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Pregnenol ketopyrrole compound and preparation method thereof

A compound and drug technology, applied in the field of steroid compounds and their preparation, can solve the problems of complex yield and operation process, and achieve the effects of cheap and easily available raw materials and mild conditions

Inactive Publication Date: 2011-12-21
NORTH CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The loss of oxime synthesis due to subsequent separation is unavoidable, which will affect the yield and complicate the operation process

Method used

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  • Pregnenol ketopyrrole compound and preparation method thereof
  • Pregnenol ketopyrrole compound and preparation method thereof
  • Pregnenol ketopyrrole compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1: the preparation of compound I and II:

[0022] Compound IV was purchased from ACROS ORGANICS, and hydroxylamine, sodium bicarbonate, DMSO, potassium hydroxide, and acetylene were commercially available analytical reagents.

[0023]

[0024] Add 5mmol (349mg) NH in a 50ml two-necked bottle 2 OH·HCl, 10ml DMSO, then add 5mmol (421mg) NaHCO under stirring at room temperature 3 and 5 mmol (1582 mg) of pregnenolone in white powdery crystals, with a strong CO 2 Released, the solution was colorless, and a large amount of white powdery solid was suspended in the solution, and the mixture was reacted at room temperature for 5h. Then heat up to 100°C, stir, pass through acetylene under normal pressure for 0.5h, add 7.5mmol of KOH·0.5H 2 O, continue to stir at 100 ° C, with about 15 cm 3 / min speed into acetylene. After the mixture was cooled, it was diluted with water to 35ml. There were more insoluble reddish-brown massive substances at the bottom, and then...

Embodiment 2

[0032] Embodiment 2: the antibacterial activity test of compound I and II

[0033] The strains to be tested were provided by the Bioassay Laboratory of the Fine Chemical Center of Guizhou University, and were purified and cultivated for later use.

[0034] Adopt growth rate method (Kong Fanbin etc., " 9 kinds of medicaments are to the indoor bacteriostasis test of maize spot bacterium ", Guangxi Agricultural Science, 2006, 37 (2): 148-149) with poisonous potato agar medium (PDA) to The target compounds were tested for their antibacterial activity against Fusarium graminearum, Fusarium oxysporum and Cytosporam and shurica.

[0035] Compounds I and II were diluted with quantitative sterile water to the desired concentration respectively, and placed in a high-speed centrifuge to rotate for 5 minutes to form a drug solution. Pour 10mL of the drug solution (10 times the final concentration of the drug solution) into 90mL of PDA in a molten state (200g of potatoes, 20g of agar, 20g...

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Abstract

The invention relates to a steroid compound and a preparation method thereof, and in particular relates to a pregnenolone pyrrole compound and a preparation method thereof. The starting raw material is cheap and easily available, the conditions of the reaction process are mild, the equipment has no special requirements and the compound is suitable for industrialized production. The method uses a new synthetic intermediate for synthesis, thus the obtained compound can inhibit the wheat scab pathogen, the chili fusarium oxysporum and the apple Valsa mali.

Description

technical field [0001] The invention relates to a steroidal compound and a preparation method thereof, in particular to a pregnenolone pyrrole compound and a preparation method thereof. Background technique [0002] With the continuous development of marine chemistry, people have isolated many polyhydroxy steroid oximes with novel structures and strong physiological activities from marine organisms. Among them, (3E)-cholest-4-ene-3,6- Diketo-3-oxime has strong inhibitory activity on hepatitis B virus HepG cells, and (6E)-cholest-4-ene-3,6-diketo-6-oxime not only has a strong inhibitory activity on leukemia (P-388), human Lung cancer (A-549), human colon cancer (HT-29) and other cell lines have strong cytotoxic activity131, and can also be used as an aromatase inhibitor to prepare anti-breast cancer drugs141. Due to the strong physiological activity of steroid oxime, many steroid oxime derivatives with different structures have been prepared by chemical synthesis. Pregnenol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J43/00C07J41/00A01N45/00A01P3/00
Inventor 刘焕梅
Owner NORTH CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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