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S-DABO compound, synthesizing method and usage

A compound and alkyl technology, applied in organic chemistry, antiviral agents, etc., can solve the problems of unfavorable binding, large electron cloud density, and large rigidity of naphthalene ring, and achieve the effect of strong inhibition, low cytotoxicity, and convenient synthesis.

Inactive Publication Date: 2009-07-29
YUNNAN UNIV +1
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  • Abstract
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Problems solved by technology

The structure-activity relationship study found that although the 6-naphthalene ring of this type of compound has a large electron cloud density, it is beneficial to the π-π stacking effect of the small molecule ligand and the amino acid residue in the RT enzyme binding cavity, but at the same time the naphthalene ring is rigid. Larger, unfavorable for binding to RT enzymes

Method used

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  • S-DABO compound, synthesizing method and usage
  • S-DABO compound, synthesizing method and usage
  • S-DABO compound, synthesizing method and usage

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Embodiment Construction

[0023] The following examples will help to understand the present invention, but cannot limit the scope of the present invention.

[0024] Synthesis of 5-alkyl-6-phenyl-2-(substituted arylcarbonylmethylthio)uracils. General operation of the reaction: 5-alkyl-6-phenyl-2-thiouracil (3mmol) and K 2 CO 3 Place in a flask, add 15ml of dry DMF, stir at room temperature for half an hour, add α-bromoketone R 1 COCH 2 Br (3.6mmol), continue to stir the reaction at a suitable temperature, TLC traces the disappearance of the raw material point to stop the reaction, pour the reaction solution into 30mL ice water, stir and precipitate the precipitate, filter, wash the precipitate with water, suction filter and dry to obtain the crude product, further Various white powders can be obtained by column chromatography purification. Recrystallization with an appropriate solvent can give white crystals of 5-alkyl-6-phenyl-2-(substituted arylcarbonylmethylthio)uracil.

[0025] Different 5-alky...

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Abstract

The S-DABO compound, its synthesis method and application belong to the technical field of medicine. The invention relates to a 5-alkyl-6-phenyl-2-(substituted arylcarbonylmethylthio)uracil compound, which has the following general formula: wherein: R1 is a C1-3 alkyl group; R2=C1-6 alkyl, substituted furan ring, thiophene ring, benzene ring (substituents on the aromatic ring are H, OH, C1-3 alkoxy). The product of the present invention is obtained by reacting 5-alkyl-6-phenylthiouracil with a-halogenated ketone under K2CO3 catalysis. The synthesis method is simple and easy, and the product has significant anti-HIV virus activity, low toxicity and high selectivity index, and can be used as a candidate anti-HIV drug.

Description

technical field [0001] The invention belongs to the technical field of medicines, in particular to dihydroalkoxybenzylpyrimidinedione (S-DABO) compounds as anti-HIV medicines. Background technique [0002] At present, the design of anti-HIV drugs is mainly based on the various links of the HIV virus replication cycle, and various inhibitors are designed to block the replication of the virus. According to their mechanism of action, there are mainly nucleoside reverse transcriptase inhibitors (NRTIs), non-nuclear Glycoside reverse transcriptase inhibitors (NNRTls), proteolytic enzyme inhibitors, fusion enzyme inhibitors, etc. Although these medicines have the clinical efficacy of anti-HIV infection and AIDS, there are defects such as relatively large toxic and side effects and expensive prices. In particular, HIV is a highly variable virus that is prone to drug resistance, which has become a difficult problem for all anti-HIV drugs today. At present, the more effective clini...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/56C07D409/12C07D407/12A61K31/506A61P31/18
Inventor 何严萍郑永唐李聪龙晶饶之坤张虽栓欧灵澄
Owner YUNNAN UNIV
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