CN103880623A - 4,2',4'-triethoxy-5' substituted chalcone derivatives and preparation method and application thereof - Google Patents

4,2',4'-triethoxy-5' substituted chalcone derivatives and preparation method and application thereof Download PDF

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CN103880623A
CN103880623A CN201410071796.XA CN201410071796A CN103880623A CN 103880623 A CN103880623 A CN 103880623A CN 201410071796 A CN201410071796 A CN 201410071796A CN 103880623 A CN103880623 A CN 103880623A
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trimethoxy
derivative
triethoxy
cinnamophenone
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郁彭
陈哲民
王浩猛
杨尧
宋彬彬
芦逵
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Tianjin University of Science and Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration

Abstract

The invention relates to 4,2',4'-triethoxy-5' substituted chalcone derivatives, a preparation method and application of the derivatives to an antitumor medicines. Two compounds refer to 4,2',4'-triethoxy-5' (p-methoxyphenyl) chalcone and 4,2',4'-triethoxy-5' (p-fluorophenyl) chalcone. Two 4,2',4'-triethoxy-5' substituted chalcone derivatives are synthesized for the first time, and the in-vitro tumor cell inhibiting activities of the derivatives are tested. As indicated by results, the derivatives have high inhibiting activity to human erythroleukemia cells (K562) and human colon cancer cells (HT-29).

