CN104016956A - 5,2',4'-trihydroxyl-7-methyl-3-hydrocarbyl flavone analogue as well as preparation method and application thereof - Google Patents
5,2',4'-trihydroxyl-7-methyl-3-hydrocarbyl flavone analogue as well as preparation method and application thereof Download PDFInfo
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- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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Abstract
The invention discloses a 5,2',4'-trihydroxyl-7-methyl-3-hydrocarbyl flavone analogue. Based on 5,2',4'-trihydroxyl-7-methyl-3-geranylated (isopentene group) flavone, the inventor researches and prepares the 5,2',4'-trihydroxyl-7-methyl-3-hydrocarbyl flavone analogue with a skeleton structure of a flavonoids compound and lucubrated total synthesis and the activities of anti-cervical cancer cells and anti-liver cancer cells. An in-vitro cancer cell inhibitory activity test verifies that the compound disclosed by the invention has a relatively remarkable inhibiting effect to cervical cancer cells and liver cancer cells and can be used as a candidate medicine for treating cervical cancer and liver cancer.
Description
Technical field
The invention belongs to the technical field of flavonoid compound, relate in particular to 5,2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones and its preparation method and application.
Background technology
Cancer is to one of dangerous maximum disease of human health and quality of life, thereby finds efficient, highly selective and the little cancer therapy drug of side effect is the main direction of medicament research and development.Flavonoid compound, particularly 3-alkyl flavonoid compound have good antitumour activity and by extensively concerned.
The people such as American scholar McLean have found that in research in 2008 7, a kind of A ring is the chromocor compound of methyl---Aminoflavone, and it has the anti-tumor activity of wide spectrum, as a kind of novel antitumor drug, is applied to clinical experiment.The people such as American scholar Chandramouli have synthesized 7, a series of A rings in 2012 be the flavonoid compound of methyl, and HT22 cell has been done to active testing, all shows good activity, wherein the active EC of 4 pairs of HT22 cells of compound
50value reaches 30 μ M/L.
Summary of the invention
The technical problem to be solved in the present invention is to provide 5,2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones and its preparation method and application, the specifically total synthesis method of these analogues and applying in the medicine of preparation treatment cervical cancer and liver cancer.
For solving the problems of the technologies described above, the present invention by the following technical solutions: 5,2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones, this analogue is compound or its pharmacy acceptable salt with following general formula,
Wherein, R
1for
r
2for-OH, R
3, R
4for-OCH
3or-OH;
Or R
1for
r
2, R
3, R
4for-OCH
3.
This analogue is 5-hydroxyl-2 ', 4 '-dimethoxy-7-methyl-3-geranyl flavones, 5, 2 '-dihydroxyl-4 '-methoxyl group-7-methyl-3-geranyl flavones, 5, 4 '-dihydroxyl-2 '-methoxyl group-7-methyl-3-geranyl flavones, 5, 2 ', 4 '-trimethoxy-7-methyl-3-(3, 7-dimethyl-2 octene) flavones, (±) 5, 2 ', 4 '-trimethoxy-7-methyl-3-(3, 7-dimethyl octene) flavones, 5-hydroxyl-2, , 4,-dimethoxy-7-methyl-3-isoamylene radical chromocor, 5, 2 '-hydroxyl-4 '-methoxyl group-7-methyl-3-isoamylene radical chromocor, 5, 2 ', 4 '-trimethoxy-7-methyl-3-(3-methyl butene) flavones.
This analogue is one of following compound:
Above-mentioned 5, the preparation method of 2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones; with 2; 4-dihydroxyl-4-methyl acetophenone is the acetylize of starting raw material process, resets, and methylates; 2; 4-dibenzoyl chlorine acidylate, Baker-Venkataraman resets, 3 geranyls or isopentene group; acid catalysis is closed ring, and demethylation or shortening form.
