CN110041204A - A kind of resveratrol nitroethylene class compound and its preparation method and application - Google Patents

A kind of resveratrol nitroethylene class compound and its preparation method and application Download PDF

Info

Publication number
CN110041204A
CN110041204A CN201910284930.7A CN201910284930A CN110041204A CN 110041204 A CN110041204 A CN 110041204A CN 201910284930 A CN201910284930 A CN 201910284930A CN 110041204 A CN110041204 A CN 110041204A
Authority
CN
China
Prior art keywords
preparation
resveratrol
pterostilbene
nitroethylene
added
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
CN201910284930.7A
Other languages
Chinese (zh)
Inventor
阮班锋
郭伟云
李遥
葛为为
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hefei University of Technology
Original Assignee
Hefei University of Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hefei University of Technology filed Critical Hefei University of Technology
Priority to CN201910284930.7A priority Critical patent/CN110041204A/en
Publication of CN110041204A publication Critical patent/CN110041204A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/32—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups bound to acyclic carbon atoms and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a kind of resveratrol nitroethylene class compounds and its preparation method and application, are related to drug design and synthesis technical field, have following general formula:

Description

A kind of resveratrol nitroethylene class compound and its preparation method and application
Technical field:
The present invention relates to drug design and synthesis technical fields, and in particular to a kind of resveratrol nitroethylene class compound And its preparation method and application.
Background technique:
The hollow tubular structure that micro-pipe is made of tubulin and micro-pipe auxilin.Tubulin includes α and β sub- single Position, micro-pipe auxilin include MAP protein family, Tau albumen, micro-pipe anode tracking albumen etc..Micro-pipe is to constitute cytoskeleton One of main component, be almost present among all eukaryotic cells, maintain cellular morphology, intracellular matter transport, It plays a significant role in the physiology courses such as cell division and differentiation.Recent study discovery, the composition of micro-pipe and depolymerization etc. are abnormal Expression influences cell mitogen process, and abnormal protein expression causes the unbalance of micro-pipe dynamical system, plays to tumour Important function.Therefore, developing novel has more strongly active, more hypotoxicity and more effectively novel to cells of resistant tumors Antitubulin has great application prospect.
Resveratrol (3-4'-5-trihydroxystilbene), also known as resvertrol are a kind of natural polyphenol class chemical combination Object.The 1970s isolates and purifies from the root of hair leaf black false hellebore plant for the first time and is obtained, later again in polygonum cuspidate, peanut, mulberry fruit etc. This kind of composition is had found in plant.Resveratrol has been shown to have anti-oxidant, anti-inflammatory, antitumor, cardiovascular protection, nerve is protected The pharmacological actions such as shield, immunological regulation.Research has shown that resveratrol has the function of stablizing microtubule associated protein.Especially have potent Antitumaous effect, have an inhibiting effect, such as lymthoma to the growth of many tumor cell lines, myeloma, melanoma, breast cancer, Cancer of pancreas, colorectal cancer, liver cell and prostate cancer etc..
But resveratrol poorly water-soluble, bioavilability is lower, and relative activity is not high, and poor selectivity, a large amount of scientific researches Personnel are carried out modification transformation to it using resveratrol structure as parent nucleus and are desirably to obtain the higher lead compound of activity. M.Amarnath Reddy et al. design has synthesized a series of compounds containing nitroethylene based structures, and research finds that these are changed The polymerization of tubulin can effectively be inhibited by closing object, make cell cycle arrest in the G2/M phase of cell division cycle, be caused thin Born of the same parents' apoptosis is potential Antitubulin.
Summary of the invention:
Technical problem to be solved by the present invention lies in a kind of resveratrol nitroethylene class compound is provided, according to drug Principle of hybridization and structure-based drug molecule design concept, draw on the talan molecular skeleton possessed by resveratrol Enter nitroethylene based structures, obtains resveratrol nitroethylene analog derivative；And biological activity test is the result shows that this is white Veratryl alcohol nitrostyrolene class compound is to human gastric cancer cell line MGC803, Bel7402 SMMC-7721 and human breast carcinoma Cell line MDA-MB-231 has good inhibitory activity.
The following technical solution is employed for the technical problems to be solved by the invention to realize:
A kind of resveratrol nitroethylene class compound has following general formula:
R is selected from one of following groups in general formula:
The reaction equation and preparation method of above-mentioned resveratrol nitroethylene class compound include the following steps:
