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Novel anilinoquinazoline derivatives and preparation method thereof

A technology for aniline quinazoline derivatives, applied in the field of novel aniline quinazoline derivatives and their preparation, capable of solving problems such as strong toxic and side effects

Active Publication Date: 2011-08-10
SHAANXI NORMAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most traditional chemotherapeutic drugs kill normal cells while directly killing cancer cells, with strong toxic and side effects

Method used

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  • Novel anilinoquinazoline derivatives and preparation method thereof
  • Novel anilinoquinazoline derivatives and preparation method thereof
  • Novel anilinoquinazoline derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1: the preparation of compound A

[0061]

[0062] Add 6-fluoro-4-chloroquinazoline (0.11g, 0.58mmol), (E)-3,4,5-trimethoxy-4'-aminostilbene (0.17g, 0.58mmol) and absolute ethanol (20mL). Heated to reflux for 1h, cooled, and filtered to obtain a bright yellow solid. The obtained solid was washed with a mixed solvent of ethanol and triethylamine until the impurities disappeared, then washed repeatedly with water, and suction-filtered to obtain 0.19 g of a bright yellow solid, namely the target compound, with a yield of 76%. m.p.: 255.0-255.2°C; 1 H NMR (300MHz, DMSO-d 6 )δ: 3.71 (s, 3H, OCH 3 ), 3.87(s, 6H, 2OCH 3 ), 6.94(s, 2H), 7.17-7.29(m, 2H), 7.62-7.95(m, 6H), 8.46(d, 1H), 8.65(s, 1H), 9.79(s, 1H, NH);

[0063] IR v max (KBr)cm -1 : 3618, 3333, 2991, 2935, 1634, 1609, 1577, 1507, 1422, 1343, 1243, 1127, 1006, 970 (trans, CH=CH);

[0064] Elemental analysis (%): C 25 h 22 FN 3 o 3 , found (calculated): C, 69.74 (69.59); H, 5.41 (5.14); N, 9...

Embodiment 2

[0065] Embodiment 2: the preparation of compound B

[0066]

[0067] Add 6-fluoro-4-chloroquinazoline (0.16g, 0.87mmol), (E)-3,4-dimethoxy-4'-aminostilbene (0.22g, 0.87mmol) successively in a 50mL three-necked flask ) and absolute ethanol (30mL). Heated to reflux for 2h, cooled, and filtered to obtain a yellow solid. The obtained solid was washed with a mixed solvent of ethanol and triethylamine until the impurities disappeared, then washed repeatedly with water, and suction filtered to obtain 0.23 g of a light yellow solid, namely the target compound, with a yield of 66%. m.p.: 265.5-267.1°C;

[0068] 1 H NMR (300MHz, DMSO-d 6 )δ: 3.78(s, 3H, OCH 3 ), 3.84(s, 3H, OCH 3 ), 6.94-7.25(m, 5H), 7.61(d, 2H), 7.78-7.9(m, 4H), 8.46(d, 1H), 8.63(s, 1H), 9.77(s, 1H, NH);

[0069] IR v max (KBr)cm -1 : 3351 (NH), 3051, 2933, 2835, 1630, 1600, 1522, 1419, 1280, 1237, 1140, 1024, 951 (trans, CH=CH);

[0070] Elemental analysis (%): C 24 h 20 FN 3 o 2 , found (calculated):...

Embodiment 3

[0071] Embodiment 3: the preparation of compound C

[0072]

[0073] Add 6-fluoro-4-chloroquinazoline (0.91g, 5.0mmol), (E)-3,5-dimethoxy-4'-aminostilbene (1.28g, 5.0mmol) into a 50mL three-necked flask ) and isopropanol (35 mL). Heat to reflux for 4h, add 1.0mL triethylamine, continue stirring for 0.5h, evaporate to dryness, add 10mL water, stir, and filter. The obtained solid was subjected to silica gel column chromatography (ethyl acetate:petroleum ether=1:2, V / V) to obtain 1.15 g of light yellow solid with a yield of 57%. 1 H NMR (300MHz, DMSO-d 6 )δ: 3.80(s, 6H, 2OCH 3 ), 6.42(s, 1H), 6.79(s, 2H), 7.12-7.32(dd, 2H, J=16.2), 7.65-7.94(m, 5H), 8.10(s, 1H), 8.46(br s, 1H), 8.65(s, 1H), 9.79(s, 1H, NH);

[0074] 13 C NMR (75MHz, DMSO-d 6 )δ: 55.69, 100.24, 104.85, 107.73, 110.77, 122.55, 123.06, 127.20, 127.87, 129.05, 131.23, 132.91, 139.13, 139.77, 145.29, 147.35, 154.47, 157.7

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Abstract

The invention relates to anilinoquinazoline derivatives shown in the formula I, and a preparation method and application thereof for curing tumors. The preparation process of anilinoquinazoline derivatives or salts of anilinoquinazoline derivatives is simple and has good repeatability; antitumor activity experiment results show that the compounds have obvious inhibiting effect on the proliferations of human epidermal carcinoma cells, human cervical-cancer cells, human poorly deferentiated gastric adenocarcinoma cells and human breast cancer cells; the effects of most of the compounds are better than the effect of a positive control medicine-gefitinib; and the inhibiting effects of the compounds on the proliferation of human breast cancer cells is better than that of gefitinib.

Description

technical field [0001] The invention relates to a novel aniline quinazoline derivative, a preparation method thereof and their use for treating tumors. Background technique [0002] In recent years, cancer has become one of the fatal diseases of human beings. Chemotherapy is an important means to inhibit the growth of tumors and the spread of cancer cells, and to make tumors regress. Most traditional chemotherapeutic drugs kill normal cells while directly killing cancer cells, with strong toxic and side effects. In order to increase the selectivity of action on cancer cells, anticancer drugs that selectively act on tumor cells have been studied. [0003] Tyrosine kinase is an important drug target, and the overexpression of tyrosine kinase can lead to malignant tumors. Therefore, inhibiting the activity of tyrosine kinase and blocking its activated signal transduction pathway has become a new way to treat tumors. Many small molecule epidermal growth factor (EGFR) tyrosine...

Claims

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Application Information

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IPC IPC(8): A61P35/00A61K31/517C07D239/94C07D405/12
Inventor 李宝林王留昌刘小莉张喜全顾红梅徐宏江
Owner SHAANXI NORMAL UNIV
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