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Allyl sulfonium amino p-benzoquinone compound and preparation and application thereof

An allylthio compound technology, applied in the field of compounds with antitumor activity, can solve the problems of difficult control, many steps in the synthesis method, complicated reactions and the like

Inactive Publication Date: 2016-11-23
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the synthesis of S-substituted p-benzoquinones, mono-substituted and multi-substituted products are difficult to control, and thiols, which are not easy to obtain, are irritating and toxic, are often used as sulfur sources
There are few studies on the synthesis of N, S-di

Method used

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  • Allyl sulfonium amino p-benzoquinone compound and preparation and application thereof
  • Allyl sulfonium amino p-benzoquinone compound and preparation and application thereof
  • Allyl sulfonium amino p-benzoquinone compound and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: 2-allylthio-5-benzylamino-p-benzoquinone

[0047]

[0048] Red solid, yield 69%, m.p.109.0-109.9°C

[0049] 1 H NMR (400MHz, CDCl 3 )δ7.41-7.30 (m, 5H), 6.26 (s, 1H), 6.19 (s, 1H), 5.87 (ddt, J=16.7, 10.1, 6.4Hz, 1H), 5.55 (s, 1H), 5.40 (dd, J=17.0, 1.0 Hz, 1H), 5.29(dd, J=10.1, 0.8Hz, 1H), 4.32(d, J=5.8Hz, 2H), 3.46(d, J=6.4Hz, 2H) ; 13 C NMR (101MHz, CDCl 3)δ181.3, 179.2, 158.4, 147.2, 135.6, 130.3, 129.0, 128.2, 127.7, 120.5, 119.9, 97.9, 46.8, 33.4; HRMS (ESI): m / z calcd for C 16 h 16 NO 2 S[M+H] + : 286.08963, found: 286.08984.

Embodiment 2

[0050] Example 2: 2-allylthio-5-(3-methoxy) propylamino-p-benzoquinone

[0051]

[0052] Red solid, yield 65%, m.p.77.3-77.6°C

[0053] 1 H NMR (400MHz, CDCl 3 )δ6.38(br, 1H), 6.23(s, 1H), 5.87(ddt, J=16.7, 10.2, 6.5Hz, 1H), 5.49(s, 1H), 5.39(d, J=17.0Hz, 1H ), 5.28(d, J=10.1Hz, 1H), 3.50(t, J=5.6Hz, 2H), 3.46(d, J=6.4Hz, 2H), 3.38(s, 3H), 3.25(dd, J =12.4, 6.3Hz, 2H), 1.97-1.87 (m, 2H); 13 C NMR (101MHz, CDCl 3 )δ181.1, 179.2, 158.6, 147.7, 130.4, 120.4, 119.8, 96.63, 70.7, 58.9, 40.8, 33.4 28.0; HRMS (ESI): m / z calcd for C 13 h 18 NO 3 S[M+H] + : 268.10019, found: 268.10042.

Embodiment 3

[0054] Example 3: 2-allylthio-5-cyclohexylamino-p-benzoquinone

[0055]

[0056] Red solid, yield 73%, m.p.92.5-93.4°C

[0057] 1 H NMR (400MHz, CDCl 3 )δ6.23(s, 1H), 5.87(ddt, J=16.6, 10.1, 6.4Hz, 2H), 5.51(s, 1H), 5.39(dd, J=17.0, 1.1Hz, 1H), 5.28(dd , J=10.1, 1.0Hz, 1H), 3.45(d, J=6.4Hz, 2H), 3.33-3.16(m, 1H), 2.08-1.88(m, 2H), 1.90-1.72(m, 2H), 1.66(d, J=5.8Hz, 1H), 1.31(ddd, J=24.4, 14.5, 2.9Hz, 5H); 13 C NMR (101MHz, CDCl 3 )δ181.0, 179.4, 158.7, 146.2, 130.4, 120.3, 119.81, 96.8, 51.3, 33.4, 31.8, 25.4, 24.5; HRMS (ESI): m / z calcd for C 15 h 20 NO 2 S[M+H] + : 278.12093, found: 278.12107.

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Abstract

The invention discloses an allyl sulfonium amino p-benzoquinone compound and preparation and application thereof, relates to a compound shown in the general formula (I) or pharmaceutically acceptable salts and solvates thereof, and further relates to a preparation method of the compound and application of the compound in preparation of anti-tumor medicine.

Description

technical field [0001] The present invention relates to a compound with antitumor activity. Specifically, the present invention relates to the compound of general formula (I) and its preparation method, and also relates to the anti-tumor application of the compound of general formula (I). Background technique [0002] Due to the special structure and properties of quinones, their potential medicinal value and mechanism of action are constantly being discovered, researched and revealed, and they play an important role in maintaining human health and treating diseases. However, due to the high redox and bioalkylation properties of quinone itself, it is easy to cause multiple side effects on the body; the strong lipophilicity affects its effect; the tolerance of tumor cells and pathogenic microorganisms to it It is also an urgent problem to be solved in the study of quinone (candidate) drugs. [0003] S- / N-substituted p-benzoquinone compounds, as an important class of p-benzo...

Claims

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Application Information

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IPC IPC(8): C07C323/36C07D213/36C07D307/52C07D211/46C07C323/35C07D213/32C07D207/08C07D233/36C07D295/26C07F9/40A61K31/145A61K31/216A61K31/4406A61K31/341A61K31/445A61K31/402A61K31/165A61K31/417A61K31/495A61K31/662A61P35/00
Inventor 李润涛葛泽梅卢艺欢
Owner PEKING UNIV
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