Above-mentioned 5, the application of 2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones in preparing medicament for resisting cervical cancer.
Above-mentioned 5, the application of 2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones in preparing medicines resistant to liver cancer.
5, 2 ', on the basis of 4 '-trihydroxy--7-methyl-3-geranyl (isopentene group) flavones, according to 7, A ring, there is good anti-tumor activity and alkylation medicine has inhibition well to malignant cell for the flavonoid compound of methyl, eliminate the effect of tumour cell, contriver studies and prepared has 5 of flavonoid compound skeleton structure, 2 ', 4 '-hydroxyl (methoxyl group)-7-methyl-3-geranyl (isopentene group) flavones, 5, 2 ', 4 '-trimethoxy-7-methyl-3-(3, 7-dimethyl-2 octene) flavones or 5, 2 ', 4 '-trimethoxy-7-methyl-3-alkane flavones, and it has been carried out to further investigation complete synthesis and anti-cervical cancer cell and liver cancer cell activity.Cancer cell in vitro suppresses activity test and shows, compound of the present invention has obvious restraining effect to s, Liver cancer cell SMMC-7721 cell and BEL-7404 cell, can be used as the drug candidate of screening preparation treatment cervical cancer and liver cancer.
Accompanying drawing explanation
Fig. 1 is the present invention 5,2 ', 4 '-hydroxyl (methoxyl group)-7-methyl-3-geranyl (isopentene group) flavones (compound 6a1,6b1,6b2,6a2,6a3), 5,2 ', 4 '-trimethoxy-7-methyl-3-(3,7-dimethyl-2 octene) flavones (compound 6c1) and 5, preparation method's process flow sheet of 2 ', 4 '-trimethoxy-7-methyl-3-alkane flavones (compound 6c2,6d).
Fig. 2 is the present invention 5,2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones to the inhibiting rate of s to drug level figure, in figure: 1 compound 6a1,2 compound 6b1,3 compound 6b2,6 compound 6c1,7 compound 6c2,8 compound 6d.
Fig. 3 is the present invention 5,2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones to the inhibiting rate of hepatoma cell strain BEL-7404 cell to drug level figure, in figure: 1 compound 6a1,2 compound 6b1,3 compound 6b2.
Fig. 4 is the present invention 5,2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones to the inhibiting rate of Liver cancer cell SMMC-7721 cell to drug level figure, in figure: 4 compound 6a2,5 compound 6a3,8 compound 6d.
Embodiment
Fig. 1 has shown the present invention 5, and preparation method's technical process of 2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones, is elaborated to this below in conjunction with example.
Embodiment 15, the preparation of 2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones
The preparation of <1> intermediate product (2)
1.66g compound (1) is dissolved in 15ml acetone, under 56 ℃ of oil baths, adds 1.5g salt of wormwood return stirring 10min, with syringe, drip 0.75ml methyl iodide back flow reaction 6h.Evaporate to dryness acetone, pours in dilute hydrochloric acid and salt of wormwood, ethyl acetate extraction, and then washing successively, saturated common salt water washing, anhydrous sodium sulfate drying, column chromatography sherwood oil obtains 1.56g yellow-green colour product (2), productive rate 87%.Product structure is through IR, NMR and MS Analysis deterrmination.
The preparation of <2> intermediate product (3)
Take 2.7g2,4-dimethoxybenzoic acid, in 100ml round-bottomed flask, and is placed in 70 ℃ of oil baths, adds 7.2g thionyl chloride stirring and refluxing 1h.Underpressure distillation goes out excessive thionyl chloride, then be added dropwise in the 15ml pyridine that has dissolved 1.93g (2), at 80 ℃, react 2h, product is not purified, again be dissolved in 15ml pyridine, add 0.9g (16mmol) KOH, at 100 ℃, react 30min, cooling, add ethyl acetate and pour dilute hydrochloric acid into, wash with water successively, saturated common salt water washing, merge organic phase, anhydrous sodium sulfate drying, column chromatography [V (sherwood oil): V (ethyl acetate)=5:1] obtains 2.015g yellow solid compound (3) (productive rate 58%).Product structure is through IR, NMR and MS Analysis deterrmination.
