Pyrimidotriazole compounds containing hydrazone bonds as well as preparation method and application of pyrimidotriazole compounds
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A triazole and compound technology, applied in the field of medicinal chemistry, can solve the problem of less research on anti-tumor activity
Inactive Publication Date: 2017-02-22
ZHENGZHOU UNIV
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[0004] However, there are few reports on the combination of hydrazone and pyrimidotriazole for antitumor activity research. Therefore, it is of great value to st
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Embodiment 1
[0075] Example 1 compound 2b, R 1 = Preparation of Propargyl
[0076] Add barbituric acid (3g, 1eq) and triethylamine (2.9ml, 1eq) to 30ml of methanol, heat to reflux, slowly add propyne bromide (1.8ml, 1eq) dropwise, and continue to reflux for 1 hour after the addition , cooled, and filtered with suction to obtain 3.7g of pink solid with a yield of 97%.
Embodiment 2
[0077] Example 2 Compound 3b, R 1 = Preparation of Propargyl
[0078] 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, Washed with water to obtain dark red powder 77.5%.
Embodiment 3
[0079] Example 3 Compound 4b, R 1 = Preparation of Propargyl
[0080] At room temperature, compound 3b (12.4g, 1eq) was dissolved in toluene, and added to 50ml of phosphorus oxychloride in batches, 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, then wash with saturated sodium carbonate solution, and dry the organic phase to obtain 13 g of brown crude compound 4 with a yield of 90.2%.
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Abstract
The invention belongs to the field of medicinal chemistry and discloses pyrimidotriazole compounds containing hydrazine bonds as well as a preparation method and an application of the pyrimidotriazole compounds in drug preparation. The general formula I of the compounds is shown in the specification. The compounds have remarkable inhibition and killing functions on multiple tumor cells such as MGC-803, MCF-7 and EC-109, can serve as candidate or lead compounds for further development and are applied to preparation of an anti-tumor drug.
Description
technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of novel pyrimidotriazole compounds containing hydrazone bonds, their preparation method and their application as a class of new antitumor drug lead compounds. Background technique [0002] Purine analogs are widely used in the treatment of various diseases, especially cancer. For example, 6-mercaptopurine and 6-mercaptoguanine, which are clinically used as antineoplastic drugs, have good effects on acute leukemia, and also have certain effects on chronic myeloid leukemia, malignant lymphoma and multiple myeloma. As an analogue of purine structure, pyrimidotriazole also has a variety of biological activities, such as anti-inflammatory, antibacterial, antiviral, anti-HIV, anticoagulant, and antitumor biological activities. Recently, the lead compounds of antitumor drugs based on pyrimidotriazole as the backbone have attracted more and more attention. The synthesis and a...
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