Novel thiazole derivatives, and preparation method and application thereof
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A technology of thiazoles and derivatives, applied in the field of medicinal chemistry, can solve the problems of many adverse reactions, unsatisfactory overall therapeutic effect, and small side effects
Inactive Publication Date: 2017-05-10
SHANDONG UNIV
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Both of these two drugs have the disadvantages of long treatment course and many adverse reactions, and the overall therapeutic effect is not ideal.
In view of the fact that there is still
Method used
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Embodiment 1
[0119] Example 1: 4-(2-((5-nitrothiazol-2-yl)amino)-2-oxoethyl)-N-phenylpiperazine-1-carboxamide (compound I-1, code XQH-3-13) preparation method
[0120] Preparation of intermediate 2-chloro-N-(5-nitrothiazol-2-yl) (1-1)
[0121] Dissolve 5-nitro2-aminothiazole (1eq) and triethylamine (1.2eq) in dichloromethane, add chloroacetyl chloride (1.2eq) dropwise at 0°C, and continue the reaction from the temperature rise after the addition After 5 h, the reaction was detected by TLC, and the reaction was stopped because there was no raw material remaining. Add 100ml of distilled water to the reaction solution, the aqueous phase was extracted three times with dichloromethane (3×100ml), the combined organic layer was washed twice with saturated sodium chloride solution (2×100ml), dried over anhydrous magnesium sulfate, and then evaporated Concentrated crude. The crude product was purified and separated by silica gel column (dichloromethane:methanol=150:1) to obtain the target compo...
Embodiment 2
[0129] Embodiment 2: N-(4-fluorophenyl)-4-(2-((5-nitrothiazol-2-yl)amino)-2-oxoethyl)piperazine-1-carboxamide (I -2, the code name is the preparation method of XQH-2-78)
[0130] The preparation method is the same as I-1, and the yield is 72%. 1 H NMR (400MHz, DMSO-d6 ): δ8.63(s,1H),8.57(s,1H),7.48-.42(m,2H),7.07(t,J=8.9Hz,2H),3.53(s,2H),3.52-3.48 (m,5H),2.67-2.62(m,4H)ppm; ESI-MS: 408.1[M-H] - .
Embodiment 3
[0131] Embodiment 3: N-(4-chlorophenyl)-4-(2-((5-nitrothiazol-2-yl)amino)-2-oxoethyl)piperazine-1-carboxamide (I -3, code name is the preparation method of XQH-2-80)
[0132] The preparation method is the same as I-1, and the productive rate is 70%, 1 H NMR (400MHz, DMSO-d 6 ): δ8.67(s,1H),8.63(s,1H),7.49(d,J=8.6Hz,2H),7.28(d,J=8.6Hz,2H),3.52(m,6H),2.64 (s,4H).ESI-MS: 423.0[M-H] - .
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Abstract
The invention relates to a structure of novel thiazole derivatives, a preparation method of the thiazole derivatives and application of the thiazole derivatives in the aspect of bioactivities. The invention also relates to pharmaceutically acceptable salts, a solvate or prodrug, and a pharmaceutical composition of the derivatives. Thiazolyl, uramido, thioureido and other active groups are introduced to obtain the series thiazole derivatives (I) and (II). The test on the activities of the compounds for some representative pathogenic bacteria and parasites shows that the series compounds have parasite resisting activities; and the CC50/IC50 of partial compounds for Toxoplasma gondii is greater than 1 or even higher, so the partial compounds have favorable inhibiting activities. Besides, the compounds XQH-2-97, XQH-3-13 and XQH-3-14 have obvious inhibitory effects on Streptococcus mutans, have obviously higher bactericidal capacities than nitazoxanide in the positive control group, and thus, are hopeful to be developed into new antibacterial compounds.
Description
technical field [0001] The invention discloses a class of novel compounds and applications thereof, and in particular relates to the structure, preparation method and application of biological activity of a class of novel thiazole derivatives. The present invention also relates to the derivative, its pharmaceutically acceptable salt, solvate or prodrug and the above-mentioned pharmaceutical composition, belonging to the technical field of medicinal chemistry. Background technique [0002] One of the most important impacts of microorganisms on humans is the prevalence of infectious diseases. About 50% of human diseases are caused by microbial infection. The history of microorganisms causing human disease is the history of human beings' continuous struggle against them. Although humans have made remarkable progress in the prevention and treatment of diseases, new or resistant microbial infections have always existed, such as the increasingly serious problem of antibiotic res...
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