<3> intermediate product 4a, the preparation of 4b
360mg (3) is dissolved in 15ml acetone, is placed in 56 ℃ of oil baths, under stirring, add 220mg salt of wormwood, stir 10min, drip 320mg geranyl bromide, reaction 2h.Cooling, solvent evaporated, pours ethyl acetate into, adds dilute hydrochloric acid to remove salt of wormwood, washes successively saturated common salt water washing, anhydrous sodium sulfate drying with water.Column chromatography [V (sherwood oil): V (ethyl acetate)=5:1] obtains yellow oil product 4a (600mg, productive rate 74%).Same method obtains yellow oil product 4b (281mg, productive rate 64%).Product structure is all through IR, NMR and MS Analysis deterrmination.
<4> intermediate product 5a, the preparation of 5b
461mg (1mmol) compound 4a is dissolved in 10ml methyl alcohol, under 65 ℃ of stirrings, drip 1 vitriol oil, back flow reaction 2h, the cooling water of pouring into, ethyl acetate extraction, saturated common salt water washing, anhydrous sodium sulfate drying, column chromatography [V (sherwood oil): V (ethyl acetate)=2:1] obtains 364mg yellow oil product 5a (productive rate 82.7%).Same method obtains 165mg yellow oil product 5b (productive rate 80.1%) by 200mg4b.Product structure is all through IR, NMR and MS Analysis deterrmination.
<5> target product 6a1,6a2,6a3,6b1, the preparation of 6b2
The dry round-bottomed flask of 25ml of 48mg (0.1mmol) compound 5a and 35mg pyridine hydrochloride will be housed, load onto air set pipe and rubber plug, the displacement of Ar gas is placed on for 3 times in 190 ℃ of oil baths reacts 6h, be cooled to room temperature and pour saturated sodium bicarbonate solution into, ethyl acetate extraction, saturated common salt water washing, anhydrous sodium sulfate drying, column chromatography [V (sherwood oil): V (ethyl acetate)=32:1] obtains yellow oil product 6a1 (38mg, productive rate 81.7%).Same method obtains yellow oil product 6b1 (36mg, productive rate 83.7%); At 0 ℃, 0.1mlEtSH is dissolved in 2ml HMPA and stirs 10min, N
2under protection, add 0.7ml n-BuLi (2M, 1.4mmol) and stir 30min at this temperature, by being dissolved in 140mg (0.3mmol) 5a in 2ml HMPA, joining in system, to stir after 5min and move at 70 ℃ and react 7h, cooling saturated NH
4cl cancellation reaction, ethyl acetate is extracted organic phase, use successively saturated LiCl, saturated NaCl washing, anhydrous sodium sulfate drying, silica gel column chromatography [V (sherwood oil): V (ethyl acetate)=5:1] obtains 55mg yellow oily liquid 6a2 (productive rate 41.9%) and 30mg yellow oily liquid 6a3 (productive rate 22.9%).Same method obtains 28mg yellow oil product 6b2 (productive rate 32.9%) by 92mg5b.Product structure is all through IR, NMR and MS Analysis deterrmination.Data are as follows:
Compound 6a1, IR (KBr): 3358; 2922; 2844; 1764; 1654; 1616; 1493; 1459; 1380; 1338; 1268; 1209; 1135; 1039; 923; 829; 755; 675; 614.
