CN100420690C - Benzofuran compound, prepn. method and application thereof - Google Patents
Benzofuran compound, prepn. method and application thereof Download PDFInfo
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- CN100420690C CN100420690C CNB2005100204796A CN200510020479A CN100420690C CN 100420690 C CN100420690 C CN 100420690C CN B2005100204796 A CNB2005100204796 A CN B2005100204796A CN 200510020479 A CN200510020479 A CN 200510020479A CN 100420690 C CN100420690 C CN 100420690C
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Abstract
The present invention relates to a benzfuran compound which has a structure in a general formula I, a preparation method of the benzfuran compound, and application of the compound for preparing medicinal preparations used for preventing or treating premature ovarian failure, climacteric syndrome, osteoporosis, puberty hypofunction of ovary, polycystic ovary syndrome, sterility and diseases caused by deficient oestrogens or relatively insufficient oestrogens.
Description
Technical field
The present invention relates to a kind of new compound and its production and use.Specifically, relate to a kind of new benzofuran compound and preparation method thereof and the application of this compound in the preparation medicine.Belong to the pharmaceutical chemistry technical field.
Background technology
Oestrogenic hormon (particularly oestrogenic hormon) is one of most important hormone in people and other higher animal body, has physiological function widely.Women 90% E2,50%E1 are respectively from ovary and suprarenal gland before climacterium, women after climacterium, because ovarian atrophy, ovarian function significantly reduces, thereby estrogen secretion significantly reduces, and at this moment the oestrogenic hormon that produces of adipocyte becomes the main source of E2 in the body, if this originates not enough, E1, E2 only were equivalent to before climacterium women's level of follicular phase early in the blood, so just caused easily that bone density reduces, and caused the osteoporosis type to be fractured.The mean lifetime of supposing the women is 80 years old, after the women has time of 1/3 to be in climacterium throughout one's life so, and has 1/4 people can get osteoporosis approximately after 65 years old.Along with being on the rise of aging population, the patient who suffers from climacteric syndrome and osteoporosis will get more and more.In addition, diseases such as some non-climacteric womens trouble ovarian hypofunction, polycystic ovary syndrome, Infertility are also lowly relevant with estrogen level.Therefore, seek to improve ovarian function, promote the medicine of estrogen synthesis to cause people's very big concern.
Modern medicine is used for post-menopausal osteoporosis, and (postmenopausal osteoporosis, control medicine PMOP) mainly contain bone resorption inhibitor and bone formation-promoter two classes.Bone resorption inhibitor comprises oestrogenic hormon, selective estrogen receptor modulators, calcium agent, vitamins D, Diphosphonate, thyrocalcitonin, vitamin K and phytoestrogen etc.Bone formation-promoter comprises fluorochemical, Rat parathyroid hormone 1-34, tethelin and rhIGF-1 etc.Wherein some medicine may have the bone resorption of inhibition simultaneously and promote osteoplastic effect.Though it is effective in cure that present modern medicine is used to control the medicine of preventing PMOP, and side effect is in various degree arranged more; The price of some new drugs is very expensive again.Because the patient of PMOP is the crowd at advanced age, and control PMOP is a secular process, the needs of patients long-term prescription.At present, at premature ovarian failure, involution syndrome, osteoporosis and disease that pubescence, ovarian hypofunction, polycystic ovary syndrome, Infertility etc. caused because of estrogen deficiency or relative deficiency, clinically still lack medicine evident in efficacy, cheap, easy to use.
Summary of the invention
Technical program of the present invention lies in providing a kind of new benzofuran compound and preparation method thereof and this compound preparation prevention or treatment premature ovarian failure, involution syndrome, osteoporosis and pubescence the disease that ovarian hypofunction, polycystic ovary syndrome, Infertility etc. cause because of estrogen deficiency or relative deficiency pharmaceutical preparation in application.