Description

4,2 ', 4 '-trimethoxy-5 ' replacement chalcones derivative and preparation method thereof and application
Technical field
The invention belongs to new compound synthetic with medicinal application field, relate in particular to a kind of novel 4,2', 4'-trimethoxy-5' replaces chalcones derivative and preparation method thereof, and application in antitumor drug.
Background technology
Cinnamophenone (Chalcones) compounds is that a class is mainly generated through cross-aldol condensation by aromatic aldehyde ketone, contains the compound of 1,3-diphenylprop ketenes structure in structure.
Its 1,3-diphenylprop ketene structures shape its have numerous replacement sites and the derivative of different loci different substituents group has diversified pharmacological property.In known bibliographical information, in chalcone derivative synthetic, overwhelming majority be all hydroxyl taking different loci as basis, formation C-O coupled derivative.And C-C coupling based on cinnamophenone phenyl ring, with other phenyl ring be directly connected to key report comparatively rare.Therefore the phenyl chalcone derivative of the C-C coupling of synthetic different loci, and carry out bioactive test, can offer help to the research of the structure activity relationship of this type of cinnamophenone compound and antitumor mechanism.That therefore, studies this compounds syntheticly has a more important meaning.
Summary of the invention
The object of the present invention is to provide a kind of 4,2', 4'-trimethoxy-5' replaces chalcones derivative and preparation method thereof, with and application in antitumor drug, the application synthesizes two kind 4 first, 2', and 4'-trimethoxy-5' replaces chalcones derivative, and it has been carried out to tumor cell in vitro and suppressed active test, result shows that this analog derivative has good inhibition active to human leukemia cell (K562), human colon cancer cell (HT-29).
The object of the invention is to be achieved through the following technical solutions:
A kind of 4,2', 4'-trimethoxy-5' replaces chalcones derivative, and the structural formula of derivative is as follows:
Figure BDA0000471435060000011
4,2', 4'-trimethoxy-5'(p-methoxyphenyl) cinnamophenone.
A kind of 4,2', 4'-trimethoxy-5' replaces chalcones derivative, and the structural formula of derivative is as follows:
Figure BDA0000471435060000021
4,2', 4'-trimethoxy-5'(is to fluorophenyl) cinnamophenone.
A kind of 4,2', 4'-trimethoxy-5' replaces the preparation method of chalcones derivative, and synthetic route is as follows:
Figure BDA0000471435060000022
Wherein R is p-methoxyphenyl, to fluorophenyl.
A kind of 4,2', 4'-trimethoxy-5' replaces chalcones derivative in the application of preparing in antitumor drug.
And described antitumor drug is the medicine of anti-human leukemia cell and human colon cancer cell.
Beneficial effect of the present invention and advantage are:
1, the present invention is taking a phenylene dimethyl ether as raw material; through acylation reaction; iodide reaction; aldol reaction; suzuki linked reaction has synthesized a series of 4 first; 2', 4'-trimethoxy-5' chalcone derivative, relate to simple to operate, reaction conditions is gentle, productive rate is high, product purity is high, synthesis technique and the advantage such as purification process is simple.
2, compound involved in the present invention has inhibition or killing off tumor cells, can be used as preparation treatment people liver cancer, human leukemia and human colon carcinoma antitumor drug, derivative 4,2', 4'-trimethoxy-5'(is to fluorophenyl) the tumour cell IC of cinnamophenone to human leukemia cell (K562) 50(μ M) is 1.88, to the tumour cell IC of human colon cancer cell (HT-29) 50(μ M) is 22.54, derivative 4,2', 4'-trimethoxy-5'(p-methoxyphenyl) the tumour cell IC of cinnamophenone to human leukemia cell (K562) 50(μ M) is 7.09, to the tumour cell IC of human colon cancer cell (HT-29) 50(μ M) is 3.52.
Brief description of the drawings
Fig. 1 is 2,4-dimethoxy-acetophenone nmr spectrum.
Fig. 2 is 2,4-dimethoxy-5-iodobenzene ethyl ketone nmr spectrum.
Fig. 3 is 4,2', 4'-trimethoxy-5' iodine cinnamophenone nmr spectrum.
Fig. 4 is 4,2', 4'-trimethoxy-5'(p-methoxyphenyl) cinnamophenone nmr spectrum.
Fig. 5 is 4,2', and 4'-trimethoxy-5'(is to fluorophenyl) cinnamophenone nmr spectrum.
Embodiment
Below by specific embodiment, the invention will be further described, and following examples are descriptive, is not determinate, can not limit protection scope of the present invention with this.
A class of the present invention is novel 4,2', and the general structure of 4'-trimethoxy-5' chalcone derivative is as follows:
Wherein R is p-methoxyphenyl, to fluorophenyl;
The present invention be more particularly directed to following two kinds of derivatives:
(1) 4,2', 4'-trimethoxy-5'(p-methoxyphenyl) cinnamophenone
(2) 4,2', 4'-trimethoxy-5'(is to fluorophenyl) cinnamophenone
The synthetic route of above-claimed cpd is as follows:
Figure BDA0000471435060000032
Illustrate synthetic method below by embodiment.
Embodiment 1:
R is p-methoxyphenyl, 4,2', 4'-trimethoxy-5'(p-methoxyphenyl) preparation process of cinnamophenone is as follows
(1) synthetic intermediate 2,4-dimethoxy-acetophenone
By AlCl 3(25g; 159.23mmol) be dissolved in 150mL anhydrous methylene chloride; system argon shield; under condition of ice bath with slowly splashing into Acetyl Chloride 98Min. (15g, 188.18mmol) under constant voltage dropping liquid, after Acetyl Chloride 98Min. all dropwises; phenylene dimethyl ether (20g between inciting somebody to action; 144.8mmol) be dissolved in 10mL anhydrous methylene chloride, slowly splash in reaction system by constant voltage dropper.Under room temperature, stir 3～4h.After TLC monitoring reacts completely, reaction system is poured in frozen water into cancellation Acetyl Chloride 98Min..With 50mLDCM extraction 3 times, merge organic phase, 5% caustic wash(ing) 2 times for organic phase, organic phase anhydrous sodium sulfate drying, evaporate to dryness, silicagel column purifying (sherwood oil: ethyl acetate=25:1), obtains 2,4-dimethoxy benzaldehyde is white solid, 15.60g, yield 60%.
1HNMR(400MHz,CDCl 3):δ/ppm2.57(s,3H),3.85(s,3H),3.89(s,3H),6.45(d,J=2.4Hz,1H),6.52(dd,J=8.8Hz,2.4Hz,1H),7.83(d,J=8.8Hz,1H)。
(2) synthetic intermediate 2,4-dimethoxy-5-iodobenzene ethyl ketone
By 2,4-dimethoxy-acetophenone (5g, 27.75mmol), be dissolved in 15mLN, dinethylformamide, adds nitrogen N-iodosuccinimide (7.5g, 33.30mmol), and 83 DEG C are stirred 6h.After the monitoring of TLC thin-layer chromatography reacts completely, add water, the each 50mL extraction of ethyl acetate 3 times, merges organic phase, anhydrous sodium sulfate drying, evaporate to dryness, purification by silica gel column chromatography (sherwood oil: ethyl acetate=7:1), obtaining 2,4-dimethoxy-5-iodobenzene ethyl ketone is white solid 6.4g, yield 80%.
1HNMR(400MHz,CDCl 3):δ/ppm2.56(s,3H),3.94(s,3H),3.94(s,3H),6.39(s,3H),8.32(s,3H)
(3) synthetic intermediate 4,2', 4'-trimethoxy-5' iodine cinnamophenone
By (2g, 6.53mmol) 2,4-dimethoxy-5-iodobenzene ethyl ketone is dissolved in 10mL ethanol, adds aubepine (935mg, 6.86mmol).Under condition of ice bath, add 5mL60% potassium hydroxide solution, stirring at room temperature 12h.After the monitoring of TLC thin-layer chromatography reacts completely, add 50mL water, 50mL ethyl acetate extraction 3 times, merges organic phase, anhydrous sodium sulfate drying, evaporate to dryness, purification by silica gel column chromatography (sherwood oil: ethyl acetate=15:1), obtains 4,2', 4'-trimethoxy-5' iodine cinnamophenone is yellow solid, 2.5g, yield 90%.
1HNMR(400MHz,CDCl3):δ/ppm3.85(s,3H),3.94(s,3H),3.96(s,3H),6.44(s,1H),6.91(d,J=8.8Hz,2H),7.32(d,J=15.6Hz,1H),7.55(d,J=8.8Hz,2H),7.65(d,J=16Hz,1H),8.13(s,1H)
(4) synthetic product 4,2', 4'-trimethoxy-5'(p-methoxyphenyl) cinnamophenone
4,2', 4'-trimethoxy-5' iodine cinnamophenone (200mg, 471.44 μ mol), is dissolved in 1.5mL methyl-sulphoxide.Add successively to methoxyphenylboronic acid (86mg, 565.73 μ mol) anhydrous acetic acid potassium (92.5mg, 942.89 μ mol), catalyzer [two (diphenylphosphino) ferrocene of 1,1'-] palladium chloride (17mg, 23.57 μ mol), argon shield.90 DEG C of reaction 1.5h of microwave.After the monitoring of TLC thin-layer chromatography reacts completely, add water, the each 20mL of ethyl acetate, extracts 3 times, merges organic phase, anhydrous sodium sulfate drying, evaporate to dryness, purification by silica gel column chromatography (sherwood oil: ethyl acetate=8:1) obtains 4,2', 4'-trimethoxy-5'(p-methoxyphenyl) cinnamophenone is yellow solid 100mg, yield 65%.
1HNMR(400MHz,CDCl 3):δ/ppm3.85(s,3H),3.90(s,3H),3.99(s,3H),6.57(s,3H),6.92(d,J=8.4Hz,2H),7.08(t,J=8.8Hz,2H),7.40～7.48(m,3H),7.56(d,J=8.4Hz,2H),7.68(d,J=15.6Hz,1H),7.74(s,1H)
Embodiment 2:
R is to fluorophenyl, and 4,2', 4'-trimethoxy-5'(is to fluorophenyl) synthetic method of cinnamophenone is as follows:
