2,6-bis(1,4,7-triazacyclonon-1-ylmethyl)-4-methylphenol | 111976-20-6

• 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: 2,6-bis(1,4,7-triazacyclonon-1-ylmethyl)-4-methylphenol
• 英文别名: 4-Methyl-2,6-bis[(1,4,7-triazonan-1-yl)methyl]phenol；4-methyl-2,6-bis(1,4,7-triazonan-1-ylmethyl)phenol
• CAS: 111976-20-6
• 化学式: C₂₁H₃₈N₆O
• 分子量: 390.572
• InChiKey: NQXKPFDGBQSMDD-UHFFFAOYSA-N

物化性质

• 沸点：
  564.0±45.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  74.8
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  zinc perchlorate 、 2,6-bis(1,4,7-triazacyclonon-1-ylmethyl)-4-methylphenol 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以73%的产率得到[Zn₂{bcmp(-H)}(μ-Cl)](ClO₄)₂
  参考文献：
  名称：

  双金属双(1,4,7-三氮杂环壬烷)锌配合物的磷酸二酯裂解、DNA相互作用和细胞毒活性

  摘要：

  非常感谢欧盟委员会和爱尔兰科学基金会（玛丽居里 FP7-IEF，授予 DM 和斯托克斯讲座给 AE，授予编号 07/SK/B1225b）的财政支持。

  DOI：

  10.1002/ejic.201402319
• 作为产物：
  描述：

  1,4,7-三氮杂环壬烷 在 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 22.0h， 生成 2,6-bis(1,4,7-triazacyclonon-1-ylmethyl)-4-methylphenol
  参考文献：
  名称：

  双金属双(1,4,7-三氮杂环壬烷)锌配合物的磷酸二酯裂解、DNA相互作用和细胞毒活性

  摘要：

  非常感谢欧盟委员会和爱尔兰科学基金会（玛丽居里 FP7-IEF，授予 DM 和斯托克斯讲座给 AE，授予编号 07/SK/B1225b）的财政支持。

  DOI：

  10.1002/ejic.201402319

文献信息

• Simulation strategies for unusual EPR spectra of binuclear mixed-valence manganese complexes: synthesis, properties, and x-ray structures of the MnIIMnIII complexes [Mn2(bpmp)(.mu.-OAc)2](ClO4)2.cntdot.H2O and [Mn2(bcmp)(.mu.-OAc)2](ClO4)2.cntdot.CH2Cl2
  作者：Habibe Diril、Hsiu Rong Chang、Mark J. Nilges、Xiaohua Zhang、Joseph A. Potenza、Harvey J. Schugar、Stephan S. Isied、David N. Hendrickson

  DOI：10.1021/ja00196a013

  日期：1989.7

  group P2sub 1}/n with a = 12.493 (1) angstrom}, b = 21.583 (2) angstrom}, c = 16.631 (2) angstrom}, beta} = 95.31 (1)degree}, Z = 4; Rsub F} = 0.061 and Rsub wF} = 0.085 for 4298 unique reflections (I > 3sigma}(I)) at 297 (1) K. (Mnsub 2}(bcmp)(mu}-OAc)sub 2})(ClOsup minus}}sub 4})sub 2}center dot}CHsub 2}Clsub 2}, where bcmpsup minus}} is the monoanion of 2,6-bis(1,4,67-triazac

  介绍了两种混合价 Mnsup II}Mnsup III} 配合物的制备、单晶 X 射线结构、变温磁化率和新的 EPR 数据。(Mnsub 2}(bpmp)(mu}-OAc)sub 2})(ClOsub 4})sub 2}center dot}Hsub 2}O，其中 bpmpsup minus} } 是 2,6-bis(bis(2-pyridylmethyl)aminomethyl)-4-methylphenol 的单阴离子，在单斜空间群 P2sub 1}/n 中结晶，a = 12.493 (1) 埃}，b = 21.583 (2) 埃}, c = 16.631 (2) 埃}, β} = 95.31 (1)度}, Z = 4; Rsub F} = 0.061 和 Rsub wF} = 0.085 对于 297 (1) K. (Mnsub 2}(bcmp)(mu})
• Acceleration of Hydrolytic DNA Cleavage by Dicopper(II) Complexes with<i>p</i>-Cresol-Derived Dinucleating Ligands at Slightly Acidic pH and Mechanistic Insights
  作者：Masahito Kodera、Yuki Kadoya、Kenta Aso、Katsuki Fukui、Akiko Nomura、Yutaka Hitomi、Hiroaki Kitagishi

  DOI：10.1246/bcsj.20180353

  日期：2019.4.15

  Four dicopper(II) complexes, [Cu2(µ-X)(bcmp)](ClO4)2 [X = OH (1a) and X = Cl (1b)], [Cu2(µ-OH)(Me4bcmp)](ClO4)2 (2), and [Cu2(bcc)](ClO4)3 (3), were synthesized with three p-cresol-derived ligands,...