Reaction reagent and reaction condition: (i) R-Br, K2CO3, TABA, acetone, reflux, overnight；(ii)DMF,POCl3, second Nitrile, 0 DEG C of to room temperature, 2h；(iii)CH3NO2,NH4OAc,100℃,2h.
Step 1: pterostilbene being added in acetone, then Anhydrous potassium carbonate, tetrabutylammonium bromide and bromine is added in sequence respectively For alkane, oil bath heating to 55-58 DEG C of return stirring is reacted, and TLC contact plate monitors reaction process；It is filtered by vacuum after fully reacting, Filtrate is taken, column chromatography for separation (ethyl acetate: petroleum ether=1:4, v/v) obtains pterostilbene hydroxyl substitution derivative after concentrate drying Object；
Step 2: pterostilbene hydroxyl substitutive derivative and n,N-Dimethylformamide are added in acetonitrile, is placed in ice bath, Phosphorus oxychloride is slowly added dropwise, restores after being added dropwise to reacting at room temperature, is stirred to react 1h, TLC monitors response situation, works as pterostilbene Hydroxyl substitutive derivative stops reaction after having reacted immediately；Ice water is added into reaction system after reaction to be quenched, under stirring Sodium hydroxide solution tune pH is added to neutrality, faint yellow solid is precipitated after being stirred overnight, filters, drying, column chromatography for separation (dichloro Methane: petroleum ether=3:1, v/v) obtain pterostilbene hydroxyl substitution hydroformylation product；
Step 3: replacing hydroformylation product to be dissolved in nitromethane step 2 gained pterostilbene hydroxyl, ammonium acetate is added, instead System is answered to be heated to 100 DEG C of reflux under oil bath, TLC monitoring reaction is cooled to room temperature, with ethyl acetate and water after fully reacting It is extracted, collect organic phase and anhydrous Na is added2SO4Water removal, vacuum concentration, column chromatographic isolation and purification (ethyl acetate: petroleum Ether=1:5, v/v) obtain resveratrol nitrostyrolene analog derivative.
The ratio between pterostilbene, Anhydrous potassium carbonate, tetrabutylammonium bromide and amount of substance of brominated alkanes are 1 in the step 1: 1.2:1.2:1.2。
The ratio between amount of substance of pterostilbene hydroxyl substitutive derivative and phosphorus oxychloride is 1:1 in the step 2.
Every mM of pterostilbene hydroxyl substitutive derivative adds N,N-dimethylformamide 0.15mL in the step 2.
Pterostilbene hydroxyl replaces the ratio between amount of substance of hydroformylation product and ammonium acetate to be 1:2 in the step 3.
Above-mentioned resveratrol nitroethylene class compound is preparing the application in anticancer drug, especially to human gastric cancer cell line MGC803, Bel7402 SMMC-7721 and human breast cancer cell line MDA-MB-231 have good inhibitory activity.
The beneficial effects of the present invention are: the present invention designs and is prepared for resveratrol nitroethylene class compound, and by institute Resveratrol nitroethylene class compound processed be applied to anticancer drug preparation, and biological activity test as the result is shown its to people's stomach Cancerous cell line MGC803, Bel7402 SMMC-7721 and human breast cancer cell line MDA-MB-231 have good inhibition Activity, therefore the preparation of the resveratrol nitroethylene class compound is of great significance to new anticancer drug is filtered out.
Specific embodiment:
In order to be easy to understand the technical means, the creative features, the aims and the efficiencies achieved by the present invention, tie below Specific embodiment is closed, the present invention is further explained.
Embodiment 1
1,5- dimethoxy -3- ((E) -4- (methoxyl group) styryl) -2- (E)-nitroethenyl group) benzene (compound 1) Preparation
It weighs pterostilbene A (1.28g, 5mmol) to be dissolved in 100mL round-bottomed flask with acetone, is separately added into Anhydrous potassium carbonate (1.38g, 6mmol), tetrabutylammonium bromide (1.94g, 6mmol), bromomethane (380uL, 6mmol), back flow reaction, TLC contact plate Reaction process is monitored, to filter removing potassium carbonate after the reaction was completed, vacuum concentration, column chromatography for separation (ethyl acetate: petroleum ether= 1:5), white solid B is obtained.
B (811mg, 3mmol) is weighed to be dissolved in 100mL round-bottomed flask with acetonitrile, addition n,N-Dimethylformamide (DMF, 458 μ L), phosphorus oxychloride (280 μ L, 3mmol) is then slowly added dropwise；Restore after being added dropwise to reacting at room temperature, be stirred to react 1h, Stop immediately after system has been reacted.1000mL beaker is taken, 500mL ice water is added, then reaction solution is added dropwise wherein, stirring Lower addition sodium hydroxide solution is adjusted to neutrality, and faint yellow solid is precipitated after being stirred overnight, and filters, is dry, column chromatography for separation (dichloro Methane: petroleum ether=3:1) obtain yellow solid C.
