Novel quinazoline mustard compound and its preparation method and tumor treatment application

A quinazoline mustard, tumor treatment technology, applied in anti-tumor drugs, organic chemistry, drug combination and other directions, can solve the problem of not fully excavating the potential of anti-cancer drugs, and achieve good anti-cancer activity and good anti-tumor effect, low toxicity effect

Inactive Publication Date: 2016-02-24
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

As of today, there are only a few reports on the research of nitrogen mustard compounds with quinazoline derivatives as anticancer drugs, and the potential of these compounds as anticancer drugs has not been fully tapped

Method used

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  • Novel quinazoline mustard compound and its preparation method and tumor treatment application
  • Novel quinazoline mustard compound and its preparation method and tumor treatment application
  • Novel quinazoline mustard compound and its preparation method and tumor treatment application

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Effect test

Embodiment

[0093] According to the following steps, the substituents R1=meta nitrogen mustard, R2=methoxyethoxy, R3=methoxyethoxy compounds in formula A are prepared.

[0094] 1.1N, the synthesis of N-bis(2-hydroxyethyl)-3-nitroaniline

[0095] 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 HNMR (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 CNMR (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(KBrpellet, cm -1 ): 3265, 3173, 2959, 2863, 1618, 1565, 1525, 1486, 1341, 129...

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Abstract

A novel quinazoline nitrogen mustard compound, 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, 2-, 3-, 4- nitrogen mustard groups; substituents R2, R3 are respectively located on the 6 and 7 positions of the quinazoline parent, and are methoxyethoxy, methoxy, morpholine propoxy, 3-tetrahydrofuryloxy and hydroxyl. The structure is as formula A. Experiments show that this kind of compound can cause cross-linking of DNA and is a 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. All these advantages show that this kind of compound has great potential to be a tumor treatment drug.

Description

technical field [0001] The invention relates to a class of novel quinazoline mustard compounds, a preparation method thereof and an application as a drug for treating tumors. 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/94C07D405/12C07D405/14A61P35/00
Inventor 齐传民王潇李石磊贺勇陈玉蓉
Owner BEIJING NORMAL UNIVERSITY
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