Chrysin non-natural amino acid derivative as well as preparation method and application thereof
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An unnatural amino acid, chrysin technology, applied in the field of medicine, can solve the problems of poor water solubility, less intestinal absorption, easy metabolic inactivation and so on
Active Publication Date: 2018-06-01
SHIJIAZHUANG UNIVERSITY
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However, due to its poor water solubility and low intestinal a
Method used
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Embodiment 1
[0025] Preparation of compound (1)
[0026] 2.5g (10 mmol) chrysin and 3.36g (20 mmol) K 2 CO 3 Added to the reactor containing 100mL of anhydrous acetone, slowly added 2 mL of propyne bromide under vigorous stirring, and refluxed for 3h. After the reaction was completed, 50 mL of water was added, acetone was removed under reduced pressure, filtered, the filter cake was washed with water, 1M HCl solution and water in sequence, and dried to obtain a yellow solid, which was compound (I), with a yield of 95%. mp:153.7-154.5℃; 1 HNMR (CDCl 3 ,400MHz)δ:12.72(s,1H), 7.89(d, J =4Hz,2H),7.53(m,3H),6.68(s,1H),6.59(d, J =1.6Hz,1H),6.45(d, J = 2.0 Hz,1H),4.77(d, J = 2.0 Hz, 2H), 2.61(s, 1H); ESI-MS(m / z): 293[M+H] + .
[0027] 3.58g (10mmol) of (L)-4-Br-Boc-PheOMe and 0.78g (12 mmol) of NaN 3 Add 15 mL of DMSO, then add 0.19 g (1 mmol) of CuI and 0.41 g (3 mmol) of L-proline sodium, heat to 90 ° C, react for 5 h, add 50 mL of H 2 O, filter, then add 50mL CH 2 Cl 2 , layered...
Embodiment 2
[0032] Preparation of compound (2)
[0033] (D)-4-Br-Boc-PheOMe was used instead of (L)-4-Br-Boc-PheOMe, and other operations were the same as in Example 1 to obtain compound (2) with a yield of 86%.
Embodiment 3
[0035] Preparation of compound (3)
[0036] (L)-4-Br-Boc-PheOMe was replaced by (L)-3-I-Boc-PheOMe, and other operations were the same as in Example 1 to obtain compound (3) with a yield of 88%.
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Abstract
The invention discloses a chrysin non-natural amino acid derivative or pharmacologically-acceptable hydrate and salt thereof. The chrysin non-natural amino acid derivative comprises a stereoisomer ora tautomer. The chrysin non-natural amino acid derivative comprises the following preparation steps: preparing 5-hydroxy-7-propargylflavone by chrysin and propargyl bromide under the action of alkali;preparing (L/D)-N3-Boc amino acid methyl ester by (L/D)-halogenated-Boc amino acid methyl ester and NaN3 under the action of CuI/L-proline sodium; reacting the 5-hydroxy-7-propargylflavone and the (L/D)-N3-Boc amino acid methyl ester under the action of CuSO4.5H2O/sodium ascorbate, removing Boc groups and hydrolyzing to prepare the chrysin amino acid derivative. The chrysin non-natural amino acidderivative disclosed by the invention has an anti-cancer effect and can be used in preparation of an anti-cancer drug.
Description
technical field [0001] The invention relates to unnatural amino acid derivatives of chrysin and their application in pharmacy, belonging to the technical field of medicine. Background technique [0002] Chrysin (5,7-dihydroxyflavone) is a flavonoid compound that widely exists in nature and has a wide range of pharmacological activities such as antibacterial, antioxidant, antitumor, anti-inflammatory, antidiabetic, and anxiolytic. Recent studies have shown that it can also prevent cisplatin-induced organ toxicity and improve cognitive deficits and brain damage caused by intermittent hypoxia. However, due to its poor water solubility and low intestinal absorption, it is easily metabolized and inactivated in the body. In order to improve its pharmacological activity, its structural modification and transformation are of great significance for obtaining new drug candidates with high efficiency and low toxicity. [0003] Amino acid is the basic unit of protein, and as an import...
Claims
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