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Matrine amide derivative and its preparation method and use
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A technology of matrine amide and derivatives, which is applied in the field of synthesis of new derivatives of matrine amide, can solve problems such as unreported activity, and achieve the effects of improving reaction selectivity, less system side reactions, and simple reaction operation
Active Publication Date: 2020-11-24
CHANGZHOU UNIV
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[0006] In 1957, Tsuda et al. (K.Tsuda, et al., J.Org.Chem., 1958, 23(8), 1179–1183) hydrolyzed matrine in potassiumhydroxide to obtain the potassium salt of matrine; Matrine was obtained through lithiumaluminum hydride or catalytic hydrogenation reduction to obtain matrine, and then the two were subjected to methylation reactions to prepare two quaternaryammonium salts of matrine derivatives (Formula 3), but no activity was observed. to report
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Embodiment 1
[0028] Example 1: Compound 1 (20g, 80.5mmol) was dissolved in water (456mL), sodiumhydroxide (9.1g, 228mmol) was added to dissolve, and heated to reflux at 90°C for 12h. After the reaction was completed, the pH was adjusted to 5-7 with 2N hydrochloric acid solution, the solvent was concentrated, and 460 mL of ethanol was added, stirred at room temperature for 30 min, and 21 g of a white solid was obtained by suction filtration, with a yield of 99%. 1 H NMR (300MHz,D 2 O): δ1.61-1.80(m,9H),1.83-2.01(m,4H),2.16-2.20(t,1H),2.26-2.34(m,4H),2.90-2.97(q,J 1 =12.6Hz,J 2 =4.5Hz, 1H), 2.71(s, 1H), 3.23-3.31(t, J=12.9Hz, 1H), 3.37-3.41(q, 1H). 13 C NMR (75MHz, D 2 O): δ22.00, 22.26, 23.16, 27.27, 28.33, 32.52, 35.32, 39.68, 40.25, 46.18, 58.64, 58.70, 64.32. HRMS (ESI): m / z [M-H] - calcd for C 15 h 25 N 2 o 2 :265.1922; found: 265.1924.
Embodiment 2
[0029] Embodiment 2: other conditions are the same as embodiment 1, and alkali used is changed into potassiumhydroxide from sodium hydroxide, and the productive rate of gained product is 70%.
Embodiment 3
[0030] Embodiment 3: other conditions are the same as embodiment 1, the reaction solvent is changed from water to tetrahydrofuran, and the yield of the product obtained is 70%.
[0031] Step 2: Preparation of methyl 4-(decahydro-1H, 4H-pyrido[1,6]naphthyridin-1-yl)butanoate (compound 3)
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Abstract
The invention discloses matrineamide derivatives as well as a preparation method and the application thereof, and belongs to the field of pharmaceutical chemistry. A series of novel compounds synthesized by the invention has anti-tumor activity. According to the method, a series of novel matrine derivatives is finally obtained by using matrine as a raw material, performing hydrolytic ring openingunder alkaline conditions and performing esterification reaction, hydrolysis reaction and amidecoupling reaction. As the matrine self has a certain pharmacological effect, the synthesized novel derivatives are subjected to anti-cancer activity test by using a MTT colorimetric method, and the anti-cancer activity of each of the novel derivatives is obviously better than that of the matrine.
Description
technical field [0001] The invention relates to the synthesis of a series of new derivatives of matrine amide, and the biological activity test of the synthesized compounds belongs to the field of medicinal chemistry. Background technique [0002] Tumor is a common clinical disease at present, the refractory of tumor lies in the recurrence and metastasis of tumor, and the formation of tumor angiogenesis is one of the important conditions for tumor recurrence and metastasis. Therefore, controlling the development of tumor diseases by inhibiting tumor angiogenesis has become a hot spot in anti-tumor therapy today. Matrine (Formula 1) is an active ingredient isolated from the traditional medicinal plantSophora flavescens, which has attracted much attention due to its wide range of biological activities, such as anti-tumor, anti-inflammatory, and anti-viral. In China, matrine injection is clinically used to treat hepatitis and liver cancer, and matrine suppository can treat va...
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