It weighs C (2298mg, 1mmol) to be dissolved in 50mL round-bottomed flask with 15mL nitromethane, ammonium acetate is added (77.1mg, 1mmol), is heated to reflux and stirs, and TLC monitoring reaction, after fully reacting, reaction solution is extracted through ethyl acetate/water Afterwards, organic phase is taken, anhydrous Na is added2SO4It after water removal, filters, vacuum concentration, column chromatographic isolation and purification (ethyl acetate: petroleum ether =1:5), obtain target compound 1.Product 1 is yellow solid powder, yield 96%, fusing point: 152-157 DEG C.1H NMR (600MHz,DMSO-d6) δ 8.31 (d, J=13.3Hz, 1H), 7.89 (d, J=13.2Hz, 1H), 7.60 (d, J=8.7Hz, 2H), 7.43 (d, J=16.0Hz, 1H), 7.06 (d, J=16.0Hz, 1H), 6.97 (d, J=8.7Hz, 2H), 6.85 (d, J= 2.1Hz, 1H), 6.62 (d, J=1.9Hz, 1H), 3.94 (s, 3H), 3.89 (s, 3H), 3.77 (s, 3H)13C NMR(151MHz, CDCl3)δ165.90,164.44,146.63,140.45,136.86,135.14,130.92,126.07,116.97,107.22, 100.25,58.43,58.22,58.01.MS(ESI):342.1336.(C19H20NO5,[M+H]+).
Embodiment 2
1,5- dimethoxy -3- ((E) -4- (ethyoxyl) styryl) -2- (E)-nitroethenyl group) benzene (compound 2) Preparation
The preparation method is the same as that of Example 1.Bromomethane is replaced with bromoethane, obtains yellow solid powder target compound, yield 91%, 149-153 DEG C of fusing point.1H NMR(600MHz,DMSO-d6) δ 8.31 (d, J=13.3Hz, 1H), 7.89 (d, J= 13.2Hz, 1H), 7.58 (d, J=8.6Hz, 2H), 7.41 (dd, J=16.1,7.9Hz, 1H), 7.05 (d, J=16.0Hz, 1H), 6.95 (d, J=8.6Hz, 2H), 6.85 (d, J=1.9Hz, 1H), 6.63 (s, 1H), 4.04 (q, J=6.9Hz, 2H), 3.94 (d, J=5.3Hz, 3H), 3.89 (s, 3H), 1.32 (t, J=7.0Hz, 3H)13C NMR(151MHz,CDCl3)δ 165.89,164.44,140.44,136.93,135.16,130.92,125.92,117.52,107.20,100.22,66.23, 58.43,58.22,32.32,17.42.MS(ESI):365.1492.(C20H22NO5,[M+H]+).
Embodiment 3
1,5- dimethoxy -2- ((E) -2- nitroethenyl group) -3- ((E) -4- (propoxyl group) styryl) benzene (compound 3) preparation
The preparation method is the same as that of Example 1.Bromomethane is replaced with N-Propyl Bromide, obtains yellow solid powder target compound, yield 91%, 100-102 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.40 (d, J=13.3Hz, 1H), 7.91 (d, J=13.3Hz, 1H), 7.46 (d, J=8.1Hz, 2H), 7.25 (d, J=16.0Hz, 1H), 6.94-6.88 (m, 3H), 6.72 (s, 1H), 6.42 (s, 1H), 3.96 (t, J=6.5Hz, 2H), 3.93 (s, 3H), 3.90 (s, 3H), 1.86-1.79 (m, 2H), 1.06 (t, J= 7.4Hz,3H).13C NMR(151MHz,CDCl3)δ165.89,136.95,135.15,130.90,125.89,117.55, 107.18,100.22,72.30,58.42,58.21,32.32,25.20,13.12.MS(ESI):392.1648.(C21H23NO5, [M+Na]+).
Embodiment 4
1- ((E) -4- (butoxy) styryl) -3,5- dimethoxy -2- ((E) -2- nitroethenyl group) benzene (compound 4) preparation
The preparation method is the same as that of Example 1.Bromomethane is replaced with bromobutane, obtains yellow solid powder target compound, yield 82%, 98-101 DEG C of fusing point.1H NMR(600MHz,DMSO-d6) δ 8.30 (d, J=13.3Hz, 1H), 7.88 (d, J= 13.3Hz, 1H), 7.57 (d, J=8.4Hz, 2H), 7.40 (d, J=16.0Hz, 1H), 7.04 (d, J=16.0Hz, 1H), 6.95 (d, J=8.3Hz, 2H), 6.84 (s, 1H), 6.62 (s, 1H), 3.97 (dd, J=13.1,6.7Hz, 2H), 3.94 (s, 3H), 3.88 (s, 3H), 1.72-1.66 (m, 2H), 1.42 (dq, J=14.7,7.3Hz, 2H), 0.92 (t, J=7.3Hz, 3H)13C NMR(151MHz,CDCl3)δ165.89,136.95,135.15,130.89,125.89,117.54,107.19,100.22, 70.49,58.31 (d, J=31.7Hz), 33.93,21.87,16.45.MS (ESI): 384.1805. (C22H26NO5,[M+H]+).
Embodiment 5
1- ((E) -4- (sec-butoxy) styryl) -3,5- dimethoxy -2- ((E) -2- nitroethenyl group) benzene (chemical combination Object 5) preparation
The preparation method is the same as that of Example 1.Bromomethane is replaced with 2- bromobutane, obtains yellow solid powder target compound, is received Rate 87%, 88-91 DEG C of fusing point.1H NMR(600MHz,DMSO-d6) δ 8.30 (d, J=13.3Hz, 1H), 7.88 (d, J= 13.2Hz, 1H), 7.55 (d, J=8.6Hz, 2H), 7.39 (d, J=16.0Hz, 1H), 7.04 (d, J=16.0Hz, 1H), 6.93 (d, J=8.7Hz, 2H), 6.83 (d, J=2.1Hz, 1H), 6.61 (d, J=2.0Hz, 1H), 4.41 (dt, J=12.0, 6.0Hz, 1H), 3.93 (s, 3H), 3.88 (s, 3H), 1.67-1.53 (m, 2H), 1.22 (d, J=6.0Hz, 3H), 0.91 (t, J =7.4Hz, 3H)13C NMR(151MHz,CDCl3) δ 165.89,164.43,140.45,136.95,135.15,130.93, 125.88,118.83,107.21,100.20,77.84-75.70 (m), 58.31 (d, J=32.1Hz), 32.32,31.80, 21.88,12.35.MS(ESI):384.1805.(C22H26NO5,[M+H]+).
Embodiment 6
1- ((E) -4- (isobutoxy) styryl) -3,5- dimethoxy -2- ((E) -2- nitroethenyl group) benzene (chemical combination Object 6) preparation
The preparation method is the same as that of Example 1.Bromomethane is replaced with 2- methyl N-Propyl Bromide, obtains yellow solid powder target chemical combination Object, yield 84%, 113-115 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.41 (d, J=13.3Hz, 1H), 7.92 (d, J= 13.3Hz, 1H), 7.47 (d, J=8.6Hz, 2H), 7.27 (s, 1H), 6.95-6.89 (m, 3H), 6.73 (d, J=2.2Hz, 1H), 6.43 (d, J=2.1Hz, 1H), 3.94 (s, 3H), 3.91 (s, 3H), 3.76 (d, J=6.6Hz, 2H), 2.15-2.07 (m, 1H), 1.04 (d, J=6.7Hz, 6H)13C NMR(151MHz,CDCl3) δ 165.89,164.43,162.45,146.69, 140.45,136.95,135.15,130.88,125.86,117.57,107.19,100.22,77.22,58.43,58.31(d,J =31.3Hz), 30.92,21.87.MS (ESI): 384.1805. (C22H26NO5,[M+H]+).
Embodiment 7
1- ((E) -4- (hexyloxy) styryl) -3,5- dimethoxy -2- ((E) -2- nitroethenyl group) benzene (compound 7) preparation
The preparation method is the same as that of Example 1.Bromomethane is replaced with bromohexane, obtains yellow solid powder target compound, yield 80%, 99-101 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.41 (d, J=13.3Hz, 1H), 7.92 (d, J=13.4Hz, 1H), 7.47 (d, J=8.6Hz, 2H), 7.26 (dd, J=10.5,5.3Hz, 2H), 6.92 (dd, J=12.1,3.4Hz, 3H), 6.72 (d, J=2.0Hz, 1H), 6.42 (d, J=1.8Hz, 1H), 3.99 (t, J=6.5Hz, 2H), 3.93 (s, 3H), 3.91 (s, 3H), 1.84-1.77 (m, 2H), 1.60-1.44 (m, 4H), 1.35 (dd, J=9.9,6.3Hz, 4H), 0.91 (dd, J= 13.5,6.6Hz,3H).13C NMR(151MHz,CDCl3)δ165.90,164.44,162.30,146.68,140.41, 136.94,135.16,131.74,130.90,125.85,117.54,113.30,107.18,100.20,70.81,58.42, 58.21,34.22,32.32,31.85,28.34,25.23,16.64.MS(ESI):434.1938.(C24H29NO5,[M+Na]+).
