CN103864734A - Synthesis and application of novel 4,6-dihydroxy-3(2H)-benzofuranone derivatives - Google Patents

Synthesis and application of novel 4,6-dihydroxy-3(2H)-benzofuranone derivatives Download PDF

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CN103864734A
CN103864734A CN201210531573.8A CN201210531573A CN103864734A CN 103864734 A CN103864734 A CN 103864734A CN 201210531573 A CN201210531573 A CN 201210531573A CN 103864734 A CN103864734 A CN 103864734A
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dimethoxy
benzofuranone
benzofuranones
analog derivative
nitrophenyl
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郁彭
吕蕾
王义乾
贾海永
吕建
苑鹏
温少鹏
邢建波
郭娜
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Tianjin University of Science and Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
    • C07D307/83—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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Abstract

The invention relates to a preparation method and an activity research of novel substituted 4,6-dihydroxy-3(2H)-benzofuranone derivatives. With m-trihydroxybenzene as a raw material and through a Friedel-Crafts acylation reaction, an alkali catalytic cyclization reaction, an electrophilic substitution reaction, an aldol condensation reaction and a series of reactions, the aurone derivatives with potential biological activity are obtained.

Description

4 of a kind of novelty, the synthetic and application of 6-dihydroxyl-3 (2H)-benzofuranone analog derivative
Technical field
The present invention relates to 4 of new replacement, the preparation method of 6-dihydroxyl-3 (2H)-benzofuranone derivatives and active research.
Technical background
Aurones is the secondary metabolite of plant, belongs to the one of flavonoid, and aurones is less in distributed in nature, is mainly present in the flower and fruit of plant, and typical aurones class natural product has aureusidin, maritimetin, sulphuretin etc.The bioactivity research of benzofuran compounds and derivative thereof is scarcely out of swaddling-clothes at present, and the report of existing antitumor, anti-oxidant aspect medical, anti-Alzheimer disease etc., agriculturally finds that aurones has the activity of weeding.Aurones analog derivative can be found lead compound and obtain through structural modification from natural phant, and polytype reaction can occur on its furan nucleus and phenyl ring, therefore very active with the synthetic and active research of cumarone and derivative thereof at present.
Be exactly take Phloroglucinol as raw material herein, the series reaction such as ring-closure reaction by friedel-crafts acylation, base catalysis, electrophilic substitution reaction, aldol reaction obtain having the aurones analog derivative of potential source biomolecule activity.
Invention summary
First, the invention provides formula (I) compound
Figure BSA00000821194100011
Formula (I)
Wherein R 1representative replace five, six-ring.
R 1be preferably: phenyl ring, para hydroxybenzene, a hydroxybenzene, o-hydroxy, to methylbenzene, p-nitrophenyl, ortho-nitrophenyl, to fluorobenzene, to chlorobenzene, to bromobenzene, to anisole, meta-methoxy benzene, O-methoxy benzene, to cyano group benzene, to trifluoromethylbenzene, cumic aldehyde, to propenylbenzene, furan nucleus, thiphene ring, pyridine ring.
R 2be preferably: bromine, iodine.
Specilization compound of the present invention comprises
1) 2-phenylmethylene-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
2) 2-(4-phenol methylene)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
3) 2-(3-phenol methylene)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
4) 2-(2-phenol methylene)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
5) 2-(4-methylbenzene methylene radical)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
6) 2-(4-oil of mirbane methylene radical)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
7) 2-(3-oil of mirbane methylene radical)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
8) 2-(4-fluorobenzene methylene radical)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
9) 2-(4-chlorobenzene methylene radical)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
10) 2-(4-bromobenzene methylene radical)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
11) 2-(4-anisole methylene radical)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