  四种二铜 (II) 配合物，[Cu2(µ-X)(bcmp)](ClO4)2 [X = OH (1a) 和 X = Cl (1b)]，[Cu2(µ-OH)(Me4bcmp)]( )2 (2) 和 [Cu2(bcc)]( )3 (3) 是用三个对甲酚衍生的配体合成的，...
• DNA damage and induction of apoptosis in pancreatic cancer cells by a new dinuclear bis(triazacyclonane) copper complex
  作者：Diego Montagner、Valentina Gandin、Cristina Marzano、Andrea Erxleben

  DOI：10.1016/j.jinorgbio.2015.01.013

  日期：2015.4

  The dinuclear copper(II) complex [Cu-2bcmp(-H)}(mu-OH)](NO3)(2)center dot H2O (1, bcmp = 2,6-bis(1,4,7-triazacyclonon-1-ylmethyl)-4-methylphenol) has been synthesized and characterized by electrospray ionization mass spectrometry, potentiometric titration and cyclovoltammetry. The X-ray structure of the analogous perchlorate salt [Cu-2bcmp(-H)}(mu-OH)](ClO4)(2)center dot 2.5H(2)O (2) was determined. Cytotoxicity studies showed very promising activity of 1 against various pancreatic tumor cell lines with IC50 values comparable or even lower than those of cisplatin. The Cu complex displayed low toxicity against a human non-tumor cell line (HEM 293) demonstrating selectivity for cancer cells. 1 converts supercoiled pUC19 plasmid DNA into the nicked form at micromolar concentrations in the absence of added reductants. A detailed kinetic study on the hydrolysis of the DNA model bis(2,4-dinitrophenyl) phosphate (BDNPP) has been performed. 1 hydrolyses BDNPP with a second order rate constant of 0.047 M s(-1) at pH 8 and 40 degrees C. Finally, single cell electrophoresis (comet assay) and fluorescence microscopy analysis showed that 1 interacts with cellular DNA and induces apoptotic cell death of Capan-1 pancreatic cancer cells. Western blotting analysis indicated that the Cu complex activates the p53 dependent pathway of apoptosis. (C) 2015 Elsevier Inc. All rights reserved.
• DNA binding, cleavage and cytotoxicity of a novel dimetallic Fe(III) triaza-cyclononane complex
  作者：Thaylan Pinheiro Araujo、Valentina Gandin、Paul Kavanagh、Jeremy Phillip Braude、Luca Nodari、Diego Montagner、Andrea Erxleben

  DOI：10.1016/j.ica.2016.02.044

  日期：2016.10

  A novel bimetallic Fe(III) complex with the bis(triaza-cyclononane) ligand 2,6-bis(1,4,7-triazacyclonon-1-ylmethyl)-4-methylphenol (bcmp) is reported. [Fe-2(bcmp(-H))(mu-OH)Cl-2]Cl-2 (2) contains two octahedral Fe(III) centers bound to the two triaza-cyclononane rings of bcmp. The coordination sphere is completed by one chlorine, one bridging phenolate oxygen and one bridging hydroxide group. The complex has been characterized by elemental analysis, Mossbauer spectroscopy, UV-Vis spectroscopy, pH potentiometric titration, ESI mass spectrometry and cyclic voltammetry. The complex hydrolyzes the DNA model bis (2,4-dinitrophenyl) phosphate (BDNPP) with a maximum activity a pH 7. Michaelis-Menten behavior is observed with k(cat) = 3.56 x 10(-4)s(-1) and K-m = 0.56 mM (pH 7.0, 40 degrees C). The interaction of 2 with CT DNA was studied by electronic absorption spectroscopy and gel electrophoresis. Notably, the complex relaxes supercoiled pUC19 DNA into the nicked form at low micromolar concentration (10 mu M) in the presence of an external reducing agent (ascorbic acid). Finally, the in vitro antiproliferative activity of 2 was assessed on a panel of human cancer cell lines and results revealed that the complex exhibited a significant cytotoxic effects in particular versus colon LoVo cancer cells, wih IC50 value 2.5 times lower than that shown by the reference metallodrug cisplatin (3.54 versus 8.53 mu M). (C) 2016 Elsevier B.V. All rights reserved.
• US6545147B1
  申请人：——

  公开号：US6545147B1

  公开（公告）日：2003-04-08