2H,6H-pyrimido[2,1-b][1,3]thiazine derivative and application thereof

A technology of thiazides and derivatives, applied in the field of preparation of antibacterial drugs, can solve problems such as the crisis of effective clinical application of antibacterial drugs

Inactive Publication Date: 2015-08-19
SHIJIAZHUANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The emergence of these drug-resistant strains puts the effective clinical use of existing antibacterial drugs in crisis

Method used

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  • 2H,6H-pyrimido[2,1-b][1,3]thiazine derivative and application thereof
  • 2H,6H-pyrimido[2,1-b][1,3]thiazine derivative and application thereof
  • 2H,6H-pyrimido[2,1-b][1,3]thiazine derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Preparation of 4-{4-[2-(1-piperidinyl)ethoxy]phenyl}-5-acetyl-6-phenyl-3,4-dihydropyrimidine-2(1H)-thione

[0019] Add 0.1 mol of 4-[2-(1-piperidinyl)ethoxy]benzaldehyde, 0.1 mol of thiourea, 0.11 mol of 1-phenyl-1,3-butanedione into a 250 ml round bottom flask, Add 30 mL of acetic acid, stir, and react at 60°C for 10 h. Cool, filter with suction, and recrystallize the filter cake from absolute ethanol to obtain 30.4 g of yellow crystals, with a yield of 69.7%. ESI-MS (m / z): 436.2 (M+H) + .

Embodiment 2

[0021] Preparation of 4-{4-[2-(4-morpholinyl)ethoxy]phenyl}-5-acetyl-6-phenyl-3,4-dihydropyrimidine-2(1H)-thione

[0022] In a 250 ml round bottom flask, add 0.1 mol of 4-[2-(4-morpholinyl)ethoxy]benzaldehyde, 0.1 mol of thiourea, 0.11 mol of 1-phenyl-1,3-butanedione, Add 30 mL of acetic acid, stir, and reflux for 10 h. Cool, filter with suction, and recrystallize the filter cake from absolute ethanol to obtain 33.5 g of yellow crystals, with a yield of 76.7%. ESI-MS (m / z): 438.1 (M+H) + .

Embodiment 3

[0024] Preparation of 4-[4-(2-diethylaminoethoxy)phenyl]-5-acetyl-6-phenyl-3,4-dihydropyrimidine-2(1H)-thione

[0025] Add 0.1 mol of 4-(2-diethylaminoethoxy)benzaldehyde, 0.1 mol of thiourea, 0.11 mol of 1-phenyl-1,3-butanedione, and 30 mL of acetic acid into a 250 ml round bottom flask , stirred, and refluxed for 10 h. Cool, filter with suction, and recrystallize the filter cake from absolute ethanol to obtain 34.6 g of yellow crystals, with a yield of 81.8%. ESI-MS (m / z): 424.3 (M+H) + .

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Abstract

The invention discloses an application of a 2H,6H-pyrimido[2,1-b][1,3]thiazine derivative in antibacterial drugs, wherein the 2H,6H-pyrimido[2,1-b][1,3]thiazine derivative has the general formula (I), wherein in the formula I, R1 and R3 independently are hydrogen, methyl, halogen, hydroxyl, methoxyl, nitro, acetyl, propionyl or alkoxy, and R2 is methyl or ethyoxyl. The compound has an obvious inhibiting effect on methicillin-resistant staphylococcus aureus, escherichia coli, pseudomonas aeruginosa and various bacteria and can be used in preparation of the antibacterial drugs.

Description

technical field [0001] The invention relates to the field of chemical and pharmaceutical technology, in particular to 2H,6H-pyrimido[2,1-b][1,3]thiazine derivatives and their application in the preparation of antibacterial drugs. Background technique [0002] Since penicillin was used clinically in the 1940s, antibiotics have saved countless lives, and penicillin has thus become one of the greatest human discoveries in the 20th century, and opened up a new era of antibiotic research. Cephalosporins, quinolones, Various types of antibiotics such as macrolides and aminoglycosides. It is true that we have such a wide variety of antibacterial drugs, but with the abuse of antibiotics, the problem of bacterial drug resistance has become increasingly prominent. In fact, almost all antibiotics have been challenged by corresponding drug-resistant strains. Since New Grinea discovered penicillin-resistant Streptococcus pneumoniae in 1967, a variety of drug-resistant bacteria have bee...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04A61P31/04
CPCC07D513/04Y02A50/30
Inventor 刘斯婕张宝华何敬宇史兰香周冉岳红坤
Owner SHIJIAZHUANG UNIVERSITY
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