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Bisfatty amido substituted quinazolone derivatives as well as preparation method and use thereof as anti-cancer drugs

A technology of quinazolones and derivatives, which is applied in the field of new drug compounds, can solve problems such as reports on the anti-cancer effects of di-fatty amino-substituted quinazolones derivatives, etc., and achieve cheap raw materials, simple preparation methods, and low cost. Toxic effects

Inactive Publication Date: 2008-08-27
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there is no report on the bis-aliphatic amino-substituted quinazolones derivatives and their anticancer efficacy

Method used

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  • Bisfatty amido substituted quinazolone derivatives as well as preparation method and use thereof as anti-cancer drugs
  • Bisfatty amido substituted quinazolone derivatives as well as preparation method and use thereof as anti-cancer drugs
  • Bisfatty amido substituted quinazolone derivatives as well as preparation method and use thereof as anti-cancer drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis of embodiment 1 compound 2

[0029] Dissolve 0.01mol of dry 4-nitro-2-aminobenzoic acid and 0.005mol of pyrrolidone in 250ml of toluene, add 2ml of phosphorus oxychloride dropwise at room temperature, raise the temperature to 110°C and react at this temperature for 5-12 hours . The reaction solution was slowly poured into ice water, adjusted to pH = 7, and suction filtered to obtain a yellow solid powder. The crude product was recrystallized with acetone to obtain a light yellow solid powder, namely compound 2, whose chemical formula is shown in formula (IIa):

[0030]

[0031] Yield: 60%; 1 H-NMR (300MHz, CDCl 3 )δ (ppm): 2.30-2.40 (m, 2H); 3.23 (t, J = 7.8Hz, 2H); 4.24 (t, J = 7.2Hz, 2H); 8.17 (dd, J = 8.7, 2.1Hz, 1H); 8.40(d, J=8.7Hz, 1H); 8.45(d, J=2.1Hz, 1H); ESI-MS m / z: 232[M+H] + .

Embodiment 2

[0032] The synthesis of embodiment 2 compound 2

[0033] The method is the same as in Example 1, except that 5-nitro-2-aminobenzoic acid is used instead of 4-nitro-2-aminobenzoic acid to obtain a light yellow solid that is compound 2, and its chemical formula is as shown in formula (IIb) :

[0034]

[0035] Yield: 65%; 1 H-NMR (300MHz, CDCl 3 )δ (ppm): 2.29-2.40 (m, 2H); 3.23 (t, J = 7.8Hz, 2H); 4.24 (t, J = 7.2Hz, 2H); 7.72 (d, J = 8.7Hz, 1H) ; 8.48 (dd, J = 8.7, 2.7Hz, 1H); 9.11 (d, J = 2.7Hz, 1H); ESI-MS m / z: 232 [M+H] + .

Embodiment 3

[0036] The synthesis of embodiment 3 compound 3

[0037] In molar ratio, dissolve 0.001 mol of compound 2 prepared in Example 1 and 8 to 10 times the amount of 4-nitrobenzaldehyde in 10 ml of acetic anhydride, reflux for 24 to 32 hours, cool to room temperature, suction filter, and use for solid Wash with ethanol, chloroform, and acetone several times. Dissolve the obtained intermediate product in 10ml of ethanol and heat to nearly reflux, add 16ml of aqueous solution dissolved with 0.004mol sodium sulfide nonahydrate and 0.01mol sodium hydroxide, reflux for 4-8 hours, cool to room temperature, and stand overnight. Ethanol was removed by rotary evaporation, and then cooled at 0-5°C, filtered with suction, washed with water several times to obtain a dark red crude product. The crude product was recrystallized with ethanol / acetone to obtain an orange-red solid, namely compound 3, whose chemical formula is shown in formula (IIIa):

[0038]

[0039] Yield: 60%; 1 H-NMR (500M...

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Abstract

The invention discloses a dual fatty ammonia substituted quinazolinone derivative, represented as formula (I), wherein n is 1, 2, 3, 4 or 5, R1 and R2 are same or different, selected from the alkyl of H and C1-6, and naphthenic group, piperidyl, morpholinyl, piperazinyl or quinoxaline of C3-6. The derivative has strong interaction on the telomere DNA rich with guanine and c-myc DNA of proto-oncogene, strong inhibition on telomere / telomerase of cancer cell and strong inhibition on the c-myc expression of proto-oncogene. The derivative has low toxicity and side effect, which can be developed to a new anti-tumor drug. The derivative has simple preparation method, cheap materials and strong inhibition on various cancer cell lines, which can be prepared into anti-tumor drug, with wide application.

Description

technical field [0001] The present invention relates to a new drug compound, in particular to a bis-fatty amino-substituted quinazolon derivative, its preparation method and its application as an anticancer drug. Background technique [0002] Cancer is one of the major diseases that threaten human health and life safety. The research and development of anticancer drugs has always been a hot spot for chemists and pharmacologists. Finding anticancer drugs with high efficiency, high selectivity and less toxic side effects is one of the important directions of drug research and development. [0003] Designing and synthesizing anticancer drugs with DNA as the target, especially designing and synthesizing small molecule inhibitors for the special high-level structures of telomere DNA and proto-oncogene DNA, which have important physiological significance, is an important method for the development of new anticancer drugs. The small molecular compounds that interact with telomere...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/519A61P35/00
Inventor 黄志纾古练权谭嘉恒欧田苗
Owner SUN YAT SEN UNIV
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