Embodiment 8
1- ((E) -4- (cyclo propyl methoxy) styryl) -3,5- dimethoxy -2- ((E) -2- nitroethenyl group) benzene The preparation of (compound 8)
The preparation method is the same as that of Example 1.Bromomethane is replaced with bromomethyl cyclopropane, obtains yellow solid powder target chemical combination Object, yield 77%, 100-102 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.41 (d, J=13.3Hz, 1H), 7.92 (d, J= 13.3Hz, 1H), 7.47 (d, J=8.6Hz, 2H), 7.26 (d, J=16.0Hz, 1H), 6.92 (dd, J=12.3,6.8Hz, 3H), 6.72 (d, J=2.1Hz, 1H), 6.43 (d, J=1.9Hz, 1H), 3.94 (s, 3H), 3.91 (s, 3H), 3.84 (d, J= 6.9Hz, 2H), 1.34-1.26 (m, 2H), 0.70-0.63 (m, 2H), 0.37 (d, J=4.5Hz, 2H)13C NMR(151MHz, CDCl3)δ165.89,164.43,146.66,140.45,136.90,135.14,131.88,130.90,125.97,117.64, (107.20,100.23,75.52,58.43,58.31 d, J=31.7Hz), 32.32,12.89,5.83.MS (ESI): 404.1468(C22H23NO5,[M+Na]+).
Embodiment 9
1- ((E) -4- (cyclobutenyl oxygen) styryl) -3,5- dimethoxy -2- ((E) -2- nitroethenyl group) benzene (chemical combination Object 9) preparation
The preparation method is the same as that of Example 1.Bromomethane is replaced with bromobutene, obtains yellow solid powder target compound, yield 87%, 110-113 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.40 (d, J=13.3Hz, 1H), 7.92 (d, J=13.3Hz, 1H), 7.47 (d, J=8.6Hz, 2H), 7.26 (d, J=16.0Hz, 1H), 6.92 (dd, J=12.4,6.2Hz, 3H), 6.72 (d, J=2.1Hz, 1H), 6.42 (d, J=1.9Hz, 1H), 5.92 (ddt, J=17.0,10.2,6.7Hz, 1H), 5.19 (dd, J =17.2,1.4Hz, 1H), 5.13 (d, J=10.3Hz, 1H), 4.06 (t, J=6.7Hz, 2H), 3.93 (s, 3H), 3.90 (s, 3H), 2.57 (q, J=6.6Hz, 2H)13C NMR(151MHz,CDCl3)δ165.89,164.4,162.39-161.51(m), (140.45,136.90 d, J=5.0Hz), 135.14,130.91,126.03,119.75,117.61,107.20,100.24, 70.00,58.32 (d, J=31.5Hz), 36.23,32.39-31.75 (m) .MS (ESI): 404.1468 (C22H23NO5,[M+Na]+).
Embodiment 10
1,5- dimethoxy -3- ((E) -4- ((2- methacrylic) oxygen) styryl) -2- ((E) -2- nitroethylene Base) benzene (compound 10) preparation
The preparation method is the same as that of Example 1.Bromomethane is replaced with 2- methyl bromopropene, obtains yellow solid powder target chemical combination Object, yield 87%, 144-148 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.40 (d, J=13.3Hz, 1H), 7.92 (dd, J =13.3,0.8Hz, 1H), 7.47 (d, J=8.5Hz, 2H), 7.27 (d, J=16.0Hz, 1H), 6.93 (dd, J=18.3, 12.2Hz, 3H), 6.72 (d, J=1.3Hz, 1H), 6.43 (s, 1H), 5.11 (s, 1H), 5.01 (d, J=0.5Hz, 1H), 4.48 (s, 2H), 3.94 (d, J=0.6Hz, 3H), 3.91 (d, J=0.7Hz, 3H), 1.85 (s, 3H)13C NMR(151MHz, CDCl3)δ165.90,164.44,146.63,140.45,136.86,135.14,130.92,126.07,116.97,107.22, 100.25,58.43,58.22,58.01.MS(ESI):404.1468(C22H23NO 5,[M+Na]+).
Embodiment 11
1,5- dimethoxy -2- ((E) -2- nitroethenyl group) -3- ((E) -4- (amylene oxygroup) styryl) benzene (chemical combination Object 11) preparation
The preparation method is the same as that of Example 1.Bromomethane is replaced with 5- bromine amylene, obtains yellow solid powder target compound, is received Rate 79%, 110-113 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.40 (d, J=13.3Hz, 1H), 7.91 (d, J= 13.2Hz, 1H), 7.47 (d, J=8.6Hz, 2H), 7.27 (s, 1H), 7.24 (s, 1H), 6.95-6.88 (m, 3H), 6.72 (d, J =2.1Hz, 1H), 6.42 (d, J=2.0Hz, 1H), 5.87 (ddt, J=16.9,10.1,6.7Hz, 1H), 5.08 (dd, J= 17.1,1.2Hz, 1H), 5.02 (d, J=10.2Hz, 1H), 4.01 (t, J=6.4Hz, 2H), 3.93 (s, 3H), 3.90 (s, 3H), 2.26 (dd, J=14.3,7.0Hz, 2H), 1.94-1.88 (m, 2H)13C NMR(151MHz,CDCl3)δ165.89, 164.4,125.95,117.89,117.56,107.20,100.23,69.96,58.42,584,162.20,146.67,140.40 (d, J=14.8Hz), 136.91,135.15,131.85,130.91,125.95,117.89,117.56,107.20,100.23, 69.96,58.42,58.21,32.72,32.33,31.05.MS(ESI):418.1625.(C23H25NO5,[M+Na]+).
Embodiment 12
1,5- dimethoxy -3- ((E) -4- (2- methoxy ethoxy) styryl) -2- ((E) -2- nitroethenyl group) The preparation of benzene (compound 12)
The preparation method is the same as that of Example 1.Bromomethane is replaced with 2- bromo-ethyl-methyl ether, obtains yellow solid powder target chemical combination Object, yield 79%, 108-112 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.40 (d, J=13.3Hz, 1H), 7.92 (d, J= 13.3Hz, 1H), 7.47 (d, J=8.3Hz, 2H), 7.26 (d, J=16.0Hz, 1H), 6.95 (t, J=8.7Hz, 2H), 6.91 (d, J=15.9Hz, 1H), 6.72 (s, 1H), 6.43 (s, 1H), 4.18-4.14 (m, 2H), 3.93 (s, 3H), 3.90 (s, 3H), 3.78 (dd, J=4.7,3.5Hz, 2H), 3.47 (d, J=1.1Hz, 3H)13C NMR(151MHz,CDCl3)δ165.90, 164.44,161.88,146.62,140.44,136.84,135.14,132.18,130.90,126.14,117.66,107.22, 100.26,73.63,70.06,61.87,58.43,58.23,32.32.MS(ESI):408.1418.(C21H23NO6,[M+Na]+).
Embodiment 13
1,5- dimethoxy -3- ((E) -4- (2- methoxy propoxy) styryl) -2- ((E) -2- nitroethenyl group) The preparation of benzene (compound 13)
The preparation method is the same as that of Example 1.Bromomethane is replaced with the bromo- 3- methoxy propane of 1-, obtains yellow solid powder target Compound, yield 79%, 97-101 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.40 (dd, J=13.3,1.4Hz, 1H), 7.94-7.89 (m, 1H), 7.46 (d, J=8.2Hz, 2H), 7.27 (d, J=16.0Hz, 1H), 6.92 (t, J=10.8Hz, 3H), 6.72 (s, 1H), 6.42 (s, 1H), 4.10 (t, J=6.2Hz, 2H), 3.93 (s, 3H), 3.90 (s, 3H), 3.57 (t, J =6.0Hz, 2H), 3.37 (d, J=0.7Hz, 3H), 2.10-2.03 (m, 2H)13C NMR(151MHz,CDCl3)δ165.90 (s),164.44,162.14,146.65,140.41,136.89,135.14,131.89,130.90,125.96,117.55, (107.20,100.22,71.82,67.65,61.35,58.32 d, J=31.1Hz), 32.29 (d, J=9.6Hz) .MS (ESI): 422.1574.(C22H25NO6,[M+Na]+).
