CN109748828B - 1, 8-dihydroxy-9, 10-anthraquinone derivative, preparation method and application thereof - Google Patents
1, 8-dihydroxy-9, 10-anthraquinone derivative, preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a 1, 8-dihydroxy-9, 10-anthraquinone derivative, a preparation method and application thereof. The invention provides an application of a 1, 8-dihydroxy-9, 10-anthraquinone derivative shown as a formula I or a pharmaceutically acceptable salt thereof in preparing a medicament for treating and/or preventing hepatitis C; wherein R is C1～C6Alkoxycarbonyl, R1Substituted or unsubstituted phenylsulfonyl, or, R2Substituted or unsubstituted benzyl; all of R1And R2Independently is C1～C4Alkyl, or, C1～C4An alkoxy group. The 1, 8-dihydroxy-9, 10-anthraquinone derivative provided by the invention shows better anti-HCV activity.
Description
Technical Field
The invention relates to a 1, 8-dihydroxy-9, 10-anthraquinone derivative, a preparation method and application thereof
Background
Hepatitis c is caused by infection with Hepatitis C Virus (HCV), primarily transmitted from blood/body fluids. According to the world health organization, 1.7 million people are infected with HCV worldwide. The positive rate of anti-HCV of healthy people in China is 0.7-3.1%, and about 3800 ten thousand people. Due to various factors such as the biological characteristics of viruses and the immune function of a host, the immunity of the organism is difficult to effectively eliminate the viruses, so that about 50 to 80 percent of HCV infected persons develop chronic hepatitis, and 20 to 30 percent of the HCV infected persons develop liver cirrhosis. Hepatocellular carcinoma develops in 1-4% of cirrhosis patients each year. Due to the fact that HCV is transmitted by blood and has the characteristics of chronic and secret nature, part of HCV infected persons can develop chronic hepatitis, and serious persons can even develop liver cirrhosis, liver failure or liver cancer (Chinese AIDS, 2017 (5): 461-plus 462; Jilin medical institute, 2017, 38 (2): 123-plus 126).
Physcion (physcion) belonging to anthraquinone is widely present in many plants of Polygonaceae, Leguminosae, Labiatae, Compositae, Orchidaceae and Rosaceae. The physcion has the inhibiting effect on 26 bacteria such as staphylococcus aureus, escherichia coli, pseudomonas aeruginosa, streptococcus, dysentery bacillus and the like; the physcion is a high-activity botanical fungicide and has good control effects on powdery mildew, downy mildew, gray mold, anthracnose and the like. (2015 (4): 938 and 940) in the journal of Chinese materia medica. Patent CN200810203112.1 also discloses that physcion has a certain inhibitory effect on hepatitis c virus, but the effect strength is general, and further structural modification is required to increase activity.
Disclosure of Invention
The invention aims to solve the technical problem of providing a 1, 8-dihydroxy-9, 10-anthraquinone derivative, a preparation method and application thereof. The 1, 8-dihydroxy-9, 10-anthraquinone derivatives show better anti-HCV activity.
The invention provides an application of a 1, 8-dihydroxy-9, 10-anthraquinone derivative shown as a formula I or a pharmaceutically acceptable salt thereof in preparing a medicament for treating and/or preventing hepatitis C;
wherein R is C1～C6Alkoxycarbonyl group (said "C1～C6Alkoxy "for example methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy", and for example methoxy), R1Substituted or unsubstituted benzenesulfonyl (said R1The number of (A) can be one or more, and can also be 1, 2 or 3; when there are more than one R1When there are two arbitrary R1The same or different; all of R1May be independently located at the ortho, meta or para position, e.g. para, of the sulfonyl group, or, R2Substituted or unsubstituted benzyl (said R2The number of (A) can be one or more, and can also be 1, 2 or 3; when there are more than one R2At any rate twoR is2The same or different; all of R2Can be independently positioned on the benzene ring of the benzyl; when said R is2When located on the phenyl ring of a benzyl group, it is located ortho, meta or para, e.g., para, to the methylene group of the benzyl group);
all of R1And R2Independently is C1～C4Alkyl (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl, also e.g. methyl), or, C1～C4Alkoxy (e.g., methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, or tert-butoxy, also e.g., methoxy).
In one embodiment, the compound I can be of any of the following structures:
in one embodiment, certain groups of compound I are defined as follows, and groups not mentioned are defined as in any of the above embodiments:
r is R1A substituted benzenesulfonyl group; all of R1Independently is C1～C4An alkyl group.