4,2', 4'-trimethoxy-5' iodine cinnamophenone (200mg, 471.44 μ mol), is dissolved in 1.5mL methyl-sulphoxide.Add successively to fluorobenzoic boric acid (79.2mg, 565.73 μ mol) anhydrous acetic acid potassium (92.5mg, 942.89 μ mol), catalyzer [two (diphenylphosphino) ferrocene of 1,1'-] palladium chloride (17mg, 23.57 μ mol), argon shield.90 DEG C of reaction 1.5h of microwave.After the monitoring of TLC thin-layer chromatography reacts completely, add water, the each 20mL of ethyl acetate, extracts 3 times, merges organic phase, anhydrous sodium sulfate drying, evaporate to dryness, purification by silica gel column chromatography (sherwood oil: ethyl acetate=8:1) obtains yellow solid 4,2', 4'-trimethoxy-5'(is to fluorophenyl) cinnamophenone 110mg, yield 58%.
1HNMR(400MHz,CDCl 3):δ/ppm3.85(s,3H),3.90(s,3H),3.99(s,3H),6.57(s,3H),6.92(d,J=8.4Hz,2H),7.08(t,J=8.8Hz,2H),7.40～7.48(m,3H),7.56(d,J=8.4Hz,2H),7.68(d,J=15.6Hz,1H),7.74(s,1H)
The antitumor cytolytic activity of two kinds of compounds provided by the invention
The preparation of solution:
The preparation of DMEM low glucose nutrient solution: buy HyClone MEM low glucose substratum, every bottle of 500mL, add 10% foetal calf serum and 1% mycillin solution, be that every bottle of substratum adds the foetal calf serum of 50mL and the mycillin of 5mL, being configured in Bechtop of substratum carried out, 4 DEG C of preservations of rear placement refrigerator.
The preparation of DMEM/F-12 nutrient solution: buy HyClone MEM/F-12 substratum, every bottle of 500mL, add 10% foetal calf serum and 1% mycillin solution, be that every bottle of substratum adds the foetal calf serum of 50mL and the mycillin of 5mL, being configured in Bechtop of substratum carried out, 4 DEG C of preservations of rear placement refrigerator.
The preparation of PBS damping fluid: in 1000mL Erlenmeyer flask, take sodium-chlor 8g, Repone K 0.2g, disodium hydrogen phosphate dodecahydrate 2.9g, potassium primary phosphate 0.2g, is settled to 1000mL after adding the abundant stirring and dissolving of 800mL pure water, places 4 DEG C of preservations of refrigerator after autoclaving.
The preparation of MTT solution: take MTT dry powder 0.5g, be dissolved in 100mL PBS damping fluid, with after 0.22 μ M membrane filtration degerming, place refrigerator-12 DEG C preservation.
The concrete steps of antitumor cytolytic activity:
Antitumor cytolytic activity of the present invention 2 tumour cells used: leukemia cell (K562) and human colon cancer cell (HT-29).
Utilization utilizes Leukemia K562 cell active testing
The nutrient solution that K562 cell uses is containing penicillin-Streptomycin sulphate solution of 1%, the PRMI1640 cell culture fluid of 10% foetal calf serum, and culture condition is 37 DEG C, containing 5%CO 2constant incubator.Concrete steps:
(1), after cell being counted with blood counting chamber, be diluted to 5x10 with RPMI nutrient solution 4individual/mL;
(2) in each hole of 96 orifice plates, add 100 μ L cell suspensions, 37 DEG C of incubation 2h of incubator;
(3) wanted test compounds is diluted to 5 kinds of concentration: 2mM, 0.2mM, 20 μ M, 2 μ M, 0.2 μ M, according to concentration successively dosing 0.5 μ L/ hole, 37 DEG C of incubation 48h of incubator;
(4) adding concentration is the MTT of 5mg/mL, 37 DEG C of incubations of incubator 4 hours;
(5) add Virahol and hydrochloric acid lysate, microplate reader is surveyed the OD value under 570nm and 630nm;
(6) processing data, calculates IC according to OD value 50value.
Utilization utilizes human colon cancer cell HT-29 active testing
The nutrient solution that HT-29 cell uses is containing penicillin-Streptomycin sulphate solution of 1%, the DMEM/F-12 cell culture fluid of 10% foetal calf serum, and culture condition is 37 DEG C, containing 5%CO 2constant incubator.Concrete steps:
(1) after cell being counted with blood counting chamber, with being diluted to 5x10 with DMEM/F-12 nutrient solution 4individual/mL;
(2) in each hole of 96 orifice plates, add 100 μ L cell suspension piping and druming to mix, 37 DEG C of incubation 24h of incubator;
(3) wanted test compounds is diluted to 5 kinds of concentration: 2mM, 0.2mM, 20 μ M, 2 μ M, 0.2 μ M, according to concentration successively dosing 0.5 μ L/ hole, 37 DEG C of incubation 48h of incubator;
(4) adding concentration is the MTT of 5mg/mL, 37 DEG C of incubation 4h of incubator;
(5) add DMSO by cytolysis, microplate reader is surveyed the OD value under 490nm and 630nm;
(6) processing data, calculates IC according to OD value 50value.
The novel 42'4'-trimethoxy of table 1-5' replaces the anti-tumor activity test result of chalcones derivative
Figure 201410071796X100002DEST_PATH_IMAGE001
Involved in the present invention novel 4,2', 4'-trimethoxy-5' replaces chalcones derivative and can suppress or killing off tumor cells, has anti-tumor activity, can in the medicine for the treatment of tumour, apply.