Embodiment 14
1- ((E) -4- (2- ethoxy ethoxy) styryl) -3,5- dimethoxy -2- ((E) -2- nitroethenyl group) The preparation of benzene (compound 14)
The preparation method is the same as that of Example 1.Bromomethane is replaced with 2- chloroethyl ethyl ether, obtains yellow solid powder target chemical combination Object, yield 82%, 109-112 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.41 (d, J=13.3Hz, 1H), 7.92 (d, J= 13.3Hz, 1H), 7.47 (d, J=8.6Hz, 2H), 7.27 (d, J=14.7Hz, 1H), 6.96 (d, J=8.6Hz, 2H), 6.92 (d, J=15.9Hz, 1H), 6.72 (d, J=2.1Hz, 1H), 6.42 (t, J=5.5Hz, 1H), 4.18-4.15 (m, 2H), 3.94 (s, 3H), 3.91 (s, 3H), 3.83-3.80 (m, 2H), 3.62 (q, J=7.0Hz, 2H), 3.42 (s, 3H)13C NMR (151MHz,CDCl3)δ165.89,164.44,161.88-160.45(m),140.45,136.87,135.15,130.88, 126.10,117.70,107.21,100.26,71.52,70.27,69.53,58.43,58.22,32.65-31.23(m), 17.79.MS(ESI):422.1574.(C22H25NO6,[M+Na]+).
Embodiment 15
1,5- dimethoxy -3- ((E) -4- (4- methoxybutoxy) styryl) -2- ((E) -2- nitroethenyl group) The preparation of benzene (compound 15)
The preparation method is the same as that of Example 1.Bromomethane is replaced with the bromo- 4- methyl butyl ether of 1-, obtains yellow solid powder target Compound, yield 82%, 105-108 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.41 (d, J=13.3Hz, 1H), 7.92 (d, J=13.3Hz, 1H), 7.47 (d, J=8.6Hz, 2H), 7.27 (d, J=16.0Hz, 1H), 6.92 (dd, J=12.3, 7.2Hz, 3H), 6.73 (d, J=2.1Hz, 1H), 6.43 (d, J=2.0Hz, 1H), 4.10 (t, J=6.3Hz, 2H), 3.94 (s, 3H), 3.91 (s, 3H), 3.57 (t, J=6.2Hz, 2H), 3.37 (s, 3H), 2.86 (m, 2H), 2.07 (m, 2H)13C NMR (151MHz,CDCl3)δ165.91,164.44,146.57,140.48,136.78,135.11,132.15,130.95, (126.30,123.82,117.76,117.41,107.25,100.29,69.23 d, J=42.2Hz), 58.43,58.23, 39.21,34.56,34.07,32.33,31.98,25.31.MS(ESI):414.4652.(C23H28NO6,[M+H]+).
Embodiment 16
1,5- dimethoxy -2- ((E) -2- nitroethenyl group) -3- ((E) -4- (2- phenoxy group) styryl) The preparation of benzene (compound 16)
The preparation method is the same as that of Example 1.Bromomethane is replaced with bromoethyl phenyl ether, obtains yellow solid powder target chemical combination Object, yield 87%, 149-152 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.41 (d, J=13.3Hz, 1H), 7.92 (d, J= 13.3Hz, 1H), 7.49 (d, J=8.6Hz, 2H), 7.34-7.27 (m, 2H), 7.01-6.95 (m, 5H), 6.92 (d, J= 15.9Hz, 2H), 6.74 (t, J=5.0Hz, 1H), 6.43 (t, J=4.4Hz, 1H), 4.39-4.33 (m, 4H), 3.93 (s, 3H),3.91(s,3H).13C NMR(151MHz,CDCl3)δ165.91,164.44,161.88-160.85(m),160.85- 159.74(m),146.57,140.48,136.78,135.11,132.15,130.95,126.30,123.82,117.76, (117.41,107.25,100.29,69.23 d, J=42.2Hz), 58.43,58.23,34.56,34.07,32.33,31.98, 25.31.MS(ESI):470.1574.(C26H25NO6,[M+Na]+).
Embodiment 17
1- ((E) -4- (cyclohexyl methoxy) styryl) -3,5- dimethoxy -2- ((E) -2- nitroethenyl group) benzene The preparation of (compound 17)
The preparation method is the same as that of Example 1.Bromomethane is replaced with bromomethylcyclohexane, obtains yellow solid powder target chemical combination Object, yield 75%, 111-114 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.40 (d, J=13.3Hz, 1H), 7.91 (d, J= 13.3Hz, 1H), 7.46 (d, J=8.5Hz, 2H), 7.24 (d, J=16.0Hz, 1H), 6.91 (dd, J=12.0,3.3Hz, 3H), 6.72 (d, J=1.9Hz, 1H), 6.42 (d, J=1.7Hz, 1H), 3.93 (s, 3H), 3.90 (s, 3H), 3.79 (d, J= 6.4Hz, 2H), 1.36-1.17 (m, 6H), 1.07 (qd, J=12.6,2.9Hz, 2H)13C NMR(151MHz,CDCl3)δ 165.89,164.43,162.91-161.48(m),140.44,136.97,135.15,130.88,125.83,117.56, 107.18,100.21,76.27,58.42,58.21,40.34,32.54,29.16,28.45.MS(ESI):424.2118. (C25H30NO5,[M+H]+).
Embodiment 18
1,5- dimethoxy -2- ((E) -2- nitroethenyl group) -3- ((E) -4- (benzene ethyoxyl) styryl) benzene (chemical combination Object 18) preparation
The preparation method is the same as that of Example 1.Bromomethane is replaced with 2 bromoethyl benzene, obtains yellow solid powder target compound, Yield 88%, 102-106 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.41 (d, J=13.3Hz, 1H), 7.92 (d, J= 13.3Hz, 1H), 7.47 (d, J=8.4Hz, 2H), 7.37-7.29 (m, 4H), 7.26 (t, J=7.7Hz, 2H), 6.92 (dd, J =12.3,6.5Hz, 3H), 6.72 (s, 1H), 6.43 (s, 1H), 4.22 (t, J=7.1Hz, 2H), 3.94 (s, 3H), 3.91 (s, 3H), 3.13 (t, J=7.1Hz, 2H)13C NMR(151MHz,CDCl3)δ165.89,164.44,162.19-160.85, 140.46,136.87,135.14,131.62,131.15,130.93,129.18,126.07,117.62,113.53-112.10 (m),107.20,100.25,71.45,58.42,58.21,38.39,32.33.MS(ESI):454.1625.(C26H25NO5,[M+ Na]+)
Embodiment 19
1,5- dimethoxy -2-2- ((E) -2- nitroethenyl group) -3- ((E) -4- ((4- (trifluoromethyl) benzyl) oxygen) benzene Vinyl) benzene (compound 19) preparation
The preparation method is the same as that of Example 1.Bromomethane is replaced with 4- (trifluoromethyl) bromobenzyl, obtains yellow solid powder target Conjunction object, yield 78%, 102-105 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.41 (d, J=13.3Hz, 1H), 7.92 (d, J =13.3Hz, 1H), 7.49 (d, J=8.6Hz, 2H), 7.42 (dd, J=8.4,5.5Hz, 2H), 7.26 (d, J=16.0Hz, 1H), 7.09 (t, J=8.7Hz, 2H), 6.99 (d, J=8.7Hz 2H), 6.92 (d, J=15.9Hz, 1H), 6.72 (d, J= 2.1Hz, 1H), 6.43 (d, J=2.0Hz, 1H), 5.07 (s, 2H), 3.94 (s, 3H), 3.91 (s, 3H)13C NMR(151MHz, CDCl3)δ165.90,164.44,161.89,146.62,140.44,136.83,135.13,132.18,130.90,126.14, 117.66,113.32,107.22,100.26,73.63,70.06,61.86,58.42,58.22,32.32.MS(ESI): 486.1560.(C26H23F3NO5,[M+H]+).
