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A technology of thiazolone and group, applied in the field of pharmaceutical compounds
Active Publication Date: 2017-07-28
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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[0003] The synthesis of {4-oxo-3-(substituted)phenyl-2-[(substituted)phenylimino]thiazolidin-5-enylidene}(substituted)phenyl compounds and their Sap2 inhibitory activity have not been seen yet and related reports of antifungal activity in vivo
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Embodiment 1
[0098] Example 1: Preparation of 1,3-diphenylthiourea (II, R 1 =H) Preparation
[0099] Weigh aniline (2.33g, 25mmol, 2equiv), carbon disulfide (1.24g, 16.25mmol, 2equiv), triethanolamine (2.5mL) and sulfurpowder (100mg) in 50mL of water, stir and reflux for 6h. The reaction solution was cooled to room temperature, and a white precipitate precipitated out. Filtered and washed with cold water to obtain 1.46 g of white solid, yield: 51%. 1 H-NMR (300MHz, DMSO-d 6 )δ:9.78(s,2H,NH),7.47(m,4H,Ar-H),7.32(m,4H,Ar-H),7.11(m,2H,Ar-H).ESI-MS(m / z):229.28[M+1].
Embodiment 2
[0100] Example 2: 3-phenyl-2-(phenylimino)thiazolidin-4-one (Ⅲ, R 1 =H) Preparation
[0101] Weigh 1,3-diphenylthiourea (1.14g, 4.0mmol, 1equiv), anhydroussodium acetate (1.64g, 20.0mmol, 5equiv), 0.85mL ethyl chloroacetate (0.98g, 8.0mmol, 2equiv) In 20 mL of absolute ethanol, the mixture was stirred at 60° C. for 6 h. The reaction solution was cooled to room temperature, and a precipitate appeared. The precipitate was filtered, washed with ethanol, and recrystallized with ethyl acetate to obtain 0.68 g of an orange solid, yield: 64%, which was directly used in the next reaction without further purification. 1 H-NMR (300MHz, DMSO-d 6 )δ:7.47-7.59(m,2H),7.37-7.46(m,3H),7.25-7.36(m,2H),7.08(t,1H,J=7.8Hz),6.81-6.92(m,2H) ,4.15(s,2H).ESI-MS(m / z):269.35[M+1].
Embodiment 3
[0102] Example 3: Ethyl 2-(2-{[4-oxo-3-phenyl-2-(phenylimino)thiazolidin-5-enylidene]methyl}phenoxy)acetate (IV, R 1 =H) Preparation
[0103] Weigh 3-phenyl-2-(phenylimino)thiazolidin-4-one (0.3g, 1.12mmol, 1equiv), ethyl 2-formylphenoxy acetate (0.28g, 1.35mmol, 1.2equiv) , piperidine (0.095g, 1.12mmol, 1equiv) in 5mL of absolute ethanol, the mixture was stirred at 60°C for 8h. Purification by flash preparative chromatography (PE-EtOAc, 5:1) gave 0.48 g of light yellow solid, yield: 95%. 1 H-NMR (300MHz, DMSO-d 6 )δ:8.07(s,1H),7.44-7.62(m,5H),7.30-7.43(m,4H),7.02-7.22(m,3H),6.90-7.01(m,2H),4.94(s, 2H), 4.16(dd, 2H, J=7.06, 14.02Hz), 1.20(t, 3H, J=7.31Hz). ESI-MS (m / z): 459.40[M+1].
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Abstract
The invention relates to a substituted thiazole ketones secretory aspartic protease inhibitor and a preparation method thereof, and particularly provides a novel thiazole ketones compound. The general structural formula of the novel thiazole ketones compound is shown as follows. The thiazole ketones compound is high in Sap2 enzyme inhibiting activity and nematode and mouse in-vivo antifungal activity, and has good antifungalmedicine combination effect on fluconazoleresistant bacteria, thereby being capable of being used for preparing medicine for preventing fungal infection or being combined with existing antifungalmedicine. A new approach is created for deeply studying and developing novel antifungal medicine.
Description
technical field [0001] The present invention relates to the technical field of pharmaceutical compounds, in particular to a novel substituted thiazolone secretory aspartic acidprotease inhibitor——{4-oxo-3-(substituted)phenyl-2-[(substituted ) phenylimino] thiazolidine-5-enylene} (substituted) phenyl compounds and their preparation methods and applications. Background technique [0002] In recent years, with the widespread application of antibiotics, tumor radiotherapy and chemotherapy, and organ transplantation, as well as the sharp increase in the prevalence of AIDS, a large number of patients with deep fungal infections such as Candida albicans, Aspergillus fumigatus, and Cryptococcus neoformans increase in magnitude. The increase of drug-resistant Candida has become a major challenge for clinical antifungal treatment, and the existing antifungal drugs have certain limitations. At present, antifungal drugs mainly target four target enzymes: lanosterol 14α-demethylase (a...
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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/54A61K31/426A61P31/10
CPCC07D277/54
Inventor 盛春泉张万年刘杨董国强姚建忠缪震元刘娜
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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