Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF3 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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

Examples

Experimental program
Comparison scheme
Effect test

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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com