Benzofuran compound provided by the invention has the structure of general formula I:
R wherein
1For-H or-CH
3R
2For-CH
2(CH
2)
2OH ,-CH
2(CH
2)
2COO (CH
2)
2CH
3Or-CH
2CH
2CHO.Work as R
1For-H, R
2Be HO (CH
2)
2CH
2-time is compound 1 5-(3-hydroxyl) propyl group-7-hydroxyl-2-(3,4-dioxy methylene radical phenyl) cumarone; R
1For-CH
3, R
2Be CH
3(CH
2)
2COO (CH
2)
2CH
2-time is compound 2 egonol butyl esters; R
1For-CH
3, R
2During for-CHCHCHO is compound 3 5-acryl-7-methoxyl group-2-(3, the 4-methylenedioxyphenyl) cumarone.
The preparation method of benzofuran compound provided by the invention comprises:
A, the Styrax plant seed is pulverized, water, alcohol or aqueous alcohol are for extracting solvent extraction, and concentrated extracting solution gets total medicinal extract;
B, the total medicinal extract of a step gained is molten diffusing with hot water uses each extracted several times of sherwood oil, chloroform and propyl carbinol successively, gets the each several part extract after concentrating.
Silica gel column chromatography on c, the chloroform extracted solution, earlier carry out gradient elution with sherwood oil/acetone system, obtain compound 6,3, use chloroform/methanol system wash-out again, obtain compound 1, wherein said sherwood oil/acetone-inso is the volume ratio sherwood oil: acetone=1: 0～5: 1, described chloroform/methanol system is the volume ratio chloroform: methyl alcohol=1: 0～10: 1.
The present invention also provides a kind of pharmaceutical composition, and it contains the above-claimed cpd and the pharmaceutically acceptable carrier for the treatment of significant quantity.
The invention provides above-claimed cpd preparation prevention or treatment premature ovarian failure, involution syndrome, osteoporosis and pubescence the disease that ovarian hypofunction, polycystic ovary syndrome, Infertility etc. cause because of estrogen deficiency or relative deficiency medicine in application.
Purposes of the present invention is achieved in that above-mentioned benzofuran compound regulates the Western medicine of estrogen synthesis or the compound that the active ingredient of Chinese herbs compatibility becomes as activeconstituents or with other, add pharmaceutically receivable carrier or auxiliary material, be prepared into oral tablet, capsule, oral liquid or injection liquid.
New compound of the present invention is a natural extract, compares at similar medicine with other aspect treatment osteoporosis, ovarian hypofunction or the diseases such as polycystic ovary syndrome, Infertility, and it is little to have toxic side effect, good effect, low cost and other advantages.
The embodiment of form is described in further detail foregoing of the present invention again by the following examples.But this should be interpreted as that the scope of the above-mentioned theme of the present invention only limits to following example.All technology that realizes based on foregoing of the present invention all belong to scope of the present invention.
Embodiment
The separation of embodiment 1 compound 1,2,3 and structure are identified.
Watt benzoic seed 2.2kg in mountain (dry weight) pulverizes the back with 80-90% industrial spirit 25L lixiviate at room temperature 3 times, each 7 days.Vat liquor gets total medicinal extract 550g behind vacuum concentration, it is suspended in the 5L hot water, respectively extracts 5 times with sherwood oil, chloroform and propyl carbinol successively, each 5L solvent, concentrated extract gets medicinal extract respectively: sherwood oil part 16g, chloroform part 200g, propyl carbinol part 120g.The external activity screening is carried out in sampling, and chloroform and propyl carbinol part show that all having the oestrogenic hormon of promotion generates active.Chloroform is partly gone up silica gel column chromatography, use sherwood oil successively: acetone=10: 1,5: 1,0: 1 wash-out was divided into three sections Fr.1-3 with it.Fr.1 (30 g) goes up silicagel column, and use sherwood oil: acetone=10: 1 wash-outs obtains compound (2) (60mg).Fr.2 (150g) goes up silicagel column, and use sherwood oil: acetone=5: 1 wash-outs obtains compound (3) (60mg).Fr.3 (15g) goes up silicagel column, uses CHCl
3: MeOH=50: 1 wash-out, obtain compound (1) (45mg) and.