In one embodiment, certain groups of compound I are defined as follows, and groups not mentioned are defined as in any of the above embodiments:
r is R2Substituted or unsubstituted benzyl; all of R2Independently is C1～C4An alkoxy group.
The hepatitis c can be HCV type 2a (e.g., caused by the JFH1 strain).
The invention also provides application of the compound I in preparation of HCV inhibitors. Such as HCV type 2a (e.g., caused by the JFH1 strain).
The invention also provides a pharmaceutical composition, which comprises the 1, 8-dihydroxy-9, 10-anthraquinone derivative or the pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier. The pharmaceutical composition can be used for treating hepatitis C.
The invention also provides an anthraquinone derivative shown as a formula II or a pharmaceutically acceptable salt thereof;
wherein R' is C1～C6Alkoxycarbonyl group (said "C1～C6Alkoxy "for example methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy", and for example methoxy), R1Substituted or unsubstituted benzenesulfonyl (said R1The number of (A) can be one or more, and can also be 1, 2 or 3; when there are more than one R1When there are two arbitrary R1The same or different; all of R1May be independently located at the ortho, meta or para position, e.g. para, of the sulfonyl group, or, R2Substituted benzyl (said R2The number of (A) can be one or more, and can also be 1, 2 or 3; when there are more than one R2When there are two arbitrary R2The same or different; all of R2Can be independently positioned on the benzene ring of the benzyl; when said R is2When located on the phenyl ring of a benzyl group, it is located ortho, meta or para, e.g., para, to the methylene group of the benzyl group);
all of R1And R2Independently is C1～C4Alkyl (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl, also e.g. methyl) or C1～C4Alkoxy (e.g., methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, or tert-butoxy, also e.g., methoxy).
In one embodiment, the compound II can be of any of the following structures:
the invention also provides a preparation method of the compound of the formula II, which comprises the step of carrying out substitution reaction on the compound 1 (emodin) and the compound 2 under the action of alkali to obtain the compound of the formula II
X is halogen.
The halogen can be fluorine, chlorine, bromine or iodine; and may also be chlorine or bromine.
The base may be a base conventional to such reactions in the art, such as an inorganic base (e.g., an alkali metal carbonate, again such as potassium carbonate) and/or an organic base (e.g., an organic amine, again such as triethylamine).
The reaction conditions for the substitution reaction may be those conventional in the art for such reactions, for example the following reaction conditions:
the substitution reaction can be carried out in ketone or ether solvents. The ketone solvent may be a ketone solvent conventional in the reactions of this type in the art, such as acetone; the ethereal solvent may be one conventional in the art for such reactions, such as tetrahydrofuran and/or dioxane. The volume mol ratio of the ketone or ether solvent to the compound 1 can be the volume mol ratio which is conventional in the reaction in the field, such as 3 mL/mmol.
In the substitution reaction, the molar ratio of the compound 2 to the compound 1 can be a molar ratio conventional in the reaction of this type, for example, 2 to 3.
In the substitution reaction, the molar ratio of the compound 2 to the base may be a molar ratio conventional in the art such as 1 to 1.5.
The temperature of the substitution reaction can be any temperature conventional in the art, such as from 0 ℃ to 100 ℃ (e.g., room temperature).
The progress of the substitution reaction can be monitored by monitoring methods conventional in the art (e.g., TLC, HPLC, or NMR), and is generally terminated when compound 1 is no longer reacted, and the reaction time can be from 5h to 15h (e.g., 12 h).
The term "pharmaceutically acceptable salt" refers to a salt formed from a suitable non-toxic organic acid, inorganic acid, organic base, or inorganic base and a compound, which retains the biological activity of the compound. The organic acid may be any of various organic acids capable of forming a salt, which are conventional in the art, such as one or more of methanesulfonic acid, p-toluenesulfonic acid, maleic acid, fumaric acid, citric acid, tartaric acid, malic acid, lactic acid, formic acid, acetic acid, propionic acid, trifluoroacetic acid, oxalic acid, succinic acid, benzoic acid, isethionic acid, naphthalenesulfonic acid, and salicylic acid. The inorganic acid may be any of various inorganic acids capable of forming a salt, such as one or more of hydrochloric acid, sulfuric acid, and phosphoric acid, which are conventional in the art. The organic base can be various organic bases which are conventional in the field and can form salts, such as one or more of pyridines, imidazoles, pyrazines, indoles, purines, tertiary amines and anilines. The tertiary amine organic base is triethylamine and/or N, N-diisopropylethylamine. The aniline organic base is, for example, N-dimethylaniline. The pyridine organic base is one or more of pyridine, picoline, 4-dimethylamino pyridine and 2-methyl-5-ethyl pyridine. The inorganic base may be any of various inorganic bases capable of forming a salt, which are conventional in the art, such as one or more of alkali metal hydride, alkali metal hydroxide, alkali metal alkoxide, potassium carbonate, sodium carbonate, lithium carbonate, cesium carbonate, potassium hydrogen carbonate, and sodium hydrogen carbonate. Such as sodium hydride and/or potassium hydride. Such as one or more of sodium hydroxide, potassium hydroxide and lithium hydroxide. The alkoxide of alkali metal is one or more of sodium methoxide, sodium ethoxide, potassium tert-butoxide and sodium tert-butoxide.