Embodiment 20
1,5- dimethoxy -2-2- ((E) -2- nitroethenyl group) -3- ((E) -4- ((3,4- difluorobenzyl) oxygen) styrene Base) benzene (compound 20) preparation
The preparation method is the same as that of Example 1.Bromomethane is replaced with 3,4- difluoro benzyl bromo, obtains yellow solid powder target chemical combination Object, yield 89%, 100-103 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.40 (d, J=13.3Hz, 1H), 7.92 (d, J= 13.3Hz, 1H), 7.49 (d, J=8.6Hz, 2H), 7.28 (d, J=18.9,3.0Hz, 2H), 7.21-7.14 (m, 2H), 6.96 (t, J=11.2Hz, 2H), 6.91 (d, J=15.9Hz, 1H), 6.72 (d, J=2.0Hz, 1H), 6.43 (t, J=5.4Hz, 1H),5.05(s,2H),3.94(s,3H),3.91(s,3H).13C NMR(151MHz,CDCl3)δ167.25,165.46, 160.96,147.32,141.14,136.75,135.63,132.08,131.02,127.24,120.34,116.96,114.62, 110.12,103.92(s),100.13,78.63,70.46,62.76,59.62,57.32,33.35.MS(ESI):454.1440. (C25H22F2NO5,[M+H]+).
Embodiment 21
1,5- dimethoxy -2-2- ((E) -2- nitroethenyl group) -3- ((E) -4- ((to luorobenzyl) oxygen) styryl) The preparation of benzene (compound 21)
The preparation method is the same as that of Example 1.Bromomethane is replaced with 4- fluorobenzyl bromide, obtains yellow solid powder target compound, is received Rate 87%, 103-106 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.40 (d, J=13.3Hz, 1H), 7.92 (d, J= 13.3Hz 1H), 7.66 (d, J=8.0Hz, 2H), 7.57 (d, J=8.0Hz, 2H), 7.49 (d, J=8.6Hz, 2H), 7.28 (d, J=15.9Hz, 1H), 6.99 (d, J=8.6Hz, 2H), 6.92 (d, J=15.9Hz, 1H), 6.72 (d, J=1.8Hz, 1H), 6.43 (t, J=5.8Hz, 1H), 5.17 (s, 2H), 3.94 (s, 3H), 3.91 (s, 3H)13C NMR(151MHz,CDCl3) δ165.91,164.56,161.58,146.90,140.97,136.65,135.09,132.62,131.00,129.99, 128.20,126.65-125.61,117.88,107.30,100.29,71.87,58.32,32.32.MS(ESI):436.4460. (C25H23FNO5,[M+H]+).
Embodiment 22
1,5- dimethoxy -2-2- ((E) -2- nitroethenyl group) -3- ((E) -4- ((to luorobenzyl) oxygen) phenethyl) benzene The preparation of (compound 22)
The preparation method is the same as that of Example 1.Bromomethane is replaced with 2,4- difluoro benzyl bromo, obtains yellow solid powder target chemical combination Object, yield 90%, 102-105 DEG C of fusing point.1H NMR(600MHz,CDCl3) δ 8.40 (d, J=13.3Hz, 1H), 7.92 (d, J= 13.3Hz, 1H), 7.51-7.46 (m, 3H), 7.28 (d, J=16.0Hz, 1H), 7.00 (d, J=8.4Hz, 2H), 6.94-6.89 (m,2H),6.89-6.84(m,1H),6.72(s,1H),6.43(s,1H),5.12(s,2H),3.94(s,3H),3.91(s, 3H).13C NMR(151MHz,CDCl3)δ165.90,164.65-163.62,161.88-160.45,146.68-146.41, 140.59-140.32,136.70,135.10,130.98,126.48,117.87,107.29,106.17-105.46,100.30, 65.99,58.58-58.47,58.32.MS(ESI):454.4350.(C25H22F 2NO5,[M+H]+).
Embodiment 23
Resveratrol nitrostyrolene analog derivative (compound 1-22) is to MGC803, SMMC-7721 and MDA-MB-231 The action activity evaluation of three plants of tumor cell lines.
We using MTT determine resveratrol nitrostyrolene analog derivative (compound 1-22) for MGC803, The growth inhibition ability of tri- kinds of tumor cell lines of SMMC-7721 and MDA-MB-231.Tested tumor cell line is trained in culture medium Support logarithmic growth phase.It is seeded in 96 orifice plates, is continued in cell incubator after the cell dilution of logarithmic growth phase Culture is for 24 hours.In primary dcreening operation, sample is added in 96 orifice plates, and each compound is respectively provided with 3 as parallel examination It tests.MTT solution will be added by placing in each hole after cultivating 48h in incubator, be discarded the supernatant in each hole after 4h, Mei Gekong Middle addition DMSO is used to dissolve first a ceremonial jade-ladle, used in libation.It is placed on shaking table after shaking, detects absorbance in the case where wavelength is 578nm using microplate reader (OD value) calculates sample to be tested to the survival rate of tumor cell line.The IC measured50Value is shown in Table 1.
Inhibitory activity IC of 1. compound of table to MGC803, SMMC-7721 and MDA-MB-231 tumor cell line50(μM)
Note: " a " indicates IC50Value is expressed as the average value of independent experiment three times, and " b " indicates that gastric carcinoma cells, " c " indicate people Liver cancer cells, " d " indicate that human breast cancer cell, " NA " indicate IC50>100μM。
Most compounds are to tri- plants of tumor cell lines of MGC803, SMMC-7721 and MDA-MB-231 as can be seen from Table 1 All have inhibitory activity, especially compound 12 best to the inhibitory activity of MGC803, SMMC-7721 tumor cell line, is expected to As potential treatment gastric cancer or the lead compound of liver cancer, and 3,5,8,18 pairs of MDA-MB-231 mammary gland cancerous swellings of compound Oncocyte system has very strong inhibitory activity, especially 3 and 5, is expected to become the drug leads chemical combination of potential treatment breast cancer Object.
The above shows and describes the basic principles and main features of the present invention and the advantages of the present invention.The technology of the industry Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the above embodiments and description only describe this The principle of invention, without departing from the spirit and scope of the present invention, various changes and improvements may be made to the invention, these changes Change and improvement all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and its Equivalent thereof.

