CN100436475C - Process for synthesizing cholester-5-ylene-3bata-hydroxy-24-one and derivative - Google Patents
Process for synthesizing cholester-5-ylene-3bata-hydroxy-24-one and derivative Download PDFInfo
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- CN100436475C CN100436475C CNB2005101213773A CN200510121377A CN100436475C CN 100436475 C CN100436475 C CN 100436475C CN B2005101213773 A CNB2005101213773 A CN B2005101213773A CN 200510121377 A CN200510121377 A CN 200510121377A CN 100436475 C CN100436475 C CN 100436475C
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Abstract
The present invention discloses a method for synthesizing cholest-5-alkene-3 bata-hydroxy-24-ketone and derivatives thereof. In the method, hyodesoxycholic acid which can be obtained easily is used as a raw material to prepare 3 beta-acetoxy-cholest-5-alkene-24-acid; the 3 beta-acetoxy-cholest-5-alkene-24-acid reacts with sulfoxide chloride to prepare 3 beta-acetoxy-cholest-5-alkene-24-acyl chloride; the 3 beta-acetoxy-cholest-5-alkene-24-acyl chloride reacts with isopropyl cadion under ultrasonic radiation to produce 3 beta-acetoxy-cholest-5-alkene-24-ketone; the 3 beta-acetoxy-cholest-5-alkene-24-ketone is treated by alkaline hydrolysis to obtain cholest-5-alkene-3 beta-hydroxy-24-ketone; the cholest-5-alkene-3 beta-hydroxy-24-ketone respectively reacts with methyl triphenyl phosphine bromide to synthesize 24-methylene-cholest-5-alkene-3 beta-alcohol and with hydrazine to synthesize cholest-5-alkene-3 beta-hydroxy-24-dihydrazone. The synthetic method of the present invention has the advantages of cheap and available raw materials, scientific and reasonable synthetic route, high synthesis yield in each step, etc.
Description
Technical field
The present invention relates to the synthetic method of courage steroid-5-alkene-3 beta-hydroxies-24-ketone and derivative thereof.
Background technology
Steroidal compounds has multiple important physiological function in vivo, as anticancer, and anti-inflammatory; neuroprotective etc.; courage steroid-5-alkene-3 beta-hydroxies-24-ketone is the important intermediate (structure is suc as formula I, hereinafter to be referred as the I compound) of synthetic many steroidal compounds, and people such as Cui Jianguo once were that raw material is through synthetic this compound (the JianGuo Cui of multistep with the Stigmasterol; LongMei Zeng; JingYu Su, et al., Steroids; 2001; 66,33-38), and synthetic thus a series of polyhydroxy ocean steroidal compound (Lu Weigang with multiple pharmacologically active function; the Su Jing joy; once Gansu Province plum, applied chemistry, 2002; 19 (5), 471-473).
Different 17-position side-chain structures often show different pharmacologically actives, obtain a series of derivatives by courage steroid-5-alkene-3 beta-hydroxies-24-ketone is synthetic, are expected to become potential neuroprotective class medicine.
Summary of the invention
The synthetic method that the purpose of this invention is to provide a kind of courage steroid-5-alkene-3 beta-hydroxies-24-ketone and derivative thereof.
Synthetic method of the present invention is to be raw material with the Hyodeoxycholic Acid, prepare 3 β-acetoxyl group-courage steroid-5-alkene-24-acid, by become 3 β-acetoxyl group-courage steroid-5-alkene-24-acyl chlorides with the sulfur oxychloride prepared in reaction, under the ultrasonic wave radiation and the sec.-propyl cadion react 3 β-acetoxyl group-courage steroid-5-alkene-24-ketone, get courage steroid-5-alkene-3 beta-hydroxies-24-ketone by alkaline hydrolysis; Courage steroid-5-alkene-3 beta-hydroxies-24-ketone synthesizes the two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-with methyltriphenylphosphonium bromide reaction Synthetic 2 4-methylene radical-courage steroid-5-alkene-3 β-alcohol and hydrazine reaction respectively.Reaction scheme is as shown below:
I. courage steroid-5-alkene-3 beta-hydroxies-24-ketone;
II.3 β-acetoxyl group-courage steroid-5-alkene-24-acid;
III.3 β-acetoxyl group-courage steroid-5-alkene-24-acyl chlorides;
IV.3 β-acetoxyl group-courage steroid-5-alkene-24-ketone;
V.24-methylene radical-courage steroid-5-alkene-3 β-alcohol;
