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2,3-dioxyethyl-5-methyl-8,9-dimethoxy benzophenanthridine derivative, and preparation method and application thereof

A technology of dimethoxytriphenanthridine and dioxyethyl is applied in the field of preparing anti-tumor pharmaceutical compositions, which can solve the problem of low tumor cell selectivity and achieve good anti-tumor activity and significant cytotoxic activity Effect

Inactive Publication Date: 2013-01-23
GUANGXI NORMAL UNIV
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AI Technical Summary

Problems solved by technology

It has been found that current anticancer drugs generally have the disadvantage of low selectivity to tumor cells, and almost all anticancer drugs kill normal cells as well as cancer cells

Method used

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  • 2,3-dioxyethyl-5-methyl-8,9-dimethoxy benzophenanthridine derivative, and preparation method and application thereof
  • 2,3-dioxyethyl-5-methyl-8,9-dimethoxy benzophenanthridine derivative, and preparation method and application thereof
  • 2,3-dioxyethyl-5-methyl-8,9-dimethoxy benzophenanthridine derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1: Synthesis of 2-bromo-4,5-dimethoxybenzaldehyde (compound 1)

[0017] Add methanol (20mL) and 3,4-dimethoxybenzaldehyde (1.42g, 8.55mmol) into a round bottom flask, slowly add liquid bromine (0.5mL, 9.76mmol), react for 1 hour, and remove by rotary evaporation solvent. Water (50 mL) was added under constant stirring, and the resulting paste was suction-filtered with a Buchner funnel, washed with water and methanol, and dried to obtain 1.76 g of a colorless to slightly yellow product, with a yield of 84%. M.p.143~145℃, 1 H NMR (500MHz, CDCl 3 ) δ: 10.21 (s, 1H, CHO), 7.44 (s, 1H, ArH), 7.08 (s, 1H, ArH), 3.97 (s, 3H, OCH 3 ), 3.94 (s, 3H, OCH 3 ). The structural formula of compound 1 is as follows:

[0018]

Embodiment 2

[0019] Example 2: Synthesis of 2,3-dioxoethyl-5-aminonaphthalene (compound 2)

[0020] Add absolute ethanol (170mL), 2,3-dioxoethyl-5-nitronaphthalene (1.56g, 7.18mmol) and 0.15g of 10% Pd / C into a round-bottomed flask, and pass through hydrogen to react 8 hours, filtered to remove ethanol, and the resulting residue was purified by silica gel column chromatography to obtain 1.11 g of lavender solid, with a yield of 82%. M.p.169~173℃, 1 H NMR (500MHz, CDCl 3 ) δ: 7.28 (s, 1H, ArH), 7.26 (s, 1H, ArH), 7.18 (m, 2H, ArH), 6.65 (m, 1H, ArH), 4.36 (s, 4H, OCH 2 CH 2 O), 3.97 (s, 2H, NH 2 ), 13 C NMR (CDCl 3 , 125MHz) δ: 143.92, 143.28, 140.94, 130.62, 124.78, 119.90, 117.80, 113.25, 108.20, 106.54 (10C, 2Ar), 64.54, 64.52 (2C, OCH 2 CH 2 O); IR (KBr) ν: 3838 (N-H), 3735 (N-H), 3368, 1636 (Ar-H), 1517 (Ar-H), 1475 (Ar-H), 1290 (C-O), 1252 (C-O ), 1067 (C-O), 904, 864cm -1 ;APCIMS m / z:201.83[M+H] + . The structural formula of compound 2 is as follows:

[0021]

Embodiment 3

[0022] Example 3: Synthesis of N-(2-bromo-4,5-dimethoxybenzylidene)-6,7-(dioxyethyl)-1-naphthylamine (Compound 3)

[0023] Add absolute ethanol (150mL), compound 1 (2.19g, 8.97mol) and compound 2 (1.68g, 8.97mol) into a round bottom flask, heat for 10 hours, filter after cooling, wash with ethanol, and dry 3.05 g of a khaki solid were obtained, yield 82%. M.p.218~221℃, 1 H NMR (500MHz, CDCl 3 ) δ: 8.81 (s, 1H, CHN), 7.94 (s, 1H, ArH), 7.76 (s, 1H, ArH), 7.57 (d, J=8.2Hz, 1H, ArH), 7.33 (m, 2H, ArH), 7.09 (s, 1H, ArH), 6.95 (d, J=7.2Hz, 1H, ArH), 4.37 (brs, 4H, OCH 2 CH 2 O), 4.03 (s, 3H, OCH 3 ), 3.97 (s, 3H, OCH 3 ); 13 C NMR (CDCl 3 , 125MHz) δ: 158.40 (1C, CHN), 152.33, 148.87, 148.01, 144.38, 143.74, 130.29, 127.42, 125.08, 124.53, 118.03, 115.51, 115.22, 112.49, 111.43, 110.439 (1, Ar, 110.43) (2C, OCH 2 CH 2 O), 56.32, 56.23 (2C, 2OCH 3 ); IR (KBr) ν: 1592 (Ar-H), 1564 (Ar-H), 1505 (Ar-H), 1465 (Ar-H), 1288 (C-O), 1248 (C-O), 1214 (C-O) , 900, 862cm -1 ;APC...

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Abstract

The invention relates to a 2,3-dioxyethyl-5-methyl-8,9-dimethoxy benzophenanthridine derivative disclosed as Formula I, a synthesis method and application thereof in preparing medicines for inhibiting tumor cell activity. The 50% inhibition concentrations IC50 of the 2,3-dioxyethyl-5-methyl-8,9-dimethoxy benzophenanthridine-hydrochloride and hydrobromide for four cancer cell strains of stomach cancer (MGC-803), liver cancer (BEL7402), human nasopharyngeal carcinoma (CNE) and human lung adenocarcinoma (A549) are respectively lower than those of nitidine chloride, and are much lower than those of 5-FU (control drug).

Description

technical field [0001] The present invention relates to 2,3-dioxoethyl-5-methyl-8,9-dimethoxybenzophenanthridine derivatives, a preparation method thereof, and an anti-tumor pharmaceutical composition containing the above substances . Background technique [0002] Tumor is a common and frequently-occurring disease that seriously threatens human health. It is one of the most important diseases that endanger human life at present, and its death has ranked first among various causes of death. Among the three major therapies for malignant tumors, drug therapy occupies an important position. Most of the synthetic chemical anti-tumor drugs are compounds with natural anti-tumor active ingredients as the lead. Finding anti-tumor lead products from natural products and carrying out structural modification to make them new anti-tumor drugs is the current anti-tumor research. hotspots (Chinese Oncology, 2007, 16(9), 705-708). It has been found that current anticancer drugs generally...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/056A61K31/4741A61P35/00
Inventor 苏桂发潘成学冯凯曦戴支凯覃江克唐煌刘华钢
Owner GUANGXI NORMAL UNIV
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