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Compound with anti-tuberculosis activity and its preparation method and application
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A compound, the technology of tuberculosis, applied in the field of biomedicine, can solve the problems of shortening the treatment cycle, difficulty in curing tuberculosis, and no antagonism, and achieves high drug value and good anti-susceptible tuberculosis activity.
Active Publication Date: 2015-11-25
FUDAN UNIV
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Problems solved by technology
[0004] At present, due to the long treatment time and the side effects of chemotherapy drugs, it is difficult to cure tuberculosis. The emergence of drug-resistant strains and co-infection with AIDS further increase the difficulty of tuberculosis treatment
Therefore, the current situation of tuberculosis treatment makes it necessary to develop new anti-tuberculosis drugs. The main purposes are: first, to shorten the treatment cycle; second, to resistdrug-resistant strains; third, to target dormant Mycobacterium tuberculosis; no antagonistic effect
Method used
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Embodiment 1
[0031] Embodiment 1: Preparation of 1-propenyl-3-(4-ethylphenyl)thiourea
[0032]
[0033] 4-Ethylaniline (5.0 g, 41.3 mmol) was dissolved in tetrahydrofuran and added to saturated sodiumbicarbonate solution. Then Zhudichloride dissolved in tetrahydrofuran was added dropwise and stirred at room temperature for 2 hours. TLC chromatography showed that no starting components appeared. Add allylamine to the above mixed solution under the condition of 0-10°C to react. When the TLC chromatography showed that the reaction was complete, it was extracted three times with methyl tert-butyl ether, and the organic phase was dried with anhydroussodiumsulfate, filtered and dehydrated to obtain a crude product. The crude product was recrystallized with methyl tert-butyl ether to obtain the desired pure target product. The yield of the target product was 83.5%. It was a white solid with a melting point of 72.15-72.60°C. 1 HNMR(DMSO): 1.17(t, J=7.8Hz, 3H), 2.49-2.58(m, 2H), 4.12(s, 2H...
Embodiment 2
[0034] Embodiment 2: Preparation of 1-propenyl-3-[4-(isopropyl)phenyl]thiourea
[0035]
[0036] 4-Ethylaniline (5.0g, 41.3mmol) was replaced with 4-(isopropyl)aniline (5.0g, 37.0mmol), and the rest of the required reagents and preparation methods were the same as in Example 1 to obtain the target product. The yield of the target product was 81.7%, a white solid with a melting point of 72.4-72.8°C. 1 HNMR (CDCl 3 ): 1.21(d, J=6.9Hz, 6H), 2.88(t, J=6.9Hz, 1H), 4.24-4.28(m, 2H), 5.09-5.15(m, 2H), 5.77-5.90(m, 1H), 5.95(br, 1H), 7.09(d, J=8.4Hz, 2H), 7.27(d, J=8.4Hz, 2H), 7.58(br, 1H).
Embodiment 3
[0037] Embodiment 3: Preparation of 1-propenyl-3-(4-butylphenyl)thiourea
[0038]
[0039] 4-Ethylaniline (5.0g, 41.3mmol) was replaced by 4-butylaniline (5.0g, 33.6mmol), and the remaining reagents and preparation methods were the same as in Example 1 to obtain the target product. The target product yield was 82.8%, white solid. The melting point is 56.85-57.6°C. 1 HNMR(DMSO): 0.89(t, J=7.2Hz, 3H), 1.26-1.34(m, 2H), 1.51-1.56(m, 2H), 2.49-2.56(m, 2H), 4.12(s, 2H) , 5.07-5.20(m, 2H), 5.83-5.93(m, 1H), 7.14(d, J=8.4Hz, 2H), 7.27(d, J=8.4Hz, 2H), 7.73(br, 1H), 9.45(br, 1H).
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Abstract
The invention belongs to the technical field of biological medicine and relates to a compound with antituberculous activity, and in particular relates to a thiourea type compound for inhibiting growth of mycobacteriumtuberculosis in a formula (I) structure as well as a preparation method and application of the compound. An extracorporal mycobacteriumtuberculosis inhibition test proves that the compound prepared by the method disclosed by the invention not only has remarkably good anti-sensitive mycobacteriumtuberculosis activity (MIC 0.09-1.5 mug / ml), but also has quite remarkable inhibition effect on drug resisting mycobacterium tuberculosis (MIC 0.37-1.5 mug / ml). The compound shows extremely high medicine preparation value and can be further used for preparing medicaments for inhibiting mycobacterium tuberculosis and treating tuberculosis caused by the mycobacterium tuberculosis.
Description
technical field [0001] The invention belongs to the technical field of biomedicine and relates to compounds with anti-tuberculosis activity. It specifically relates to a thiourea compound for inhibiting the growth of Mycobacterium tuberculosis and its preparation method and application. Background technique [0002] The prior art discloses that Mycobacterium tuberculosis is a pathogenic microorganism that causes tuberculosis, a major infectious disease, and tuberculosis is one of the main killers that endanger human health. According to the report of the World Health Organization, nearly one-third of the world's population has been infected with Mycobacterium tuberculosis, and tuberculosis can also lead to poverty due to illness and return to poverty due to illness. In addition, tuberculosis is a zoonotic infectious disease. Therefore, TB is not only a public health problem, but also a socioeconomic problem. The World Health Organization declared a global tuberculosis eme...
Claims
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Application Information
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