VI. two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-.
The concrete steps of synthetic method of the present invention are:
(1) the II reference literature (Bharucha KR, Buckley GC, Cross CK, et al.Can J Chem., 1955,34:982-990.) synthetic;
(2) II is dissolved in the dry-out benzene, adds sulfur oxychloride, add the pyridine of catalytic amount again, at room temperature stirred 2～4 hours, be evaporated to driedly, add benzene again and continue to concentrate, boil off residual sulfur oxychloride, yellow heavy-gravity liquid III;
(3) take by weighing dry magnesium powder, add anhydrous diethyl ether, drip different N-PROPYLE BROMIDE/anhydrous ether solution, add back ultrasonic wave radiation 15～30 minutes, after the ice bath cooling, equimolar Cadmium chloride fine powder is added in batches, under 25～40 ℃, the ultrasonic wave radiation, stir, frozen water cooling slowly is added drop-wise to 30～40% dry-out benzene solution of product III of last step in the reaction system, drips off the back and continues ultrasonic backflow 1～2 hour, after the ice bath cooling, drip 1: 1 aqueous hydrochloric acid, with the benzene extraction, the benzene layer is washed till neutrality with distilled water, dry, concentrating under reduced pressure, silica gel column chromatography gets white solid IV;
(4) will go up the step product IV and be dissolved in the methyl alcohol, add strong base solution, reflux 15～30 minutes, it is neutral transferring pH, methyl alcohol is removed in underpressure distillation, ethyl acetate extraction, organic layer drying, pressure reducing and steaming solvent, get light yellow solid, silica gel column chromatography gets white solid I;
(5) methyltriphenylphosphonium bromide is added in the anhydrous tetrahydrofuran solution, inject n-Butyl Lithium, its injection rate just is dissolved as suitable with methyltriphenylphosphonium bromide, stirring reaction is 4～6 hours under the room temperature, I in the last step is added reaction system, continue reaction 2～3 hours, reaction solution is poured into rapidly in the saturated ammonium chloride solution, use extracted with diethyl ether, ether layer drying, the pressure reducing and steaming solvent gets light yellow solid, silica gel column chromatography gets white solid V;
(6) I is dissolved in the ethanol, the aqueous solution reflux of adding hydrazine 2～4 hours, the pressure reducing and steaming solvent adds entry, and it is neutral transferring pH, and ethyl acetate extraction gets white solid, and silica gel column chromatography gets white solid VI.
In the above-mentioned reactions steps, the concentration of the benzole soln of II is 25～45% in the step (2), and the amount of sulfur oxychloride is 1.0～2.0 times of mole number of II; The amount of magnesium powder is 1.2～3.0 times of mole number of II in the step (3); Strong base solution in the step (4) is the methanol solution of potassium hydroxide or sodium methylate, and concentration is 3～6%; The concentration of the ethanolic soln of I is 5～10% in the step (6), and the concentration of aqueous solution of hydrazine is 50%～80%.
Synthetic method of the present invention has that raw material is cheap and easy to get, synthetic route is scientific and reasonable, respectively go on foot characteristics such as synthetic yield height.Synthetic product courage steroid-5-alkene-3 beta-hydroxies-24-ketone is the important intermediate of synthetic many steroidal compounds, and steroidal compounds has multiple important physiological function in vivo, as anticancer, and anti-inflammatory, neuroprotective etc.; By the synthetic series derivates that obtains of courage steroid-5-alkene-3 beta-hydroxies-24-ketone such as 24-methylene radical-courage steroid-5-alkene-3 β-alcohol, courage steroid-5-alkene-3 beta-hydroxies-24-pair hydrazones, be expected to become potential neuroprotective class medicine.
