CN102796023A - Hydrogenated amide ferulate compounds, and synthesis method and application thereof - Google Patents

Hydrogenated amide ferulate compounds, and synthesis method and application thereof Download PDF

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CN102796023A
CN102796023A CN201210262931XA CN201210262931A CN102796023A CN 102796023 A CN102796023 A CN 102796023A CN 201210262931X A CN201210262931X A CN 201210262931XA CN 201210262931 A CN201210262931 A CN 201210262931A CN 102796023 A CN102796023 A CN 102796023A
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acid amides
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刘幸海
赵卫光
翁建全
曹耀艳
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Zhejiang University of Technology ZJUT
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Zhejiang University of Technology ZJUT
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Abstract

The invention provides hydrogenated amide ferulate derivatives (I) with tobacco mosaic virus activity, and a preparation method and application thereof. The compounds provided by the invention have favorable effect for preventing and treating tobacco mosaic virus and the like, and thus, have wide application prospects.

Description

A kind of Hydroferulic acid amides, its compound method and application
Technical field
The present invention provides a kind of Hydroferulic acid amides, its preparation method and application.
 
Background technology
The carboxylic acid amide series bactericidal agent is the new series bactericidal agent of dividing of sterilant resistance Action Committee (FRAC) in 2005, comprising mandelic acidamide, cinnamide and Xie Ansuan acid amides three series bactericidal agents.Can know that from fig1 mandipropamid amine and HSDB 6915 not only have identical pharmacophore, and have similar skeleton structure.The position that is not both amido linkage wherein of two compounds skeleton structures is just opposite, and the group counter-rotating is medicinal design, particularly the extremely successful method in the amino acid drug design.Particularly the skeleton structure of mandelic acidamide compd A and HSDB 6915 is more similar, and the fungicidal activity of Phytophthora infestans is then improved 5 times than the sterilization of mandipropamid amine.It is reported that in addition mandelamide type compound still has better activity after the carbochain with amidocarbonylation one side prolongs.(hydrogenation) asafoetide acyl phenyl ethyl amine compounds that in view of the above acid amides of mandipropamid amine is overturn; Find that this compounds has good activity of resisting tobacco mosaic virus; When concentration is 500 mg/L, has the active and live body therapeutic action activity of live body provide protection that tobacco mosaic virus(TMV) infects.
 
Summary of the invention
The object of the present invention is to provide a kind of Hydroferulic acid amide derivatives, preparation method and use with excellent antiviral activity.
The structural formula of Hydroferulic acid amide derivatives of the present invention is following:
Figure 941719DEST_PATH_IMAGE001
formula (I)
Wherein, R 1Be selected from one or more C1 ~ C4 alkoxyl group, benzyloxy, nitro, preferably be selected from 3-methoxyl group, 3-nitro or 4-benzyloxy; R 2Be selected from benzyl, allyl group, propargyl.
The preparation method of Hydroferulic acid amide derivatives of the present invention, shown in following reaction equation:
Figure 7633DEST_PATH_IMAGE002
Wherein, R 1, R 2Definition as previously mentioned.Concrete; The final step reaction can be: the compound shown in compound shown in the formula II and the formula (III) is under the basic catalyst effect; React in organic solvent at 0-100 ℃, reaction finishes the Hydroferulic acid amides that the back separation and purification obtains formula (I); Compound (II): compound (III): the mol ratio of basic catalyst is 1:0.1-10:0.05-0.2, is preferably 1:1-5:0.05-0.2; Said basic catalyst be selected from following one or more: salt of wormwood, sodium hydrogencarbonate, sodium hydroxide; Said organic solvent be selected from following one or more: N, N N, THF, 1,4-dioxane, acetone, methylene dichloride.
Hydroferulic acid amide derivatives of the present invention can be used for preparing antiviral agent, plant virus agent especially, more particularly resisting tobacco mosaic virus agent.
 
