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6-(2-amino-1H-benzo[d]imidazole-6-yl)quinazoline-4(3H)-one compound

A ketone compound, quinazoline technology, applied in the pharmaceutical field, to achieve the effect of high yield

Active Publication Date: 2020-01-07
THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no research and report on the synthesis and druggability of 6-(2-amino-1H-benzo[d]imidazol-6-yl)quinazolin-4(3H)-ones

Method used

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  • 6-(2-amino-1H-benzo[d]imidazole-6-yl)quinazoline-4(3H)-one compound
  • 6-(2-amino-1H-benzo[d]imidazole-6-yl)quinazoline-4(3H)-one compound
  • 6-(2-amino-1H-benzo[d]imidazole-6-yl)quinazoline-4(3H)-one compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] N-(6-(3-(2-morpholinoethyl)-4-oxo-3,4-dihydroquinazolin-6-yl)-1H-benzo[d]imidazol-2-yl) The synthetic (compound number is a) of propionamide comprises the following steps:

[0044] (1) Synthesis of 6-bromo-3-(2-morpholinoethyl)quinazolin-4(3H)-one:

[0045] 2-Amino-4-bromobenzoic acid (10.8g, 50mmol) was dissolved in 150mL of absolute ethanol, triethyl orthoformate (11.1g, 75mmol) was added, and N-(2-aminoethyl)morpholine was added (9.75g, 75mmol), iodine (0.127g, 0.5mmol), heated to reflux in an argon environment and protected from light, and reacted for 5 hours. After the reaction was cooled to room temperature, and concentrated under reduced pressure to remove ethanol, 200 mL of ethyl acetate was added, and after dissolution, it was washed once with 1N sodium hydroxide solution, and the aqueous layer was extracted three times with ethyl acetate. After the solution and saturated brine were washed three times each, the organic layer was collected and dried overnight ...

Embodiment 2

[0057] 1,1-diethyl-3-(6-(3-(2-morpholinoethyl)-4-oxo-3,4-dihydroquinazolin-6-yl)-1H-benzo[ d] the synthesis of imidazol-2-yl) urea (the compound number is b), comprising the following steps:

[0058] (1) Synthesis of 6-bromo-3-(2-morpholinoethyl)quinazolin-4(3H)-one:

[0059] As in step (1) in Example 1.

[0060] (2) Synthesis of 2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline:

[0061] As in step (2) in Example 1.

[0062] (3) Synthesis of 6-(4-amino 3-nitrophenyl)-3-(2-morpholine ethyl)quinazolin-4(3H)-one:

[0063] As in step (3) in Example 1, a yellow solid was obtained, 4.81 g, with a yield of 81.1%.

[0064] (4) Synthesis of 6-(3,4-diaminophenyl)-3-(2-morpholine ethyl)quinazolin-4(3H)-one:

[0065] As in step (4) in Example 1, a yellow solid was obtained, 3.37 g, with a yield of 92.3%.

[0066] (5) Synthesis of 6-(2-amino-1H-benzo[d]imidazol-6-yl)-3-(2-morpholine ethyl)quinazolin-4(3H)-one:

[0067] As in step (5) in Example 1, a light yellow solid ...

Embodiment 3

[0071] N-(6-(3-(2-morpholinoethyl)-4-oxo-3,4-dihydroquinazolin-6-yl)-1H-benzo[d]imidazol-2-yl) The synthetic (compound numbering is c) of cyclopropyl formamide comprises the following steps:

[0072] (1) Synthesis of 6-bromo-3-(2-morpholinoethyl)quinazolin-4(3H)-one:

[0073] As in step (1) in Example 1.

[0074] (2) Synthesis of 2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline:

[0075] As in step (2) in Example 1.

[0076] (3) Synthesis of 6-(4-amino 3-nitrophenyl)-3-(2-morpholine ethyl)quinazolin-4(3H)-one:

[0077] As in step (3) in Example 1, a yellow solid was obtained, 4.81 g, with a yield of 81.1%.

[0078] (4) Synthesis of 6-(3,4-diaminophenyl)-3-(2-morpholine ethyl)quinazolin-4(3H)-one:

[0079] As in step (4) in Example 1, a yellow solid was obtained, 3.37 g, with a yield of 92.3%.

[0080] (5) Synthesis of 6-(2-amino-1H-benzo[d]imidazol-6-yl)-3-(2-morpholine ethyl)quinazolin-4(3H)-one:

[0081] As in step (5) in Example 1, a light yellow solid ...

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Abstract

The invention discloses a 6-(2-amino-1H-benzo[d]imidazole-6-yl)quinazoline-4(3H)-one compound,a preparation method and applications thereof, wherein the structural general formula (I) of the compoundis defined in the specification, R1 is hydrogen atom, morpholinomethyl, piperazinomethyl or substituted piperazinomethyl, R2 is hydrogen atom, butyl, morpholine substituted alkyl, benzyl, substitutedbenzyl, tryptamine, substituted tryptamine or N,N-dimethylamino, R3 is-C(O)R4 or-SO2R5, R4 and R5 are alkyl (C3-C6 alkyl), cycloalkyl (3-6-membered ring), alkoxy or alkyl substituted amino, and n is 1, 2, 3 or 4. The compound of the invention has inhibition activity on breast cancer, prostate cancer and human neuroblastoma.

Description

technical field [0001] The invention belongs to the field of pharmacy, and specifically relates to a quinazolin-4(3H)-one compound substituted by a 6-(2-amino-1H-benzo[d]imidazole aromatic group, and also relates to the 6- (2-Amino-1H-benzo[d]imidazol-6-yl)quinazolin-4(3H)-one compound preparation method, and the 6-(2-amino-1H-benzo[d] Application of imidazol-6-yl)quinazolin-4(3H)-one compounds in the preparation of antitumor drugs. Background technique [0002] The Aurora kinase family is an important class of serine / threonine kinases in the cell mitosis regulatory network, including three family members of Aurora kinase A, B, and C. In cell mitosis, Aurora kinases are involved in multiple processes such as centrosome maturation and separation, chromosome condensation, spindle assembly and maintenance, chromosome segregation, and cytokinesis. Abnormal expression and activation appear in rectal cancer, prostate cancer, lung cancer, glioma and leukemia. At present, it is b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04C07D403/14A61P35/00
CPCC07D403/04C07D403/14A61P35/00
Inventor 范艳华樊成成许永男钟婷阳华容
Owner THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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