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Method for synthesizing androstane-17(20)-alkenyl-21-ketone

A synthesis method and technology of androstane are applied in the field of synthesis of androst-17-en-21-one, can solve problems such as difficulty in structural modification, and achieve the effects of fewer synthesis steps, high yield and low cost

Inactive Publication Date: 2013-08-14
YANGZHOU UNIV
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  • Abstract
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Problems solved by technology

There have been many reports on the design and modification of the double bond structure of the 16-position side chain of steroids, and a certain structure-activity relationship has been established, but there are very few reports on the 17(20)-ene-α,β-unsaturated carbonyl steroid Related reports on the compound, from the perspective of steroid synthesis, due to the influence of the angle methyl group at the 13-position, it is more difficult to modify the structure at the 17-position of the steroid than at the 16-position

Method used

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  • Method for synthesizing androstane-17(20)-alkenyl-21-ketone
  • Method for synthesizing androstane-17(20)-alkenyl-21-ketone
  • Method for synthesizing androstane-17(20)-alkenyl-21-ketone

Examples

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Embodiment 1

[0034] Example 1: Synthesis of 17α-(2-phenyl-1-ethynyl)-5α-androst-3β, 17β-diol (2a)

[0035] Under nitrogen protection, phenylacetylene (0.66mL, 6mmol) and anhydrous tetrahydrofuran THF 10mL were added to a dry round-bottomed flask, and after the temperature dropped to -20°C, 2.7M n-butyllithium n-BuLi (2.22 mL, 6mmol), after the drop was completed, when the temperature dropped to -78°C, 3β-hydroxy-5α-androstan-17-one (0.58g, 2mmol) was dissolved in 20mL THF and slowly added dropwise to the reaction system. After the dropwise addition, the reaction was changed to room temperature and stirred for 3 h (the reaction progress was tracked and detected by TLC). After the reaction was completed, the reaction was quenched with 20 mL of water, and most of the solvent was removed by rotary evaporation, followed by CH 2 Cl 2 (2×15mL) was extracted, and the organic phase was washed with water and saturated brine successively, and dried over anhydrous sodium sulfate until clear. The so...

Embodiment 2

[0036] Example 2: Synthesis of 17α-(2-p-methoxyphenyl-1-ethynyl)-5α-androst-3β, 17β-diol (2b)

[0037] The synthesis method is the same as 2a, using p-methoxyphenylacetylene instead of phenylacetylene to obtain the target compound 2b, a white solid, with a yield of 85%; mp 81-83°C (EtOAc-hexanes); IR (KBr, cm -1 )v 3333, 2931, 2855, 2219, 1571, 1510, 1445, 1383, 1247, 1132, 1035, 831; 1 H-NMR (CDCl 3 , 600MHz) δ (ppm): 7.30 (d, J = 6.6Hz, 2H), 6.76 (d, J = 6.6Hz, 2H), 3.73 (s, 3H, Ar-OMe), 3.52-3.47 (m, 1H , 3α-H), 0.80(s, 3H), 0.74(s, 3H); 13 C-NMR (CDCl 3 , 150MHz) δ (ppm): 158.51, 132.07 (2C), 114.28, 112.90 (2C), 90.66, 84.52, 79.27, 70.24, 54.29, 53.08, 49.70, 46.37, 43.87, 38.12, 37.16, 36.03, 345.26, 32.07, 30.61, 30.48, 27.61, 22.26, 20.00, 12.04, 11.34; MS (EI): 423 (M+1, 52%); Anal.Calcd.forC 28 h 38 o 3 : C, 79.58; H, 9.06; Found C, 79.80; H, 9.17.

Embodiment 3

[0038] Example 3: Synthesis of 17α-(2-p-tolyl-1-ethynyl)-5α-androst-3β, 17β-diol (2c)

[0039] The synthesis method is the same as 2a, using p-tolueneacetylene instead of phenylacetylene to obtain the target compound 2c, a white solid, with a yield of 81%, mp 93-95°C (EtOAc-hexanes); IR (KBr, cm -1 ) v 3400, 2928, 2857, 1578, 1510, 1451, 1379, 1283, 1136, 1043, 817; 1 H-NMR (CDCl 3 , 600MHz) δ (ppm): 7.33 (d, J = 6.6Hz, 2H), 7.12 (d, J = 6.6Hz, 2H), 3.61-3.56 (m, 1H, 3α-H), 2.35 (s, 3H , Ar-CH 3 ), 0.88(s, 3H), 0.83(s, 3H); 13 C-NMR (CDCl 3 , 150MHz) δ (ppm): 137.27, 130.54 (2C), 128.00 (2C), 119.00, 91.21, 84.87, 79.37, 70.32, 53.09, 49.72, 46.41, 43.89, 38.10, 37.23, 36.04, 35.25, 32.05, 30.61, 30.55, 27.61, 22.25, 20.43, 20.00, 12.00, 11.35; MS (EI): 407 (M+1, 28%); Anal.Calcd.forC 28 h 38 o 2 : C, 82.71; H, 9.42; Found C, 82.63; H, 9.55.

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Abstract

The invention relates to a method for synthesizing androstane-17(20)-alkenyl-21-ketone. The method comprises the following steps of: taking 3beta-hydroxyl-5alpha-androstane-17-ketone as the raw material; carrying out nucleophilic addition reaction with terminal alkyne in the presence of strong base n-BuLi at first; producing 3beta,17-bihydroxyl-20-alkynyl-21-subsitituted phenyl-5alpha-androstane;and then, carrying out addition reaction of exocyclic triple bond and water under the catalysis of HgSO4 / H2SO4, and producing 3beta-hydroxyl-21-subsitituted phenyl-5alpha-androstane-17(20)-alkenyl-21-ketone. Compared with the prior art, the method disclosed by the invention has the advantages of being few in synthesis step, low in cost, easy for reaction condition control, high in yield and applied to preparing androstane-17(20)-alkenyl-21-ketone greatly.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a synthesis method of androst-17(20)-en-21-one. Background technique [0002] Many steroid compounds have been widely used as drugs in clinical treatment due to their strong biological activity. With the study of the mechanism of action of steroid drugs, it was found that the change of the 17-position substituent of the steroid nucleus is more than that of the substituents at other positions. Changes play a more important role in drug activity. Clinical application studies have shown that the 17-position substituent determines the type of pharmaceutical activity of the entire compound, while changes in other positions of the substituent usually only change the activity intensity of the compound, so it is of great significance to modify the 17-position of steroids and study biological activity. more important meaning. In 2008, Moreira et al. used 3β-hydroxyandrostan...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J13/00A61P35/00
Inventor 王存德李艳孙倩刘金良王兴斌蒋澄刚
Owner YANGZHOU UNIV
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