Aromatic heterocyclic pyridine derivatives and analogs and preparation method and application thereof
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A technology of aromatic heterocycles and analogues, applied in the application field of disease drugs
Active Publication Date: 2010-03-17
LIAONING LIFENG SCI & TECH DEV
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[0007] In summary, in terms of active research, the patents and documents at home and abroad have not been found in the present invention to have antibacterial activity and antibacterial activity to the aromatic heterocyclic pyrimidine derivatives and analogs of the compound structure represented by structural formula I. Invention patents and reports of fungi
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preparation example Construction
[0057] ②Preparation of aromatic ring fused pyrimidinone ring: use o-amino aromatic ring as intermediate to provide cyclization substrate, use carbonyl-substituted ester analog as cyclization agent, and use one of the following reagents (ethanol, tetrahydrofuran, 1,4 -dioxane, N, N-dimethylformamide, toluene, etc.) as solvent or solvent-free, the reaction temperature is at room temperature to 180 ° C, using one or more of the following catalysts: p-toluenesulfonate Acid, Lewis acid, sulfuric acid, molecular sieve, alumina, silica gel, dehydrating agent, etc. These catalysts can catalyze the formation of C-C bonds, C-O bonds, C-S bonds, and C-N bonds, resulting in cyclization reactions to form pyrimidine rings to obtain aromatic ring fused pyrimidinones Ring analogs, the reaction formula is as follows:
[0058]
[0059] ③Preparation of heterocyclic fused pyrimidinone cyclization analogues: use o-amino heterocyclic or aromatic cyclic amide derivatives as intermediates to provi...
Embodiment 1
[0089] Preparation of Example 1
[0090] In a 100ml eggplant-shaped bottle, sequentially add 0.964g of 5-methyl-4-(4-(trifluoromethyl)phenyl)-4-hydropyrazol-3-amine, 0.55g of sodium ethoxide, and 20ml of ethanol, and reflux After reacting for 10 hours, the solid target product was obtained by filtration. IR (KBr, cm -1 )3446, 2986, 2933, 1701, 1617, 1595, 1557, 1468, 1326, 1261, 1191, 1164, 1108, 1070, 1009; 1 H NMR (DMSO-d 6 )δ8.50(s, 1H), 8.02(d, J=8.1Hz, 2H), 7.72(d, J=8.4Hz, 2H), 4.18(q, J=6.9Hz, 2H), 2.50(m, 3H), 1.27 (t, J = 7.2 Hz, 3H).
Embodiment 2
[0091] Preparation of Example 2
[0092] In a 25ml eggplant-shaped bottle, add 723mg of 5-methyl-4-(4-(trifluoromethyl)phenyl)-4-hydropyrazol-3-amine, 882mg of dicarbonyl compound, and react at 100°C for 2 hours. The solid was filtered to obtain the desired white product. IR (KBr, cm -1 )3434, 3055, 2774, 1691, 1632, 1585, 1571, 1521, 1494, 1448, 1326, 1172, 1129, 1065;1 H NMR (DMSO-d 6 ) δ 12.30 (s, 1H), 7.93 (br, 4H), 7.56 (s, 1H), 7.53 (br, 2H), 6.10 (s, 1H), 2.19 (s, 3H).
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Abstract
The invention aims at providing chemical synthesis and preparation of an aromatic heterocyclic pyridine and the analogs thereof to obtain derivatives and analogs of a plurality of series of aromatic heterocyclic pyridine and medicinal salts or salts having the following formulas or prodrugs, and the preparation, a pharmacologically activity experimental method and pharmacologically activity thereof are provided. The definitions of dotted line, ring A, ring B, X1, X2, X3, X4, R1, R2 and R3 in formula I are shown in the description. The invention provides the aromatic heterocyclic pyridine derivatives and analogue with antibacterial and antifungal activities, also provides the application thereof as antibacterial and antifungal drugs and the application thereof in concomitant use with other known antibacterial and antifungal drugs and with drugs for curing bacteria infection coupled with various complicating diseases such as inflammation, virus, immune system diseases and the like, and also provides the preparation method of the aromatic heterocyclic pyridine analogs.
Description
field of invention [0001] The present invention relates to the discovery of aromatic heterocyclic pyrimidine derivatives and analogs as antibacterial and antifungal activities, medicinal chemistry research and preparation methods. The present invention also relates to the application of the compounds as antibacterial, antifungal and other disease drugs. Background technique [0002] Since Alexander Fleming discovered penicillin in 1929, the clinical use of a large number of antibacterial drugs has shown that all effective antibacterial drugs may have drug-resistant strains, and many pathogenic bacteria will also show resistance to multiple antibacterial drugs Resistance, that is, "multi-drug resistance", such as methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant enterococcus (VRE), etc., which are called "super bacteria". The number of people infected with "super bacteria" is also increasing, and its spread has constituted a serious threat to human hea...
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