1HNMR(400MHz,CDCl
3)δppm:12.80(s,1H)；7.255(m,J＝12Hz,1h)；6.67(s,1H)；7.255(m,J＝12Hz,1h)；6.59(d,J＝16Hz,3h)；5.13(t，J＝12Hz，1h)；5.02(t，J＝12Hz，1h)；3.90(s，3h)；3.81(s，3h)；3.08(d,J＝8Hz,2h)；2.14(m，4h)；
13CNMR(100MHz,CDCl
3)δppm：182；162；160；156；146；135；131；124；123.7；123.2；122；121.6；121.3；115；111；108；107；104；98；55.59；55.53；39；26；25；24；22；17；15。(ESI)-MS,m/z:449.2323[M+H]
+。
Compound 6a2, IR (KBr): 3376; 2922; 2853; 1646; 1619; 1492; 1432; 1334; 1295; 1207; 1148; 1080; 1035; 951; 828; 754; 939; 828; 574.
1HNMR(400MHz,CDCl
3)δppm：12.66(s，1h)；7.24(d,J＝8Hz,1h)；6.64(s，1h)；6.58(m，2h)；6.53(s，1h)；5.16(t，J＝12Hz，1h)；5.15(t，J＝12Hz，1h)；3.86(s，3h)；3.16(d，J＝8Hz,2h)；2.35(s，3h)；2.03-1.94(m，4h)；1.65(s，3h)；1.58(s，3h)；1.46(s，3h)；
13CNMR(100MHz，CDCl
3)δppm：182；162；160；159；156；155；146；136；131.38；131.25；121.6；111；108；107.4；107；104；55；39；29；26；25；24；22；17；15。(ESI)-MS,m/z:434.2172[M+H]
+。
Compound 6a3, IR (KBr): 3458; 3000; 2917; 2853; 1741; 1654; 1614; 1459; 1379; 1295; 1202; 1165; 1088; 1018; 951; 828; 721.
1HNMR(400MHz,CDCl
3)δppm：12.89(s，1h)；7.19(d,J＝8Hz,1h)；6.71(s，1h)；6.64(s，1h)；6.555(d，J＝8Hz，2h)；5.14(t，J＝12Hz，1h)；5.06(t，J＝12Hz，1h)；3.78(s，3h)；3.10(d，J＝8Hz,2h)；2.40(s，3h)；2.0(t，J＝12Hz，2h)；1.92(t，J＝12Hz，2h)；1.66(s，3h)；1.58(s，3h)；1.42(s，3h)；
13CNHM(100MHz，CDCl
3)δppm：183；161；160；159；158；156；146；135；131.4；131.3；124；121.6；121.1；114；111；108；107.5；107.2；99；55；39；29；26；25；24；22；17；15。(ESI)-MS,m/z:434.2159[M+H]
+。
Compound 6b1, IR (KBr): 2922; 2852; 1733; 1654; 1615; 1589; 1495; 1455; 1372; 1339; 1280; 1209; 1157; 1081; 1032; 939; 826; 755; 673; 616.
1HNMR(400MHz,CDCl
3)δppm：12.78(s，1h)；6.75(s，1h)；7.28(s，1h)；6.67(s，1h)；6.59(d,J＝16Hz,3h)；5.12(t，J＝12Hz，1h)；3.90(s，3h)；3.81(s，3h)；3.06(d，J＝8Hz，2h)；2.39(s，3h)；1.64(s，3h)；1.44(s，3h)；
13CNMR(100MHz，CDCl
3)δppm：183；162；161；160；158；156；146；131.9；131.2；121.6；121.4；115；111；108；107；104；98；55.58；55.54；25；24；22；17。(ESI)-MS,m/z:381.1694[M+H]
+。
Compound 6b2, IR (KBr): 3409; 2955; 2922; 2853; 1723; 1654; 1611; 1487; 1459; 1374; 1334; 1282; 1210; 1085; 1025; 823; 766.
