Two nitrogen mustard derivatives, as well as preparation method and application therefore in tumor treatment

A tumor treatment and derivative technology, applied in anti-tumor drugs, drug combinations, pharmaceutical formulations, etc., can solve problems such as failure to fully tap the potential of anti-tumor drugs, and achieve good anti-cancer activity, easy preparation, and yield. high effect

Inactive Publication Date: 2015-04-29
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there are only a few reports on the research of nitrogen mustard compounds with quinazoline derivatives as anti-tumor drugs, and the potential of these compounds as anti-tumor drugs has not been fully tapped.

Method used

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  • Two nitrogen mustard derivatives, as well as preparation method and application therefore in tumor treatment
  • Two nitrogen mustard derivatives, as well as preparation method and application therefore in tumor treatment
  • Two nitrogen mustard derivatives, as well as preparation method and application therefore in tumor treatment

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Embodiment

[0068] Compounds of the formula A in which the substituents R1=hydrogen, R2=nitrogen mustard are prepared according to the following steps.

[0069] 1.1 Synthesis of N, N-bis(2-hydroxyethyl)-3-nitroaniline

[0070] Take 5.52 g (0.04 mol) of 3-nitroaniline, add it to 80 mL of 25% acetic acid aqueous solution, and add 10 mL of ethylene oxide dropwise under ice cooling. Warm up to room temperature, stir for 72 hours, filter with suction, wash the filter cake with water, and dry to obtain 8.02 g of a yellow-orange solid, with a yield of 88%. mp94-96℃, 1 H NMR (400MHz, CDCl 3 )δ7.53 (d, J=8.0Hz, 1H, ArH), 7.48 (s, 1H, ArH), 7.33 (t, J=8.2Hz, 1H, ArH), 6.97 (dd, J=8.4, 2.2Hz , 1H, ArH), 3.89 (t, J=4.8Hz, 4H, -NCH 2 CH2-), 3.65(t, J=4.8Hz, 4H, -CH 2 CH 2 OH). 13 C NMR (100MHz, CDCl 3 )δ149.43, 148.63, 129.84, 118.10, 111.34, 106.48, 60.35, 55.06.MS (ESI + ) m / z: 227.3 (M+H + ).IR(KBr pellet, cm -1 ): 3265, 3173, 2959, 2863, 1618, 1565, 1525, 1486, 1341, 1290, 1040.

[007...

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Abstract

The novel nitrogen mustard derivative is characterized in that: one end has a nitrogen mustard alkylating group; the other end has a 6,7-substituted quinazoline structure, and the substituent R1 is located at the 4-position of the quinazoline parent, which is 2- or 3 - the nitrogen mustard group; the 6 and 7 positions of the quinazoline parent are morpholine propoxy and methoxy. The structure is as formula A. Experiments show that this kind of compound can inhibit cell cycle in G2 / M phase, and is a kind of bifunctional alkylating agent. Anti-tumor activity experiments in vivo show that the compound has good activity. Not only that, this type of compound also has the advantage that nitrogen mustards do not have, namely less toxicity. Simultaneously, the compounds are easy to synthesize, and the total yield is high. Various advantages show that this kind of compound has great potential to be a tumor treatment drug.

Description

Technical field: [0001] The invention relates to two novel nitrogen mustard derivatives, their preparation method and their application as tumor treatment drugs. Background technique: [0002] Tumor is a disease that seriously threatens human health. Over the years, scientists from various countries have made unremitting efforts to find out more suitable tumor chemotherapy drugs for tumor treatment. [0003] Nitrogen mustards are the earliest anti-tumor alkylating agents used clinically. Since their inception, the development of new nitrogen mustards has been going on for a long time. In the development process of nitrogen mustard drugs, how to introduce new drug carriers to reduce drug toxicity and increase tumor selectivity, thereby improving the therapeutic index, is the common goal of scientists from all over the world. At present, research based on this idea is mainly focused on the following three directions: introducing sugars and their derivatives into drug molecul...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/94A61P35/00
CPCA61K31/5377A61P35/00C07D239/94
Inventor 齐传民李石磊王潇贺勇陈玉蓉赵明霞宁红玉
Owner BEIJING NORMAL UNIVERSITY
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