On the basis of the common knowledge in the field, the above preferred conditions can be combined randomly to obtain the preferred embodiments of the invention.
The reagents and starting materials used in the present invention are commercially available.
The positive progress effects of the invention are as follows: the 1, 8-dihydroxy-9, 10-anthraquinone derivative provided by the invention shows better anti-HCV activity.
Detailed Description
The invention is further illustrated by the following examples, which are not intended to limit the scope of the invention. The experimental methods without specifying specific conditions in the following examples were selected according to the conventional methods and conditions, or according to the commercial instructions.
Example 1
Dissolving 5mmol of emodin in 15mL of tetrahydrofuran, adding 10mmol of triethylamine and 10mmol of p-toluenesulfonyl chloride, reacting at room temperature for 5 hours, distilling off the solvent under reduced pressure, adding 15mL of water, extracting with 15mL of ethyl acetate for three times, combining organic phases, washing with 15mL of water once, and performing column chromatography (PE/EA-4/1) to obtain the compound 1 with the yield of 59%.
1H NMR(500MHz，CDCl3)δ12.17(s，1H)，11.88(s，1H)，7.79(d，J＝6.5 Hz，2H)，7.63(s，1H)，7.44(s，1H)，7.36(d，J＝6.5Hz，2H)，7.11(s，1H)，7.00(s， 1H)，2.46(s，6H，overlapped)；13C NMR(126MHz，CDCl3)δ191.5，180.7， 163.88，162.9，155.5，149.7，146.2，135.3，132.8，132.1，130.1，128.4，124.7， 121.7，117.0，114.7，113.8，113.4，22.2，21.7；ESI-MS：m/z 422.9[M-H]-。
Example 2
Dissolving 5mmol of emodin in 15mL of acetone, adding 10mmol of potassium carbonate and 15mmol of methyl chloroformate, heating to 45 ℃, reacting for 12 hours, decompressing, evaporating the solvent, adding 15mL of water, extracting with 15mL of ethyl acetate for three times, combining organic phases, washing with 15mL of water once, and performing column chromatography (PE/EA is 4/1) to obtain the compound 1 with the yield of 65%.
1H NMR(500MHz，CDCl3)δ12.21(s，1H)，11.95(s，1H)，7.66(s，1H)， 7.64(d，J＝2.5Hz，1H)，7.15(d，J＝2.0Hz，1H)，7.18(d，J＝1.0Hz，1H)，3.96 (s，3H)，2.47(s，3H)；13C NMR(126MHz，CDCl3)δ191.5，181.1，164.1，162.8，157.1，152.8，149.4，135.2，133.0，124.7，121.7，115.9，114.0，113.5，113.2，55.9， 22.2；ESI-MS：m/z 329.2[M+H]+；351.1[M+Na]+；326.9[M-H]-。
Example 3
Dissolving 5mmol of emodin in 15mL of acetone, adding 10mmol of potassium carbonate and 15mmol of 4-methoxy benzyl chloride, heating to 45 ℃ for reaction for 12 hours, decompressing and distilling off the solvent, adding 15mL of water, extracting with 15mL of ethyl acetate for three times, combining organic phases, washing with 15mL of water once, and performing column chromatography (PE/EA-4/1) to obtain the compound 1 with the yield of 53%.