Compound 1:5-(3-hydroxyl) propyl group-7-hydroxyl-2-(3,4-dioxy methylene radical phenyl) cumarone, promptly the structure of demethyl egonol is identified:
CF: white amorphous powder; Fusing point: 196-199 ℃;
Infrared spectra: main key band is positioned at 3456,2946,2919,1600,1504,1482,1459,1236,1042,928cm
-1
UV spectrum (MeOH): λ
Max(log ε)=204 (4.69), 302 (4.47), 317 (4.54) nm;
Mass spectrum (HRESIMS): m/z=335.0886[M+Na]
+(calcd.:335.0890);
Proton nmr spectra (600MHz, DMSO-d
6): δ 6.83 (1H, s, H-3), 7.45 (1H, d, J=1.6Hz, H-4), 6.57 (1H, d, J=1.6Hz, H-6), 9.88 (1H, s, H-7-OH), 7.17 (1H, d, J=1.6Hz, H-2 '), 7.05 (1H, d, J=8.0Hz, H-5 '), 7.42 (1H, dd, J=8.0,1.6Hz, H-6 '), 2.60 (2H, t, J=7.4Hz, H-1 "), 1.72 (2H, m, H-2 "), 3.42 (2H, m, H-3 "); 4.46 (1H, t, J=5.0Hz, H-3 " OH), 6.10 (2H, s, H-(O-CH
2-O-));
Carbon-13 nmr spectra (150MHz, DMSO-d
6): δ 32.2 (C-2 "), 35.2 (C-1 "), 60.6 (C-3 "), 101.9 (O-CH
2-O-), 105.4 (C-2 '), 111.0 (C-5 '), 119.1 (C-6 '), 124.8 (C-1 '), (148.2 C-4 '), 148.4 (C-3 '), 101.5 (C-3), 109.3 (C-6), 111.6 (C-4), 131.1 (C-9), 138.4 (C-5), 141.8 (C-8); 142.3 (C-7), 155.3 (C-2).
High resolution mass spectrum quasi-molecular ion peak m/z=335.0886[M+Na from compound 1]
+Extrapolating its molecular formula is C
18H
16O
5UV spectrum is at λ
MaxMaximum absorption band appears in=204,302 and 317nm places, and is similar with the ultra-violet absorption spectrum of 5-(3-hydroxyl) propyl group-7-methoxyl group-2-(3,4-dioxy methylene radical phenyl) cumarone (be egonol, that is egonol), prompts for benzofuran derivative.Compound 1
1The H-NMR signal is similar to egonol also, just than egonol Duo a phenolic hydroxyl group signal δ 9.88 (1H, s, H-7-OH), and methyl signals less.The methylation reaction of compound 1 (KOH-(CH
3)
2SO
4) obtained egonol, show that its phenolic hydroxyl group is in the C-7 position.Therefore compound 1 is 5-(3-hydroxyl) propyl group-7-hydroxyl-2-(3,4-dioxy methylene radical phenyl) cumarone, i.e. demethyl egonol.
5-(3-hydroxyl) propyl group-7-hydroxyl-2-(3,4-dioxy methylene radical phenyl) cumarone, i.e. demethyl egonol
Compound 2: the structure of egonol butyl ester is identified:
CF: light yellow solid; Fusing point: 76-79 ℃;
Infrared spectra: main key band is positioned at 2959,1729,1599,1504,1477,1449,1236,1186,1042,930cm
-1
UV spectrum (MeOH): λ
Max(log ε)=220 (3.97), 300 (3.86), 315 (4.01) nm;
Mass spectrum (HRESIMS): m/z=419.1459[M+Na]
+(calcd.:419.1465);
Proton nmr spectra (600MHz, CDCl
3): δ 6.74 (1H, s, H-3), 7.28 (1H, d, J=1.2 Hz, H-4), 6.55 (1H, d, J=1.2Hz, H-6), 6.90 (1H, d, J=1.6Hz, H-2 '), 6.82 (1H, d, J=8.2Hz, H-5 '), 7.35 (1H, dd, J=8.2,1.6Hz, H-6 '), 2.70 (2H, t, J=7.4Hz, H-1 "), 1.95 (2H, m, H-2 "), 4.07 (2H, t, J=6.5Hz, H-3 "), 5.96 (2H, s, H-(O-CH
2-O-)), 3.98 (3H, s, H-7-OMe), 2.26 (2H, t, J=7.8Hz, H-2 " '), 1.62 (2H, m, H-3 " '), 0.92 (3H, t, J=8.5Hz, H-4 " ');
Carbon-13 nmr spectra (150MHz, CDCl
3): δ 13.9 (C-4 ' "), 18.7 (C-3 " '), 36.5 (C-2 " '), 31.0 (C-2 "), 32.7 (C-1 "), 63.8 (C-3 "), 56.4 (OMe-7), 101.5 (O-CH
2-O-), 105.8 (C-2 '), 108.8 (C-5 '), 119.4 (C-6 '), 124.9 (C-1 '), (148.2 C-4 '), 148.3 (C-3 '), 100.6 (C-3), 107.6 (C-6), 112.6 (C-4), 131.3 (C-9), 137.2 (C-5), 142.7 (C-8); 145.0 (C-7), 156.3 (C-2), 174.0 (C-1 " ').