Embodiment
Following examples are in order to explanation the present invention, but protection scope of the present invention is not only for following examples.Unless otherwise specified, in following examples: I represents courage steroid-5-alkene-3 beta-hydroxies-24-ketone; II represents 3 β-acetoxyl group-courage steroid-5-alkene-24-acid; III represents 3 β-acetoxyl group-courage steroid-5-alkene-24-acyl chlorides; IV represents 3 β-acetoxyl group-courage steroid-5-alkene-24-ketone; V represents 24-methylene radical-courage steroid-5-alkene-3 β-alcohol; VI represents the two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-.
Embodiment 1
Synthesizing of courage steroid-5-alkene-3 beta-hydroxies-24-ketone
(1) get compound (II) 100 gram, add 300ml benzene, the 20ml sulfur oxychloride, the 1ml pyridine at room temperature stirred 2 hours, was evaporated to driedly, removed residual sulfur oxychloride, compound (III), with the dissolving of 200ml benzene, standby.
(2) get 37 gram exsiccant magnesium powder, add the 120ml anhydrous diethyl ether, the anhydrous ether solution of the different N-PROPYLE BROMIDE of instillation 140ml adds to keep and refluxed 30 minutes, and cooling adds 137 gram Cadmium chloride fine powdeies in four batches, refluxes 30 minutes down at 40 ℃.The ice bath cooling slowly drips the benzene mixed solution that compound (III) is made into down, drips the ultrasonic backflow of Bi Jixu 2 hours.After water-cooled on the rocks is frozen 30 minutes, drip 1: 1 aqueous hydrochloric acid of 150ml, with benzene extraction three times, the benzene layer is washed till neutrality with distilled water, anhydrous sodium sulfate drying, and concentrating under reduced pressure, silica gel column chromatography gets white solid (IV).
(3) will go up the potassium hydroxide methanol solution that step product (IV) 10g is added to 500mL3%, reflux 30 minutes, pH with 5% hydrochloride adjusted solution is neutral, methyl alcohol is removed in underpressure distillation, ethyl acetate extraction three times, organic layer merge uses anhydrous sodium sulfate drying, pressure reducing and steaming solvent, get light yellow solid, the white solid of silica gel column chromatography (I).
Embodiment 2
Synthesizing of courage steroid-5-alkene-3 beta-hydroxies-24-ketone
(1) get compound (II) 100 gram, add 400ml benzene, the 32ml sulfur oxychloride, the 1ml pyridine at room temperature stirred 4 hours, was evaporated to driedly, removed residual sulfur oxychloride, compound (III), with the dissolving of 200ml benzene, standby.
(2) step (2) with embodiment 1 is identical.
(3) step (3) with embodiment 1 is identical.
Embodiment 3
Synthesizing of courage steroid-5-alkene-3 beta-hydroxies-24-ketone
(1) step (1) with embodiment 1 is identical.
(2) get 20 gram exsiccant magnesium powder, add the 60ml anhydrous diethyl ether, the anhydrous ether solution of the different N-PROPYLE BROMIDE of instillation 73ml under 60% ultrasonic wave radiation adds and continued ultrasonic 15～30 minutes, add 78 gram Cadmium chloride fine powdeies after the cooling in four batches, under 25～40 ℃, opened for 60% ultra-sonic oscillation half an hour.The frozen water cooling slowly drips the benzene mixed solution of compound (III) down, drips the ultrasonic backflow of Bi Jixu 2 hours.After water-cooled on the rocks is frozen 30 minutes, drip 150ml (1: 1) aqueous hydrochloric acid, with benzene extraction three times, the benzene layer is washed till neutrality with distilled water, anhydrous sodium sulfate drying, and concentrating under reduced pressure, silica gel column chromatography gets white solid (IV).
(3) step (3) with embodiment 1 is identical.
