1,4-naphthoquinone compounds and application thereof

A compound, naphthoquinone technology, applied in 1 field, can solve the problems of limiting clinical application, toxicity and water solubility, etc., and achieve significant anti-tumor activity

Inactive Publication Date: 2010-09-22
GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Shikonin compounds are a class of natural naphthoquinone compounds that widely exist in nature and have significant antit

Method used

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  • 1,4-naphthoquinone compounds and application thereof
  • 1,4-naphthoquinone compounds and application thereof
  • 1,4-naphthoquinone compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

Example one:

In a 50 mL round-bottom flask were added 20 mL of absolute ethanol, 158 mg (1 mmol) of 1,4-naphthoquinone, 162 mg (1 mmol) of phenylpiperazine and 14 mg (0.1 mmol) of potassium carbonate, protected by nitrogen, and heated to reflux for 2 hours. After the reaction is complete, cool to room temperature, extract with ethyl acetate (100mL*2), combine the organic phases, wash with water, wash with saturated brine, dry and spin dry, and separate by column chromatography to obtain a red product 242mg (76%)

1 H NMR(CDCl 3 ).3.39(t, J=4.8Hz, 4H), 3.76(t, J=4.8Hz, 4H), 6.05(s, 1H), 6.93(m, 3H), 7.15(m, 1H), 7.31(m , 3H), 12.31 (s, 1H), 13.06 (s, 1H).

Example Embodiment

Table 2.

In a 50 mL round-bottom flask were added 20 mL of absolute ethanol, 158 mg (1 mmol) of 1,4-naphthoquinone, 162 mg (1 mmol) of phenylpiperazine and 14 mg (0.1 mmol) of potassium carbonate, protected by nitrogen, and heated to reflux for 2 hours. After the reaction is complete, cool to room temperature, extract with ethyl acetate (100mL*2), combine the organic phases, wash with water, wash with saturated brine, dry and spin dry, and separate by column chromatography to obtain a red product 242mg (76%)

1 H NMR(CDCl 3 ).2.28(t, J=4.8Hz, 4H), 3.68(t, J=4.8Hz, 4H), 6.08(s, 1H), 6.91(m, 2H), 7.00(m, 2H), 7.68(m , 2H), 8.04 (m, 2H).

Example Embodiment

Embodiment three:

In a 50 mL round-bottom flask were added 20 mL of absolute ethanol, 158 mg (1 mmol) of 1,4-naphthoquinone, 162 mg (1 mmol) of phenylpiperazine and 14 mg (0.1 mmol) of potassium carbonate, protected by nitrogen, and heated to reflux for 2 hours. After the reaction is complete, cool to room temperature, extract with ethyl acetate (100mL*2), combine the organic phases, wash with water, wash with saturated brine, dry and spin dry, and separate by column chromatography to obtain a red product 242mg (76%)

1 H NMR(CDCl 3 ).3.23(t, J=5.2Hz, 4H), 3.67(t, J=5.2Hz, 4H), 3.78(s, 3H), 6.07(s, 1H), 6.86(d, J=9.2Hz, 2H ), 6.93 (d, J=9.2 Hz, 2H), 7.67 (m, 2H), 8.03 (m, 2H).

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Abstract

The invention provides 1,4-naphthoquinone compounds with a formula II, and the definition of substituents of the naphthoquinone compounds are described as the specification. The compounds have the connecting ring structures of piperazine or piperidine, have notable antitumor activity, and provide a new choice for preparing antitumor drugs in clinical practice.

Description

technical field The invention relates to a class of 1,4-naphthoquinone compounds and applications thereof. Background technique Worldwide, the cost of new drug research and development is increasing year by year, but the number of new drugs on the market is decreasing, and the efficiency of new drug research and development is decreasing year by year. In recent years, the number of new drugs approved by countries around the world has shown a new "trough" in the past 20 years. The process of drug innovation is very complicated. First, the development cycle of new drugs is long. It usually takes 10 to 15 years from the synthesis of active compounds to the launch of drugs. Second, the investment in new drug research and development is large. In the United States, it takes about 8 Thirdly, the success rate of new drug research and development is low. Of the 10,000 compounds with in vitro activity synthesized, only 250 can enter animal experiments, only 5 can enter clinical tri...

Claims

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Application Information

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IPC IPC(8): C07D295/116C07D211/14C07D211/18A61K31/495A61K31/451A61P35/00
Inventor 丁克裴端卿周净段磊
Owner GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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