12) 2-(3-anisole methylene radical)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
13) 2-(2-anisole methylene radical)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
14) 2-(4-cyano group α-tolylene)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
15) 2-(4-trifluoromethyl α-tolylene)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
16) 2-(4-isopropyl benzene methylene radical)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
17) 2-(4-tert.-butylbenzene methylene radical)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
18) 2-(styryl methylene radical)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
19) 2-(2-furyl methylene radical)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
20) 2-(2-thienyl methene)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
21) 2-(4-pyridyl methylene radical)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
22) 2-(2-naphthyl methylene)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
23) 2-phenylmethylene-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
24) 2-(4-phenol methylene)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
25) 2-(3-phenol methylene)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
26) 2-(2-phenol methylene)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
27) 2-(4-methylbenzene methylene radical)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
28) 2-(4-oil of mirbane methylene radical)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
29) 2-(3-oil of mirbane methylene radical)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
30) 2-(4-fluorobenzene methylene radical)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
31) 2-(4-chlorobenzene methylene radical)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
32) 2-(4-bromobenzene methylene radical)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
33) 2-(4-anisole methylene radical)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
34) 2-(3-anisole methylene radical)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
35) 2-(2-anisole methylene radical)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
36) 2-(4-cyano group α-tolylene)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
37) 2-(4-trifluoromethyl α-tolylene)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
38) 2-(4-isopropyl benzene methylene radical)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
39) 2-(4-tert.-butylbenzene methylene radical)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
40) 2-(styryl methylene radical)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
41) 2-(2-furyl methylene radical)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
42) 2-(2-thienyl methene)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
43) 2-(4-pyridyl methylene radical)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
44) 2-(2-naphthyl methylene)-4, bromo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
Detailed Description Of The Invention
The synthetic route of formula (I)
Figure BSA00000821194100031
Illustrate 1
The chloro-1-of 2-(2,4,6-trihydroxy-phenyl) ethyl ketone
Under anhydrous condition, by Phloroglucinol (10.0g, 79.30mmol) with 1 of 80mL, 2-ethylene dichloride dissolves, under 0 ℃ of stirring, slowly add aluminum chloride (21g, 158.59mmol) to stir after 5 minutes, dropwise drip chloroacetyl chloride (10.8g, 95.15mmol) dropwise half an hour, the reflux at 90 ℃ that slowly heats up stirs 10h.After reacting completely, reaction mixture is poured in the frozen water of the 300mL that contains 12mL concentrated hydrochloric acid configuring in advance, vigorous stirring, leaves standstill, and separates out orange/yellow solid, and suction filtration obtains the chloro-1-of 2-(2,4,6-trihydroxy-phenyl) ethyl ketone.Yield 85%.
1H-NMR(d6-DMSO?400MHz)：δ/ppm?4.98(s，2H)，5.85(s，2H)，10.54(s，1H)，12.07(s，2H).
Illustrate 2
4,6-dihydroxyl-3 (2H)-benzofuranone
In the 100mL round-bottomed flask that reflux condensing tube is housed, add anhydrous methanol 50mL, under constantly stirring, add successively the chloro-1-(2 of 2-in normal temperature, 4,6-trihydroxy-phenyl) ethyl ketone (5.0g, 24.68mmol), sodium-acetate (4.3g, 51.83mmol), after by round-bottomed flask at 65 ℃ of back flow reaction 3h.After reacting completely, be spin-dried for methyl alcohol, add water to stir, leave standstill, separate out orange red solid, suction filtration, obtains solid 4,6-dihydroxyl-3 (2H)-benzofuranone, yield 86%.
