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Beta-trifluoromethyl vinyl sulfone compounds as well as preparation method and application thereof

A technology of trifluoromethyl alkenyl sulfone and trifluoromethyl, which is applied in the application field of β-trifluoromethyl alkenyl sulfone and its preparation, anti-tumor cell proliferation, and can solve the reaction configuration selection difficult to control, harsh reaction conditions, narrow substrate range, etc., to achieve good application prospects, mild reaction conditions, and easy operation.

Active Publication Date: 2017-12-15
FUDAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these methods have been widely used to a certain extent, their shortcomings cannot be avoided, such as harsh reaction conditions, narrow substrate range, difficult control of reaction configuration selectivity, etc.
At the same time, in the methods reported in the literature, there is no synthetic route for combining trifluoromethyl and alkenyl sulfone to obtain β-trifluoromethyl alkenyl sulfone compounds, and this type of new structural compound with bifunctional groups can be expected to be used in It has certain application and development prospects in the fields of biochemistry and medicine

Method used

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  • Beta-trifluoromethyl vinyl sulfone compounds as well as preparation method and application thereof
  • Beta-trifluoromethyl vinyl sulfone compounds as well as preparation method and application thereof
  • Beta-trifluoromethyl vinyl sulfone compounds as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] Add DABCO.(SO 2 ) 2 (0.16mmol), p-chlorophenylacetylene (0.2mmol), TMSCF 3 (0.24mmol), p-chlorophenyldiazotetrafluoroborate (0.24mmol) and dimethyl sulfoxide (2mL), under the protection of argon, stirred at room temperature for 8 hours, TLC detected that the reaction was complete, and the reaction solution was used Extracted with ethyl acetate, washed with saturated brine, concentrated and purified by column chromatography to obtain compound Ia.

[0028] Characterization of Compound Ia: 1 H NMR (400MHz, CDCl 3 )δ7.53–7.45(m,4H),7.33–7.28(m,2H),7.23–7.13(m,1H),7.05–6.89(m,2H); 19 F NMR (376MHz, CDCl 3 )δ-58.3(d, J=6.8Hz); 13 C NMR (100MHz, CDCl 3 )δ151.8, 141.5, 136.8, 134.6, 130.9, 130.5, 129.6, 128.6, 126.2 (q, J = 36.2Hz), 126.0, 121.3 (q, J = 274.1Hz); HRMS (ESI) calcd for C 15 h 10 Cl 2 f 3 o 2 S:380.9725(M+H + ), found: 380.9708..

Embodiment 2

[0030]

[0031] Add DABCO.(SO 2 ) 2 (0.16mmol), 3-ethynylpyridine (0.2mmol), TMSCF 3(0.24mmol), phenyldiazonium tetrafluoroborate (0.24mmol) and dimethyl sulfoxide (2mL), under the protection of argon, stirred at room temperature for 8 hours, TLC detected that the reaction was complete, and the reaction solution was washed with ethyl acetate The ester was extracted, washed with saturated brine, concentrated and purified by column chromatography to obtain compound Ib.

[0032] Characterization of compound Ib: 1 H NMR (400MHz, CDCl 3 )δ8.47(s,1H),7.74(s,1H),7.65–7.60(m,3H),7.47–7.43(m,3H),7.30(d,J=6.0Hz,1H),7.26–7.16 (m,1H); 19 F NMR (376MHz, CDCl 3 )δ-59.2(d, J=5.5Hz).; 13 C NMR (100MHz, CDCl 3 )δ151.5, 149.4, 141.5, 136.4, 134.4, 132.7, 129.2, 129.1, 126.4 (q, J = 36.7Hz), 125.5, 124.3, 121.3 (q, J = 273.8Hz); HRMS (ESI) calcdfor C 14 h 11 f 3 NO 2 S:314.0457(M+H + ), found: 314.0463..

Embodiment 3

[0034]

[0035] Add DABCO.(SO 2 ) 2 (0.16mmol), p-acetylphenylacetylene (0.2mmol), TMSCF 3 (0.24mmol), phenyldiazonium tetrafluoroborate (0.24mmol) and dimethyl sulfoxide (2mL), under the protection of argon, stirred at room temperature for 8 hours, TLC detected that the reaction was complete, and the reaction solution was washed with ethyl acetate The ester was extracted, washed with saturated brine, concentrated and purified by column chromatography to obtain compound Ic.

[0036] Characterization of Compound Ic: 1 H NMR (400MHz, CDCl 3 )δ7.85(d, J=8.5Hz, 2H), 7.63(t, J=7.3Hz, 1H), 7.58–7.55(m, 2H), 7.45(t, J=7.8Hz, 2H), 7.19( q, J=7.1Hz, 1H), 7.10(d, J=8.3Hz, 2H), 2.59(s, 3H); 19 F NMR (376MHz, CDCl 3 )δ-58.3(d, J=7.2Hz); 13 C NMR (100MHz, CDCl 3 )δ197.2, 152.3, 137.9, 135.9, 134.6, 132.5, 129.9, 129.3, 129.1, 127.8, 125.8 (q, J = 36.1Hz), 121.3 (q, J = 273.5Hz), 26.6; HRMS (ESI) calcd for C 17 h 14 f 3 o 3 S:355.0610(M+H + ), found: 355.0617..

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Abstract

The invention belongs to the technical field of organic compounds and particularly provides beta-trifluoromethyl vinyl sulfone compounds, a preparation method thereof and an application of the compounds to tumor cell proliferation resistance. The beta-trifluoromethyl vinyl sulfone compounds are prepared from a multicomponent reagent (trifluoromethyl) trimethylsilane (TMSCF3), alkyne, diazonium salt and DABCO.(SO2)2 in an organic solvent DMSO through a one-step reaction. Reaction conditions are quite mild, alkyne bi-functionalization is realized directly through the one-step cascade reaction of the four raw materials, the operation is simple, defects of tedious steps, low operability and yield and poor selectivity of the traditional synthesis method of vinyl sulfone derivatives are overcome, and the method is applicable to large-scale preparation and has quite good application prospect. In-vitro pharmacological activity screening tests show that the compounds have an anti-proliferation effect on tumor cells, part of the compounds have an obvious tumor inhibition activity, the half maximal inhibitory concentration IC50 value can reach mu m level, and the compounds can be used for preparing a kind of novel anti-tumor reagents.

Description

technical field [0001] The invention belongs to the technical field of organic compounds, and in particular relates to novel beta-trifluoromethyl alkenyl sulfone compounds and their preparation methods, as well as their application in anti-tumor cell proliferation. Background technique [0002] In recent years, the preparation of structurally diverse olefin derivatives through the 1,2-difunctionalization reaction of alkynes is one of the research hotspots in organic chemistry. Alkenyl sulfone compounds due to sulfonyl or sulfone group (-SO 2 The electron-pulling effect of -) and the polarity of the C-S bond activate the carbon-carbon double bond, so that alkenyl sulfone molecules can be widely used in organic synthesis as a good Michael electron acceptor. On the other hand, sulfonyl or sulfone moieties are also important pharmacophores in many bioactive molecules, the most common being sulfonamide, sulfonate and sulfone compounds widely used in clinical medicine, pesticide ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/14C07D213/34C07C315/00A61P35/00
CPCC07C317/14C07D213/34
Inventor 向远超匡云艳周伟吴劼
Owner FUDAN UNIV
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