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Novel benzanthracene cyclic compounds and preparation method and use thereof

A technology of benzanthracene and compounds, which is applied in the field of benzanthracycline compounds, can solve the problems of difficult synthesis, difficult derivatization, and no report on the synthesis of MarmycinA, etc., and achieve the effect of short reaction steps and high yield

Inactive Publication Date: 2012-11-28
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And so far, there is no report about the synthesis of Marmycin A
Since the natural product Marmycin A has a quaternary carbon center, its synthesis is difficult and it is difficult to rapidly derivatize in drug screening and discovery

Method used

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  • Novel benzanthracene cyclic compounds and preparation method and use thereof
  • Novel benzanthracene cyclic compounds and preparation method and use thereof
  • Novel benzanthracene cyclic compounds and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1L-rhamnocene is the preparation of the glycosylation product Ia-1, Ia-2 and IIa-1, IIa-2 of the sugar moiety

[0052] Step 1: 2-Bromo-5-acetoxy-1,4-p-naphthoquinone (compound 1)

[0053] Dissolve 1,5-diacetoxynaphthalene (1220mg, 5mmol) in 50mL glacial acetic acid, heat to dissolve it, then weigh NBS (3560mg, 20mmol) and dissolve it in 50mL glacial acetic acid and 100mL water, use a dropping funnel The solution of glacial acetic acid and water of NBS was added dropwise to the glacial acetic acid solution of the reactant, and stirred while dropping, for a total of 5 minutes. During the dropwise addition, a yellow solid was produced, and then the reaction solution was stirred at 65° C. for 2 hours. After the reaction, add 100 mL of water to the reaction solution, then extract three times with ethyl acetate, combine the organic phases, wash twice with saturated sodium bicarbonate solution, then wash with saturated brine, dry over anhydrous sodium sulfate, spin ...

Embodiment 2

[0094] Example 2D-Glucosene is the glycosylation product Ib-1, IIb-1 and Ib-2, IIb-2 of the sugar moiety

[0095]

[0096] The acetylated glycosidation products Ib-1 and IIb-1 and the deacetylated Glycosidation products Ib-2 and lib-2.

[0097] Acetylated glycosidation product Ib-1, dark red solid, 1 H-NMR (300MHz, CDCl 3 ): δ9.80(d, 1H, J=3.9Hz), 9.54(d, 1H, J=8.7Hz), 8.33(d, 1H, J=8.7Hz), 8.08(d, 1H, J=8.4Hz ), 7.65(s, 1H), 7.55(m, 3H), 4.90(m, 2H), 4.18(m, 2H), 4.06(dd, 1H, J=2.1, 12.0Hz), 3.61(ddd, 1H, J=2.4, 4.2, 10.2Hz), 2.54(s, 3H), 2.38(dd, 1H, J=1.5, 12.0Hz), 2.16(s, 3H), 2.06(s, 3H), 2.01(m, 1H ); 13 C-NMR (75MHz, CDCl 3 ): δ186.2, 185.6, 170.8, 170.1, 148.3, 138.7, 136.8, 136.5, 136.2, 134.6, 134.4, 132.1, 128.7, 128.4, 128.2, 127.6, 126.1, 122.3, 115.9, 111.7, 9.5 62.9, 46.2, 27.2, 21.5, 21.1, 20.8; MS (EI-LR) 499 (M+).

[0098] Acetylated glycosidation product IIb-1, dark red solid, 1 H-NMR (300MHz, CDCl 3 ): δ10.04(d, 1H, J=5.4Hz), 9.55(d, 1H, J=9Hz)...

Embodiment 3

[0101] Example 3D-Galactosene is the glycosylation product Ic-1, IIc-1 and Ic-2, IIc-2 of the glycan

[0102]

[0103] The acetylated glycosidation products Ic-1 and IIc-1 were prepared according to Step 9 of Example 1, except that the acetylated L-rhamnosene was replaced by acetylated D-galactosene 13 and deacetylated The glycosylation products Ic-2 and IIc-2.

[0104] Acetylated glycosidation product Ic-1, dark red solid, 1 H-NMR (300MHz, CDCl 3 ): δ9.90(d, 1H, J=5.1Hz), 9.53(d, 1H, J=8.7Hz), 8.32(d, 1H, J=8.1Hz), 8.07(d, 1H, J=8.7Hz ), 7.65(s, 1H), 7.58(m, 3H), 4.93(br s, 1H), 4.80(br s, 1H), 4.18(dd, 1H, J=6.0, 11.1Hz), 4.04(m, 2H), 3.77(m, 1H), 2.56(m, 4H), 2.16(s, 3H), 1.96(s, 3H), 1.70(d, 1H, J=13.2Hz). MS(EI-LR): 499(M + ).

[0105] Acetylated glycosidation product IIc-1, dark red solid, 1 H-NMR (300MHz, CDCl 3 ): δ9.82(d, 1H, J=5.1Hz), 9.55(d, 1H, J=9.0Hz), 8.33(d, 1H, J=8.4Hz), 8.07(d, 1H, J=9.0Hz ), 7.64(s, 1H), 7.55(q, 3H, J=7.8, 17.7Hz), 5.10(t, 1H, J=...

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Abstract

The invention relates to novel benzanthracene cyclic compounds and a preparation method and use thereof. The benzanthracene cyclic compounds have the structure shown in a general formula I or II. The compounds can be used as topoisomerase inhibitors for preparing anti-tumor, cell growth-resistant, antibacterial and antimalarial medicaments. The invention also relates to a method for preparing thecompounds. In the formula I, C1' and C3' have an S structure simultaneously, and in the formula II, C1' and C3' have an R structure simultaneously.

Description

technical field [0001] The invention relates to a class of benzanthracycline compounds, which can be used as topoisomerase inhibitors to prepare anti-tumor, anti-cell growth and other drugs. The invention also relates to processes for the preparation of such compounds. Background technique [0002] [0003] The natural product Marmycin A is a new type of anthraquinone derivative extracted and isolated from marine actinomycetes by Fenical et al. It can be divided into benzanthracycline compounds structurally, that is, polyketone-derived angular tetracycline anthraquinone class of compounds. Such compounds have a wide range of biological activities, mainly including antitumor, antibacterial, antiviral, enzyme inhibitors, antiplatelet aggregation, cell growth inhibitors, and immunomodulators. Such as kanglemycin C (Kanglemycin C) has significant immunosuppressive activity; oleandomycin A (Landomycin A) has excellent antitumor activity, once in the United States NCI for ant...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/08A61K31/4748A61P35/00A61P31/00A61P33/06
CPCY02A50/30
Inventor 张翱蒙凌华谢华丁春勇李付营
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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