CN117903049A - Resveratrol derivative and preparation method and application thereof - Google Patents

Resveratrol derivative and preparation method and application thereof Download PDF

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CN117903049A
CN117903049A CN202311698434.9A CN202311698434A CN117903049A CN 117903049 A CN117903049 A CN 117903049A CN 202311698434 A CN202311698434 A CN 202311698434A CN 117903049 A CN117903049 A CN 117903049A
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acid
resveratrol
compound
formula
derivative
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汤有志
卢佳勋
靳珍
孙永学
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South China Agricultural University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/86—Hydrazides; Thio or imino analogues thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/86—Hydrazides; Thio or imino analogues thereof
    • C07D213/87—Hydrazides; Thio or imino analogues thereof in position 3

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  • Life Sciences & Earth Sciences (AREA)
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Abstract

The invention belongs to the technical field of anti-inflammatory and antioxidant drug development, and discloses a resveratrol derivative, a preparation method and application thereof. The resveratrol derivative is a compound with a structure shown in a formula 2 or pharmaceutically acceptable salt thereof, and a solvent compound of the compound with the structure shown in the formula 2 or pharmaceutically acceptable salt thereof. The resveratrol derivative belongs to novel compounds, and is designed for the first time and successfully synthesized, and meanwhile, the structure of the resveratrol derivative is characterized; the preparation method of the resveratrol derivative is simple and convenient to operate, and can rapidly synthesize the compounds; the research shows that the resveratrol derivative has good anti-inflammatory and antioxidant activities and has good application prospects in the treatment of inflammation and oxidative stress.

