meso-[4-(pyridin-2-ylmethoxy)phenyl]dipyrromethene | 1426854-96-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: meso-[4-(pyridin-2-ylmethoxy)phenyl]dipyrromethene
• 英文别名: 2-pcdpm；2-[[4-[1H-pyrrol-2-yl(pyrrol-2-ylidene)methyl]phenoxy]methyl]pyridine
• CAS: 1426854-96-7
• 化学式: C₂₁H₁₇N₃O
• 分子量: 327.385
• InChiKey: WVWCIQFWDSIXNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  50.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 meso-[4-(pyridin-2-ylmethoxy)phenyl]dipyrromethene 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 以55%的产率得到[(η5-C5Me5)IrCl(2-pcdpm)]
  参考文献：
  名称：

  DNA Binding and Anti-Cancer Activity of Redox-Active Heteroleptic Piano-Stool Ru(II), Rh(III), and Ir(III) Complexes Containing 4-(2-Methoxypyridyl)phenyldipyrromethene

  摘要：

  The synthesis of four novel heteroleptic dipyrrinato complexes [(eta(6)-arene)RuCl(2-pcdpm)] (eta(6)-arene = C6H6, 1; C10H14, 2) and [(eta(5)-C5Me5)MCl(2-pcdpm)] (M = Rh, 3; Ir, 4) containing a new chelating ligand 4-(2-methoxypyridyl)-phenyldipyrromethene (2-pcdpm) have been described. The complexes 1-4 have been fully characterized by various physicochemical techniques, namely, elemental analyses, spectral (ESI-MS, IR, H-1, C-13 NMR, UV/vis) and electrochemical studies (cyclic voltammetry (CV) and differential pulse voltammetry (DPV)). Structures of 3 and 4 have been determined crystallographically. In vitro antiproliferative and cytotoxic activity of these complexes has been evaluated by trypan blue exclusion assay, cell morphology, apoptosis, acridine orange/ethidium bromide (AO/EtBr) fluorescence staining, and DNA fragmentation assay in Dalton lymphoma (DL) cell lines. Interaction of 1-4 with calf thymus DNA (CT DNA) has also been supported by absorption titration and electrochemical studies. Our results suggest that in vitro antitumor activity of 1-4 lies in the order 2 > 1 > 4 > 3.

  DOI：

  10.1021/ic302196v
• 作为产物：
  描述：

  4-(吡啶-2-甲氧基)苯甲醛 在 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.0h， 生成 meso-[4-(pyridin-2-ylmethoxy)phenyl]dipyrromethene
  参考文献：
  名称：

  DNA Binding and Anti-Cancer Activity of Redox-Active Heteroleptic Piano-Stool Ru(II), Rh(III), and Ir(III) Complexes Containing 4-(2-Methoxypyridyl)phenyldipyrromethene

  摘要：

  The synthesis of four novel heteroleptic dipyrrinato complexes [(eta(6)-arene)RuCl(2-pcdpm)] (eta(6)-arene = C6H6, 1; C10H14, 2) and [(eta(5)-C5Me5)MCl(2-pcdpm)] (M = Rh, 3; Ir, 4) containing a new chelating ligand 4-(2-methoxypyridyl)-phenyldipyrromethene (2-pcdpm) have been described. The complexes 1-4 have been fully characterized by various physicochemical techniques, namely, elemental analyses, spectral (ESI-MS, IR, H-1, C-13 NMR, UV/vis) and electrochemical studies (cyclic voltammetry (CV) and differential pulse voltammetry (DPV)). Structures of 3 and 4 have been determined crystallographically. In vitro antiproliferative and cytotoxic activity of these complexes has been evaluated by trypan blue exclusion assay, cell morphology, apoptosis, acridine orange/ethidium bromide (AO/EtBr) fluorescence staining, and DNA fragmentation assay in Dalton lymphoma (DL) cell lines. Interaction of 1-4 with calf thymus DNA (CT DNA) has also been supported by absorption titration and electrochemical studies. Our results suggest that in vitro antitumor activity of 1-4 lies in the order 2 > 1 > 4 > 3.

  DOI：

  10.1021/ic302196v

文献信息

• Structural diversity in heteroleptic dipyrrinato copper(II) complexes
  作者：Rakesh Kumar Gupta、Rampal Pandey、Amit Kumar、K.V. Ramanujachary、Samuel E. Lofland、Daya Shankar Pandey

  DOI：10.1016/j.ica.2013.09.044

  日期：2014.1

  Synthesis and characterization of the heteroleptic dipyrrinato complexes [Cu-2(2-pcdpm)(2)(acac)(2)] (1), [Cu-2(2-pcdpm)(2)(hfacac)(2)] (2), [Cu-3(4-OHdpm)(2)(acac)(4)] (3), [Cu-3(4-OHdpm)(2)(hfacac) 4] (4), [Cu-2(3-OHdpm)(acac)(3)] (5), [Cu-2(3-OHdpm)(hfacac)(3)] (6), [Cu(2-OHdpm)(acac)] (7) and [Cu((2)OHdpm)(hfacac)] (8) (acac = acetylacetone; hfacac = hexafluoroacetylacetone; 2-pcdpm = 4-(2-methoxypyridyl) phenyldipyrromethene; 3-pcdpm = 4-(3-methoxypyridyl) phenyldipyrromethene; 4-pcdpm = 4-(4-methoxypyridyl) phenyldipyrromethene; 4-/3-/2-OHdpm = 4-/3-/(2-hydroxyphenyl)dipyrromethene) have been described. The complexes 1-8 have been characterized by elemental analyses, ESI-MS, IR, UV-Vis, EPR and electrochemical (CV and DPV) studies. Electronic absorption spectra of 1-8 clearly suggested that position of the absorption bands depend on the nuclearity and coordination geometry about the copper(II) centres. Structures of 1, 2, 3 and 7 have been determined by X-ray single crystal analyses. The spectral and structural studies revealed that copper(II) in 1 and 2 adopted square pyramidal geometry, whereas in 7 a square planar geometry. On the other hand in trinuclear complex 3 one copper(II) adopted square planar, while other two square pyramidal geometry. In their cyclic voltammo-grams, 1-6 exhibited an irreversible oxidation and two reduction waves whereas 7 and 8 displayed one oxidation and reduction wave. Variable temperature magnetic susceptibility measurements suggested paramagnetic nature of the complexes 1-3. The X-ray photoelectron spectroscopic (XPS) studies indicated that copper(II) centres in complex 3 are present in two different coordination environments. Room temperature EPR studies on 1-8 (g(parallel to) > g(perpendicular to) > 2.003) suggested a typical d(9) copper(II) with unpaired electron lying in a d(x2-y2) orbital. (C) 2013 Elsevier B. V. All rights reserved.