Claims (8)

1. a kind of resveratrol nitroethylene class compound, it is characterised in that: have following general formula:
R is selected from one of following groups in general formula:
2. the preparation method of resveratrol nitroethylene class compound as described in claim 1, it is characterised in that: including as follows Step:
Step 1: pterostilbene being added in acetone, then Anhydrous potassium carbonate, tetrabutylammonium bromide and bromoalkane is added in sequence respectively Hydrocarbon, oil bath heating to 55-58 DEG C of return stirring are reacted, and TLC contact plate monitors reaction process；It is filtered by vacuum after fully reacting, takes filter Liquid, column chromatography for separation (ethyl acetate: petroleum ether=1:4, v/v) obtains pterostilbene hydroxyl substitutive derivative after concentrate drying；
Step 2: pterostilbene hydroxyl substitutive derivative and n,N-Dimethylformamide being added in acetonitrile, is placed in ice bath, slowly Phosphorus oxychloride is added dropwise, restores after being added dropwise to reacting at room temperature, is stirred to react 1h, TLC monitors response situation, when pterostilbene hydroxyl Substitutive derivative stops reaction after having reacted immediately；Ice water is added into reaction system after reaction to be quenched, is added with stirring Sodium hydroxide solution tune pH is precipitated faint yellow solid, filters, drying, column chromatography for separation (dichloromethane to neutrality after being stirred overnight Alkane: petroleum ether=3:1, v/v) obtain pterostilbene hydroxyl substitution hydroformylation product；
Step 3: replacing hydroformylation product to be dissolved in nitromethane step 2 gained pterostilbene hydroxyl, ammonium acetate, reactant is added It ties up under oil bath and is heated to 100 DEG C of reflux, TLC monitoring reaction is cooled to room temperature after fully reacting, is carried out with ethyl acetate and water Extraction collects organic phase and anhydrous Na is added2SO4Water removal, vacuum concentration, column chromatographic isolation and purification (ethyl acetate: petroleum ether= 1:5, v/v) obtain resveratrol nitrostyrolene analog derivative.
3. preparation method according to claim 1, it is characterised in that: pterostilbene, Anhydrous potassium carbonate, four in the step 1 The ratio between butylammonium bromide and the amount of substance of brominated alkanes are 1:1.2:1.2:1.2.
4. preparation method according to claim 1, it is characterised in that: pterostilbene hydroxyl substitutive derivative in the step 2 It is 1:1 with the ratio between the amount of substance of phosphorus oxychloride.
5. preparation method according to claim 1, it is characterised in that: every mM of pterostilbene hydroxyl takes in the step 2 N,N-dimethylformamide 0.15mL is added for derivative.
6. preparation method according to claim 1, it is characterised in that: pterostilbene hydroxyl replaces formylated in the step 3 The ratio between amount of substance of product and ammonium acetate is 1:2.
7. resveratrol nitroethylene class compound as described in claim 1 is preparing the application in anticancer drug.
8. application according to claim 7, it is characterised in that: the resveratrol nitroethylene class compound is to human gastric cancer Cell line MGC803, Bel7402 SMMC-7721 and human breast cancer cell line MDA-MB-231 live with good inhibition Property.
CN201910284930.7A 2019-04-10 2019-04-10 A kind of resveratrol nitroethylene class compound and its preparation method and application Withdrawn CN110041204A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201910284930.7A CN110041204A (en) 2019-04-10 2019-04-10 A kind of resveratrol nitroethylene class compound and its preparation method and application