Claims (5)

1. one kind 4,2', 4'-trimethoxy-5' replaces chalcones derivative, it is characterized in that: the structural formula of derivative is as follows:
Figure FDA0000471435050000011
4,2', 4'-trimethoxy-5'(p-methoxyphenyl) cinnamophenone.
2. one kind 4,2', 4'-trimethoxy-5' replaces chalcones derivative, it is characterized in that: the structural formula of derivative is as follows:
Figure FDA0000471435050000012
4,2', 4'-trimethoxy-5'(is to fluorophenyl) cinnamophenone.
3. one kind 4,2', 4'-trimethoxy-5' replaces the preparation method of chalcones derivative, it is characterized in that: synthetic route is as follows:
Figure FDA0000471435050000013
Wherein R is p-methoxyphenyl, to fluorophenyl.
One kind as claimed in claim 14,2', 4'-trimethoxy-5' replaces chalcones derivative in the application of preparing in antitumor drug.
5. according to claim 44,2', 4'-trimethoxy-5' replaces chalcones derivative in the application of preparing in antitumor drug, it is characterized in that: described antitumor drug is the medicine of anti-human leukemia cell and human colon cancer cell.
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CN104288133A (en) * 2014-09-19 2015-01-21 天津科技大学 3,5-diisoamylene, 2,4,4'-trihydroxyl chalcone as well as use and preparation method of derivative of the 3,5-diisoamylene, 2,4,4'-trihydroxyl chalcone
CN105967991A (en) * 2016-05-12 2016-09-28 哈尔滨医科大学 Compound with antitumor activity and preparation method and application of compound
CN110734367A (en) * 2019-10-24 2020-01-31 贵州医科大学 diphenyl ether chalcone tubulin inhibitor and preparation method and application thereof
CN112961096A (en) * 2021-02-05 2021-06-15 安徽医科大学 Chalcone tryptophan derivatives with improved cisplatin nephrotoxicity and antitumor activity
CN115624544A (en) * 2022-12-02 2023-01-20 甘肃中医药大学 Application of chalcone analogue as active substance in preparation of antitumor drugs

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104288133A (en) * 2014-09-19 2015-01-21 天津科技大学 3,5-diisoamylene, 2,4,4'-trihydroxyl chalcone as well as use and preparation method of derivative of the 3,5-diisoamylene, 2,4,4'-trihydroxyl chalcone
CN105967991A (en) * 2016-05-12 2016-09-28 哈尔滨医科大学 Compound with antitumor activity and preparation method and application of compound
CN110734367A (en) * 2019-10-24 2020-01-31 贵州医科大学 diphenyl ether chalcone tubulin inhibitor and preparation method and application thereof
CN110734367B (en) * 2019-10-24 2022-06-24 贵州医科大学 Diphenyl ether chalcone tubulin inhibitor and preparation method and application thereof
CN112961096A (en) * 2021-02-05 2021-06-15 安徽医科大学 Chalcone tryptophan derivatives with improved cisplatin nephrotoxicity and antitumor activity
CN112961096B (en) * 2021-02-05 2023-05-30 安徽医科大学 Chalcone tryptophan derivatives with cisplatin nephrotoxicity and antitumor activity
CN115624544A (en) * 2022-12-02 2023-01-20 甘肃中医药大学 Application of chalcone analogue as active substance in preparation of antitumor drugs

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