1HNMR(400MHz,CDCl
3)δppm：12.89(s，1h)；7.19(d,J＝8Hz,1h)；6.71(s，1h)；6.64(s，1h)；6.555(d，J＝8Hz，2h)；5.14(t，J＝12Hz，1h)；5.06(t，J＝12Hz，1h)；3.78(s，3h)；3.10(d，J＝8Hz,2h)；2.40(s，3h)；2.0(t，J＝12Hz，2h)；1.92(t，J＝12Hz，2h)；1.66(s，3h)；1.58(s，3h)；1.42(s，3h)；
13CNMR(100MHz，CDCl
3)δppm：183；161；160；159；158；156；146；135；131.4；131.3；124；121.6；121.1；114；111；108；107.5；107.2；99；55；39；29；26；25；24；22；17；15。(ESI)-MS,m/z:381.1694[M+H]
+。
<6> target product 6c1,6c2, the preparation of 6d
92mg (0.2mmol) compound 5a is obtained being dissolved in 7ml anhydrous methanol, hydrogen exchange 3 times, room temperature hydrogenation 3,5h, column chromatography [V (sherwood oil): V (ethyl acetate)=2:1] obtains 78mg yellow oil product 6c1 (productive rate 85%).Under similarity condition, react 7h, obtain 82mg yellow oil product 6c2 (productive rate 90%); By 40mg (0.1mmol) compound 5b and 4mgPtO
2be dissolved in 5ml anhydrous methanol, hydrogen exchange 3 times, room temperature hydrogenation 3.5h, column chromatography [V (sherwood oil): V (ethyl acetate)=2:1] obtains 36mg yellow oil product 6d (productive rate 91.6%).
Product structure is all through IR, NMR and MS Analysis deterrmination.Data are as follows:
Compound 6c1, IR (KBr): 3444; 2952; 2922; 2850; 2357; 1634; 1457; 1377; 1212; 1155; 1100; 1030; 584.
1HNMR(400MHz,CDCl
3)δppm：7.265(d，J＝12Hz；1h)；6.78(s，1h)；,6.57(t，J＝8Hz，3h)；5.18(t，J＝12Hz，1h)；3.99(s，3h)；3.89(s，3h)；3.79(s，3h)；3.05(d，J＝8Hz，2h)；2.42(s，3h)；1.84(d，J＝8Hz，2h)；1.37-1.07(m，5h)；0.86(s，3h)；0.84(s，3h)；
13CNMR(100MHz，CDCl
3)δppm：177；162；159；158.5；158.3；157.9；144；134；131；123；121；115；111；110；106；104；98；56；55.6；55.5；39；38；29；27；25；24；22.6；22.2；15。(ESI)-MS,m/z:465.2630[M+H]
+。
Compound 6c2, IR (KBr): 3446; 2952; 2927; 2863; 1636; 1571; 1506; 1459; 1414; 1339; 1212; 1115; 1030; 828; 754.
1HNMR(400MHz,CDCl
3)δppm：7.25(d，J＝8Hz；1h)；6.76(s，1h)；,6.57(t，J＝8Hz，3h)；3.98(s，3h)；3.88(s，3h)；3.79(s，3h)；2.40(s，3h)；2.37-2.21(m，2h)；1.50-1.41(m，2h)；1.29-1.04(m，8h)；0.84(s，3h)；0.83(s，3h)；0.75(d，J＝8Hz；3h)；
13CNMR(100MHz，CDCl
3)δppm：177；162；159；158.5；158.2；157；144；131；125；115；111；110；106；104；98；56；55.6；55.4；39；36；35；32；27；24；22.7；22.6；22.1；19。(ESI)-MS,m/z:467.2787[M+H]
+。
Compound 6d, IR (KBr): 3446; 2957; 2927; 2850; 1736; 1634; 1467; 1379; 1302; 1157; 1115; 1035; 823.
