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6-(2-Amino-1h-benzo[d]imidazol-6-yl)quinazolin-4(3h)-ones

A technology of ketone compounds and quinazoline, which is applied in the field of pharmaceuticals to achieve the effect of high yield

Active Publication Date: 2022-06-21
THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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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]imidazol-6-yl)quinazolin-4(3h)-ones
  • 6-(2-Amino-1h-benzo[d]imidazol-6-yl)quinazolin-4(3h)-ones
  • 6-(2-Amino-1h-benzo[d]imidazol-6-yl)quinazolin-4(3h)-ones

Examples

Experimental program
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Effect test

Embodiment 1

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

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

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

Embodiment 2

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

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

[0059] Step (1) as in Example 1.

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

[0061] Step (2) as in Example 1.

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

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

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

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

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

[0067] According to step (5) in Example 1, a pale yellow solid was obtained, 2.25 g, and the yie...

Embodiment 3

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

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

[0073] Step (1) as in Example 1.

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

[0075] Step (2) as in Example 1.

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

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

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

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

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

[0081] According to step (5) in Example 1, a pale yellow solid was obtained, 2.25 g, and...

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Abstract

The invention discloses a 6-(2-amino-1H-benzo[d]imidazol-6-yl)quinazolin-4(3H)-ketone compound, its preparation method and application, its general structural formula ( Ⅰ) as follows, wherein: R 1 is a hydrogen atom, morpholinomethyl, piperazinemethyl or substituted piperazinemethyl; R 2 is a hydrogen atom, butyl, morpholine substituted alkyl, benzyl, substituted benzyl, tryptamine, substituted tryptamine or N,N-dimethylamino; R 3 for-C(O)R 4 or‑SO 2 R 5 , where R 4 , R 5 It is an alkyl group (3-6 carbon atoms), a cycloalkyl group (3-6 membered ring), an alkoxy group or an alkyl-substituted amino group; n is 1, 2, 3 or 4. The invention has the activity of inhibiting breast cancer, prostate cancer and human neuroblastoma.

Description

technical field [0001] The invention belongs to the field of pharmacy, in particular to a 6-(2-amino-1H-benzo[d]imidazole aromatic group-substituted quinazoline-4(3H)-one compound, and also 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 cellular mitotic 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 pyknosis, spindle assembly and maintenance, chromosome segregation, and cytokinesis. Aurora kinases A and B are involved in many tumor tissues such as breast cancer, Abnormal expression and activation are found in rectal cancer, prostate ...

Claims

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Application Information

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Patent Type & Authority Patents(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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