N,N,N’,N’-tetrakis(2-quinolylmethyl)-2-hydroxy-1,3-propanediamine | 868668-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N,N,N’,N’-tetrakis(2-quinolylmethyl)-2-hydroxy-1,3-propanediamine
• 英文别名: 1,3-Bis[bis(quinolin-2-ylmethyl)amino]propan-2-ol；1,3-bis[bis(quinolin-2-ylmethyl)amino]propan-2-ol
• CAS: 868668-01-3
• 化学式: C₄₃H₃₈N₆O
• 分子量: 654.814
• InChiKey: VHWWFLPEGNQCJV-UHFFFAOYSA-N

物化性质

• 熔点：
  196-198 °C
• 沸点：
  839.1±65.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  50
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  78.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  烟酸 、 N,N,N’,N’-tetrakis(2-quinolylmethyl)-2-hydroxy-1,3-propanediamine 、 cobalt(II) perchlorate hexahydrate 在 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以36%的产率得到
  参考文献：
  名称：

  Bio-relevant cobalt(II) complexes with compartmental polyquinoline ligand: Synthesis, crystal structures and biological activities

  摘要：

  Three new Co(II) complexes, [Co-4(L)(2)(mu(3)-CrO4)(2)](ClO4)(2)center dot 2CH(3)CN (1), [Co-2(L)(mu(2)-na)(H2O)](ClO4)(2) (2) and [Co-2(L)(mu(2)-ba)](ClO4)(2)center dot 0.5CH(3)CN (3) (Hna = nicotinic acid, Hba = benzoic acid, HL = N,N,N',N'-tetrakis (2-quinolylmethyl)-1,3-diaminopropan-2-ol), have been synthesized and characterized by various physicochemical techniques. The Co(II) centers are connected by endogenous alkoxy bridge from L- and various extrinsic auxiliary linkers, some of which display coordination number asymmetry (5, 6-coordinated for 1 and 2; 5, 5-coordinated for 3). It is worth mentioning that complex 1 contains two rare reported mu(3)-eta(1), eta(1), eta(1)-CrO42- moieties. Susceptibility data of three complexes indicated intramolecular antiferromagnetic coupling of high-spin Co(II) atoms with exchange integral values (J) -14.94 cm(-1), -11.26 cm(-1) and -13.66 cm(-1) for 1,2 and 3, respectively. Interaction of compounds with calf thymus DNA (CT-DNA) have been investigated by absorption spectral titration, ethidium bromide (EB) displacement assay and viscosity measurement, which revealed that compounds bound to CT-DNA with a moderate intercalative mode, accompanied the affinities order: 1 > 2 approximate to 3. Three complexes exhibit oxidative cleavage of pBR322 plasmid DNA including a reliance on H2O2 as the activator. Compound 1 demonstrates an increased DNA cleavage activity as compared with 2 and 3, which could degrade super coiled DNA (SC DNA) into nicked coiled DNA (NC DNA) in lower concentration (5 mu M). Moreover, all compounds could quench the intrinsic fluorescence of bovine serum albumin (BSA) in a static quenching process. Complex 1 also shows higher anticancer activity than cisplatin with lower IC50 value of incubation for both 24 h and 48 h. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2014.11.003
• 作为产物：
  描述：

  2-氯甲基喹啉盐酸盐 、 1,3-二氨基-2-羟基丙烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成 N,N,N’,N’-tetrakis(2-quinolylmethyl)-2-hydroxy-1,3-propanediamine
  参考文献：
  名称：

  Bio-relevant cobalt(II) complexes with compartmental polyquinoline ligand: Synthesis, crystal structures and biological activities

  摘要：

  Three new Co(II) complexes, [Co-4(L)(2)(mu(3)-CrO4)(2)](ClO4)(2)center dot 2CH(3)CN (1), [Co-2(L)(mu(2)-na)(H2O)](ClO4)(2) (2) and [Co-2(L)(mu(2)-ba)](ClO4)(2)center dot 0.5CH(3)CN (3) (Hna = nicotinic acid, Hba = benzoic acid, HL = N,N,N',N'-tetrakis (2-quinolylmethyl)-1,3-diaminopropan-2-ol), have been synthesized and characterized by various physicochemical techniques. The Co(II) centers are connected by endogenous alkoxy bridge from L- and various extrinsic auxiliary linkers, some of which display coordination number asymmetry (5, 6-coordinated for 1 and 2; 5, 5-coordinated for 3). It is worth mentioning that complex 1 contains two rare reported mu(3)-eta(1), eta(1), eta(1)-CrO42- moieties. Susceptibility data of three complexes indicated intramolecular antiferromagnetic coupling of high-spin Co(II) atoms with exchange integral values (J) -14.94 cm(-1), -11.26 cm(-1) and -13.66 cm(-1) for 1,2 and 3, respectively. Interaction of compounds with calf thymus DNA (CT-DNA) have been investigated by absorption spectral titration, ethidium bromide (EB) displacement assay and viscosity measurement, which revealed that compounds bound to CT-DNA with a moderate intercalative mode, accompanied the affinities order: 1 > 2 approximate to 3. Three complexes exhibit oxidative cleavage of pBR322 plasmid DNA including a reliance on H2O2 as the activator. Compound 1 demonstrates an increased DNA cleavage activity as compared with 2 and 3, which could degrade super coiled DNA (SC DNA) into nicked coiled DNA (NC DNA) in lower concentration (5 mu M). Moreover, all compounds could quench the intrinsic fluorescence of bovine serum albumin (BSA) in a static quenching process. Complex 1 also shows higher anticancer activity than cisplatin with lower IC50 value of incubation for both 24 h and 48 h. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2014.11.003