1HNMR(400MHz,CDCl
3)δppm：7.26(d，J＝8Hz；1h)；6.77(s，1h)；,6.68(m，3h)；3.98(s，3h)；3.88(s，3h)；3.79(s，3h)；2.41(s，3h)；2.29(t，J＝16Hz，2h)；1.35(d，J＝8Hz，2h)；0.78(s，3h)；0.76(s，3h)；
13CNMR(100MHz，CDCl
3)δppm：177；162；159；158.5；158.3；157.9；144；131；124；115；111；110；106；104；98；56；55.5；55.4；37；28；23；22.3；22.2；14。(ESI)-MS,m/z:397.2015[M+H]
+。Embodiment 25,2 ', 4 '-hydroxyl (methoxyl group)-7-methyl-3-geranyl (isopentene group) flavones, 5,2 ', 4 '-trimethoxy-7-methyl-3-(3,7-dimethyl-2 octene) flavones and 5, the pharmacologically active of 2 ', 4 '-trimethoxy-7-methyl-3-alkane flavones.
Adopt the target product (6a1,6b1,6b2,6a2,6a3,6c1,6c2,6d) of embodiment 1 to carry out anti-tumor activity experiment to s, Liver cancer cell SMMC-7721 cell and BEL-7404, adopt mtt assay, carry out cell in vitro determination of activity.
The tumour cell of taking the logarithm vegetative period is with 10
4the density of individual/mL is inoculated in 96 orifice plates, 200 μ L are inoculated in every hole, being placed in CO2gas incubator cultivates 24 hours, then target compound (the 6a1 that adds different concns in 96 orifice plates in the logarithmic phase cell of cultivating, 6b1, 6b2, 6a2, 6a3, 6c1, 6c2, 6d), each gradient is established three parallel holes, set up contrast (first three hole adds the RPM I1640 liquid base 200 μ L that do not contain sample simultaneously, rear three holes do not add and do not contain the RPM I1640 liquid base 200 μ L of sample containing cell), cultivate 72 hours, every hole adds the MTT (5mg/mL) of 20 μ L, then be placed in 37 ℃ of incubator incubations 4 hours, extract the DMSO that supernatant liquid adds 200 μ L, concussion 10min dissolution precipitation, by microplate reader, detect OD value subsequently, wavelength 570nm.According to following formula, obtain the inhibiting rate of sample to cell under finite concentration:
Inhibiting rate=[(contrasting the blank OD of blank OD-)-(the blank OD of administration OD-)]/(contrasting the blank OD of blank OD-) * 100%
With inhibiting rate, to drug level mapping (seeing Fig. 2 to 4), obtain the IC of each sample
50value, the results are shown in Table shown in 1 to 4:
Table 1 target compound 6a1,6b1, the IC of 6b2 extracorporeal suppression tumor cell growing multiplication activity
50value (mtt assay)
Table 2 target compound 6a2, the IC of 6a3 extracorporeal suppression tumor cell growing multiplication activity
50value (mtt assay)
Table 3 target compound 6c1, the IC of 6c2 extracorporeal suppression tumor cell growing multiplication activity
50value (mtt assay)
The IC of table 4 target compound 6d extracorporeal suppression tumor cell growing multiplication activity
50value (mtt assay)
Data from table, the present invention 5,2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones has obvious growth-inhibiting effect to s, Liver cancer cell SMMC-7721 cell and BEL-7404 cell, can be for the medicine of screening treatment cervical cancer and liver cancer.
Claims (6)
1.5,2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones, is characterized in that this analogue is compound or its pharmacy acceptable salt with following general formula,
Wherein, R
1for
r
2for-OH, R
3, R
4for-OCH
3or-OH;
Or R
1for
r
2, R
3, R
4for-OCH
3.