The UV spectrum of compound 2 is at λ
Max=220,300, maximum absorption band appears in the 315nm place, and is similar to the ultra-violet absorption spectrum of egonol, prompts for benzofuran derivative.The major part of compound 2
1H,
13The C-NMR signal is similar to egonol, just has more than egonol
1H-NMR signal δ 0.92 (3H, J=8.2Hz, H-4 " '), 2.26 (2H, t, J=7.8Hz, H-2 " '), 1.62 (2H, m, H-3 " ') and corresponding
13C-NMR signal δ 13.9 (C-4 " '), 36.5 (C-2 " '), 18.7 (C-3 " '), 174.0 (C-1 " ') (according to HMQC), show that compound 2 has more a butyl ester base than egonol.Compound 2 basic hydrolysiss (10%KOH ethanolic soln) obtain egonol, and therefore, the structure of this compound is 5-(3-butyl propionate base)-7-methoxyl group-2-(3,4-dioxy methylene radical phenyl) cumarone, i.e. egonol butyl ester.High resolution mass spectrum quasi-molecular ion peak m/z=419.1459[M+Na]
+Extrapolating its molecular formula is C
23H
24O
6, further proved conclusively the exactness of this structure.
The structure of compound 3:5-acryl-7-hydroxyl-2-(3, the 4-methylenedioxyphenyl) cumarone is identified:
CF: colourless acicular crystal (acetone); Fusing point: 187-189 ℃;
Infrared spectra: main key band is positioned at 2923,1673,1620,1474,1234,1129,1038cm
-1
UV spectrum (MeOH): λ
Max(log ε)=216 (4.08), 299 (4.30), 319 (4.40) nm;
Mass spectrum (HRESIMS): m/z=345.0730[M+Na]
+(calcd.:345.0733);
Proton nmr spectra (600MHz, CDCl
3): δ 6.87 (1H, s, H-3), 7.38 (1H, d, J=1.6 Hz, H-4), 6.99 (1H, d, J=1.6 Hz, H-6), 7.33 (1H, d, J=1.4Hz, H-2 '), 6.90 (1H, d, J=8.2Hz, H-5 '), 7.42 (1H, dd, J=8.2,1.4Hz, H-6 '), 7.54 (1H, d, J=15.8Hz, H-1 "); 6.72 (1H, dd, J=15.8,7.6Hz, H-2 "), 9.7 1 (1H, d, J=7.6Hz, H-3 "), 6.03 (2H, s, H-(O-CH
2-O-)), 4.08 (3H, s, H-7-OMe);
Carbon-13 nmr spectra (150MHz, CDCl
3): δ 56.2 (OMe-7), 100.4 (C-3), 101.4 (O-CH
2-O-), 105.6 (C-6), 105.7 (C-2 '), (108.7 C-5 '), 115.2 (C-4), 119.6 (C-6 '), (124.0 C-1 '), 127.6 (C-2 "), 130.2 (C-5); 131.5 (C-9), 145.7 (C-7), 145.6 (C-8); 148.2 (C4 '), 148.5 (C-3 '), 153.7 (C-1 "), 157.3 (C-2), 193.6 (C-3 ").