Description

Resveratrol derivative and preparation method and application thereof
Technical Field
The invention belongs to the technical field of anti-inflammatory and antioxidant drug development, and particularly relates to a resveratrol derivative, a preparation method and application thereof.
Background
Resveratrol (Resveratrol), chemical name 3,4', 5-trihydroxy-1, 2-diphenylethylene, molecular formula C 14H12O3, molecular weight 228.23, CAS number: 501-36-0, and has a structure shown in formula 1. Resveratrol was originally isolated from the roots of resveratrol by japanese scientists and is an antitoxin secreted by plants in adverse conditions or when encountering pathogenic attack. Common sources at present are peanuts, grapes, mulberries, cranberries and the like.
Resveratrol as a non-flavonoid polyphenol compound has various biological activities such as anti-inflammatory, antioxidant, anticancer, cardiovascular protection, etc. Research shows that resveratrol can scavenge free radicals to protect biomacromolecules from damage, increase the expression of antioxidant enzyme through multiple ways, activate SIRT1 and improve mitochondrial function. In anti-inflammatory terms, resveratrol inhibits cyclooxygenase COX1 and COX2, and also inhibits tumor necrosis factor alpha (TNF-alpha) and interleukin 1 beta (IL-1 beta) against inflammation. However, resveratrol has a relatively low oral bioavailability of about 12% and requires the use of a relatively large dosage to achieve an effective concentration of drug in plasma or tissue. Therefore, rapid absorption, low bioavailability and poor water solubility are key factors limiting the clinical use of resveratrol.
Molecular hybridization (Molecular hybridization) refers to the formation of a novel active compound by chemically ligating two active molecular fragments. Molecular hybridization can enhance the pharmacological activity of active molecules and reduce their toxic side effects. Therefore, by paying out an aldehyde group on the benzene ring of resveratrol, the resveratrol is connected with benzoyl hydrazine to form a novel compound on the basis of the aldehyde group, so that the pharmacological activity and bioavailability of the resveratrol are improved.
Disclosure of Invention
In order to overcome the drawbacks and disadvantages of the prior art, a primary object of the present invention is to provide a resveratrol derivative which can enhance the anti-inflammatory and anti-oxidative activity of resveratrol.
Another object of the present invention is to provide a method for preparing the resveratrol derivative.
It is still another object of the present invention to provide the use of the resveratrol derivative, which has good anti-inflammatory and antioxidant activity in vitro, and is suitable for being used as a novel medicine for inflammatory or oxidative stress diseases.
The invention aims at realizing the following technical scheme:
a resveratrol derivative which is a compound with a structure shown in a formula 2 or a pharmaceutically acceptable salt thereof, and a solvent compound of the compound with the structure shown in the formula 2 or the pharmaceutically acceptable salt thereof:
wherein R is one of the following groups:
The specific groups of the above compounds are summarized in Table 1:
Table 1 Compound numbering and Structure
The pharmaceutically acceptable salt is preferably a salt of the compound of formula 2 with hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, fumaric acid, maleic acid, oxalic acid, malonic acid, succinic acid, citric acid, malic acid, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, toluenesulfonic acid, glutamic acid or aspartic acid.
The preparation method of the resveratrol derivative comprises the following steps:
(1) Reacting resveratrol with N, N dimethylformamide and phosphorus oxychloride to obtain an intermediate I with a structure shown in a formula 3;
(2) Intermediate I and different benzoyl hydrazine derivatives are used as raw materials, and resveratrol derivatives with the structure shown in the formula 2 are obtained through heating reaction and purification.
The mol ratio of resveratrol, N dimethylformamide and phosphorus oxychloride in the step (1) is 1:1.1:1.1.
The step (1) is specifically carried out according to the following steps: acetonitrile is used as a solvent, N dimethylformamide and phosphorus oxychloride are added under the stirring of an ice salt bath, resveratrol is added, and the reaction is carried out overnight; filtering to obtain red solid, and washing with cold acetonitrile; transferring the obtained solid to a new reaction bottle, adding water to react for 3-5 h at 55 ℃, and carrying out suction filtration to obtain an intermediate I.
The molar ratio of the intermediate I to the benzoyl hydrazine derivative in the step (2) is 1:1; the reaction condition is 70 ℃ for 1-5 h.
The synthetic route of the resveratrol derivative is shown in the following formula, and R groups are all groups in table 1:
the resveratrol derivative is applied to the preparation of medicines for preventing and treating inflammatory diseases and oxidative stress.
Compared with the prior art, the invention has the following advantages:
(1) The resveratrol derivatives provided by the invention are novel compounds which are not reported, and the invention designs and successfully synthesizes the compounds for the first time, and simultaneously characterizes the structures of the compounds.
(2) The preparation method of the resveratrol derivative is simple and convenient to operate, and the resveratrol derivative can be quickly synthesized.
(3) Through extensive and intensive research, a large number of resveratrol derivatives with brand new structures and anti-inflammatory and antioxidant activities are synthesized, and anti-inflammatory and antioxidant activity screening is performed, so that the compounds have good in-vitro anti-inflammatory and antioxidant activities for the first time, and are suitable for being used as novel medicines for preventing and treating inflammatory diseases and oxidative stress.
Drawings
FIG. 1 is a nuclear magnetic resonance image spectrum of Compound 1.
FIG. 2 is a nuclear magnetic resonance spectrum of Compound 2.
FIG. 3 is a nuclear magnetic resonance image of compound 19.
FIG. 4 is a cytotoxicity assay of resveratrol and derivatives thereof on RAW264.7 cells using MTT assay.
FIG. 5 is a graph showing the inhibition of NO content in RAW264.7 cells by resveratrol and its derivatives as determined by Griess.
Fig. 6 is a flow cytometry analysis of the inhibition of reactive oxygen species ROS production by resveratrol and its derivatives in RAW264.7 cells.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but embodiments of the present invention are not limited thereto.
Example 1 preparation of intermediate I
30ML of acetonitrile was added to a single-diameter round bottom flask, the ice-salt bath was continued for 5min, N dimethylformamide (1.76 g,24.1 mmol), phosphorus oxychloride (3.69 g,24.1 mmol), resveratrol (5 g,21.9 mmol) was added after stirring for 5min, and the solid was collected by suction filtration after stirring overnight and washed with cold acetonitrile. Transferring the obtained solid to a new single-diameter round-bottom flask, adding 30mL of water, reacting for 3-5 h at 55 ℃, filtering, collecting the solid by suction, washing with cold water, and drying to obtain the intermediate I with the structure shown in the formula 3, wherein the yield is 80%.
Example 2 Synthesis of N' - (Z) -2, 4-dihydroxy-6- ((E) -4-hydroxystyryl) benzylidene) benzoyl hydrazine (Compound 1)
