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5,6-dihydro-choleste compound

A technology of steroidal compounds and compounds, applied in the field of a class of 5,6-dihydro-cholesteric compounds, can solve the problems of cumbersome operation steps, outdated degradation process, waste of resources, etc.

Inactive Publication Date: 2007-09-05
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Obviously, this synthesis strategy using steroidal sapogenins has many disadvantages, such as outdated degradation process, cumbersome operation steps, serious environmental pollution, etc., and more importantly, the carbon skeleton and functional groups of steroidal sapogenins have not been fully utilized. , which will inevitably result in a great waste of resources

Method used

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  • 5,6-dihydro-choleste compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of Example 1 Compound 14

[0039]

[0040] Dissolve 10g Tigogenin in 25ml Py, add 6ml Ac 2 O(2.5eq) reacted at 40°C for 2.5h, the raw materials disappeared, stopped heating, cooled at room temperature, added ice water to it, and stirred to make Ac 2 O was completely decomposed, and 10.89 g of white solid 14 (99%) was obtained by suction filtration.

[0041] Compound 14: C 29 h 46 o 4 ; FW 458; m.p 187-190°C; [α] D 25 -146.96° (c 0.98, CHCl 3 );

[0042] 1 H-NMR (300MHz, CDCl 3 ): δ4.68 (1H, m, 3-H), 4.40-4.37 (1H, q, 16-H), 3.46-3.37 (2H, dd, 26-H), 2.02 (3H, s, CH 3 CO), 0.97 (3H, d, J=7.2Hz, 21-CH 3 ), 0.83 (3H, s, 19-CH 3 ), 0.79 (3H, d, J=6.8Hz, 27-CH 3 ), 0.0.76 (3H, s, 18-CH 3 )

Embodiment 2

[0043] Synthesis of Example 2 Compound 15

[0044]

[0045] Dissolve 11g compound 14 in 50ml DCM, add 150ml acetone, 50ml 4×10 -4 mol / L of EDTA-Na 2 Solution, add 88g Oxone and 47g NaHCO several times under ice-water bath condition 3 The mixture was reacted for 6 days, the raw materials disappeared, filtered, the inorganic salt was washed several times with DCM, the organic solvent was evaporated to dryness, and the organic matter was washed with hot water to obtain a white solid 15 with a yield of about 80%.

[0046] Compound 15: C 29 h 46 o 5 ; FW 474; mp 170-171°C; [α] D 25 -46.97° (c 0.98, CHCl 3 );

[0047] 1 H-NMR (300MHz, CDCl 3 )δ4.68 (1H, m, 3-H), 3.58-3.56 (2H, dd, 26-H), 2.06 (3H, s, CH 3 CO), 2.03 (3H, s, CH 3 CO), 1.25 (3H, s, 19-CH 3 ), 1.02 (3H, d, J=6.4Hz, 21-CH 3 ), 0.81 (3H, d, J=6.8Hz, 27-CH 3 ), 0.73 (3H, s, 18-CH 3 )

Embodiment 3

[0048] Synthesis of Example 3 Compound 16

[0049]

[0050] Dissolve 1.205g of compound 15 in 20ml of dry DCM, add 0.32ml of 30% HBr / HOAc solution dropwise at room temperature under the protection of argon, stir at room temperature for 18h without starting material, add saturated NaHCO 3 Quench the reaction with aqueous solution, extract with DCM, combine the organic phases, wash the organic phases with saturated brine twice, anhydrous MgSO 4 Drying, spin-drying and separation by column chromatography (PE:EA=20:1) gave 1.209 g of white solid 16 (88.9%).

[0051] Compound 16: C 29 h 45 BrO 4 ; FW 537; mp 144-145°C; [α] D 25 -134.5° (c 0.965, CHCl 3 );

[0052] 1 H-NMR (300MHz, CDCl 3 )δ4.70 (1H, m, 3-H), 3.45-3.44 (2H, d, 26-H), 2.03 (3H, s, CH 3 CO), 1.06 (3H, d, J=6.4Hz, 21-CH 3 ), 1.03 (3H, d, J=6.8Hz, 27-CH 3 ), 0.85 (3H, s, 19-CH 3 ), 0.77 (3H, s, 18-CH 3 );

[0053] 13 C-NMR (75MHz, CDCl 3 )δ 218.24, 213.07, 73.35, 66.34, 53.66, 5...

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Abstract

A 5,6-bihydro-cholesteroid compound with 5,6-bihydro-cholesterol structure used for synthesizing 5,6-bihydro-OSW-1 and its preparing process are disclosed.

Description

technical field [0001] The present invention relates to a class of novel structure steroid molecules with 5,6-dihydro-cholesterol skeleton and their synthesis method. This type of compound can be used to synthesize OSW-1 analogue 5,6-dihydro-OSW-1 . Synthesizing 5,6-dihydro-OSW-1 by using the method described in the invention has simple operation and more atom economy. technical background [0002] In 1992, the Y.Sashida research group of the Faculty of Medicine, University of Tokyo isolated a series of saponins with a cholesterol skeleton from the underground corm of an evergreen ornamental plant Ornithogalum saunderside native to South Africa, which are only in the 3-position of the aglycone Slightly different from the 2”-position of diglycoside, both of them have strong antitumor activity. As the main extract, the saponins of tiger eye (OSW-1, compound 1) have strong antitumor activity against various malignant tumor cells. The lethality is 10-100 times higher than that...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
Inventor 田伟生陈丽君许启海
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI