Pyrimidine and triazole containing LSD1 inhibitor and preparation method and application thereof
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A technology of triazole and inhibitor, applied in the field of medicinal chemistry
Active Publication Date: 2017-02-22
ZHENGZHOU UNIV
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However, there are few reports on the combination of new compounds combining pyrimidine and triazole s
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Embodiment 1
[0080] Example 1 compound 2b, R 1 = Preparation of Propyl
[0081] Barbituric acid (3g, 1eq) and triethylamine (2.9ml, 1eq) were added to 30ml of methanol, under reflux, bromopropane (1.8ml, 1eq) was slowly added dropwise, and reflux was continued for 1 hour after the addition , cooled, and suction filtered to obtain 3.7g of pink solid compound 2b with a yield of 97%.
Embodiment 2
[0082] Example 2 Compound 3b, R 1 = Preparation of Propyl
[0083] Under ice bath, carefully dissolve 3ml of fuming nitric acid in 6ml of acetic acid, then add 2.9g of compound 2b in batches, after the addition, continue to stir for 2 hours, then add the reaction solution to 18ml of ice water, filter with suction, After washing with water, a dark red powder compound 3b was obtained with a yield of 77.5%.
Embodiment 3
[0084] Example 3 Compound 4b, R 1 = Preparation of Propyl
[0085] Compound 3b (12.4g, 1eq) was dissolved in 50ml of phosphorus oxychloride, and DMA (12ml, 1.8eq) was slowly added dropwise, then heated to reflux, and reacted for 5 hours. Cool to room temperature, hydrolyze, then extract with EA, wash with water, and then wash with saturated sodium carbonate solution, and dry the organic phase to obtain 13 g of crude brown compound 4b with a yield of 90.2%.
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Abstract
The invention belongs to the field of medicinal chemistry, and discloses a pyrimidine and triazole containing compound and a preparation method and application thereof in preparation of anti-cancer medicine with lysine specific demethylase 1 (LSD1) being a target. The general formula of the compound is shown in the drawing I. In-vitro LSD1 enzyme inhibition activity experiments prove that by inhibiting LSD1 activity, the compound has obvious inhibiting and killing effects on kinds of cancer cells and can be applied to preparation of the anti-cancer medicine as a further developed lead compound.
Description
technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to pyrimidotriazole compounds, their preparation methods and their use in antitumor drugs targeting histone lysine specific demethylase (hereinafter referred to as LSD1) application. Background technique [0002] Tumor is a disease that seriously endangers human health and is difficult to overcome. There are many anti-tumor drugs that have been marketed, but there are still some problems in these drugs, such as high toxicity, weak targeting, and easy drug resistance. Therefore, the research and development of new anticancer drugs is particularly important. [0003] Histone covalent modification is an important epigenetic mode, including histone acetylation, methylation, phosphorylation, and ubiquitination, among which acetylation and methylation are more frequently studied for the mechanism of histone modification. histone modification. Before 2004, histone methylati...
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