4,4'-methylenebis[1-(2-bromoethyl)-3-(4-nitrophenyl)pyrazole] | 444805-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,4'-methylenebis[1-(2-bromoethyl)-3-(4-nitrophenyl)pyrazole]
• 英文别名: 1-(2-bromoethyl)-4-[[1-(2-bromoethyl)-3-(4-nitrophenyl)pyrazol-4-yl]methyl]-3-(4-nitrophenyl)pyrazole
• CAS: 444805-71-4
• 化学式: C₂₃H₂₀Br₂N₆O₄
• 分子量: 604.258
• InChiKey: ZAOWNLDKUYGALP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  121.92
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4,4'-methylenebis[1-(2-bromoethyl)-3-(4-nitrophenyl)pyrazole] 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 36.0h， 生成 [(2-{1'-[2-(biscarboxymethylamino)ethyl]-3,3'-bis(4-nitrophenyl)-1'H-[4,4']bipyrazolyl-1-yl}ethyl)carboxymethylamino]acetic acid tetrasodium salt
  参考文献：
  名称：

  A novel series of complexones with bis- or biazole structure as mixed ligands of paramagnetic contrast agents for MRI

  摘要：

  We describe the syntheses, physicochemical properties and biological evaluation of a novel series of complexones containing bis- or biazoles moieties and two iminodiacetic acid units as novel ligands for paramagnetic lanthanides. The complexones were prepared by reaction of the corresponding 1,1'-bishaloethylbi- or bispyrazoles with methyl iminodiacetate and subsequent NaOH hydrolysis. 1,1'-Bisbromoethyl precursors were obtained by direct alkylation with an excess of 1,2-dibromoethane, or by heating the corresponding alcohol in HCl. Sigmoidal binding isotherms and MO calculations supported as most stable structures in solution, those containing two Gd(III) atoms bound per molecule of complexone with half saturation values S-0.5 (M-1, 22degreesC, pH 7.2) in the range 6.5 10(-6) < S-0.5 < 36.1 10(-6). Relaxivity properties [r(1), r(2), s(-1) mM(-1) Gd(III)] determined at 1.5 Tesla gave values (12.0 < r(1) < 17.7, 12.2 < r(2) < 20), improving significantly the relaxivities of reference compounds such as Gd(III)EDTA (5.2, 5.6) or Gd(III)DTPA (4.30, 4.30). These improvements involve mainly increased hydration and slower rotational motions. In vitro toxicity experiments are reported. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.07.002
• 作为产物：
  描述：

  3,4-二氢-2-甲基-吡喃 在 哌啶 、 sodium hydroxide 、 N-butyl-3,4,5-trimethoxybenzamide 、 sodium methylate 、 溶剂黄146 作用下， 以 水 、 三乙二醇 为溶剂， 反应 29.5h， 生成 4,4'-methylenebis[1-(2-bromoethyl)-3-(4-nitrophenyl)pyrazole]
  参考文献：
  名称：

  A novel series of complexones with bis- or biazole structure as mixed ligands of paramagnetic contrast agents for MRI

  摘要：

  We describe the syntheses, physicochemical properties and biological evaluation of a novel series of complexones containing bis- or biazoles moieties and two iminodiacetic acid units as novel ligands for paramagnetic lanthanides. The complexones were prepared by reaction of the corresponding 1,1'-bishaloethylbi- or bispyrazoles with methyl iminodiacetate and subsequent NaOH hydrolysis. 1,1'-Bisbromoethyl precursors were obtained by direct alkylation with an excess of 1,2-dibromoethane, or by heating the corresponding alcohol in HCl. Sigmoidal binding isotherms and MO calculations supported as most stable structures in solution, those containing two Gd(III) atoms bound per molecule of complexone with half saturation values S-0.5 (M-1, 22degreesC, pH 7.2) in the range 6.5 10(-6) < S-0.5 < 36.1 10(-6). Relaxivity properties [r(1), r(2), s(-1) mM(-1) Gd(III)] determined at 1.5 Tesla gave values (12.0 < r(1) < 17.7, 12.2 < r(2) < 20), improving significantly the relaxivities of reference compounds such as Gd(III)EDTA (5.2, 5.6) or Gd(III)DTPA (4.30, 4.30). These improvements involve mainly increased hydration and slower rotational motions. In vitro toxicity experiments are reported. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.07.002