Embodiment 4
Synthesizing of courage steroid-5-alkene-3 beta-hydroxies-24-ketone
(1) step (1) with embodiment 1 is identical;
(2) step (2) with embodiment 3 is identical;
(3) will go up the methanol solution that step product (IV) 10g is added to the sodium methylate of 300mL3%, stirring at room 1 hour, pH with 5% hydrochloride adjusted solution is neutral, methyl alcohol is removed in underpressure distillation, ethyl acetate extraction three times, organic layer merge uses anhydrous sodium sulfate drying, pressure reducing and steaming solvent, get light yellow solid, the white solid of silica gel column chromatography (I).
Embodiment 5
Synthesizing of 24-methylene radical-courage steroid-5-alkene-3 β-alcohol
(1) identical with step (1)～(3) of embodiment 4.
(2) in the 25mL anhydrous tetrahydrofuran solution, add 1.2 gram methyltriphenylphosphonium bromides, logical nitrogen injects an amount of n-Butyl Lithium, and stirring reaction is 4～6 hours under the room temperature, the tetrahydrofuran solution that to go up (I) in the step injects reaction system, continue reaction 23 hours, reaction solution is poured into rapidly in the saturated ammonium chloride solution, use extracted with diethyl ether, ether layer anhydrous sodium sulfate drying, the pressure reducing and steaming solvent gets light yellow solid, the white solid of silica gel column chromatography (V).
Embodiment 6
Synthesizing of 24-methylene radical-courage steroid-5-alkene-3 β-alcohol
(1) identical with step (1)～(3) of embodiment 4.
(2) in the 50mL anhydrous tetrahydrofuran solution, add 5 gram methyltriphenylphosphonium bromides, logical nitrogen injects an amount of n-Butyl Lithium, and stirring reaction is 4 hours under the room temperature, the tetrahydrofuran solution of 1 gram (I) is injected reaction system, continue reaction 2 hours, reaction solution is poured into rapidly in the saturated ammonium chloride solution, use extracted with diethyl ether, ether layer anhydrous sodium sulfate drying, the pressure reducing and steaming solvent gets light yellow solid, the white solid of silica gel column chromatography (V).
Embodiment 7
Synthesizing of 24-methylene radical-courage steroid-5-alkene-3 β-alcohol
(1) identical with step (1)～(3) of embodiment 4.
(2) in the 50mL anhydrous tetrahydrofuran solution, add 2 gram methyltriphenylphosphonium bromides, logical nitrogen injects an amount of n-Butyl Lithium, and stirring reaction is 6 hours under the room temperature, the tetrahydrofuran solution of 1 gram (I) is injected reaction system, continue reaction 4 hours, reaction solution is poured into rapidly in the saturated ammonium chloride solution, use extracted with diethyl ether, ether layer anhydrous sodium sulfate drying, the pressure reducing and steaming solvent gets light yellow solid, the white solid of silica gel column chromatography (V).
Embodiment 8
Synthesizing of the two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-
(1) identical with step (1)～(3) of embodiment 4.
(2) 1g is used the 10mL dissolve with ethanol, add the aqueous solution of 5mL50% hydrazine, reflux 4 hours, the pressure reducing and steaming solvent adds suitable quantity of water, and it is neutral transferring pH, and ethyl acetate extraction gets white solid, the white solid of silica gel column chromatography (VI).
Embodiment 9
Synthesizing of the two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-
(1) identical with step (1)～(3) of embodiment 4.
(2) 1g (I) is used the 20mL dissolve with ethanol, add the aqueous solution of 5mL80% hydrazine, reflux 2 hours, the pressure reducing and steaming solvent adds suitable quantity of water, and it is neutral transferring pH, and ethyl acetate extraction gets white solid, the white solid of silica gel column chromatography (VI).
Purpose product 1: the structural identification of courage steroid-5-alkene-3 beta-hydroxies-24-ketone
Fusing point: 135-137 ℃
Ultimate analysis: C:80.94, H:11.07, calculated value: C
27H
44O
2: C:81.00,11.00, O:8.00.
MS：[M
+]＝401，[M
+-1]＝401，
IR(cm
-1)：3409，2936，2870，1710，1466，1378，1056
1HNMR(CDCl
3)：
5.37(1H，t，6β-CH)，3.54(1H，m，3-CH)，2.60(1H，m，25-CH)，1.13(3H，d，26-CH
3，27-CH
3)，1.01(3H，s，19-CH
3)，0.91(3H，d，21-CH
3)，0.68(3H，s，18-CH
3).