Embodiment
3,4-dimethoxyphenylacetic acid synthetic: with 3,4-dimethoxy-cinnamic acid (15 g, 72 mmol) is dissolved in 150 mL ETHYLE ACETATE and the 150 mL ethanol mixed solvent, is heated to backflow, and solid dissolves gradually.Standard atmosphere is depressed and is fed nitrogen and remove the air in the reaction system, adds 1.5 g, 10% palladium carbon subsequently, and hydrogen replacement nitrogen continues to feed, with bubbler keep watch on gas feed situation and once with isolate from outer air.Keep about 72 h of reflux to react completely.Suction filtration separates wherein palladium carbon, and organic solvent is sloughed in decompression, obtains white solid 13.92 g, productive rate 92%, 94 ° of C of fusing point 92 –.
N-(2-substituted-phenyl-2-hydroxyethyl)-3-(3, the 4-Dimethoxyphenyl) propionic acid amide IISynthetic: with (1.44 g, 6.84 mmol) 3-(3, the 4-Dimethoxyphenyl) propionic acid 1With 15 mL THF dissolving, cryosel is bathed 20 ° of C of its Leng Que Zhi –, under this temperature, adds N-methylmorpholine (0.7 g, 7.18 mmol) successively, and isobutyl chlorocarbonate (0.89 g, 6.84 mmol), cryosel are bathed and stirred 30 min down.With (7.18 mmol) 2-amino-4-substituted-phenyl ethanol ( IV) be dissolved in the anhydrous THF of 25 mL, slowly be added drop-wise in the above-mentioned reaction solution, dropwise and stir 1 h about 10 ° of C of ， Zai –, rise to room temperature, continue to stir 12 h.Reaction finishes back decompression precipitation and removes THF, and the solid with 40 mL methylene dichloride dissolving precipitation obtains adds 35 mL saturated nacl aqueous solutions, extraction; Merge organic layer, anhydrous magnesium sulfate drying filters; Precipitation, the quick preparative hplc of middle pressure is separated (sherwood oil+ETHYLE ACETATE), obtains white solid IIa-IIdPhysicochemical data with 1H NMR data are following:
N-[2-(3-methoxyl group) phenyl-2-hydroxyethyl]-3-(3, the 4-Dimethoxyphenyl) propionic acid amide IIa, yellow solid, yield 85%, 113 ° of C of fusing point 112 –. 1H?NMR?(400?MHz,?CDCl 3)? δ?2.49?(d,? J?=?7.7?Hz,?2H,?C H 2CH 2),?2.91?(t,?2H, ?J?=?7.7?Hz,?2H,?C H 2CH 2),?3.32?(s,?1H,?ArCHC H 2),?3.69?(s,?1H,?ArCHC H 2),?3.83?(s,9H,? p-C H 3O+p-C H 3O+p-C H 3O),?4.77?(s,?1H,?ArC H),?5.80?(br,?1H,?CON H),?7.01–6.67?(m,?6H,?Ar- H)。
N-[2-(4-benzyloxy) phenyl-2-hydroxyethyl]-3-(3, the 4-Dimethoxyphenyl) propionic acid amide IIb, yellow solid, yield 67%, 133 ° of C of fusing point 132 –. 1H?NMR?(400?MHz,?CDCl 3)? δ?2.45?(t,? J?=?7.5?Hz,?2H,?CH 2CH 2),?2.91?(t,? J?=?7.4?Hz,?2H,?CH 2CH 2),?3.24?(t,? J?=?11.2?Hz,?1H,?ArCHCH 2),?3.80–3.66?(m,?1H,?ArCHCH 2),?3.88?(s,?6H,?p-CH 3O+?o-CH 3O),?4.22?(d,? J?=?11.5?Hz,?1H,?ArCHCH 2),?4.37?(d,? J?=?8.7?Hz,?1H,?ArCH 2),?4.48?(d,? J?=?11.6?Hz,?1H,?ArCHCH 2),?5.10?(s,?2H,?ArCH 2),?5.86?(br,?1H,?CONH),?6.84–6.69?(m,?3H,?Ar-H),?7.53–7.22?(m,?10H,?Ar-H)。
N-[2-(3-nitrophenyl)-2-hydroxyethyl]-3-(3, the 4-Dimethoxyphenyl) propionic acid amide IIc, yellow oil, yield 82%. 1H?NMR?(400?MHz,?CDCl 3)? δ?2.50?(t,?2H,? J?=?7.6?Hz,?C H 2CH 2),?2.90?(t，2H,? J?=?7.6?Hz,?CH 2C H 2),?3.30–3.36?(m,?1H,?C H 2CH),?3.63–3.68?(m,?1H,?C H 2CH),?3.85?(s,?6H,?p-C H 3O+o-C H 3O),?4.90?(dd,?1H,? J?=?2.4?Hz,? J?=?7.2?Hz,?CH 2C H),?6.03?(br,?1H,?CON H),?6.70–6.79?(m,?3H,?Ar- H),?7.63–8.20?(m,?4H,?Ar- H)。
N-(2-(4-nitrophenyl)-2-hydroxyethyl)-3-(3, the 4-Dimethoxyphenyl) propionic acid amide IId, white solid, yield 51 %, 135 ° of C of fusing point 133 –. 1H?NMR?(400?MHz,?CDCl 3)? δ?2.47–2.52?(m,?2H,?C H 2CH 2),?2.92?(t,?2H,? J?=?7.2?Hz,?CH 2C H 2),?3.26–3.32?(m,?1H,?C H 2CH),?3.66–3.71?(m,?1H,?C H 2CH),?3.87?(s,?6H,?p-C H 3O+o-C H 3O),?4.91?(dd,?1H,? J?=?2.4?Hz,? J?=?6.8?Hz,?CH 2C H),?5.73?(s,?1H,?CON H),?6.71–6.81?(m,?3H,?Ar- H),?7.45?(d,?2H,? J?=?8.8?Hz,?Ar- H),?8.17?(d,?1H,? J?=?8.8?Hz,?Ar- H)。
 
