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Water-soluble maslinic acid derivative as well as preparation method and application thereof

A technology of maslinic acid and derivatives, which is applied in the field of medicine, can solve the problems of poor water solubility and low bioavailability, and achieve the effect of inhibiting activity and improving water solubility

Inactive Publication Date: 2019-01-18
JIANGXI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Maslinic acid widely exists in natural plants, and it has been reported in the literature that it has hypoglycemic activity, but its bioavailability is low due to its poor water solubility

Method used

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  • Water-soluble maslinic acid derivative as well as preparation method and application thereof
  • Water-soluble maslinic acid derivative as well as preparation method and application thereof
  • Water-soluble maslinic acid derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] (1) Synthesis of 2α,3β-diacetoxyoleanane-12-ene-28-carboxylic acid 2

[0051] Dissolve maslinic acid (0.3g, 0.63mmol) in 10ml of pyridine, slowly add 7.5ml of acetic anhydride dropwise under ice bath, and react for 24h in the bathroom after dropping the ice. After the reaction, the reaction solution was washed with 1N hydrochloric acid 50ml*3, and the organic layer was separated with saturated NaHCO 3 and distilled water, dried over anhydrous sodium sulfate, filtered, concentrated by rotary evaporation, and then subjected to silica gel column chromatography (petroleum ether: ethyl acetate = 4:1) to obtain a white solid 1 (yield 93.2%). Mp: 228~233℃. 1 H NMR (400MHz, CDCl 3 ): δ5.26(t, J=12.0Hz, 1H), 5.11-5.07(m, 1H), 4.75(d, J=12.0Hz, 1H), 2.82(dd, J=6.0, 6.0Hz, 1H) ,2.06(d,J=12.0Hz,3H),2.02-1.99(m,1H),1.98(s,3H),1.95-1.90(m,1H),1.87-1.82(m,1H),1.79-1.73 (m,1H),1.71-1.67(m,1H),1.63-1.61(m,1H),1.60(s,1H),1.58-1.57(d,J=12.0Hz,1H),1.56-1.54(m ,1H),1.48-1.45(m,1H),1.44...

Embodiment 2

[0059] (1) Synthesis of N-(2α,3β-diacetoxyoleanane-12-en-28-amide)-L-isoleucine methyl ester 4b

[0060] Referring to the method of Example 1, a white solid 4b was obtained from L-isoleucine methyl ester hydrochloride and intermediate 3 (yield 82.4%). Mp:117-136℃. 1 H NMR (600MHz, CDCl 3 ):δ6.44(d,J=6.0Hz,1H),5.42(t,J=6.0Hz,1H),5.11-5.06(m,1H),4.75(d,J=12.0Hz,1H),4.50 -4.48(m,1H),3.69(s,3H),2.65(dd,J=6.0,3.6Hz,1H),2.04(s,3H),2.03-1.98(m,2H),1.97(s,3H ),1.96-1.93(m,1H),1.89-1.84(m,2H),1.77(t,J=24.0Hz,1H),1.65-1.52(m,8H),1.48-1.44(m,2H), 1.41-1.34(m,2H),1.29-1.27(m,1H),1.21-1.17(m,3H),1.14(s,3H),1.04(s,3H),0.94(t,J=12.0Hz, 3H),0.91(s,6H),0.89(d,J=3.6Hz,6H),0.87(d,J=12.0Hz,3H),0.68(s,3H).

[0061] (2) Synthesis of N-(2α,3β-dihydroxyoleanane-12-en-28-amide)-L-isoleucine 5b

[0062] Referring to the method of Example 1, 4b was hydrolyzed to obtain white solid 5b (65.4% yield). Mp:147-184℃. 1 HNMR (600MHz, DMSO-d 6 ):δ6.99(d,J=6.0Hz,1H),5.23(t,J=12.0Hz,1H),4.08(t,J=12.0Hz,1...

Embodiment 3

[0064] (1) Synthesis of N-(2α,3β-diacetoxyoleanane-12-ene-28-amide)-L-valine methyl ester 4c

[0065] Referring to the method of Example 1, a white solid 4c was obtained with L-valine methyl ester hydrochloride and intermediate 3 (85.6% yield). Mp:168-180℃. 1 H NMR (600MHz, CDCl 3):δ6.40(d,J=6.0Hz,1H),5.43(t,J=6.0Hz,1H),5.11-5.06(m,1H),4.75(d,J=12.0Hz,1H),4.45 -4.43(m,1H),3.70(s,3H),2.66(dd,J=6.0,3.6Hz,1H),2.13-2.06(m,1H),2.05(s,3H),2.03-2.00(m ,2H),1.98(s,3H),1.97-1.93(m,1H),1.90-1.85(m,1H),1.77-1.73(m,J=24.0Hz,1H),1.70(s,1H), 1.66-1.63(m,2H),1.61-1.58(m,2H),1.56-1.52(m,1H),1.49-1.44(m,1H),1.42-1.33(m,2H),1.29-1.27(m ,1H),1.25(s,3H),1.21-1.18(m,2H),1.14(s,3H),1.08(d,J=12.0Hz,1H),1.04(s,3H),0.97-0.95( m,1H),0.93-0.89(m,15H),0.67(s,3H).

[0066] (2) Synthesis of N-(2α,3β-dihydroxyoleanane-12-en-28-amide)-L-valine 5c

[0067] Referring to the method of Example 1, 4c was hydrolyzed to obtain white solid 5c (68.4% yield). Mp:112-128℃. 1 HNMR (600MHz, DMSO-d 6 ): δ7.23(d,...

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Abstract

The invention relates to a water-soluble maslinic acid derivative as well as a preparation method and application thereof, which belongs to the field of medicines. According to the water-soluble maslinic acid derivative provided by the invention, a series of hydrophilic amino acids are respectively introduced on maslinic acid C-28 carboxyl sites. Discovered from an experiment result, the hydrophilic property is significantly improved, and the glucose reduction activity of N(2alpha,3beta-dihydroxyl oleanane-12-ene-28-amide)-L-aspartic acid is apparently higher than that of a reference drug acarbose.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a water-soluble maslinic acid derivative and its preparation method and application. Background technique [0002] Diabetes mellitus is an endocrine and metabolic disease characterized by chronic elevated blood sugar levels, accompanied by chronic damage to the eyes, kidneys, heart, blood vessels, and nervous system. In recent years, the morbidity and mortality have shown a rapid upward trend, becoming the third major disease that threatens human health after tumors and cardiovascular diseases. According to the 2013 International Diabetes Federation (IDF) statistics (Kleinberger, J.W.and T.I.Pollin, Personalized medicine in diabetes mellitus: current opportunities and future prospects. Annals of the New York Academy of Sciences, 2015.1346(1): p.45-56.) At present, there are about 382 million diabetics in the world, and the number of diabetics in my country has reached 98.4 million, rankin...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61P3/10
Inventor 洪艳平曾臻尹小莉蒋艳杨武英吴国强廖晓宁王纯荣刘小琴
Owner JIANGXI AGRICULTURAL UNIVERSITY
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