13CNMR(CDCl
3)：
215.4(C)，140.7(C)，121.6(CH)，71.7(CH)，56.7(CH)，56.0(CH)，50.1(CH)，42.3(C)，42.2(CH
2)，40.8(C)，39.7(CH
2)，37.2(CH)，36.4(CH
2)，35.7(CH)，31.9(CH)，31.6(CH
2)，30.9(CH
2)，29.8(CH
2)，29.6(CH
2)，28.2(CH
2)，24.2(CH
2)，21.0(CH
3)，19.3(CH
2)，18.7(CH
3)，18.5(CH
3)，18.3(CH
3)，11.8(CH
3).
The structural identification of purpose product 2:24-methylene radical-courage steroid-5-alkene-3 β-alcohol
Fusing point: 148-149 ℃
Ultimate analysis: C:83.36, H:11.80, calculated value: C
28H
46O:C:84.42, H:11.56; .MS:[M
+-1]=398, [M
++ 1]=399, [M
++ 1]=400
IR(cm
-1)：3416，3028，2936，2868，1642，1464，1377，1057.
1HNMR(CDCl
3)：
5.38(1H，t，6β-H)，0.71(1H，d，28-CH)，.65(1H，d，28-CH)，3.52(1H，m，3-CH)，2.25(1H，m，25-CH)，1.13(6H，d，26-CH
3，27-CH
3)，1.01(3H，s，19-CH
3)，0.91(3H，d，21-CH
3)，0.69(3H，s，18-CH
3).
13CNMR(CDCl
3)：
156.8(C)，140.7(C)，121.6(CH)，105.9(CH
2)，71.8(CH)，56.8(CH)，56.0(CH)，50.1(CH)，42.35(C)，42.30(CH
2)，39.8(C)，37.2(CH)，36.5(CH)，35.7(CH)，34.7(CH)，33.8(CH
2)，31.9(CH
2)，31.6(CH
2)，30.9(CH
2)，28.2(CH
2)，24.2(CH
2)，22.0(CH
3)，21.8(CH
2)，21.1(CH
3)，19.4(CH
3)，18.7(CH
3)，11.8(CH
3).
Purpose product 3: the structural identification of the two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-
Ultimate analysis: C:81.52, H:11.53, N:3.36;
Calculated value: C
54H
88O
2N
2C:81.34, H:11.13, N:3.51.
MS：[M]
+＝897，[M+1]
+＝898，
IR：3382，2933，2867，2859，1637，1466，1377，1058.
1HNMR(CDCl
3)：
5.35(1H，t，6β-H)，3.52(1H，m，3-CH)，2.62(1H，m，25-CH)，1.16(6H，d，26-CH
3，27-CH
3)，1.01(3H，s，19-CH
3)，0.91(3H，d，21-CH
3)，0.69(3H，s，18-CH
3).
13CNMR(DMSO)：
169.1(C)，142.1(C)，121.0(CH)，70.9(CH)，57.1(CH)，56.2(CH)，50.6(CH)，43.0(C)，42.8(CH
2)，42.4(C)，37.9(CH)，37.6(CH)，36.9(CH)，36.2(CH)，35.9(CH
2)，32.4(CH
2)，32.2(CH
2)，29.8(CH
2)，29.6(CH
2)，28.7(CH
2)，24.7(CH
2)，21.5(CH
3)，21.0(CH
2)，20.9(CH
3)，19.9(CH
3)，19.1(CH
3)，12.4(CH
3).