1H-NMR(d6-DMSO?400MHz)：δ/ppm?4.55(s，2H)，5.91(s，2H)，10.56(s，1H)，10.58(s，1H).
Illustrate 3
4,6-dimethoxy-3 (2H)-benzofuranone
In the round-bottomed flask of 50mL, add 4,6-dihydroxyl-3 (2H)-benzofuranone (0.5g, 3.01mmol), be dissolved in 6mLDMF.After at 0 ℃, add salt of wormwood (0.83g, 6.02mmol), methyl iodide (0.64g, 4.51mmol), reacts 5h at normal temperatures after adding.After reacting completely, add water, dichloromethane extraction, separates organic phase, with anhydrous sodium sulfate drying, sherwood oil: ethyl acetate=3: 1,200 order purification by silica gel column chromatography, obtain yellow look solid 4,6-dimethoxy-3 (2H)-benzofuranone 0.5g, yield 86%.
1H-NMR(d6-DMSO?400MHz)：δ/ppm?3.82(s，3H)，3.85(s，3H)，4.66(s，2H)，6.17(s，1H)，6.36(s，1H).
Illustrate 4
Iodo-3 (the 2H)-benzofuranones of 4,6-dimethoxy-7-
4,6-dimethoxy-3 (2H)-benzofuranone (0.2g, 1.03mmol) is dissolved in 1mLDMF, under constantly stirring, in adding N-iodosuccinimide (0.28g, 1.24mmol), stirs at normal temperatures 6h.After reacting completely, add unsaturated carbonate clock solution and ethyl acetate extraction, separate organic phase, with anhydrous sodium sulfate drying, sherwood oil: ethyl acetate=2: 1,200 order purification by silica gel column chromatography, obtains yellow solid 4, iodo-3 (the 2H)-benzofuranone 0.23g of 6-dimethoxy-7-, yield 68%.
1H-NMR(d6-DMSO?400MHz)：δ/ppm?3.93(s，3H)，3.98(s，3H)，4.75(s，2H)，6.38(s，1H).
Illustrate 5
2-(4-anisole methylene radical)-4, iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-
By 4, iodo-3 (2H)-benzofuranone (0.2g of 6-dimethoxy-7-, 0.62mmol) be dissolved in 15mL methyl alcohol, add aubepine (0.11g, 0.75mmol), at room temperature stir 3 hours after slowly adding 30% potassium hydroxide solution 2mL at 0 ℃.After TLC detection reaction is complete, cross filter solid, filter cake obtains yellow solid 2-(4-anisole methylene radical)-4 by a small amount of washed with methanol, iodo-3 (the 2H)-benzofuranone 0.19g of 6-dimethoxy-7-.Productive rate: 70%.
1H?NMR(CDCl 3?400MHz)：δ/ppm?6.94(s，1H)，7.28(s，1H)，7.44-7.50(m，3H)，7.75-7.78(de，1H)，7.92(s，1H)，7.94(m，2H).
Illustrate 6
The experiment that 4,6-dihydroxyl-3 (2H)-benzofuranone analog derivative suppresses K562, TH-29, HepG2 selectivity
Cell K562, HT-29, HepG2 are purchased from Shanghai cell bank, get in K562, TH-29, the HepG2 cell of growth logarithmic phase and are inoculated in 96 orifice plates, every hole 5 × 10 3individual cell/100 μ L at 37 ℃, passes into 5% CO simultaneously 2under condition, cultivate 24 hours.Medicine is dissolved in dimethyl sulfoxide (DMSO) and prepares 5 different pharmaceutical concentration in order to measuring (drug level scope is 0-10 μ M), the drug solution of getting 0.5 each concentration gradient of μ L adds in 96 orifice plates and at 37 ℃, continues to cultivate 48 hours, every hole adds the tetramethyl-azo azoles indigo plant (MTT) of 0.5g/mL, measures the optical density(OD) OD value in 96 each hole of orifice plate under 490 and 630 wavelength.3-4 parallel hole established in each test, repeats 3 times.IC 50in value representation cell to be measured, there is 50% the cell count corresponding drug level when suppressed of growing.
The inhibiting experimental result of 4,6-dihydroxyl-3 (2H)-benzofuranone analog derivative to K562, HepG2, HT-29 cell proliferation
Figure BSA00000821194100051
Medicine growth inhibition ratio (%)=(the average OD value of the average OD value-medication of solution control group group) average OD value of/control group to cell, the then IC of the growth inhibition ratio to cell (%) calculating medicine according to different pharmaceutical concentration 50value.
We choose K562, HepG2, the HT-29 cancer cells as experiment, can be found out by chart data: compound 6,15,21,30 couples of K562, HepG2 and HT-29 have optionally restraining effect.
Fig. 1 is the proton nmr spectra analysis chart of the chloro-1-of compound 2-(2,4,6-trihydroxy-phenyl) ethyl ketone;
Fig. 2 is compound 4, the proton nmr spectra analysis chart of 6-dihydroxyl-3 (2H)-benzofuranone;
Fig. 3 is compound 4, the proton nmr spectra analysis chart of 6-dimethoxy-3 (2H)-benzofuranone;
Fig. 4 is compound 4, the proton nmr spectra analysis chart of iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-;
Fig. 5 is compound 2-(4-anisole methylene radical)-4, the proton nmr spectra analysis chart of iodo-3 (the 2H)-benzofuranones of 6-dimethoxy-7-.

