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Terpyridyl ligand containing nitrogen mustard as well as preparation method and application of terpyridyl ligand

A technology of terpyridine and nitrogen mustard, which is applied in the field of pharmaceutical intermediates and anti-tumor drugs, can solve the problems of large molecular structure, and achieve the effect of easy-to-obtain raw materials, simple and easy method, and strong inhibitory ability

Active Publication Date: 2021-06-15
GUANGDONG OCEAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Mainly because the coupling of the two requires multi-step reactions, and the molecular structure of the reaction product will be too large

Method used

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  • Terpyridyl ligand containing nitrogen mustard as well as preparation method and application of terpyridyl ligand
  • Terpyridyl ligand containing nitrogen mustard as well as preparation method and application of terpyridyl ligand
  • Terpyridyl ligand containing nitrogen mustard as well as preparation method and application of terpyridyl ligand

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Embodiment 1

[0055] Take the following synthetic route to prepare 4-(4-[bis(β-chloroethyl)amino]phenyl)-2,2':6',2-terpyridine (compound L1):

[0056]

[0057] step 1.

[0058] Synthesis of 4-[bis(β-chloroethyl)amino]benzaldehyde:

[0059]

[0060] Add dry DMF 102.2mmol (7.46g) to the round bottom flask, and slowly add POCl dropwise while stirring in an ice-water bath 3 45.5mmol (6.97g), after the dropwise addition, continue to react in the ice bath for 30min. Then add N,N-bis(2-hydroxyethyl)-aniline 13.8mmol (2.50g) in DMF 13.8mmol (1.01g) solution, and react at 100°C for 3h. After cooling to room temperature, it was poured into 200 mL of ice water, and 1 mol / L NaOH was added dropwise with stirring to adjust to neutrality. After suction filtration, the filter cake was washed twice with a small amount of cold ethanol / water mixture (v:v=1:1), and finally recrystallized with ethanol / dichloromethane (v:v=1:1) mixture to obtain shallow Yellow solid, yield 85%. figure 1 For the H NMR...

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Abstract

The invention relates to the field of medical intermediates and anti-tumor drugs, in particular to a terpyridyl ligand containing nitrogen mustard and a preparation method and application of the terpyridyl ligand. The preparation method comprises the following steps: by taking N, N-bis (2-hydroxyethyl)-aniline as a raw material, carrying out Vilsmeier-Haack reaction to prepare an aromatic aldehyde intermediate containing nitrogen mustard, and then further reacting with 2-acetylpyridine to prepare the terpyridyl ligand L1 containing nitrogen mustard. The method is simple and feasible, has low requirements on equipment, and is easy to separate and purify target compounds. The compound has high symmetry in structure, and is a terpyridyl derivative which has the simplest structure and contains aromatic nitrogen mustard at present. Various metal complexes containing nitrogen mustard can be designed as ligands of various metal ions. In-vitro anti-tumor experiments show that the compound has the characteristics of excellent anti-tumor effect, capability of effectively inhibiting growth, migration, crawling, cloning and the like of tumor cells, and has wide research and development values in the field of anti-tumor drugs.

Description

technical field [0001] The invention relates to the fields of pharmaceutical intermediates and antineoplastic drugs, in particular to a terpyridine ligand of nitrogen mustard and its preparation method and application. Background technique [0002] Since 2,2':6',2-terpyridine was synthesized for the first time, the research on terpyridine derivatives and terpyridine metal complexes has been widely used in the fields of photophysics, photochemistry, supramolecular chemistry, pharmacy, materials science and supramolecular chemistry. Development and other aspects have important research value and have received extensive attention. The current research on terpyridine and its metal complexes is mainly based on the design of derivatives containing various substituents, which makes their development more practical. Common synthetic methods include cyclization and coupling. Terpyridine derivatives can coordinate with many transition metal ions, such as Zn(II), Co(II), Cu(II), Ni(I...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/36A61P35/00A61P35/04
CPCA61P35/00A61P35/04C07D213/36
Inventor 梁远维
Owner GUANGDONG OCEAN UNIVERSITY
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