L3 is 2-(2-pyridyl)benzimidazole, were prepared, characterized and their visible light-induced anti-cancer activity was studied

  铜（II）配合物[Cu（L 1 / L 2 / L 3）（A）]（1-3），其中H 2 A·HCl是维生素B 6 Schiff碱，即。3-羟基-5-（羟甲基）-4-（（（（2-羟基苯基）亚氨基）甲基）-2-甲基吡啶-1-氯，L 1和L 2是基于2-（2-吡啶基）苯并咪唑的硼二吡咯并二甲基（制备并表征了BODIPY）配体和L 3为2-（2-吡啶基）苯并咪唑，并研究了其可见光诱导的抗癌活性。通过X射线晶体学表征的配合物3表现出扭曲的方金字塔形几何形状的铜（τ= 0.33）。在20％DMSO / Dulbecco's磷酸盐缓冲盐水（DPBS）介质中，配合物1和2在500和535 nm处分别显示吸收带。复杂1个在~510纳米（展出发射λ EXC = 480纳米）（Φ ˚F在20％DMSO / DPBS = 0.1），而与不发光二碘BODIPY复杂2是一种有效的光敏剂。绿色荧光复合物1使我们能够研究