Target compound N-(2-substituted-phenyl-2-alkoxyethyl)-3-(3, the 4-Dimethoxyphenyl) propionic acid amide Ia- Ig: will go up the acid amides that a step obtains IIBe dissolved in 35 mL methylene dichloride, add 1.3 g massfractions and be 30% aqueous sodium hydroxide solution, the Tetrabutyl amonium bromide of catalytic amount, reflux dripped corresponding halides R after 15 minutes 2X (X is a halogen, is preferably Br and I).Dropwise reflux 8 h.After reaction finishes, add the dilution of 20 mL water, dichloromethane extraction (20 mL * 3) merges organic layer, anhydrous magnesium sulfate drying.Filter, precipitation, the quick preparative hplc of middle pressure separate (sherwood oil: ETHYLE ACETATE=3:2) title product, promptly formula ( I) compound.
 
Embodiment 1: N-(2-(benzyloxy)-2-(3-p-methoxy-phenyl) ethyl)-3-(3, the 4-Dimethoxyphenyl) propionic acid amide Ia: with midbody acid amide 2a(2.1 mmol) is dissolved in 35 mL methylene dichloride, adds 1.3 g massfractions and be 30% sodium hydroxide solution, the Tetrabutyl amonium bromide of catalytic amount (0.07 g, 0.21 mmol), and reflux dripped benzyl bromine (0.92 g, 5.34 mmol) after 15 minutes.Dropwise reflux 8 h.After reaction finishes, add the dilution of 20 mL water, dichloromethane extraction (20 mL * 3) merges organic layer, anhydrous magnesium sulfate drying.Filter, precipitation, the quick preparative hplc of middle pressure is separated (sherwood oil: ETHYLE ACETATE=3:2), get faint yellow oily thing ,Productive rate 85 %. 1H?NMR?(400?MHz,?CDCl 3)? δ?2.42?(t,? J?=?7.7?Hz,?2H,?CH 2CH 2),?2.88?(t,? J?=?7.7?Hz,?2H,?CH 2CH 2),?3.25–3.16?(m,?1H,?ArCHCH 2),?3.77–3.69?(m,?1H,?ArCHCH 2),?3.87–3.80?(m,?9H,?p-CH 3O?+?p-CH 3O?+?o-CH 3O),?4.22?(d,? J?=?11.6?Hz,?1H,?ArCH),?4.38?(dd,? J?=?8.8?Hz,? J?=?3.7?Hz,?1H,?ArCHCH 2),?4.49?(d,? J?=?11.6?Hz,?1H,?ArCH),?5.81?(s,?1H,?CONH),?6.80–6.70?(m,?3H,?Ar-H),?6.87–6.81?(m,?3H,?Ar-H),?7.38–7.24?(m,?5H,?Ar-H).?HRMS?(ESI)?m/z?Calcd?for?C 27H 31NO 5Na +?[M+Na] +?472.2100,?found?472.2091。
Embodiment 2: N-(2-(benzyloxy)-2-(3-nitrophenyl) ethyl)-3-(3, the 4-Dimethoxyphenyl) propionic acid amide Ib: faint yellow solid, productive rate 82 %. 1H?NMR?(400?MHz,?CDCl 3)? δ?2.44?(t,? J?=?7.6?Hz,?2H,?CH 2CH 2),?2.88?(t,? J?=?7.6?Hz,?2H,?CH 2CH 2),?3.28–3.22?(m,?1H,?CH 2CH),?3.75–3.72?(m,?1H,?CH 2CH),?3.86?(s,?3H,?o-CH 3O),?3.88?(s,?3H,?p-ArOCH 3),?4.28?(d,? J?=?11.5?Hz,?1H,?Ar-CH),?4.51?(d,? J?=?11.5?Hz,?1H,?Ar-CH),?4.56?(d,? J?=?8.0?Hz,?1H,?CH 2CH),?5.81?(br,?1H,?CONH),?6.84–6.72?(m,?3H,?Ar-H),?7.43–7.32?(m,?4H,?Ar-H),?7.57?(t,? J?=?8.0?Hz,?1H,?Ar-H),?7.67?(d,? J?=?8.0?Hz,?1H?Ar-H),?8.21?(d,? J?=?8.0?Hz,?1H,?Ar-H),?8.27?(s,?1H,?Ar-H).?HRMS?(ESI)?m/z?Calcd?for?C 26H 28N 2O 6Na +?[M+Na] +?487.1845,?found?487.1835。
Embodiment 3: N-(2-(alkynes propoxy-)-2-(3-nitrophenyl) ethyl)-3-(3, the 4-Dimethoxyphenyl) propionic acid amide Ic: faint yellow oily thing, productive rate 95 %. 1H?NMR?(400?MHz,?CDCl 3)? δ?2.40?(m,?3H,?CH 2CH 2?+?C≡CH),?2.80?(d,? J?=?7.6?Hz,?2H,?CH 2CH 2),?3.22–3.08?(m,?1H,?ArCHCH 2),?3.66?(m,?1H,?ArCHCH 2),?3.88–3.72?(m,?7H,?p-CH 3O?+o-CH 3O+OCH 2CH),?4.09?(m,?1H,?OCH 2CH),?4.64?(dd,? J?=?3.0?Hz,? J?=?8.0?Hz,?1H,?ArCHCH 2),?6.02?(br,?1H,?CONH),?6.78–6.61?(m,?3H,?Ar-H),?7.46?(s,?1H,?Ar-H),?7.56?(s,?1H,?Ar-H),?8.24–8.03?(m,?2H,?Ar-H).?HRMS?(ESI)?m/z?Calcd?for?C 22H 24N 2O 6Na +?[M+Na] +?435.1532,?found?435.1526。
