2-[3-(4-Nitro-phenyl)-propyl]-malonic acid dimethyl ester | 129619-73-4

• 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-[3-(4-Nitro-phenyl)-propyl]-malonic acid dimethyl ester
• 英文别名: dimethyl 2-[3-(4-nitrophenyl)propyl]propanedioate
• CAS: 129619-73-4
• 化学式: C₁₄H₁₇NO₆
• 分子量: 295.292
• InChiKey: OFVVNSKHLJFOJV-UHFFFAOYSA-N

物化性质

• 沸点：
  411.6±40.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  95.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-[3-(4-Nitro-phenyl)-propyl]-malonic acid dimethyl ester 在 dimethyl sulfide borane 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 40.25h， 生成
  参考文献：
  名称：

  DNA-directed alkylating agents. 2. Synthesis and biological activity of platinum complexes linked to 9-anilinoacridine

  摘要：

  Two different classes of cis-diaminedichloroplatinum(II) complexes linked to the DNA-intercalating chromophore 9-anilinoacridine have been synthesized and evaluated as DNA-targeted antitumor agents. Two different Pt chelating ligands were investigated (based on 1,2-ethanediamine and 1,3-propanediamine), designed to deliver the Pt in an orientation likely to respectively enhance either intrastrand or interstrand cross-linking. Although both sets of ligands were somewhat unstable under neutral or basic conditions with respect to disproportionation, the corresponding Pt complexes, once prepared, appeared to be quite stable. All the Pt complexes were monitored for purity by TLC, HPLC, and FAB mass spectra, and the mode of Pt coordination was established by 195Pt NMR spectroscopy. The complexes appeared to cause simultaneous platination and intercalative unwinding of plasmid DNA. In vitro studies were carried out with both wild-type and cisplatin-resistant P388 cell lines. Whereas cisplatin itself and the ethylenediamine and 1,3-propanediamine complexes used as standards were about 10-fold less active against the resistant line, the ethylenediamine-linked Pt complexes showed no differential toxicity between the two lines and the propanediamine-linked complexes showed significant differentials (up to 8-fold) in favor of the cisplatin-resistant line. However, these were no greater than those shown by the unplatinated ligands themselves. The majority of the acridine complexes were inactive in vivo against the wild-type P388 leukemia. They were very insoluble, and although a suitable formulation was found, this may have been a factor. It is also possible that these compounds bind in such a way as to direct the Pt away from the major groove.

  DOI：

  10.1021/jm00173a015
• 作为产物：
  描述：

  3-(4-硝基苯基)-1-丙醇 在 吡啶 、 sodium hydride 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 22.17h， 生成 2-[3-(4-Nitro-phenyl)-propyl]-malonic acid dimethyl ester
  参考文献：
  名称：

  DNA-directed alkylating agents. 2. Synthesis and biological activity of platinum complexes linked to 9-anilinoacridine

  摘要：

  Two different classes of cis-diaminedichloroplatinum(II) complexes linked to the DNA-intercalating chromophore 9-anilinoacridine have been synthesized and evaluated as DNA-targeted antitumor agents. Two different Pt chelating ligands were investigated (based on 1,2-ethanediamine and 1,3-propanediamine), designed to deliver the Pt in an orientation likely to respectively enhance either intrastrand or interstrand cross-linking. Although both sets of ligands were somewhat unstable under neutral or basic conditions with respect to disproportionation, the corresponding Pt complexes, once prepared, appeared to be quite stable. All the Pt complexes were monitored for purity by TLC, HPLC, and FAB mass spectra, and the mode of Pt coordination was established by 195Pt NMR spectroscopy. The complexes appeared to cause simultaneous platination and intercalative unwinding of plasmid DNA. In vitro studies were carried out with both wild-type and cisplatin-resistant P388 cell lines. Whereas cisplatin itself and the ethylenediamine and 1,3-propanediamine complexes used as standards were about 10-fold less active against the resistant line, the ethylenediamine-linked Pt complexes showed no differential toxicity between the two lines and the propanediamine-linked complexes showed significant differentials (up to 8-fold) in favor of the cisplatin-resistant line. However, these were no greater than those shown by the unplatinated ligands themselves. The majority of the acridine complexes were inactive in vivo against the wild-type P388 leukemia. They were very insoluble, and although a suitable formulation was found, this may have been a factor. It is also possible that these compounds bind in such a way as to direct the Pt away from the major groove.

  DOI：

  10.1021/jm00173a015

文献信息

• 一种用于金属锆标记的螯合剂及其合成方法与应用
  申请人：华中科技大学

  公开号：CN113880769B

  公开（公告）日：2023-03-31

  本发明涉及一种用于金属锆标记的螯合剂及其合成方法与应用，属于金属螯合剂合成领域。合成过程为：丙二酸二甲酯在碱的作用下，与1‑(溴烷基)‑4‑硝基苯反应，然后在还原剂的作用下，发生羧酸酯还原成羟基的反应，然后在溴代试剂的作用下引入Br原子，再与[1H]吡唑‑3‑羧酸乙酯发生N上的亲核取代反应，最后将吡唑羧酸酯水解，并酸化得到式I的化合物；式I的化合物在卤代试剂的作用下转化为酰氯，然后与盐酸羟胺反应，生成式II的化合物。本发明合成了一类新型的锆金属螯合剂I和II，结构简单，易于合成，解决了现有技术中螯合剂合成步骤冗长。与锆离子标记的条件温和，稳定，螯合过程不需要苛刻的条件，以及长时间的高温加热。