Benzoselenadiazole derivatives with anti-tumor and anti-oxidation activities and their preparation and application

A technology of antioxidant activity and benzoselenodiazole, which is applied in the field of medicine to achieve the effects of high yield, simple preparation method, good anti-tumor and antioxidant activity

Active Publication Date: 2011-12-21
GUANGDONG JINAN ESTABLISHED SELENIUM SOURCE NANO TECH RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the antitumor activity of the above organoselenium compounds has room for further improvement.

Method used

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  • Benzoselenadiazole derivatives with anti-tumor and anti-oxidation activities and their preparation and application
  • Benzoselenadiazole derivatives with anti-tumor and anti-oxidation activities and their preparation and application
  • Benzoselenadiazole derivatives with anti-tumor and anti-oxidation activities and their preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Preparation of 5-nitrobenzo[c][1,2,5]selenodiazole (abbreviated as NS)

[0040] Add 1 mmol 4-nitro-o-phenylenediamine to a three-necked flask, then add 95% (v / v) ethanol to dissolve it completely, heat and stir, and add an equimolar amount of SeO dissolved in a little water drop by drop. 2 , heated to 85° C. and refluxed, reacted for 3 hours and precipitated a large amount of khaki precipitate, filtered it with suction, washed three times with 95% ethanol, and dried to obtain a khaki solid with a yield of 80% (mass percentage). ESI-MS (CH 3 OH): m / z 227.1 ((M-H), 100%). 1 H NMR (DMSO): δ8.8(s 1H), δ8.2(m 1H), 8.1(d 1H). IR characteristic peak (KBr), υ / cm -1 : 449, 527, 560 (υ N-Se-N ).UV-Vis(DMSO):λ max 351nm. Fluorescence emission peak (DMSO and water): λ max 689nm.

[0041]

Embodiment 2

[0042] Example 2: Preparation of 5,6-dinitrobenzo[c][1,2,5]selenodiazole (abbreviated as DNS)

[0043] Take 1mmol of 4,5-dinitro-o-phenylenediamine in an agate mortar, then add 1mmol of SeO that is ground into fine powder 2 Solid, then grind at room temperature for half an hour, then transfer the ground mixture to 95% (v / v) ethanol solution, heat to dissolve the precipitate completely, heat filter to remove insoluble matter, and the filtrate precipitates yellow-gray needles after cooling Crystal, yield 80% (mass percentage). ESI-MS (CH 3 OH): m / z 274.2 ((M-H)-, 100%). 1 H NMR (DMSO): δ9.2 (m 1H), δ9.0 (m 1H). IR characteristic peak (KBr), υ / cm -1 : 437,583(υ N-Se-N ).UV-Vis(DMSO):λ max 364nm.

[0044]

Embodiment 3

[0045] Example 3: Preparation of 5-(3,4-diaminobenzene)-benzo[c][1,2,5]selenadiazole (abbreviated as BSBD)

[0046] Weigh 2mmol 3,3′,4,4′-biphenyltetramine in a single-necked flask, add 1.5mol / L hydrochloric acid solution to dissolve it completely, add 1mmol SeO2 dropwise at room temperature 2 Aqueous solution, after reacting for 2 hours, filter to remove impurities, adjust the filtrate to pH 8 with saturated NaOH solution under the condition of stirring in an ice bath, precipitate a gray precipitate of soil, filter with suction, wash the obtained solid several times with a small amount of water, and then dry it in vacuum to obtain The desired product, the yield is 60% (mass percentage). ESI-MS (CH 3 OH): m / z 291.1 ((M+H) + , 100%). 1 H NMR (DMSO): δ7.8(m1H), δ7.0(m 1H), δ6.6(m 1H), δ4.8(s 1H), δ4.6(s 1H), δ3.3(d 1H).IR characteristic peak (KBr), υ / cm -1 : 455,671(υ N-Se-N ).UV-Vis(DMSO):λ max 467nm. Fluorescence emission peak (DMSO and water): λ max 669nm.

[0047]...

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Abstract

The invention discloses benzoselenadiazole derivatives with antitumor and antioxidation activities, and a preparation method and application thereof. The chemical structure of the benzoselenadiazole derivatives is disclosed as Formula I, wherein R1 is -H or -NO2, R2 is -H, -NO2 or a group shown in specification, and R1 and R2 can not be H at the same time. The benzoselenadiazole derivatives are synthesized by reacting ortho-diamine compounds with selenium dioxide in a liquid phase or solid phase. The benzoselenadiazole derivatives have favorable antitumor and antioxidation activities, and have the advantages of simple preparation method and high yield. The benzoselenadiazole derivatives disclosed by the invention can be used for preparing antitumor drugs and/or antioxidation drugs. Formula I is shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a benzoselenadiazole derivative with antitumor and antioxidative activities, a preparation method and application thereof. Background technique [0002] Malignant tumors are the greatest threat to human health in this century. At present, the incidence of malignant tumors in the world continues to rise, and there are nearly 10 million new malignant tumor patients every year. According to the current trend of cancer incidence, the incidence of cancer worldwide will increase by 50% in 2020, and the number of new cancer patients worldwide will reach 15 million each year. The cause of death caused by malignant tumor accounted for 17.9%, accounting for the second cause of death. According to the 2006 Statistical Bulletin on the Development of China's Health Services, the leading cause of death among urban and rural residents in my country is malignant tumors. In 2007, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D293/10A61K31/41A61P35/00A61P39/06
Inventor 陈填烽黄晓纯郑文杰杨芳罗懿
Owner GUANGDONG JINAN ESTABLISHED SELENIUM SOURCE NANO TECH RES INST CO LTD
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