1H NMR(500MHz，CDCl3)δ12.29(s，1H)，12.11(s，1H)，7.62(s，1H)， 7.44(d，J＝2.5Hz，1H)，7.37(d，J＝8.5Hz，2H)，7.08(s，1H)，6.94(d，J＝8.5 Hz，2H)，6.75(d，J＝2.5Hz，1H)，5.12(s，2H)，3.83(s，3H)，2.45(s，3H)；13C NMR(126MHz，CDCl3)δ190.8，182.0，165.7，165.1，162.5，159.8，148.4，135.2， 133.2，129.4，127.3，124.5，121.3，120.0，114.2，113.7，110.3，108.8，107.7，70.6， 55.3，29.7，22.1；ESI-MS：m/z 389.1[M-H]-。
Effect examples Activity test for Compounds inhibiting HCV Strain
The purpose is as follows: the antiviral effect of the compound on the HCV2a type JFH1 virus was examined.
The test means is as follows: HCV infection stable cell line Huh7.5.1
Grouping tests: drug positive control (interferon alpha: morri (shanghai) biotechnology limited), drug group compounds to be tested (0, 0.625 μ M, 1.25 μ M, 2.5 μ M, 5 μ M, 10 μ M), negative control group.
Detecting items and indexes: HCV RNA content, nonstructural protein NS3 expression.
The experimental scheme is as follows:
cell: HCV susceptible cell line Huh7.5.1 (Shanghai institute of technology cell Bank) with 6-well plate (Coming, USA) cell density, 1X 105A hole;
virus: JFH1 strain (genotype 2a, institute of Wuhan virus, Chinese academy), with a viral infection count of 1 mol;
the experimental process comprises the following steps:
1. counting cells Huh7.5.1 according to an experimental scheme, then paving the cells in a 6-hole plate, and allowing the cells to adhere to the wall overnight;
2. HCV virus (JFH1) was added at the dose of infection, and after 6 hours of infection, the medium was changed and fresh medium containing derivatives at various concentrations (0, 0.625. mu.M, 1.25. mu.M, 2.5. mu.M, 5. mu.M, 10. mu.M) was added, i.e., serial drug dilutions were established at 2-fold dilutions. And changing fresh culture medium with corresponding concentration according to corresponding concentration every day to maintain the concentration of the medicine. The negative control group of the drug experiment is drug solvent (ddH2O), and the positive control group is interferon (PEG-IFN alpha, 500IU/mL, telaprevir (VX950), 10 μ M).
3. Samples were harvested 72 hours after infection with drug treatment, where the supernatant was TCID50The method detects the titer of infectious virus particles, half of cell components detect the copy number of virus genome by using real-time, and half of cell components detect the expression level of virus non-structural protein NS3 by using a western blot method, wherein GAPDH is used as a control.
Experimental results form: HCV RNA content, expression of the non-structural protein NS3, viral TCID50And (4) horizontal.
TABLE 1
Claims (30)
1. An application of 1, 8-dihydroxy-9, 10-anthraquinone derivative shown in formula I or pharmaceutically acceptable salt thereof in preparing a medicament for treating and/or preventing hepatitis C;
wherein R is R1Substituted or unsubstituted phenylsulfonyl, R2Substituted or unsubstituted benzyl;
all of R1And R2Independent of each otherGround is C1～C4Alkyl radical, C1～C4An alkoxy group.
2. The use according to claim 1, wherein when R is R1When substituted benzenesulfonyl, said R1When the number of R is one or more1When there are plural, any two R1The same or different.
3. The use according to claim 2,
when said R is1When the number of (2) is plural, the plural number is 2 or 3.
4. The use according to claim 1,
when said R is R2When substituted benzyl, said R2When the number of R is one or more2When there are plural, any two R2The same or different.
5. The use according to claim 4,
when said R is2When the number of (2) is plural, the plural number is 2 or 3.
6. The use according to claim 1,
when said R is R1Substituted benzenesulfonyl, all of R1Independently in the ortho, meta or para position relative to the sulfonyl group.
7. The use according to claim 1,
when said R is R2In the case of substituted benzyl radicals, all R2Independently at the ortho, meta or para position on the phenyl ring of the benzyl group.
8. The use according to claim 1,
when said R is R1Substituted benzenesulfonyl, R1Is C1～C4When alkyl, said C1～C4Alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl.
9. The use according to claim 1,
when said R is R1Substituted benzenesulfonyl, R1Is C1～C4At alkoxy, said C1～C4Alkoxy is methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy.
10. The use according to claim 1,
when said R is R2Substituted benzyl, R2Is C1～C4When alkyl, said C1～C4Alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl.
11. The use according to claim 1,
when said R is R2Substituted benzyl, R2Is C1～C4At alkoxy, said C1～C4Alkoxy is methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy.
12. The use according to claim 1,
the hepatitis C is HCV type 2 a.
