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A kind of 1,4-naphthoquinone derivatives and its preparation method and application

A technology of derivatives, naphthoquinones, applied in the fields of new compound synthesis and pharmaceutical application, can solve the problem of no sulfonamide group side chain, etc., achieves simple operation, good anti-human colon cancer cell activity, cheap and easily available raw materials and reagents Effect

Active Publication Date: 2020-03-20
TIANJIN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In 1968, Benjamin P. reported that a series of 2-amino derivatives of 2-chloro-1,4-naphthoquinone had antimalarial activity, but these derivatives did not have sulfonamide side chains

Method used

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  • A kind of 1,4-naphthoquinone derivatives and its preparation method and application
  • A kind of 1,4-naphthoquinone derivatives and its preparation method and application
  • A kind of 1,4-naphthoquinone derivatives and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] A preparation method of 1,4-naphthoquinone derivatives according to claim 1, the steps are as follows:

[0042] Diamine mono(Boc) 2 O is protected to obtain III, reacted with sulfonyl chloride to obtain IV, removed the Boc protecting group under acidic conditions to obtain V, reacted with 1,4-naphthoquinone and its derivatives to obtain a class of 1,4-naphthoquinone derivatives, and the reaction formula is

[0043]

[0044] Specifically related to the synthesis of compound 1.

[0045]

[0046] Will (Boc) 2 O (3.6g, 0.1eq.) was dissolved in anhydrous dichloromethane (50mL), and (Boc) 2 O solution was added dropwise to anhydrous dichloromethane solution of ethylenediamine (0.2mol / L, 1.0eq.) under the protection of argon. The reaction mixture was stirred at 0 °C for 1 h, then at room temperature for 10 h. Saturated NaCl aqueous solution (30mL) was washed, and the organic layer was washed with NaCl 2 SO 4 Drying, filtration and evaporation of the solvent gave th...

Embodiment 2

[0051]Synthesis of compound 2.

[0052]

[0053] The synthesis method of Example 2 is the same as that of Compound 1 above.

[0054] Yield: 89%; Structural parameters: 1 H NMR (400MHz, DMSO-d 6 )δ7.95(d,J=7.6Hz,3H),7.83–7.72(m,4H),7.58(d,J=8.4Hz,2H),7.30(s,1H),3.80–3.75(m,2H ),3.10–3.07(m,2H); 13 CNMR (100MHz, DMSO-d 6 )δ180.3,175.9,145.5,139.6,137.8,135.3,133.2,132.2,130.3,129.7,128.8,126.9,126.3,43.5.HRMS(ESI-TOF)m / z calcd.for C 18 h 14 N 2 o 4 SCl 2 Na + [(M+Na) + ]:446.9932, found 446.9944.

Embodiment 3

[0056] Synthesis of compound 3.

[0057]

[0058] The synthesis method of Example 3 is the same as the synthesis method of Compound 1 above.

[0059] Yield: 94%; Structural parameters: 1 H NMR (400MHz, DMSO-d 6 )δ7.94(t, J=7.2Hz, 2H), 7.82(t, J=8.4Hz, 1H), 7.76–7.71(m, 2H), 7.64(d, J=7.6Hz, 2H), 7.26( d,J=8.0Hz,3H),3.79–3.74(m,2H),3.07–3.02(m,2H),2.19(s,3H); 13 C NMR (100MHz, DMSO-d 6 )δ180.2, 175.8, 145.4, 143.0, 137.8, 135.3, 133.2, 132.2, 130.3, 130.0, 1126.9, 126.9, 126.2, 43.5, 21.2. 19 h 17 N 2 o 4 SClNa + [(M+Na) + ]:427.0480, found 427.0490.

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Abstract

The invention relates to a 1,4-naphthoquinone derivative, a preparation method and applications thereof. According to the present invention, the 1,4-naphthoquinone derivative is firstly synthesized, has good activity in the inhibition of human colon cancer cells (SW480 and HCT116), and has potential application value in the development and application of antitumor drugs; and the results of the alpha-glucosidase inhibitory activity experiment show that the 1,4-naphthoquinone derivative has a certain alpha-glucosidase inhibitory activity, such that the 1,4-naphthoquinone derivative has wide application prospects in the development and application of diabetes treating drugs.

Description

technical field [0001] The invention belongs to the field of new compound synthesis and drug application, and relates to a 1,4-naphthoquinone derivative, including synthesis, activity evaluation and application. [0002] technical background [0003] 1,4-Naphthoquinone derivatives have a variety of biological activities, such as antitumor, antimicrobial, antibacterial, antiviral, free radical cleavage, antithrombotic, trypanocidal and other activities, and have potential medicinal value, so they are widely used In agriculture, medicine and other industries. Therefore, the synthesis and activity research of 1,4-naphthoquinone derivatives has attracted much attention. [0004] In 1968, Benjamin P. reported that a series of 2-amino derivatives of 2-chloro-1,4-naphthoquinone had antimalarial activity, but these derivatives did not have sulfonamide side chains. Year 2009 M. Sebti et al. screened from the NCI compound library and found that 1,4-naphthoquinone derivative PI-083 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/36C07C311/18C07C311/51C07D295/26A61P3/10A61P35/00
CPCC07C311/18C07C311/51C07D295/26Y02P20/55
Inventor 孙华郁彭王凯丽王栋陈明珠张梦迪张一楠
Owner TIANJIN UNIV OF SCI & TECH
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