Embodiment 4: N-(2-(benzyloxy)-2-(4-nitrophenyl) ethyl)-3-(3, the 4-Dimethoxyphenyl) propionic acid amide Id: faint yellow solid ,Productive rate 77 %, 135 ° of C of fusing point 133 –. 1H?NMR?(400?MHz,?CDCl 3)? δ?2.43?(t,?2H,? J?=?7.6?Hz,?CH 2CH 2),?2.87?(t,?2H,? J?=?7.6?Hz,?CH 2CH 2),?3.19–3.26?(m,?1H,?CH 2CH),?3.67–3.73?(m,?1H,?CH 2CH),?3.83?(s,?3H,?o-ArOCH 3),?3.85(s,?3H,?p-ArOCH 3),?4.26?(d,?1H,? J?=?11.6?Hz,?Ar-CH),?4.47?(d,?1H,? J?=?11.6?Hz,?Ar-CH),?4.54(dd,?1H,? J?=?4?Hz, ?J?=?8?Hz,?CH 2CH),?5.86?(br,?1H,?CONH),?6.71–6.78?(m,?3H,?Ar-H),?7.25–7.38?(m,?5H,?Ar-H),?7.50?(d,?2H,? J?=?8.4?Hz,?Ar-H),?8.21?(d,?2H, ?J?=?8.4?Hz,?Ar-H).?HRMS?(ESI)?m/z?Calcd?for?C 26H 28N 2O 6Na +?[M+Na] +?487.1845,?found?487.1836。
Embodiment 5: N-(2-(benzyloxy)-2-(4-benzyloxy phenyl) ethyl)-3-(3, the 4-Dimethoxyphenyl) propionic acid amide Ie: white solid, productive rate 68 %, 108 ° of C of fusing point 107 –. 1H?NMR?(400?MHz,?CDCl 3)? δ?2.45?(t,? J?=?8.0?Hz,?2H,?CH 2CH 2),?2.92?(t,? J?=?8.0?Hz,?2H,?CH 2CH 2),?3.30–3.21?(m,?1H,?ArCHCH 2),?3.77–3.69?(m,?1H,?ArCHCH 2),?3.87?(s,?3H,?o-CH 3O),?3.89?(s,?3H,?p-CH 3O),?4.23?(d,? J?=?11.6?Hz,?1H,?ArCH 2),?4.38?(dd,? J?=?8.8?Hz,? J?=?3.8?Hz,?1H,?ArCHCH 2),?4.48?(d,? J?=?11.6?Hz,?1H,?ArCH 2),?5.11?(s,?2H,?ArCH 2),?5.83?(br,?1H,?CONH),?6.84–6.74?(m,?3H,?Ar-H),?7.02?(d,? J?=?8.4?Hz,?2H,?Ar-H),?7.46–7.25?(m,?8H,?Ar-H),?7.48?(d,? J?=?7.4?Hz,?2H,?Ar-H).?HRMS?(ESI)?m/z?Calcd?for?C 33H 35NO 5Na +?[M+Na] +?548.2408,?found?548.2405。
Embodiment 6: N-(2-(alkynes propoxy-)-2-(4-benzyloxy phenyl) ethyl)-3-(3, the 4-Dimethoxyphenyl) propionic acid amide If: white solid, productive rate 68 %, 94 ° of C of fusing point 93 –. 1H?NMR?(400?MHz,?CDCl 3)? δ2.41?(s,?1H,?C≡CH),?2.48?(t,?2H,? J?=?7.6?Hz,?CH 2CH 2),?2.92?(t,?2H,? J?=?7.6?Hz,?CH 2CH 2)?,?3.13–3.20?(m,?1H?,?CH 2CH),?3.70–3.78?(m,?1H,?CH 2CH),?3.82?(d,?1H,? J?=?2.0?Hz,?OCH 2),?3.86(s,?3H,?o-ArOCH 3),?3.88?(s,?3H,?p-ArOCH 3),?4.08?(d,?1H,? J?=?2.0?Hz,?OCH 2),?4.47?(dd,?1H,? J?=?7.6?Hz,? J?=?9.2?Hz,?CH 2CH),?5.06?(s,?2H,?p-ArOCH 2Ph),?5.87?(br,?1H,?NH),?6.74–6.81(m,?3H,?Ar-H),?6.96?(d,?2H,? J?=?8.8?Hz,?Ar-H),?7.21?(d,?2H,? J?=?8.8?Hz,?Ar-H),?7.32–7.44?(m,?5H,?Ar-CH).?HRMS?(ESI)?m/z?Calcd?for?C 29H 31NO 5Na +?[M+Na] +?496.2094,?found?496.2090。
Embodiment 7: N-(2-(allyloxy)-2-(4-benzyloxy phenyl) ethyl)-3-(3, the 4-Dimethoxyphenyl) propionic acid amide Ig: white solid, productive rate 65 %, 69 ° of C of fusing point 68 –. 1H?NMR?(400?MHz,?CDCl 3)? δ?2.57–2.41?(m,?2H,?CH 2CH 2),?2.92?(d,? J?=?7.1?Hz,?2H,?CH 2CH 2),?3.38–3.15?(m,?2H,?CH 2CH),?3.78–3.58?(m,?2H,?CH 2CH),?3.97–3.81?(m,?6H,?p-CH 3O+o-CH 3O),?4.74?(d,? J?=?7.8?Hz,?1H,?CH 2CH),?5.07?(s,?1H,?CH 2CH),?5.20?(dd,? J?=?21.0,?13.9?Hz,?1H,?CHPh),?5.85?(br,?1H,?CONH),?6.87–6.70?(m,?3H,?CH=CH 2),?6.96?(s,?1H,?Ar-H),?7.53–7.16?(m,?7H,?Ar-H).?HRMS?(ESI)?m/z?Calcd?for?C 29H 33NO 5Na +?[M+Na] +?498.2251,?found?498.2258。
 
