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Quinazol derivative, preparation method and application thereof

A technology of quinazolinone and quinazolinone, which is applied in the field of pharmaceutical compounds and can solve problems such as large side effects

Inactive Publication Date: 2013-08-21
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, drug contraception mainly includes hormonal drugs, which will break the metabolic balance of the normal human body and have relatively large side effects.

Method used

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  • Quinazol derivative, preparation method and application thereof
  • Quinazol derivative, preparation method and application thereof
  • Quinazol derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103] The synthetic method of 3-substituted-4 (3H)-quinazolone compound (compound 1), comprises the following steps:

[0104]

[0105] Steps:

[0106] (1) Preparation of 2-ethyl 6-methylbenzoxazin-4-one (intermediate 2)

[0107] Take 0.04mol of 2-amino-6-methylbenzoic acid and 50ml of propionic anhydride, heat, stir and reflux for 3h-5h, stop the reaction, let cool to room temperature, place in the refrigerator overnight, filter and precipitate white flaky crystals to obtain the crude product. Recrystallized from absolute ethanol to obtain light yellow intermediate 2 (5.24g).

[0108] (2) Preparation of Target 3 (Compound 1)

[0109] Take intermediate 2 (1.5g, 0.005mol), equimolar 3-substituted 4-chloroaniline 0.635g, dissolve in 10mlN, a mixed solution of N dimethylformamide (DMF) and 50ml of tetrahydrofuran, add 0.5g of Catalyst dicyclohexylcarbodiimide (DCC), stirred and refluxed for 10h. After filtration, the filtrate was rotary evaporated to remove the mixed solve...

Embodiment 2-7

[0110] Embodiment 2-7 (preparation of compound 2-7)

[0111] The method is the same as in Example 1, but the 3-substitute of compound 2-8 of step (2) is different from the target object, see the following table:,

[0112]

[0113]

Embodiment 8

[0115] The synthetic method of 6-substituted-4 (3H)-quinazolone compound (compound 8), comprises the following steps:

[0116]

[0117] Steps:

[0118] (1) Preparation of 2-ethyl 6-methylbenzoxazin-4-one (intermediate 2)

[0119] Take 6.0g (0.04mol) of 2-amino-6methylbenzoic acid and 50ml of propionic anhydride, heat, stir and reflux for 3h-5h, stop the reaction, let it cool to room temperature 25°C, put it in the refrigerator overnight, filter and precipitate white flaky crystals , 5.82g crude product was obtained. Using 8ml of absolute ethanol, recrystallized to obtain 25.24g of light yellow compound.

[0120] (2) Preparation of 2-ethyl 6-methyl-4-(3H)-quinazolinone (intermediate 3)

[0121] Take compound 2 (0.043mol) and 30ml formamide and stir for 7h. Cool to room temperature 25°C, filter out tan needle crystals, wash with a small amount of water (10ml×3), and dry to obtain compound 36.10g.

[0122] (3) Preparation of 2-ethyl 6-bromomethyl-4-(3H)-quinazolinone (int...

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Abstract

The present invention discloses a quinazol derivative of a structural formula I, comprising the 3-substituted-4(3H)-quinazol derivative (compound 1-8) and the 6- substituted-4(3H)-quinazol derivative (compound 9-27). By testing each of the target compounds of the present invention in vitro inhibition of human sperm acrosin activity, the result shows that, compared with the publically reported acrosin inhibitor TLCK (N-toluene sulfonyl-L-lysyl-chloromethyl ketone), all target compounds have inhibit activity to human sperm acrosin. The quinazol derivative can be applied for preparing anti-fertility drugs and providing a new male contraceptive medicine in clinical field, and has a great application value. The present invention further provides a preparation method of the derivative I.

Description

technical field [0001] The present invention relates to medicinal compounds, in particular to quinazolinone derivatives, preparation methods and applications. In particular, it relates to 3-substituted or 6-benzyl substituted-4(3H)-quinazolone compounds and their synthesis and application. Background technique [0002] At present, the contraceptive methods commonly used in clinical practice mainly include condoms, sterilization operations, birth control rings and drug contraception. Although condoms are widely used, a large number of men are unwilling to use them because they affect sexual pleasure and easily cause a failure rate of 3.6%. Sterilization is a big worry for a couple who only have one child, and there are problems such as bleeding and pregnancy with the IUD. And drug contraception mainly contains hormonal drugs at present, and this type of drugs will break the metabolic balance in the normal human body, and the side effects are relatively large. Therefore, it...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/91C07D239/90C07D401/04C07D413/12C07D417/12C07D401/12C07D401/06C07D403/06C07D403/12C07D473/40A61K31/517A61K31/52A61P15/16
Inventor 吕加国宁微微朱驹周有骏宋云龙薛博亮盛春泉吴蕴琦郑灿辉章玲刘雪飞祁晶晶
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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