In a single diameter round bottom flask, intermediate I (0.5 g,1.95 mmol) and benzoyl hydrazine (0.26 g,1.95 mmol) are added, dissolved in 5mL absolute ethanol, stirred for 1-5 h at 70 ℃ and solid is separated out, TLC is used for tracking and monitoring the reaction, after the reaction is completed, the solid is obtained through suction filtration, and the product N' - (Z) -2, 4-dihydroxy-6- ((E) -4-hydroxystyryl) benzylidene) benzoyl hydrazine is obtained through recrystallization and purification. The nuclear magnetic pattern of the product is shown in figure 1, and the number and displacement of hydrogen of ,1H NMR(600MHz,DMSO-d6)δ12.41(s,1H),11.94(s,1H),10.02(s,1H),9.67(s,1H),9.00(s,1H),8.02–7.89(m,2H),7.65–7.59(m,1H),7.55(dd,J＝8.3,6.9Hz,2H),7.51–7.46(m,2H),7.32(d,J＝16.0Hz,1H),6.94(d,J＝16.0Hz,1H),6.84–6.77(m,2H),6.58(d,J＝2.3Hz,1H),6.28(d,J＝2.3Hz,1H). compound 1 are similar to those of prediction, so that the structure of the product is N' - (Z) -2, 4-dihydroxy-6- ((E) -4-hydroxystyryl) benzylidene) benzoyl hydrazine.
EXAMPLE 3 Synthesis of Compounds 2 to 20
Intermediate I (0.5 g,1.95 mmol) and benzoyl hydrazine derivative 2-20 (1.95 mmol) are added into a single-diameter round-bottom flask, dissolved in 5mL absolute ethyl alcohol, stirred for 1-5 h at 70 ℃, solid is separated out, TLC is used for tracking and monitoring the reaction, after the reaction is completed, the solid is obtained through suction filtration, and the compound 2-20 is obtained through recrystallization and purification. Wherein the nuclear magnetic patterns of compounds 2 and 19 are shown in FIG. 2 and FIG. 3.
The preparation yields of the above compounds are summarized in Table 2.
Table 2 yields of Compounds 1 to 20
Effect examples
1. Experimental method
1.1DPPH radical scavenging experiments
190. Mu.L of the prepared DPPH solution of 100. Mu. Mol/L was added to each well of a 96-well plate, followed by 10. Mu.L of Compound 1-20 (resveratrol derivative prepared in examples 2-3) in a final concentration of 5 to 50. Mu. Mol/L, and a control group was set so that their total volume was kept at 200. Mu.L. The reaction was left to stand at room temperature in the absence of light for 30min, and then their absorbance was measured at 517 nm. DPPH radical scavenging was calculated as follows: DPPH clearance= [1- (Am-An)/As ] ×100%. Am represents the OD of the sample group, an represents the OD of the methanol solution, and As represents the OD of the negative control group. And taking the concentration of the resveratrol derivative as an abscissa and the clearance rate corresponding to the concentration of the resveratrol derivative respectively as an ordinate, and making a standard curve according to the clearance rate, thereby obtaining a linear regression equation and a correlation coefficient (R 2). The concentration of the sample measured when DPPH radical was removed by 50% is shown by IC 50 values and the results are shown in Table 3. Compounds 5,6, 7, 8 and 9 all showed stronger DPPH radical scavenging ability than resveratrol, with compounds 6 and 9 being the strongest scavenging ability and IC 50 being 37.8 and 39.8 μm, respectively.
1.2ABTS radical scavenging experiments
Preparing 2.45mmol/L K 2S2O8 solution by using 7mmol/L ABTS solution, placing the solution at room temperature in a dark place for 12-16 hours to obtain ABTS free radical stock solution, diluting the stock solution (50:1) by using methanol solution to ensure that the absorbance value at 734nm is 0.7+/-0.02, and obtaining the ABTS+ working solution. The prepared ABTS+ working solution was added to a 96-well plate at 195. Mu.L per well, followed by 5. Mu.L of compound 1-20 (resveratrol derivative prepared in examples 2-3) at a final concentration of 2.5-30. Mu. Mol/L, a control group was set, allowed to stand still at room temperature for reaction for 20min under light-shielding conditions, and then their absorbance was measured at 734 nm. ABTS cation radical clearance was calculated from the formula ABTS clearance = [1- (Am-An)/As ] ×100%. Am represents the OD of the sample group, an represents the OD of the methanol solution, and As represents the OD of the negative control group. The measured sample concentration when ABTS radicals were scavenged 50% is expressed as IC 50 values and the results are shown in table 3. Compounds 5, 6, 7, 8 and 9 all showed stronger ABTS radical scavenging ability than resveratrol, with most of the compounds having enhanced ABTS radical scavenging ability than resveratrol, with compounds 8 and 9 having the strongest scavenging ability and IC 50 being 9.7 and 8.5 μm, respectively.
TABLE 3 Table 3
1.3 Cytotoxicity experiments
The mouse mononuclear macrophage RAW 264.7 was sub-cultured in DMEM medium containing 10% fetal bovine serum, 100mg/L penicillin, 100mg/L streptomycin at 37℃in a 5% CO 2 incubator. RAW 264.7 cells in log phase were used, the cell density was adjusted to 1X 10 5 cells/ml, and inoculated in 96-well plates at 100. Mu.L per well. After 12h of cell attachment, the medium was replaced with DMEM without or with 50 μmol/L of compound 1-20 (resveratrol derivative prepared in examples 2-3), with 3 multiplex wells per concentration. After 24h incubation, 100. Mu.L of MTT was added to each well and incubation was continued for 4h, the supernatant was discarded, 150. Mu.L of dimethyl sulfoxide (DMSO) was added to each well, and the mixture was shaken on a shaker for 10min, and absorbance A was measured at 490nm until the crystals were sufficiently dissolved. Experiments were repeated 3 times. Cell viability was calculated as (%) = (a test well/a blank well) ×100%. The experimental results are shown in fig. 4, and compounds 5, 7, 8, 18, 19 and 20 have no significant inhibitory effect on RAW 264.7 cells.
1.4 Effect of Compounds on NO content
Taking RAW264.7 cell suspension in logarithmic growth phase, adjusting cell density to 2X 10 5/mL, inoculating to 96-well plates, attaching to 100 mu L of each well for 12h, adding 100 mu L of compound 1-20 (resveratrol derivative prepared in example 2-3) with concentration of 50 mu mol/L, incubating for 3h, adding 100ng/L of LPS, incubating for 12h, setting a blank group, an LPS+ administration group and 3 compound wells each, and detecting the NO content of the supernatant by using Griess method.
1.5 Effect of Compounds on ROS expression
Taking RAW264.7 cell suspension in logarithmic growth phase, adjusting cell density to 2X 10 5/mL, inoculating to 12-well plates, 1mL each well, attaching to wall for 12h, adding 50 mu mol/L compound 1-20 (resveratrol derivative prepared in example 2-3), incubating for 3h, adding 800 mu mol/L H 2O2, incubating for 3h, adding DCEH-DA, and treating for 1h in dark place, and detecting ROS production by using a flow cytometer.
1.6 Data analysis
Data analysis is carried out by adopting prism software, t-test is adopted for comparison among groups, and P < 0.05 is statistically significant for difference.
2. Results
Based on the MTT experimental results, 6 compounds without significant toxicity were selected, and the effect of compounds 5, 7, 8, 18, 19 and 20 on LPS-induced NO release and ROS expression in RAW264.7 cells was studied, and the results are shown in fig. 5 and 6.
The result shows that the compound 5 has NO obvious cell inhibition effect on RAW264.7, can obviously reduce the release level of RAW264.7 cell inflammatory factor NO induced by LPS and the expression level of ROS in RAW264.7 cells stimulated by H 2O2, has good anti-inflammatory and antioxidant activities, and can be used as an active ingredient of anti-inflammatory and antioxidant drugs.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.