13. The use according to any one of claims 1 to 12, wherein the 1, 8-dihydroxy-9, 10-anthraquinone derivative is of any one of the following structures:
14. the use of claim 1, wherein R is R1Substituted benzenesulfonyl, all of R1Independently is C1～C4An alkyl group;
or, R is R2Substituted or unsubstituted benzyl, all R2Independently is C1～C4An alkoxy group.
15. A pharmaceutical composition comprising a 1, 8-dihydroxy-9, 10-anthraquinone derivative of formula I as described in any one of claims 1 to 14, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
16. Use of a 1, 8-dihydroxy-9, 10-anthraquinone derivative of formula I according to any one of claims 1 to 14 for the preparation of an HCV inhibitor.
17. The use according to claim 16,
the HCV is HCV type 2 a.
18. 1, 8-dihydroxy-9, 10-anthraquinone derivative shown as formula II or pharmaceutically acceptable salt thereof;
wherein R' is R1Substituted or unsubstituted phenylsulfonyl, R2A substituted benzyl group;
all of R1And R2Independently is C1～C4Alkyl radical, C1～C4An alkoxy group.
19. The 1, 8-dihydroxy-9, 10-anthraquinone derivative II or a pharmaceutically acceptable salt thereof according to claim 18, wherein when R' is R1When substituted benzenesulfonyl, said R1When the number of R is one or more1When there are plural, any two R1The same or different.
20. The 1, 8-dihydroxy-9, 10-anthraquinone derivative II or its pharmaceutically acceptable salt according to claim 19,
the number of the plurality is 2 or 3.
21. The 1, 8-dihydroxy-9, 10-anthraquinone derivative II or its pharmaceutically acceptable salt according to claim 18,
when said R' is R2When substituted benzyl, said R2When the number of R is one or more2When there are plural, any two R2The same or different.
22. The 1, 8-dihydroxy-9, 10-anthraquinone derivative II or its pharmaceutically acceptable salt according to claim 21,
the number of the plurality is 2 or 3.
23. The 1, 8-dihydroxy-9, 10-anthraquinone derivative II or its pharmaceutically acceptable salt according to claim 18,
when said R' is R1When substituted benzenesulfonyl, said R1Independently in the ortho, meta or para position relative to the sulfonyl group.
24. The 1, 8-dihydroxy-9, 10-anthraquinone derivative II or its pharmaceutically acceptable salt according to claim 18,
when said R' is R2When substituted benzyl, said R2Independently located atOrtho, meta or para on the phenyl ring of the benzyl group.
25. The 1, 8-dihydroxy-9, 10-anthraquinone derivative II or its pharmaceutically acceptable salt according to claim 18,
when said R' is R1Substituted benzenesulfonyl, R1Is C1～C4When alkyl, said C1～C4Alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl.
26. The 1, 8-dihydroxy-9, 10-anthraquinone derivative II or its pharmaceutically acceptable salt according to claim 18,
when said R' is R1Substituted benzenesulfonyl, R1Is C1～C4At alkoxy, said C1～C4Alkoxy is methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy.
27. The 1, 8-dihydroxy-9, 10-anthraquinone derivative II or its pharmaceutically acceptable salt according to claim 18,
when said R' is R2Substituted benzyl, R2Is C1～C4When alkyl, said C1～C4Alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl.
28. The 1, 8-dihydroxy-9, 10-anthraquinone derivative II or its pharmaceutically acceptable salt according to claim 18,
when said R' is R2Substituted benzyl, R2Is C1～C4At alkoxy, said C1～C4Alkoxy is methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy.
29. The 1, 8-dihydroxy-9, 10-anthraquinone derivative II or a pharmaceutically acceptable salt thereof according to any one of claims 18 to 28, wherein said 1, 8-dihydroxy-9, 10-anthraquinone derivative is of any one of the following structures:
30. a process for the preparation of 1, 8-dihydroxy-9, 10-anthraquinone derivatives of formula II according to any one of claims 18 to 29, characterized in that it comprises the following steps: carrying out substitution reaction on the compound 1 and the compound 2 in the presence of alkali to obtain the compound shown in the formula II;
x is halogen.
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| CN104208054A (en) * | 2014-08-27 | 2014-12-17 | 浙江大学 | Application of rheum emodin in preparation of medicine for preventing acute fulminant hepatitis |
| WO2016169573A1 (en) * | 2015-04-20 | 2016-10-27 | Elsebai Mahmoud Fahmi | Sesquiterpene lactones as potent and broad spectrum antiviral compounds against all genotypes of hepatitis c virus (hcv) |
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