文献信息

• <i>N</i>,<i>N</i>,<i>N</i><i>‘</i>,<i>N</i><i>‘</i>-Tetrakis(2-quinolylmethyl)-2-hydroxy-1,3-propanediamine (Htqhpn) as a Supporting Ligand for a Low-Valent (μ-O)₂ Tetranuclear Manganese Core
  作者：Yuji Mikata、Motoko Wakamatsu、Haruka So、Yuriko Abe、Masahiro Mikuriya、Kôichi Fukui、Shigenobu Yano

  DOI：10.1021/ic050582r

  日期：2005.10.1

  ligand, N,N,N',N'-tetrakis(2-quinolylmethyl)-2-hydroxy-1,3-propanediamine (Htqhpn), was synthesized and used to generate compounds with linearly ordered MnIIMnIIIMnIIIMnII tetranuclear cores. This is the lowest valent tetranuclear manganese complex that exhibits a (mu2-O)2Mn2 core in the molecule. The electron paramagnetic resonance and magnetic measurements of these tetranuclear complexes suggest

  合成了新的七齿N6-O1配体N，N，N'，N'-四（2-喹啉基甲基）-2-羟基-1,3-丙二胺（Htqhpn），并用于生成具有线性有序MnIIMnIIIMnIIIMnII四核的化合物核心。这是最低价的四核锰配合物，在分子中具有（mu2-O）2Mn2核。这些四核配合物的电子顺磁共振和磁测量表明，中央MnIII2核具有中等强度的反铁磁耦合，而MnII和MnIII中心之间的耦合较弱。
• Quantitative Fluorescent Detection of Pyrophosphate with Quinoline-Ligated Dinuclear Zinc Complexes
  作者：Yuji Mikata、Anna Ugai、Risa Ohnishi、Hideo Konno

  DOI：10.1021/ic401605m

  日期：2013.9.16

  Dinuclear zinc complex [Zn-2(TQHPN)-(AcO)](2+) exhibits characteristic fluorescence response (lambda(ex) = 317 nm and lambda(em) = 455 nm) toward pyrophosphate (PPi) with maximum fluorescence upon 1:1 Zn-2(TQHPN)-PPi complex formation. The crystallographic investigation utilizing (PP2)-P-1-Ph(2)PPi revealed that the fluorescent response mechanism is due to intramolecular excimer formation of two quinoline rings.
• Bio-relevant cobalt(II) complexes with compartmental polyquinoline ligand: Synthesis, crystal structures and biological activities
  作者：Jun-Ling Li、Lin Jiang、Bi-Wei Wang、Jin-Lei Tian、Wen Gu、Xin Liu、Shi-Ping Yan

  DOI：10.1016/j.jinorgbio.2014.11.003

  日期：2015.4

  Three new Co(II) complexes, [Co-4(L)(2)(mu(3)-CrO4)(2)](ClO4)(2)center dot 2CH(3)CN (1), [Co-2(L)(mu(2)-na)(H2O)](ClO4)(2) (2) and [Co-2(L)(mu(2)-ba)](ClO4)(2)center dot 0.5CH(3)CN (3) (Hna = nicotinic acid, Hba = benzoic acid, HL = N,N,N',N'-tetrakis (2-quinolylmethyl)-1,3-diaminopropan-2-ol), have been synthesized and characterized by various physicochemical techniques. The Co(II) centers are connected by endogenous alkoxy bridge from L- and various extrinsic auxiliary linkers, some of which display coordination number asymmetry (5, 6-coordinated for 1 and 2; 5, 5-coordinated for 3). It is worth mentioning that complex 1 contains two rare reported mu(3)-eta(1), eta(1), eta(1)-CrO42- moieties. Susceptibility data of three complexes indicated intramolecular antiferromagnetic coupling of high-spin Co(II) atoms with exchange integral values (J) -14.94 cm(-1), -11.26 cm(-1) and -13.66 cm(-1) for 1,2 and 3, respectively. Interaction of compounds with calf thymus DNA (CT-DNA) have been investigated by absorption spectral titration, ethidium bromide (EB) displacement assay and viscosity measurement, which revealed that compounds bound to CT-DNA with a moderate intercalative mode, accompanied the affinities order: 1 > 2 approximate to 3. Three complexes exhibit oxidative cleavage of pBR322 plasmid DNA including a reliance on H2O2 as the activator. Compound 1 demonstrates an increased DNA cleavage activity as compared with 2 and 3, which could degrade super coiled DNA (SC DNA) into nicked coiled DNA (NC DNA) in lower concentration (5 mu M). Moreover, all compounds could quench the intrinsic fluorescence of bovine serum albumin (BSA) in a static quenching process. Complex 1 also shows higher anticancer activity than cisplatin with lower IC50 value of incubation for both 24 h and 48 h. (C) 2014 Elsevier Inc. All rights reserved.