High resolution mass spectrum quasi-molecular ion peak m/z=345.0730 [M+Na] from compound 3
+Extrapolating its molecular formula is C
19H
14O
5 1H-NMR signal δ 6.72 (1H, dd, J=7.6,15.8 Hz, H-2 "), 7.54 (1H, d, J=15.8Hz, H-1 "), 9.71 (1H, d, J=7.6Hz, H-3 "), and corresponding
13C-NMR signal δ 127.6 (C-2 "), 153.7 (C-1 "), 193.6 (have an acryl to exist in C-3 ") (according to HMQC) the prompting molecule; The major part of compound 3
1H,
13The C-NMR signal is similar to egonol, and difference is that compound 3 contains acryl, and egonol contains the n-propyl alcohol base." with C-4, C-6, and H-4, H-6 and C-1 " have HMBC relevant (being illustrated in fig. 1 shown below), illustrate that acryl is positioned at C-5 H-1.Therefore, the structure of compound 3 is confirmed as 5-acryl-7-methoxyl group-2-(3, the 4-methylenedioxyphenyl) cumarone.
5-acryl-7-methoxyl group-2-(3, the 4-methylenedioxyphenyl) cumarone
Embodiment 2
Tablet: The compounds of this invention 1,2 and/or 3 10mg
Lactose 187mg
W-Gum 50mg
Magnesium Stearate 3mg
The preparation method: with activeconstituents, lactose mixes with starch, and water is evenly moistening, the mixture after moistening is sieved and drying, after sieve, adds Magnesium Stearate, then with the mixture compressing tablet, and every heavy 250mg, active component content is 10mg.
Embodiment 3
Capsule: The compounds of this invention 1,2 and/or 3 10mg
Lactose 188mg
Magnesium Stearate 2mg
The preparation method: activeconstituents lactose, Magnesium Stearate are mixed, sieve, uniform mixing in suitable containers is the mixture that the obtains hard gelatin capsule of packing into, each capsule weight 200mg, active component content 10mg.
Embodiment 4 compounds 1,2,3 promote mouse ovarian granulosa cell synthetic estrogen E
2:
Collect the mouse ovarian granulosa cell, cultivate in 96 well culture plates, add estrogen synthesis raw material testosterone or Androstenedione (0.5mM), add medicine to be measured simultaneously, final concentration is 100 μ g/ml, at 37 ℃, and 5%CO
2Cultivated 48 hours under the condition, collect supernatant, 1000 rev/mins of centrifugal 3min remove residual cells, adopt enzyme to exempt from test kit and detect estradiol (E in the supernatant
2) or the content of oestrone, (maximum value that converts E2 with the 0.5mM testosterone to is as 100% production rate, the E of computerized compound
2Synthetic ratio), the results are shown in following table 1:
Table 1 compound 1,2,3 promotes the synthetic E of mouse ovarian granulosa cell
2
Embodiment 5 compounds 1,2,3 promote mouse adipocyte synthetic estrogen:
To form the mouse 3T3-L1 adipocyte of insulin resistant by 2.4 * 10
5/ hole, 1mL/ hole are inoculated in the 24 hole nutrient solutions, treat to add estrogen synthesis desired raw material testosterone or Androstenedione (0.5mM) after cell is grown to individual layer, add medicine to be measured simultaneously, and final concentration is 100 μ g/ml, continues at 37 ℃ 5%CO
2Cultivate under the condition, not add medicine (only containing testosterone) in contrast.Draw supernatant after 72 hours, 1000 rev/mins of centrifugal 3min remove residual cells, adopt enzyme to exempt from test kit and detect estrogenic content in the supernatant, and (maximum value that converts E2 with the 0.5mM testosterone to is as 100% production rate, the E of computerized compound
2Synthetic ratio), the results are shown in following table 2:
Table 2 compound 1,2,3 promotes the synthetic E of mouse adipocyte
2
By table 1-2 as can be seen, compare with control group, 1,2,3 pairs of mouse nest granulosa cells of compound, mouse 3T3-L1 adipocyte produce E
2Significant promoter action is all arranged, therefore, compound 1,2,3 of the present invention can be used for preventing or treats diseases such as the premature ovarian failure that caused by estrogen deficiency, involution syndrome, osteoporosis, ovarian hypofunction, polycystic ovary syndrome, Infertility, for clinical treatment provides a kind of new medicament selection.
