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Quinazoline ketone anticoccidial medicament

A kind of quinazolinone, halogenated quinazolinone ring technology, applied in the field of drug synthesis, can solve the problems of high compound price, affecting product use and the like

Inactive Publication Date: 2008-09-03
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] It can be seen from the above reaction formula that the synthesis of this compound requires a total of 18 steps, and the long synthetic route causes the price of the compound to be high, which affects the use of the product.

Method used

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  • Quinazoline ketone anticoccidial medicament
  • Quinazoline ketone anticoccidial medicament
  • Quinazoline ketone anticoccidial medicament

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: Synthesis of 6-bromo-3-[4-(2-methoxyphenyl)-2-butanonyl]-4-(3H)-quinazolone

[0026] Add 2.00g (0.0089mol) 6-bromo-quinazolin-4-one, 1.0gKI, 0.43g (0.0178mol) NaH, 30ml DMSO in a 50ml three-necked flask, heat up to 75°C, and add dropwise 4.57g ( 0.0178mol) the mixed solution of 1-bromo-4-(2-methoxyphenyl)butan-2-one and 5ml DMSO, stirred and reacted for 1 hour, cooled and added 100ml water, extracted with ethyl acetate, and the organic phase was washed with Dry over sodium sulfate and remove the solvent. The resulting solid is recrystallized from absolute ethanol to obtain a white flocculent solid, which is dried to obtain 1.86 g, with a yield of 52.1%. 1 HNMR (CDCl 3 , 400MHz) d: 8.41(d, J=2.4Hz, 1H), 7.85(m, 1H), 7.74(s, 1H), 7.60(q, J 1 =8.0Hz,J 2 =8.4Hz, 1H), 7.21(dd, J 1 =8.0Hz,J 2 =8.0Hz 1H), 7.15(dd, J 1 =7.2Hz,J 2 =7.6Hz, 1H), 6.90(q, J 1 =7.6Hz,J 2 =8.4Hz, 2H), 4.73(s, 2H), 3.84(s, 3H), 2.98(d, J=6.4Hz, 2H), 2.92(t, J 1 =6.4Hz,J 2 =7.2H...

Embodiment 2

[0027] Example 2: Synthesis of 8-bromo-6-chloro-3-[4-(2-methoxyphenyl)-2-butanonyl]-4-(3H)-quinazolone

[0028] Add 2.31g (0.0089mol) 8-bromo-6-chloro-quinazolin-4-one, 1.0gKI, 0.86g (0.0178mol) NaH, 30ml DMSO into a 50ml three-necked flask, heat up to 75°C, and drop under stirring Add a mixture of 4.57g (0.0178mol) 1-bromo-4-(2-methoxyphenyl)butan-2-one and 5ml DMSO, stir the reaction for 1 hour, add 100ml water under cooling, and extract with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed. The resulting solid was recrystallized from absolute ethanol to obtain a white flocculent solid, which was dried to obtain 2.21 g, with a yield of 57.1%. 1 HNMR (CDCl 3 , 400MHz) δ: 8.15 (d, J 1 =2.0Hz, 1H), 7.95(d, J 1 =2.4Hz, 1H), 7.78(s, 1H), 7.15(dd, J 1 =8.0Hz,J 2 =7.6Hz, 1H), 7.06(d, J 1 =7.2Hz), 6.82(q,J 1 =7.6Hz,J 2 =8.0Hz, 2H), 4.60(s, 2H), 3.78(s, 3H), 2.91(t, J 1 =7.2Hz,J 2 =6.8Hz, 2H), 2.83(q, J1 =6.8Hz,J 2 =7.2H...

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Abstract

A series quinazoline ketones compounds with halogeno- quinazolone ring, propa-2-ketone group or buta-2ketone group or guaiacyl are synthesized by condensing halogeno- quinazoline-4-ketone and bromium-3-(2-methoxylbenz)propa-2-ketone or 1-bromium-4-(2-methoxyl benz )buta-2-ketone at 70-80 degree C for 1-7h under existing condition of sodium hydride, potassium carbonate, potassium tert butoxide, sodium methoxide or sodium ethylate using DMSO or DMF as a dissolvent. Proved by bioactivity experiment, the compounds have anticoccidial activity.

Description

field of invention [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a class of quinazolinone anticoccidial drugs. Background technique [0002] Changshan is a kind of traditional Chinese medicine for treating malaria. It is also reported in the literature that it has anti-coccidiosis effect (China Veterinary Science and Technology, 2000, NO 05, 37; Poultry Raising and Poultry Disease Control, 2006, NO 09, 10), but it also has Side effects such as diarrhea and vomiting (J. Med. Chem. 1970, Vol 13, 867). In 1949, Chinese chemist Zhao Chenggu and others confirmed that its active ingredients were febrifugine (1) and isofebrifugine (2) (J.Am.Chem.Soc.1948, 70(5): 1765 ), they are all quinazolinone alkaloids from the chemical structure, molecular formula: C 16 h 19 N 3 o 3 . [0003] [0004] The chemical name of halofuginone (3) currently used as an anticoccidial drug in the aquaculture industry is: 7-bromo-6-chloro-3-[3...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/91A61K31/517A61P33/02
Inventor 王玉良游军辉叶长文朱基美刘建新
Owner SICHUAN UNIV
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