Novel benzothiapyran diketone compound as well as preparation method and application thereof

A technology of benzothiopyrandione and thiopyrandione, which is applied in organic chemistry, drug combination, antineoplastic drugs, etc., can solve the problems of artificial synthesis and achieve good antitumor activity

Active Publication Date: 2021-02-02
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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  • Novel benzothiapyran diketone compound as well as preparation method and application thereof
  • Novel benzothiapyran diketone compound as well as preparation method and application thereof
  • Novel benzothiapyran diketone compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthesis of 8-methylbenzothiopyrandione, concrete steps are as follows:

[0028] (1) 2-Methyl-4H-benzothiopyran-4-one

[0029] 12.5g H 3 PO 4 , 18gP 2 O 5 Stir at 70°C, and after dissolving, add a mixture of 1.5 mL of thiophenol and 1.5 mL of ethyl acetoacetate dropwise (15 min) using a constant pressure dropping funnel. After reacting for 3 hours, it was poured into ice water and extracted with ethyl acetate. The organic layer was washed with 10% NaOH aqueous solution (20 mL×3), and adjusted to pH=9. After washing with water, the organic layer was washed with anhydrous MgSO 4 dry. The obtained product was concentrated and crystallized with diethyl ether to obtain 1.6 g of yellow crystals, with a yield of 77.4%.

[0030] 1 H-NMR (CDCl 3 / TMS) δ: 8.48(1H, J=7.9Hz, d), 7.56-7.52(2H, m), 7.50(1H, J=7.6, 7.9Hz, dd), 6.82(1H, s), 2.44(3H ,s).

[0031] 13 C-NMR (CDCl 3 )δ: 180.63, 151.32, 137.64, 131.35, 130.70, 128.54, 127.48, 125.98, 124.89, 23.31.

[00...

Embodiment 2

[0045] The synthesis of 8-ethylbenzothiopyrandione is the same as in Example 1.

[0046] 1 H NMR (CDCl 3 / TMS) δ: 8.60 (d, J = 7.8Hz, 1H), 8.10 (d, J = 7.5Hz, 1H), 7.73 (d, J = 7.8Hz, 1H), 7.62 (ddd, J = 19.2, 11.0 ,4.2Hz,2H),7.46(s,1H),7.31(d,J=7.5Hz,1H),2.65(q,J=7.5Hz,2H),1.25(s,3H).

[0047] 13 C NMR (CDCl 3 )δ:192.49,177.84,145.09,145.09,142.68,141.85,138.22,135.72,134.79,134.20,131.91,130.49,129.06,128.67,128.40,124.49,124.02,125.6,767.3

Embodiment 3

[0049] The synthesis of 10-methylbenzothiopyrandione is the same as in Example 1.

[0050] 1 H NMR (CDCl 3 / TMS)δ:8.56(d,J=8.5Hz,1H),7.74–7.57(m,4H),7.52(d,J=7.1Hz,1H),7.33(d,J=7.7Hz,1H), 7.16(t,J=7.4Hz,1H),2.80(s,3H).

[0051] 13 C NMR (CDCl 3 )δ: 192.45, 177.31, 144.10, 142.58, 141.07, 140.31, 135.39, 134.61, 131.82, 131.30, 129.64, 128.40, 128.09, 122.81, 77.36, 23.34.

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Abstract

The invention relates to a novel benzothiapyran diketone compound as well as a preparation method and application thereof. The compound is 8-methyl benzothiapyran diketone, 8-ethyl benzothiapyran diketone, 10-methyl benzothiapyran diketone and 7,9-dimethyl benzothiapyran diketone. The invention discloses a method for synthesizing a series of benzothiapyran diketone compounds by taking thiophenol as an initial raw material for the first time, in-vitro anti-tumor activity experiments are carried out on the benzothiapyran diketone compounds, and results show that the compounds have an obvious inhibition effect on human cervical cancer cells (Hela), human liver cancer cells (SMMC-7721), human lung cancer cells (A549) and human breast cancer cells (MCF77); and the potential value is realized inthe aspects of anti-tumor medicine development and application.

Description

technical field [0001] The invention belongs to the field of new compound synthesis and drug application, and specifically relates to a benzothiopyrandione compound, including synthesis and application. [0002] technical background [0003] Rouge is distributed in Guangxi, Guizhou, Yunnan and other places in my country, and also in India, Myanmar, Thailand and other countries. It is recorded in "National Chinese Herbal Medicine Compilation": "Treating snake bites: fresh products of rouge, smashed and applied to the affected area." It has the effects of detoxification and swelling. Anne dione isolated from dried bark of rouge exhibits a wide range of biological activities, including the treatment of leukemia. [0004] The unique four-ring structure of carmine dione makes it an important structure in biologically active compounds and drug molecules, and has a wide range of pharmacological activities and medicinal significance. However, there is no report in China to artifici...

Claims

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Application Information

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IPC IPC(8): C07D335/04A61P35/00
CPCC07D335/04A61P35/00
Inventor 张有来张舜光张欢王琦田紫烨
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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