Claims (6)
1. benzofuran compound is characterized in that it has the structure of general formula I:
R wherein
1For H or-CH
3, R
2For-CH
2(CH
2)
2OH ,-CH
2(CH
2)
2COO (CH
2)
2Or CH
3-CH
2CH
2CHO.
2. benzofuran compound according to claim 1 is characterized in that:
R
1Be H, R
2For-CH
2(CH
2)
2OH is compound 1 5-(3-hydroxyl) propyl group-7-hydroxyl-2-(3,4-dioxy methylene radical phenyl) cumarone;
R
1For-CH
3, R
2For-CH
2(CH
2)
2COO (CH
2)
2CH
3, be compound 2 egonol butyl esters;
R
1For-CH
3, R
2For-CH
2CH
2CHO is compound 3 5-acryl-7-methoxyl group-2-(3, the 4-methylenedioxyphenyl) cumarone.
3. method for preparing claim 1 or 2 described benzofuran compounds, it comprises:
A, the Styrax plant seed is pulverized, water, alcohol or 20-95% aqueous alcohol are for extracting solvent extraction, and concentrated extracting solution gets total medicinal extract;
B, the total medicinal extract of a step gained is molten diffusing with 40-80 ℃ of hot water uses sherwood oil, chloroform extraction successively;
C, with silica gel column chromatography on the b step gained chloroform extraction liquid, earlier carry out gradient elution with sherwood oil/acetone system, obtain compound 2,3, use chloroform/methanol system wash-out again, obtain compound 1, wherein said sherwood oil/acetone-inso is the volume ratio sherwood oil: acetone=1: 0～5: 1, described chloroform/methanol system is the volume ratio chloroform: methyl alcohol=1: 0～10: 1.
4. a pharmaceutical composition wherein contains claim 1 or the 2 described benzofuran compounds and the pharmaceutically acceptable carrier for the treatment of significant quantity, the medicament that is prepared into.
5. pharmaceutical composition according to claim 4 is characterized in that: described medicament is: oral tablet, capsule, oral liquid or injection liquid.
6. claim 1 or the 2 described compounds application in the pharmaceutical preparation of the disease that preparation prevention or treatment cause because of estrogen deficiency or relative deficiency, wherein said disease be premature ovarian failure, involution syndrome, osteoporosis and pubescence ovarian hypofunction, polycystic ovary syndrome, Infertility.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100204796A CN100420690C (en) | 2005-03-08 | 2005-03-08 | Benzofuran compound, prepn. method and application thereof |
| PCT/CN2006/000341 WO2006094456A1 (en) | 2005-03-08 | 2006-03-07 | An extract of styrax linn, the preparation and uses thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100204796A CN100420690C (en) | 2005-03-08 | 2005-03-08 | Benzofuran compound, prepn. method and application thereof |
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| Publication Number | Publication Date |
|---|---|
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| CN100420690C true CN100420690C (en) | 2008-09-24 |
Family
ID=36993499
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
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| Country | Link |
|---|---|
| CN (1) | CN100420690C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1830435B (en) * | 2005-03-08 | 2010-05-12 | 成都地奥制药集团有限公司 | Oleanol type benzofuran and its glucoside applied in preparation of anti female hormone deficiency medicine |
-
2005
- 2005-03-08 CN CNB2005100204796A patent/CN100420690C/en active Active
Non-Patent Citations (4)
| Title |
|---|
| Benzofurans and another constituent from seeds of styraxofficinalis.. Akgul YY, Anil H.Phytochemistry,Vol.63 . 2003 |
| Benzofurans and another constituent from seeds of styraxofficinalis.. Akgul YY, Anil H.Phytochemistry,Vol.63 . 2003 * |
| Four benzofuran glycosides from Styrax officinalis.. Anil H.Phytochemistry,Vol.19 . 1980 |
| Four benzofuran glycosides from Styrax officinalis.. Anil H.Phytochemistry,Vol.19 . 1980 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1830435B (en) * | 2005-03-08 | 2010-05-12 | 成都地奥制药集团有限公司 | Oleanol type benzofuran and its glucoside applied in preparation of anti female hormone deficiency medicine |
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