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A kind of terpyridine ligand of nitrogen mustard and its preparation method and application

The technology of terpyridine and nitrogen mustard is applied in the field of pharmaceutical intermediates and anti-tumor drugs, which can solve problems such as large molecular structure, and achieve the effects of easy availability of raw materials, few operation steps and good anti-tumor activity.

Active Publication Date: 2021-07-30
GUANGDONG OCEAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A kind of terpyridine ligand of nitrogen mustard and its preparation method and application
  • A kind of terpyridine ligand of nitrogen mustard and its preparation method and application
  • A kind of terpyridine ligand of nitrogen mustard and its preparation method and application

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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 fields of pharmaceutical intermediates and antineoplastic drugs, in particular to a terpyridine ligand of nitrogen mustard and its preparation method and application. Using N,N-bis(2-hydroxyethyl)-aniline as raw material, the aromatic aldehyde intermediate of nitrogen mustard was prepared by Vilsmeier-Haack reaction, and then further reacted with 2-acetylpyridine to prepare the terpyridine ligand of nitrogen mustard L1. The method is simple and easy to implement, has low requirements on equipment, and is easy to separate and purify the target compound. The compound has good symmetry in structure, and is currently the terpyridine derivative with the simplest structure and aromatic nitrogen mustard. It can be used as a ligand for various metal ions to design various metal complexes of nitrogen mustards. In vitro anti-tumor experiments show that the compound has excellent anti-tumor effect, can effectively inhibit the growth, migration, crawling and cloning of tumor cells, and has extensive research and development value 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 Patents(China)
IPC IPC(8): C07D213/36A61P35/00A61P35/04
CPCA61P35/00A61P35/04C07D213/36
Inventor 梁远维
Owner GUANGDONG OCEAN UNIVERSITY
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