2. according to claim 15, 2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones, it is characterized in that this analogue is 5-hydroxyl-2 ', 4 '-dimethoxy-7-methyl-3-geranyl flavones, 5, 2 '-dihydroxyl-4 '-methoxyl group-7-methyl-3-geranyl flavones, 5, 4 '-dihydroxyl-2,-methoxyl group-7-methyl-3-geranyl flavones, 5, 2 ', 4 '-trimethoxy-7-methyl-3-(3, 7-dimethyl-2 octene) flavones, (±) 5, 2 ', 4 '-trimethoxy-7-methyl-3-(3, 7-dimethyl octene) flavones, 5-hydroxyl-2, , 4,-dimethoxy-7-methyl-3-isoamylene radical chromocor, 5, 2 '-hydroxyl-4 '-methoxyl group-7-methyl-3-isoamylene radical chromocor, 5, 2 ', 4 '-trimethoxy-7-methyl-3-(3-methyl butene) flavones.
3. according to claim 25,2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones, is characterized in that this analogue is one of following compound:
。
4. claims 1 to 3 is arbitrary described 5, the preparation method of 2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones; it is characterized in that: with 2; 4-dihydroxyl-4-methyl acetophenone is the acetylize of starting raw material process, resets, and methylates; 2; 4-dibenzoyl chlorine acidylate, Baker-Venkataraman resets, 3 geranyls or isopentene group; acid catalysis is closed ring, and demethylation or shortening form.
5. claims 1 to 3 is arbitrary described 5, the application of 2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones in preparing medicament for resisting cervical cancer.
6. claims 1 to 3 is arbitrary described 5, the application of 2 ', 4 '-trihydroxy--7-methyl-3-alkyl flavones in preparing medicines resistant to liver cancer.
Priority Applications (1)
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| CN105001191A (en) * | 2015-07-23 | 2015-10-28 | 广西师范学院 | Derivative with 5,2'-dyhydroxy-4'-methoxy-3-geranyl flavonoid skeleton and preparation method and application thereof |
| CN105130938A (en) * | 2015-07-23 | 2015-12-09 | 广西师范学院 | Derivative having apigenin framework, preparation method and application thereof |
| CN105153089A (en) * | 2015-07-23 | 2015-12-16 | 广西师范学院 | Derivative with 5,2'-dihydroxy-4'-methoxy-3-geranyl flavone skeleton and preparation method therefor and use thereof |
| CN105175374A (en) * | 2015-07-23 | 2015-12-23 | 广西师范学院 | Derivative with 5,2'-dihydroxy-4'-methoxy-3-geranylated flavone framework, and preparation method for derivative and use of derivative |
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| CN105130938A (en) * | 2015-07-23 | 2015-12-09 | 广西师范学院 | Derivative having apigenin framework, preparation method and application thereof |
| CN105153089A (en) * | 2015-07-23 | 2015-12-16 | 广西师范学院 | Derivative with 5,2'-dihydroxy-4'-methoxy-3-geranyl flavone skeleton and preparation method therefor and use thereof |
| CN105175374A (en) * | 2015-07-23 | 2015-12-23 | 广西师范学院 | Derivative with 5,2'-dihydroxy-4'-methoxy-3-geranylated flavone framework, and preparation method for derivative and use of derivative |
| CN105175374B (en) * | 2015-07-23 | 2017-10-17 | 广西师范学院 | Derivative with the geranyl lavonoid backbone of 5,2 ' dihydroxy, 4 ' methoxyl group 3 and its production and use |
| CN107827726A (en) * | 2017-11-28 | 2018-03-23 | 辽宁中医药大学 | Compound Oleracone E and its extraction separation method in purslane |
| CN107827726B (en) * | 2017-11-28 | 2020-09-15 | 辽宁中医药大学 | Compound Oleracone E in purslane and extraction and separation method thereof |
| CN112851615A (en) * | 2021-01-21 | 2021-05-28 | 厦门大学 | Preparation of isopentenyl flavone and application of isopentenyl flavone as medicine for treating cervical cancer |
| CN112851615B (en) * | 2021-01-21 | 2023-04-07 | 厦门大学 | Preparation of isopentenyl flavone and application of isopentenyl flavone as medicine for treating cervical cancer |
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