Novel quinazoline nitrogen mustard compound, and preparation method and application thereof to treatment of cancer

A technology for quinazoline mustard and tumor treatment, which is applied in the fields of antitumor drugs, organic chemistry, and drug combinations, and can solve the problems of not fully tapping the potential of anticancer drugs, and achieve good anticancer activity and high yield , low toxicity effect

Inactive Publication Date: 2013-07-10
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 nitrogen mustard compound, and preparation method and application thereof to treatment of cancer
  • Novel quinazoline nitrogen mustard compound, and preparation method and application thereof to treatment of cancer
  • Novel quinazoline nitrogen mustard compound, and preparation method and application thereof to treatment of cancer

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Experimental program
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Embodiment

[0092] According to the following steps, the substituents R1=meta nitrogen mustard, R2=methoxyethoxy, R2=methoxyethoxy compounds in formula A are prepared.

[0093] 1.1N, the synthesis of N-bis(2-hydroxyethyl)-3-nitroaniline

[0094] 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%. mp 94-96°C, 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...

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Abstract

A novel quinazoline nitrogen mustard compound is characterized in that: one end is provided with a nitrogen mustard alkylating group; the other end is provided with a 6, 7-substituted quinazoline structure; a substituent R1 is located at a site 4 of a quinazoline matrix, and represents 2-, 3-, 4- nitrogen mustard substituent; and substituents R2, R3 are located at site 6 and 7 of a quinazoline matrix, and represent methoxyethoxy, methoxy, morpholine propoxy, 3-etrahydrofuran oxygen group and hydroxyl group. The compound has a structure shown as a formula A. Experiments show that the compound can cause cross-linking of DNA, and is a bifunctional alkylating agent. In vivo antitumor activity experiment show that the compound has good activity; furthermore, the compound has the advantage of low toxicity, which a nitrogen mustard drug is lack of. At the same time, the compound is easy for synthesis, has high total yield. Advantages of the compound show that it has great potential to become a drug for treatment of cancer.

Description

Technical field: [0001] The invention involves a new type of chimodoline nitrogen mustard compounds and its preparation methods and the application of 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 and have been trying to find more suitable tumor chemotherapy drugs for tumor treatment. [0003] Nitrogen mustard drugs are the earliest anti -tumor alkylated agents for clinical clinical. Since the introduction, the development of new nitrogen mustard drugs has been lasting.During the development of nitrogen mustard drugs, how to reduce the toxicity of the drug by introducing new drug carriers and increased the selectivity of tumors, thereby improving the treatment index, which is the common efforts of scientists in various countries.At present, research based on this idea is mainly concentrated in the following three directions: the introduc...

Claims

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Application Information

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Patent Type & Authority Applications(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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