Biological activity test embodiment: the antiviral activity test of target compound
Virus is purified: adopt the Gooding method, choose more than 3 weeks of inoculation TMV systemic infection host Nicotiana glutinosaL .The plant upper blade, homogenate in phosphoric acid buffer, double gauze filters, and 1000 γ pm are centrifugal, handle through 2 polyoxyethylene glycol, and centrifugal again, deposition suspends with phosphoric acid buffer, promptly obtains the crude extract of T M V.Whole test is carried out under 4 ℃.Absorbance with ultraviolet spectrophotometer mensuration 260nm wavelength calculates virus concentration according to formula.
Wherein E representes optical extinction coefficient, and promptly during wavelength 260nm, concentration is the suspension-s of 0.1% (1mg/ml), the photoabsorption when light path is 1cm (optical density(OD)) value.The E of TMV
Figure 268030DEST_PATH_IMAGE004
is 3.1.
The stripped therapeutic action that medicament infects TMV: TMV is diluted to 6 * 10 with phosphoric acid buffer -3Mg/mL, artificial inoculation is in the of the right age blade that spreads silicon carbide (500 order), and inoculation back water washes the blade of inoculation.Treat that the blade face receive to do, cut, along arteries and veins in the blade to cuing open, about half leaf immerse respectively in test compound solution and the aqua sterilisa, represent treatment group and blank group respectively, take out behind the 30min.Place the cultivation of preserving moisture under optimal temperature and the illumination, observed and recorded incidence behind 3 ~ 4 d.
The live body provide protection that medicament infects TMV: select the consistent Nicotiana glutinosa of growing way, spread medicament at Zuo Banye gently with writing brush, right half leaf spreads aqua sterilisa and compares, 12h, treat that blade is done after, virus inoculation.Dip in writing brush and to get viral juice, concentration is 6 * 10 -3Mg/mL, artificial frictional inoculation are on the blade that spreads silicon carbide, and (full leaf) wiped 1 ~ 2 time along its offshoot direction gently on the blade face.The blade below is supported with palm or multilayer filter paper.The inoculation back is with the good blade of flowing water (or wash bottle) flushing inoculation.Promptly occur scab behind 3 ~ 4 d, when scab is counted easily, add up, the inhibiting rate calculation formula is following:
Inhibiting rate (%)=
Figure 760191DEST_PATH_IMAGE005
Table 1The tobacco mosaic disease cytotoxic activity result (500 ppm) of formula (I) compound
Figure 1817DEST_PATH_IMAGE006

