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16 alpha-bromosteroid compound and its synthesis method

A technology of steroid compound and synthesis method, which is applied in the field of a class of 16α-bromo steroid compound and its synthesis, and can solve the problem of no literature report and the like

Inactive Publication Date: 2006-09-13
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Synthesis of steroidal drugs and steroidal molecules with potential biological activity from pregesterol is a very meaningful work, but there is no literature report in this area

Method used

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  • 16 alpha-bromosteroid compound and its synthesis method
  • 16 alpha-bromosteroid compound and its synthesis method
  • 16 alpha-bromosteroid compound and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Synthesis of Example 1 Compound 2a and 2b

[0023]

[0024] Put 1 g (3 mmol) of gesterol 1a in a 25 ml dry reaction flask, and add 6 ml of 30% hydrogen bromide-acetic acid solution while stirring and controlling the temperature at 0°C. After the gesterol was dissolved in the 30% hydrogen bromide-acetic acid solution, the temperature was raised to 45° C. and the reaction was continued for 1.5 hours. TLC followed the reaction, and the reaction of gesterol was complete. Acetic acid was distilled off under reduced pressure, and the obtained residue was dissolved in ether. The diethyl ether solution was washed with saturated sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and the resulting crude reaction product was concentrated and subjected to silica gel column chromatography to obtain 1.176g of compound 2a (yield 82%) and 0.134g of compound 2b (yield rate 9%).

[0025] Compound 2a, colorless crystal, m.p.123~125℃...

Embodiment 2

[0027] Example 2 Synthesis of Compounds 2a and 2c

[0028]

[0029] Put 339mg (1mmol) gesterol 1a in a 25ml dry reaction bottle, add 1ml of anhydrous dichloromethane to dissolve. With stirring at room temperature, 2 ml of 30% hydrogen bromide-acetic acid solution (5 mmol) was added dropwise to the reaction flask. After dropping, the temperature was raised to 30° C. to continue the reaction for 1 hour. The reaction was tracked by TLC. After the reaction of gesterol was complete, acetic acid and dichloromethane were distilled off under reduced pressure to obtain a residue. The resulting residue was dissolved in ether, washed with saturated sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain a crude reaction product. The reaction crude product was subjected to silica gel column chromatography (column chromatography eluent: petroleum ether (boiling range 60-90° C.) / ethyl acetate, gradient) to obtain ...

Embodiment 3

[0032] Synthesis of Example 3 Compound 2d

[0033]

[0034] Put 0.832g (2.36mmol) gesteritol 1b in a 25ml dry reaction flask, and add 5ml of 30% hydrogen bromide-acetic acid solution while stirring and controlling the temperature at 0°C. After the gesteritol was dissolved in the 30% hydrogen bromide-acetic acid solution, the temperature was raised to 45° C. to continue the reaction for 2 hours. TLC followed the reaction, and the reaction of gesteritol was complete. Acetic acid was distilled off under reduced pressure, and the obtained residue was dissolved in ether. The ether solution was washed with saturated sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and the reaction crude product obtained was concentrated and subjected to silica gel column chromatography to obtain 1.026 g of compound 2d (yield 80.2%).

[0035] Compound 2d, 1 H-NMR (CDCl 3 , 300MHz) δ: 0.65(s, 3H), 0.80(s, 3H), 1.35(d, J=5.2Hz, 3H), 2.04(s...

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Abstract

The invention relates to 16alpha-bromization steroid compounding and the synthetic method. When the pregnant sterol and the acetlyation bromization reagent have the reaction of the regioselective acetylation,a series of 16alpha-bromization steroid compound of the novel fabric are gained. The formula of the steroid compound is the above formula, so represents the turning up or the adown; R1 is H, OH, 0Ac, OMOM or OTBDPS; R2 is H or Br; R3 is H, Br or R3 and R4 form the 5,6-double bond; R4 is H or Br; R5 is H, OH, Oac or OMOM; thereinto, Ac is the acetyl, TBDPS is the tertiary diphenyl silicone base, MOM is the methoxy methylene. The method provided by the invention is simple, fit for the industrialized produce and makes it possible to utilize effectively the pregnant sterol (the degradation product of the steroid sapogenines).

Description

technical field [0001] The present invention relates to a class of 16α-brominated steroidal compounds with novel structure and a synthetic method of such compounds, that is, the reaction of pregesterol and acetylated brominated reagent (acetyl bromide or hydrogen bromide-acetic acid solution) produces regioselective acetylated A series of 16α-brominated steroidal compounds with novel structures were obtained through the bromination reaction. This method provides the possibility for the further effective utilization of the degradation product of steroidal sapogenin—pregnsterol. technical background [0002] Steroidal sapogenins, such as diosgenin (diosgenin), sisal sapogenin (tigogenin), hecogenin (hecogenin) and timosaponin (sarsasapogenin) are the basic raw materials of my country's steroidal drug industry. To use steroidal sapogenin to synthesize steroidal drugs and steroidal compounds, it is first necessary to degrade steroidal sapogenin into pregnanes or androsteroids. ...

Claims

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Application Information

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IPC IPC(8): C07J5/00C07J75/00
Inventor 田伟生许启海
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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