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Xanthonoid glycoside compound with its benzapyrene [a] substituted by hydroxy-propyl and photochemistries synthesizing method

A compound and technology of xanthone, applied in the field of 11-carboxypropyl substituted benzo[a]xanthone compound and its photochemical synthesis method, can solve the problem of low reaction yield and the like

Inactive Publication Date: 2003-07-23
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Not only can it prepare benzoxanthone, but it is also a method for preparing polycyclic aromatic hydrocarbons, but the reaction yield is not high, generally 15-35%

Method used

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  • Xanthonoid glycoside compound with its benzapyrene [a] substituted by hydroxy-propyl and photochemistries synthesizing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1: Preparation of 3-(12-oxo-12H-benzo[a]xanthene-11-yl)propionic acid (Ia)

[0019] In 30 mL of acetonitrile, 1 mmol of pyridine and 2 mmol of CuCl were added dropwise, shaken to obtain a brown solution, and then 1 mmol of 1,1'-bi-2-naphthol (3a) was added. Stir with oxygen under normal pressure, and react at room temperature for 60 hours. The solvent was evaporated under reduced pressure, and the residue was redissolved in 50 mL of ethyl acetate, washed with 5% ammonia water (3×30 mL), and then washed with water until neutral. The organic phase was separated and dried over anhydrous sodium sulfate. Finally, it was separated by silica gel column chromatography (silica gel 100-200 mesh, eluted with ethyl acetate:petroleum ether=1:15-1:6). The product is 1-oxo-13c-hydroxy-1,13c-dihydro-dibenzo[a,kl]xanthene (2a), yellow powder. Yield 60%. m.p.>250°C (dec.). 1 HNMR (DMSO-d 6 ,500MHz)δ H : 6.28(d, J=10.0Hz, 1H), 7.17(d, J=8.5Hz, 1H), 7.19(s, 1H, OH, disappear...

Embodiment 2

[0021] Example 2: Preparation of 3-(3,9-dibromo-12-oxo-12H-benzo[a]xanthene-11-yl)propionic acid (Ib)

[0022] In 30mL of acetonitrile, add dropwise 1mmol ethanolamine and 2mmol CuCl 2 2H 2 O, shake to get a brown solution, then add 1 mmol 6,6'-dibromo-1,1'-bi-2-naphthol (3b). Stir with oxygen under normal pressure, and react at room temperature for 77 hours. The solvent was evaporated under reduced pressure, and the residue was redissolved in 50 mL of ethyl acetate, washed with 5% ammonia water (3×30 mL), and then washed with water until neutral. The organic phase was separated and dried over anhydrous sodium sulfate. Finally, it was separated by silica gel column chromatography (silica gel 100-200 mesh, eluted with ethyl acetate:petroleum ether=1:15-1:6). The product was 5,11-dibromo-1-oxo-13c-hydroxy-1,13c-dihydro-dibenzo[a,kl]xanthene (2b) as a yellow powder. Yield 62%, m.p.>250°C (dec.). 1 HNMR (DMSO-d 6 , 500MHz) δH: 6.36(d, J=10.0Hz, 1H), 7.38(d, J=10.0Hz, 1H), 7...

Embodiment 3

[0024] Example 3: Preparation of methyl 3-(12-oxo-12H-benzo[a]xanthene-11-yl)propionate (Ic)

[0025] 2a (1 mmol) of Example 1 was dissolved in 20 mL of ethyl acetate, and about 1 mmol of methanol was added as a nucleophile, irradiated under sunlight, followed by TLC until the reaction was complete. The reaction mixture was concentrated and separated by silica gel column chromatography (silica gel 100-200 mesh, eluting with ethyl acetate:petroleum ether=1:15-1:4) to obtain white needle-like crystals of Ic. Yield 75%. m.p.116-117°C. 1 HNMR (CDCl 3 ,500MHz)δ H : 2.87(t, J=7.5Hz, 2H), 3.68(s, 3H, OCH 3 ), 3.72(t, J=7.5Hz, 2H), 7.24(d, J=7.5Hz, 1H), 7.44(d, J=7.5Hz, 1H), 7.52(d, J=9.0Hz, 1H), 7.57-7.60(m, 2H), 7.76(t, J=7.5Hz, 1H), 7.90(d, J=7.5Hz, 1H), 8.10(d, J=9.0Hz, 1H), 8.97(d, J = 8.5Hz, 1H); 13 CNMR (CDCl 3 , 125MHz) δ C : 30.98 (CH 2 ), 35.51 (CH 2 ), 51.47 (OCH 3 ),108.89,115.53,116.62,117.60,121.69,125.99,126.70 ,127.12,128.45,129.41,130.22,131.05,133.07,136....

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Abstract

A kind of 11-carboxypropyl substituted benzo [a] xanthone compounds is prepared from substituted binaphthol through catalytic reaction under existance of water and copper-amine complex as catalyst toobtain 1-oxy-13c-hydroxy-1,13-dihydro-dibenzo [a,kl] xanthene compound, and optical open-loop synthesizing respectively in water, alcohol, and ammonia (or amine) contained system.

Description

technical field [0001] The invention relates to benzo[a]xanthone compounds substituted by 11-propionyl group and a preparation method thereof. Background technique [0002] Xanthone compounds are secondary metabolites of some higher plants, fungi or lichens. In recent years, xanthone compounds of various structures have been continuously isolated from plants (Peres, V.; Nagem, T.J.. Phytochemistry 1997, 44:191; (b) Petres, V.; Nagerm, T.J.; de Oliveira , F.F.; Phytochemistry 2000, 55:683). Due to the structural similarity between these compounds and flavonoids, they have good physiological activities such as: antimicrobial effect, regulating effect on organisms, antiviral and antitumor effects. Therefore, it occupies a more important position in medicinal chemistry, and has also attracted people's greater research interest, thus developing a variety of methods for synthesizing xanthone, but the methods that can be used for synthesizing benzoxantho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/86
Inventor 许遵乐黄孟炜汪波谭端明庞冀燕
Owner SUN YAT SEN UNIV
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