Claims (5)

1. Hydroferulic acid amides, structure is shown in formula I:
Figure 201210262931X100001DEST_PATH_IMAGE001
（Ⅰ）
In the formula I:
Wherein said, R 1Be selected from one or more C1-C4 alkoxyl groups, benzyloxy, nitro; R 2Be selected from benzyl, allyl group, propargyl.
2. Hydroferulic acid amides as claimed in claim 1 is characterized in that R in the formula I 1Be selected from 3-methoxyl group, 3-nitro or 4-benzyloxy.
3. the method for preparing the said Hydroferulic acid amides of claim 1; Said method comprises: the compound shown in compound shown in the formula II and the formula (III) is under the basic catalyst effect; React in organic solvent at 0-100 ℃, reaction finishes the Hydroferulic acid amides that the back separation and purification obtains formula (I);
Figure 287100DEST_PATH_IMAGE002
（Ⅱ）
Figure 201210262931X100001DEST_PATH_IMAGE003
（Ⅲ）
R in the formula (II) 1, the R in the formula (III) 2Definition is with claim 1;
Compound (II): compound (III): the mol ratio of basic catalyst is 1:0.1-10:0.05-0.2;
Said basic catalyst be selected from following one or more: salt of wormwood, sodium hydrogencarbonate, sodium hydroxide;
Said organic solvent be selected from following one or more: N, N N, THF, 1,4-dioxane, acetone, methylene dichloride.
4. according to claim 1 or claim 2 triazole class compounds is in the application of preparation in the anti-plant virus agent.
5. application as claimed in claim 4 is characterized in that said anti-plant virus agent is used to prevent and treat tobacco mosaic virus(TMV).
CN201210262931XA 2012-07-27 2012-07-27 Hydrogenated amide ferulate compounds, and synthesis method and application thereof Pending CN102796023A (en)

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CN109369594A (en) * 2018-12-04 2019-02-22 贵州大学 A kind of myricetin derivative, preparation method and the usage containing ferulic amide
CN113801022A (en) * 2021-07-23 2021-12-17 贵州大学 Ferulic acid eugenol and isoeugenol heterozygote and application thereof

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CN109369594A (en) * 2018-12-04 2019-02-22 贵州大学 A kind of myricetin derivative, preparation method and the usage containing ferulic amide
CN109369594B (en) * 2018-12-04 2023-08-22 贵州大学 Myricetin derivative containing ferulic acid amide, and preparation method and application thereof
CN113801022A (en) * 2021-07-23 2021-12-17 贵州大学 Ferulic acid eugenol and isoeugenol heterozygote and application thereof
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