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Synthesis and application of a class of acenaphtho[1,2-b]quinoxaline derivatives containing 1,2,3-triazole

A derivative, 2-b technology, used in drug combination, organic chemistry, anti-tumor drugs, etc.

Inactive Publication Date: 2016-04-13
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, they have been shown to cause side effects such as myelosuppression, vomiting, and skin rashes in clinical trials, so designing and synthesizing new and effective DNA-targeted drugs has important application value

Method used

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  • Synthesis and application of a class of acenaphtho[1,2-b]quinoxaline derivatives containing 1,2,3-triazole
  • Synthesis and application of a class of acenaphtho[1,2-b]quinoxaline derivatives containing 1,2,3-triazole
  • Synthesis and application of a class of acenaphtho[1,2-b]quinoxaline derivatives containing 1,2,3-triazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Synthesis of 4-(4-Morpholinomethyl-[1,2,3]-triazole)-acenaphtho[1,2-b]quinoxaline (K1)

[0021] ①In a 250mL three-necked flask, add 10.04g of acenaphthylquinone and 17mL of liquid bromine, heat to 65°C, and 2 SO 3 The solution absorbs tail gas, stirs and reacts for 2 hours, then cools to room temperature, and slowly adds saturated Na to the three-necked flask. 2 SO 3 The solution neutralized the liquid bromine, and a yellow solid was precipitated, filtered and washed until the filtrate was neutral, dried, recrystallized with glacial acetic acid, and dried to obtain 11.79 g of an orange-yellow product of compound b, with a yield of 82%.

[0022]

[0023] ②In a 50mL two-necked bottle, add 0.52g of compound b and 20mL of DMF, stir well at room temperature, and dissolve 0.20g of NaN 3 Dissolved in 1 mL of water, dropped into the reaction system, heated to 50°C for 6 h, poured into cold water after standing, filtered with suction, washed with water, and dried to obtain...

Embodiment 2

[0032] Synthesis of 4-(4-Morpholinomethyl-[1,2,3]-triazole)-acenaphtho-(2,3-dicyano)pyrazine (K2)

[0033] Except that diaminomaleonitrile was used instead of o-phenylenediamine, other synthesis and purification methods were the same as in Example 1 to obtain the target compound K2 as a brown solid with a yield of 61%. m.p.: 182.3-183.3°C.

[0034]

[0035] 1 HNMR (400MHz, CDCl 3 )δ8.68(d, J=8.6Hz, 1H), 8.62(d, J=7.1Hz, 2H), 8.18(s, 1H), 8.08–8.00(m, 2H), 3.90(s, 2H), 3.79(t,4H),2.69(t,4H).

[0036] TOFMS (m / z): C 23 h 17 N 8 O+, Calculated: 421.1520, Found: 421.1526.

Embodiment 1 and 2

[0038] The in vitro tumor cell growth inhibitory activity assay of the target product K1 and K2 synthesized in embodiment 1 and 2:

[0039] Three kinds of tumor cells, human breast cancer cell MCF-7, human cervical cancer cell Hela and human liver cancer cell SMMC-7721, were tested for their anti-tumor cell growth activity in vitro by using tetrazolium salt (microculturetetrozolium, MTT) reduction method. Described MTT reduction method is as follows:

[0040] 1. Cell inoculation

[0041] 1. Digest the adherent monolayer cells with trypsin, and collect the cells into the medium containing serum.

[0042] 2. Count with a counting board.

[0043] 3. Dilute the cells, each well has 2000-5000 cells, and add 100 μL of cell suspension to each well of the tenth column in the middle of the flat-bottomed 96-well plate with a sampler.

[0044] 4. Add PBS to the surrounding wells.

[0045] 5. Put the culture plate at 37°C, 5% CO 2 Incubate in an environment for 12 hours, and add drug...

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Abstract

The invention relates to synthesis and application of an acenaphthene [1,2-b] quinoxaline derivative of 1,2,3-triazole, and belongs to the field of organic synthesis. The derivative is a compound with a structure having a general formula A as shown in the specification. The preparation method of the derivative comprises the following steps: by taking acenaphthequinone as a raw material, carrying out bromination and azidation, carrying out cyclization on a product subjected to bromination and azidation and o-phenylenediamine or diaminomaleonitrile, finally reacting a product obtained from the former step with 3-morpholinyl allylene to prepare the acenaphthene [1,2-b] quinoxaline derivative. The derivative is applied to a drug for inhibiting tumor cells.

Description

technical field [0001] The invention relates to the synthesis and application of a class of acenaphtho[1,2-b]quinoxaline derivatives containing 1,2,3-triazole and belongs to the field of organic synthesis. Background technique [0002] The research on DNA intercalators is a focus of attention in the interdisciplinary disciplines of chemistry, medicine and molecular biology. The intercalator intercalates into the base pairs of DNA, changes its conformation, causes the DNA chain to unwind and lengthen, thereby restricting its replication and exhibiting anti-tumor activity. Naphthalimide derivatives have made great progress in the research of antitumor drugs, such as the famous naphthalimide lead drugs Amonafide and Mitonafide, which have entered clinical trials. However, they have been shown to cause side effects such as bone marrow suppression, vomiting, and skin rashes in clinical trials. Therefore, the design and synthesis of new and effective DNA-targeted drugs has import...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04A61K31/5377A61P35/00
CPCC07D403/04
Inventor 李晓莲于汀汀马黎明张英利孟扬马茹菲黄驰洲
Owner DALIAN UNIV OF TECH
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