Claims (7)

1. A resveratrol derivative characterized by: the derivative is a compound with a structure shown in a formula 2 or pharmaceutically acceptable salt thereof, and a solvent compound of the compound with the structure shown in the formula 2 or pharmaceutically acceptable salt thereof:
wherein R is one of the following groups:
2. Resveratrol derivative according to claim 1, characterized in that:
The pharmaceutically acceptable salt is preferably a salt of the compound of formula 2 with hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, fumaric acid, maleic acid, oxalic acid, malonic acid, succinic acid, citric acid, malic acid, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, toluenesulfonic acid, glutamic acid or aspartic acid.
3. The method for preparing resveratrol derivatives according to claim 1 or 2, characterized by comprising the steps of:
(1) Reacting resveratrol with N, N dimethylformamide and phosphorus oxychloride to obtain an intermediate I with a structure shown in a formula 3;
(2) Intermediate I and different benzoyl hydrazine derivatives are used as raw materials, and resveratrol derivatives with the structure shown in the formula 2 are obtained through heating reaction and purification.
4. A method of preparation according to claim 3, characterized in that: the mol ratio of resveratrol, N dimethylformamide and phosphorus oxychloride in the step (1) is 1:1.1:1.1.
5. A method of preparation according to claim 3, characterized in that: the step (1) is specifically carried out according to the following steps: acetonitrile is used as a solvent, N dimethylformamide and phosphorus oxychloride are added under the stirring of an ice salt bath, resveratrol is added, and the reaction is carried out overnight; filtering to obtain red solid, and washing with cold acetonitrile; transferring the obtained solid to a new reaction bottle, adding water to react for 3-5 h at 55 ℃, and carrying out suction filtration to obtain an intermediate I.
6. A method of preparation according to claim 3, characterized in that: the molar ratio of the intermediate I to the benzoyl hydrazine derivative in the step (2) is 1:1; the reaction condition is 70 ℃ for 1-5 h.
7. Use of resveratrol derivatives according to claim 1 or 2 for the manufacture of a medicament for the prevention and treatment of inflammatory diseases and oxidative stress.
CN202311698434.9A 2023-12-12 2023-12-12 Resveratrol derivative and preparation method and application thereof Pending CN117903049A (en)

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