Claims (6)
1. the synthetic method of courage steroid-5-alkene-3 beta-hydroxies-24-ketone and derivative thereof, it is characterized in that with the Hyodeoxycholic Acid being raw material, prepare 3 β-acetoxyl group-courage steroid-5-alkene-24-acid, by become 3 β-acetoxyl group-courage steroid-5-alkene-24-acyl chlorides with the sulfur oxychloride prepared in reaction, under the ultrasonic wave radiation and the sec.-propyl cadion react 3 β-acetoxyl group-courage steroid-5-alkene-24-ketone, get courage steroid-5-alkene-3 beta-hydroxies-24-ketone by alkaline hydrolysis; Courage steroid-5-alkene-3 beta-hydroxies-24-ketone synthesizes the two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-with methyltriphenylphosphonium bromide reaction Synthetic 2 4-methylene radical-courage steroid-5-alkene-3 β-alcohol and hydrazine reaction respectively.
2. synthetic method according to claim 1 is characterized in that comprising following concrete reactions steps:
(1) II is dissolved in the dry-out benzene, adds sulfur oxychloride, add the pyridine of catalytic amount again, at room temperature stirred 2～4 hours, be evaporated to driedly, add benzene again and continue to concentrate, boil off residual sulfur oxychloride, yellow heavy-gravity liquid III;
(2) take by weighing dry magnesium powder, add anhydrous diethyl ether, drip different N-PROPYLE BROMIDE/anhydrous ether solution, add back ultrasonic wave radiation 15～30 minutes, after the ice bath cooling, equimolar Cadmium chloride fine powder is added in batches, under 25～40 ℃, the ultrasonic wave radiation, stir, frozen water cooling slowly is added drop-wise to 30～40% dry-out benzene solution of product III of last step in the reaction system, drips off the back and continues ultrasonic backflow 1～2 hour, after the ice bath cooling, drip 1: 1 aqueous hydrochloric acid, with the benzene extraction, the benzene layer is washed till neutrality with distilled water, dry, concentrating under reduced pressure, silica gel column chromatography gets white solid IV;
(3) will go up the step product IV and be dissolved in the methyl alcohol, add strong base solution, reflux 15～30 minutes, it is neutral transferring pH, methyl alcohol is removed in underpressure distillation, ethyl acetate extraction, organic layer drying, pressure reducing and steaming solvent, get light yellow solid, silica gel column chromatography gets white solid I;
(4) methyltriphenylphosphonium bromide is added in the anhydrous tetrahydrofuran solution, inject n-Butyl Lithium, its injection rate just is dissolved as suitable with methyltriphenylphosphonium bromide, stirring reaction is 4～6 hours under the room temperature, I in the last step is added reaction system, continue reaction 2～3 hours, reaction solution is poured into rapidly in the saturated ammonium chloride solution, use extracted with diethyl ether, ether layer drying, the pressure reducing and steaming solvent gets light yellow solid, silica gel column chromatography gets white solid V;
(5) I is dissolved in the ethanol, the aqueous solution reflux of adding hydrazine 2～4 hours, the pressure reducing and steaming solvent adds entry, and it is neutral transferring pH, and ethyl acetate extraction gets white solid, and silica gel column chromatography gets white solid VI;
In the above-mentioned steps, I represents courage steroid-5-alkene-3 beta-hydroxies-24-ketone; II represents 3 β-acetoxyl group-courage steroid-5-alkene-24-acid; III represents 3 β-acetoxyl group-courage steroid-5-alkene-24-acyl chlorides; IV represents 3 β-acetoxyl group-courage steroid-5-alkene-24-ketone; V represents 24-methylene radical-courage steroid-5-alkene-3 β-alcohol; VI represents the two hydrazones of courage steroid-5-alkene-3 beta-hydroxies-24-.
3. synthetic method according to claim 2 is characterized in that the concentration of the benzole soln of II in the step (1) is 25～45%, and the amount of sulfur oxychloride is 1.0～2.0 times of mole number of II.
4. synthetic method according to claim 2, the amount of magnesium powder in the step (2) of it is characterized in that are 1.2～3.0 times of mole number of II.
5. synthetic method according to claim 2 is characterized in that the strong base solution in the step (3) is the methanol solution of potassium hydroxide or sodium methylate, and concentration is 3～6%.
6. synthetic method according to claim 2 is characterized in that the concentration of the ethanolic soln of I in the step (5) is 5～10%, and the concentration of aqueous solution of hydrazine is 50%～80%.
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