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201910284930.7A CN110041204A (en) 2019-04-10 2019-04-10 A kind of resveratrol nitroethylene class compound and its preparation method and application

Publications (1)

Publication Number Publication Date
CN110041204A true CN110041204A (en) 2019-07-23

Family

ID=67276729

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910284930.7A Withdrawn CN110041204A (en) 2019-04-10 2019-04-10 A kind of resveratrol nitroethylene class compound and its preparation method and application

Country Status (1)

Country Link
CN (1) CN110041204A (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108558813A (en) * 2018-03-30 2018-09-21 合肥工业大学 A kind of resveratrol analog derivative and its preparation method and application containing flavonoids

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108558813A (en) * 2018-03-30 2018-09-21 合肥工业大学 A kind of resveratrol analog derivative and its preparation method and application containing flavonoids

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
M. AMARNATH REDDY等: "Design and Synthesis of Resveratrol-Based Nitrovinylstilbenes as Antimitotic Agents", 《J.MED.CHEM.》 *
葛为为: "白藜芦醇衍生物的设计合成及活性评价", 《中国优秀博硕士学位论文全文数据库（硕士） 工程科技I辑》 *

Similar Documents

Publication Publication Date Title
CN101580477B (en) Dehydroabietylamine derivatives and application thereof in bactericidal and antineoplastic medicaments
CN108610348A (en) A kind of simultaneously [2,3-b] pyridine -3- carbonitrile derivatives and its preparation and application of the 5H- chromenes containing imidazole substituent
CN109438365A (en) N- (3- ((4- trifluoromethyl) -2- pyrimidine radicals) aminophenyl) -2,6- difluorobenzenesulfonamide derivative
CN109762034B (en) Preparation method of novel terephthalaldehyde D-glucosamine Schiff base
CN117843550A (en) 10-perfluoroalkyl-5, 10-indano [1,2-b ] indole compound and synthesis method thereof
CN110551070A (en) Synthesis of camphoryl pyrimidine compounds and antitumor activity thereof
CN113234070B (en) Honokiol thioether derivative containing oxazole ring, and preparation method and application thereof
CN107311937A (en) The licochalcone A dihydro amino-metadiazine compound and its synthetic method of one class tool antitumor activity
CN110041204A (en) A kind of resveratrol nitroethylene class compound and its preparation method and application
CN110511214B (en) Diamine substituted aromatic heterocyclic compound and preparation method and application thereof
CN107674036B (en) Asymmetric bis-1, 2, 3-triazole compound as well as preparation method and application thereof
CN107494553B (en) Agricultural bactericide derived from gallic acid and application
CN106554362B (en) It is a kind of using 1- pyridines-B-carboline as copper chloride (II) chelate and its synthetic method of ligand and application
CN110590765B (en) Structure, preparation and application of 2-thiazole formaldehyde-furfural Schiff base
CN103804273B (en) Oxoindole and double; two quaternary carbon splicing derivant of 1,2,3-indantrione monohydrate and preparation method thereof
CN107311949B (en) Sulfonamide-substituted aryl triazine compound and preparation method and application thereof
CN106234385B (en) A kind of application of 1,2,4- triazole derivatives of the structure containing benzopyrazines as fungicide
CN113861127B (en) Preparation method of benzothiazole derivative drug molecules
CN109824647A (en) The preparation and use of 4- dihydroxy benaophenonel hydrazone -2- acetyl thiophene schiff bases
CN109912491A (en) 4- dihydroxy benaophenonel hydrazone-isatin schiff bases preparation and use
CN108997149A (en) A kind of dehydroabietylamine derivatives and its preparation method and application that aryl replaces
CN104530062B (en) A kind of 1,4-naphthoquinone derivatives and synthetic method thereof
CN103539642A (en) Method for preparing 3,4,5-trimethoxy-3'-hydroxy-4'-alkoxy diphenylethane
CN103724324A (en) Imidacloprid-like ramification and preparing method thereof
CN110105260B (en) Aromatic ring ureido indole derivative and preparation method and application thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
WW01 Invention patent application withdrawn after publication

Application publication date: 20190723

WW01 Invention patent application withdrawn after publication