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Phthalazino[1,2,b]quinazolin-8-one compound and its preparation method and application in antitumor drugs

A quinazoline and compound technology, applied in the field of organic chemistry, can solve problems such as synthesis and application without literature reports

Inactive Publication Date: 2017-12-08
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] We found that phthalazino[1,2,b]quinazolin-8-ones with ω-dimethylamine-substituted aminoethyl and aminopropyl groups and ω-hexahydropyridylaminopropyl groups at the 5-position The compound is a new framework with good compounds both in vivo and in vitro, and the synthesis and application of these compounds have not been reported in the literature.

Method used

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  • Phthalazino[1,2,b]quinazolin-8-one compound and its preparation method and application in antitumor drugs
  • Phthalazino[1,2,b]quinazolin-8-one compound and its preparation method and application in antitumor drugs
  • Phthalazino[1,2,b]quinazolin-8-one compound and its preparation method and application in antitumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]5-(2-(dimethylamino)ethylamino)-8H-phthalazino[1,2-b]quinazolin-8-one

[0041]

[0042] The synthetic method comprises the steps:

[0043] 1. Under electromagnetic stirring, add the compounds anthranilic acid and THF to the reaction vessel in sequence, place the flask in an ice-water bath, add triphosgene in batches under stirring, and move the flask to room temperature and stir for 10 hours after the addition is complete. After the reaction, excess solvent was removed by filtration, and the filter cake was washed with petroleum ether to obtain a white hydrazinolysis product.

[0044] 2. Under electromagnetic stirring, add the hydrazinolysis product and hydrazine hydrate obtained in the previous step to the reaction vessel in sequence, stir evenly, and then heat and reflux in an oil bath at 105°C under nitrogen protection for 3.5h (TLC monitors the reaction process, Developing agent: V PE :V EtOAc =2:1). After the reaction was finished, cool, precipitate solid, fil...

Embodiment 2

[0050] 5-(3-(dimethylamino)propylamino)-8H-phthalazino[1,2-b]quinazolin-8-one

[0051]

[0052] The synthesis method is the same as in Example 1, and its structural characterization data is: m.p.158~159°C; 1 H NMR (500MHz, CDCl 3 )δ: 8.88(d, J=7.6Hz, 1H, ArH), 8.24(dd, J=7.6, 3.5Hz, 2H, ArH), 7.98~7.90(m, 2H, ArH), 7.83(t, J= 7.5Hz,1H,ArH),7.78(d,J=8.2Hz,1H,ArH),7.68(s,1H,NH),7.51(t,J=7.4Hz,1H,ArH),3.51(dd,J =12.5,6.6Hz,2H,CH 2 ),2.38(t,J=6.8Hz,2H,CH 2 ),2.20(s,6H,CH 3 ), 1.90 (t, J=7.0, 2H, CH 2 ); 13 C NMR (125MHz, DMSO) δ: 157.8, 149.0, 146.3, 143.6, 134.2, 133.4, 132.7, 129.0, 127.5, 127.1, 126.7, 126.0, 123.3, 122.0, 120.3, 57.7, 45.7, 40.5, 26.2. + ): m / z calcd for 347.17461, found 348.18.55 ([M+H] + ).

Embodiment 3

[0054] 5-(3-morpholinopropylamino)-8H-phthalazino[1,2-b]quinazolin-8-one

[0055]

[0056] The synthesis method is the same as in Example 1, and its structural characterization data is: m.p.158~162°C; 1 H NMR (500MHz, DMSO-d 6 )δ: 8.86(dd, J=7.5, 1.2Hz, 1H, ArH), 8.25(dd, J=19.9, 7.7Hz, 2H, ArH), 7.96~7.89(m, 2H, ArH), 7.81(d, J=8.2Hz, 1H, ArH), 7.77(d, J=7.9Hz, 1H, ArH), 7.60(s, 1H, NH), 7.49(t, J=7.5Hz, 1H, ArH), 3.74(t ,J=4.5Hz,2H,CH 2 ),3.62(t,J=4.1Hz,4H,CH 2 ),3.00(t,J=4.3Hz,2H,CH 2 ), 2.42(t, J=6.8Hz, 4H, CH 2 ),1.92(m,5.5Hz,2H,CH 2 ); 13 C NMR (125MHz, DMSO-d 6 )δ: 157.7, 149.0, 146.3, 143.6, 134.1, 133.3, 132.7, 129.0, 127.5, 127.0, 126.7, 126.0, 123.4, 122.0, 120.3, 66.6, 56.8, 53.8, 39.5, 25.1. HRMS (ESI + ): m / z calcd for 389.18518, found 390.19220 ([M+H] + ).

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Abstract

The invention discloses a phthalizine [1,2,b] quinazoline-8-ketone compound, which is characterized in that the structural general formula of the compound is shown in the description, and phthalizine [1,2,b] quinazoline-8-ketone derivatives disclosed by the invention have very strong inhibiting effect on common cancer cells such as human gastric carcinoma cells (MGC-803), human lung cancer cells (NCI-H460), human hepatoma cells (HepG-2), cervical carcinoma cells (Hela), human bladder cancer cells (T-24) and the like, can induce apoptosis of the cancer cells, hence the phthalizine [1,2,b] quinazoline-8-ketone and derivatives thereof have potential application in preparation of antitumor drugs.

Description

technical field [0001] The invention relates to organic chemistry, in particular to a phthalazino[1,2,b]quinazolin-8-one compound, a preparation method thereof and an application in antitumor drugs. Background technique [0002] Tumor is a major disease that threatens human health and life safety. The research and development of anti-tumor drugs has always been a hot spot for chemists and pharmacologists. Finding anti-tumor drugs that are more efficient, more selective, and less toxic and side effects is an anti-tumor drug. The main direction of drug research and development. [0003] We found that phthalazino[1,2,b]quinazolin-8-ones with ω-dimethylamine-substituted aminoethyl and aminopropyl groups and ω-hexahydropyridylaminopropyl groups at the 5-position The compound is a new framework with good compounds both in vivo and in vitro, and the synthesis and application of these compounds have not been reported in the literature. Contents of the invention [0004] The obje...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61K31/519A61K31/5377A61P35/00
CPCC07D487/04
Inventor 苏桂发潘成学钱刚袁静梅张国海何国学
Owner GUANGXI NORMAL UNIV
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