N,N'-(p-xylylene)di-(D,L-alanine acid) | 1224208-93-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N'-(p-xylylene)di-(D,L-alanine acid)
• 英文别名: N,N'-(p-xylylene)di-alanine acid；D,L-PDIAla
• CAS: 1224208-93-8
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: ZTGWKZKYTUWOBI-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.81
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  98.66
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,10-菲罗啉 、 copper(II) perchlorate hexahydrate 、 N,N'-(p-xylylene)di-(D,L-alanine acid) 、 水 在 LiOH 作用下， 以 甲醇 、 水 为溶剂， 以92%的产率得到[copper(II)2(1,10-phenanthroline)2(N,N'-(p-xylylene)di-D,L-alanine acid-1H)(H2O)](ClO4)2*0.5H2O
  参考文献：
  名称：

  Synthesis, crystal structures, DNA-binding properties, cytotoxic and antioxidation activities of several new ternary copper(II) complexes of N,N′-(p-xylylene)di-alanine acid and 1,10-phenanthroline

  摘要：

  Three novel ternary copper(II) complexes, [Cu-2(phen)(2)(L-PDIAla)(H2O)(2)](ClO4)(2)center dot 2.5H(2)O (1), [Cu-4(phen)(6)(D,L-PDIAla)(H2O)(2)](ClO4)(6)center dot 3H(2)O (2) and [Cu-2(phen)(2)(D,L-PDIAla)(H2O)](ClO4)(2)center dot 0.5H(2)O (3) (phen = 1,10-phenanthroline, H(2)PDIAla = N,N'-(p-xylylene)di-alanine acid) have been synthesized and structurally characterized by single-crystal X-ray crystallography and other structural analysis. Spectrometric titrations, ethidium bromide displacement experiments, CD (circular dichroism) spectral analysis and viscosity measurements indicate that the three compounds, especially the complex 3, strongly bind to calf-thymus DNA (CT-DNA). The intrinsic binding constants of the ternary copper(II) complexes with CT-DNA are 0.89 x 10(5), 1.14 x 10(5) and 1.72 x 10(5) M-1, for 1, 2 and 3, respectively. Comparative cytotoxic activities of the copper(II) complexes are also determined by acid phosphatase assay. The results show that the ternary copper(II) complexes have significant cytotoxic activity against the HeLa (Cervical cancer), HepG2 (hepatocarcinoma), HL-60 cells (myeloid leukemia), A-549 cells (pulmonary carcinoma) and L02 (liver cells). Investigations of antioxidation properties show that all the copper(II) complexes have strong scavenging effects for hydroxyl radicals and superoxide radicals. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2009.12.047
• 作为产物：
  描述：

  对苯二甲醛 、 DL-丙氨酸 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以80%的产率得到N,N'-(p-xylylene)di-(D,L-alanine acid)
  参考文献：
  名称：

  Synthesis, crystal structures, DNA-binding properties, cytotoxic and antioxidation activities of several new ternary copper(II) complexes of N,N′-(p-xylylene)di-alanine acid and 1,10-phenanthroline

  摘要：

  Three novel ternary copper(II) complexes, [Cu-2(phen)(2)(L-PDIAla)(H2O)(2)](ClO4)(2)center dot 2.5H(2)O (1), [Cu-4(phen)(6)(D,L-PDIAla)(H2O)(2)](ClO4)(6)center dot 3H(2)O (2) and [Cu-2(phen)(2)(D,L-PDIAla)(H2O)](ClO4)(2)center dot 0.5H(2)O (3) (phen = 1,10-phenanthroline, H(2)PDIAla = N,N'-(p-xylylene)di-alanine acid) have been synthesized and structurally characterized by single-crystal X-ray crystallography and other structural analysis. Spectrometric titrations, ethidium bromide displacement experiments, CD (circular dichroism) spectral analysis and viscosity measurements indicate that the three compounds, especially the complex 3, strongly bind to calf-thymus DNA (CT-DNA). The intrinsic binding constants of the ternary copper(II) complexes with CT-DNA are 0.89 x 10(5), 1.14 x 10(5) and 1.72 x 10(5) M-1, for 1, 2 and 3, respectively. Comparative cytotoxic activities of the copper(II) complexes are also determined by acid phosphatase assay. The results show that the ternary copper(II) complexes have significant cytotoxic activity against the HeLa (Cervical cancer), HepG2 (hepatocarcinoma), HL-60 cells (myeloid leukemia), A-549 cells (pulmonary carcinoma) and L02 (liver cells). Investigations of antioxidation properties show that all the copper(II) complexes have strong scavenging effects for hydroxyl radicals and superoxide radicals. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2009.12.047