Claims (7)

1.4,6-dimethoxy-3 (2H)-benzofuranone analog derivative, is characterized in that: the general structure of derivative is as follows:
Figure FSA00000821194000011
Wherein R 1representative contains any of any and heterocycle in substituent phenyl ring, R 2represent iodine and bromine.
2. the compound under claim structure 1 has the release of antitumor, antibacterial, resisting cardiovascular disease, adjusting neurotransmitter, anti-oxidant, anti-diabetic etc. and other biological activity.
3. according to claim 14,6-dimethoxy-3 (2H)-benzofuranone analog derivative is R 1for phenyl ring, para hydroxybenzene, a hydroxybenzene, o-hydroxy, to methylbenzene, p-nitrophenyl, ortho-nitrophenyl, to fluorobenzene, to chlorobenzene, to bromobenzene, to anisole, meta-methoxy benzene, O-methoxy benzene, to cyano group benzene, to trifluoromethylbenzene, cumic aldehyde, to propenylbenzene, furan nucleus, thiphene ring, pyridine ring, R 2for iodine.
4. according to claim 14,6-dimethoxy-3 (2H)-benzofuranone analog derivative is R 1for phenyl ring, para hydroxybenzene, a hydroxybenzene, o-hydroxy, to methylbenzene, p-nitrophenyl, ortho-nitrophenyl, to fluorobenzene, to chlorobenzene, to bromobenzene, to anisole, meta-methoxy benzene, O-methoxy benzene, to cyano group benzene, to trifluoromethylbenzene, cumic aldehyde, to propenylbenzene, furan nucleus, thiphene ring, pyridine ring, R 2for bromine.
5. according to claim 14,6-dimethoxy-3 (2H)-benzofuranone analog derivative synthetic route is as follows:
Figure FSA00000821194000012
Wherein R 1representative contains any of any and heterocycle in substituent phenyl ring, R 2represent bromine and iodine.
According to described in claim 4, the preparation method of 6-dihydroxyl-3 (2H)-benzofuranone, it is characterized in that: Phloroglucinol is 1: 1.2: 2 with the amount ratio of chloroacetyl chloride, aluminum chloride, reaction solvent is 1,2-ethylene dichloride, temperature of reaction is preferably 90-100 ℃, reaction times 8-10 hour.
The application of 7.4,6-dimethoxy-3 (2H)-benzofuranone analog derivative in the release of antitumor, antibacterial, the resisting cardiovascular disease of preparation, adjusting neurotransmitter, anti-oxidant, anti-diabetic.
CN201210531573.8A 2012-12-07 2012-12-07 Synthesis and application of novel 4,6-dihydroxy-3(2H)-benzofuranone derivatives Pending CN103864734A (en)

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CN110498739A (en) * 2019-09-12 2019-11-26 南华大学 A method of synthesis 6- hydroxyl -2,3,4- trimethoxy-alpha-chloro acetophenone
CN111925377A (en) * 2020-08-31 2020-11-13 上海应用技术大学 Para-substituted dihydrofurocoumarin neuraminidase inhibitor and preparation method and application thereof
US10899727B2 (en) 2016-04-11 2021-01-26 Middle Tennessee State University Therapeutic aurones
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105037305A (en) * 2015-02-05 2015-11-11 南京工业大学 5-hydroxy-2'-nitroaurone or 5-hydroxy-4'-nitroaurone derivatives and application thereof
CN105037305B (en) * 2015-02-05 2017-09-29 南京工业大学 The nitro aurones of 5 hydroxyl 2 ' or the nitro aurones derivative of 5 hydroxyl 4 ' and its application
US10899727B2 (en) 2016-04-11 2021-01-26 Middle Tennessee State University Therapeutic aurones
US11286245B2 (en) 2016-04-11 2022-03-29 Middle Tennessee State University Therapeutic aurones
CN110498739A (en) * 2019-09-12 2019-11-26 南华大学 A method of synthesis 6- hydroxyl -2,3,4- trimethoxy-alpha-chloro acetophenone
CN111925377A (en) * 2020-08-31 2020-11-13 上海应用技术大学 Para-substituted dihydrofurocoumarin neuraminidase inhibitor and preparation method and application thereof
CN111925377B (en) * 2020-08-31 2022-05-31 上海应用技术大学 Para-substituted dihydrofurocoumarin neuraminidase inhibitor and preparation method and application thereof
CN114835664A (en) * 2022-03-25 2022-08-02 湖南大学 Novel trans-styryl benzofuranone compound and efficient synthesis method thereof

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