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Method for electrochemical synthesis of alkyl sulfone compounds

A synthesis method and technology of alkyl sulfone, which is applied in the application field of alkyl sulfone compounds, can solve the problems of few reports, and achieve the effects of high atom economy, good inhibitory activity, and good functional group tolerance

Active Publication Date: 2022-02-08
GUILIN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Direct sulfonylation of C(sp3)-H bonds is the most efficient synthesis of C(sp3)-sulfonyl compounds from the perspective of atom and step economy method, but there are few reports on this research

Method used

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  • Method for electrochemical synthesis of alkyl sulfone compounds
  • Method for electrochemical synthesis of alkyl sulfone compounds
  • Method for electrochemical synthesis of alkyl sulfone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 9-(Benzenesulfonyl)-9 H - Synthesis and characterization of xanthene (3aa):

[0025]

[0026] 0.6 mmol benzenesulfonyl hydrazide, 0.3 mmol 9 H -Xanthene, 0.06 mmol ammonium iodide and 0.6 mmol potassium carbonate were added to a 25 mL three-necked flask, and 6 mL of a mixed solution of 1,2-dichloroethane and hexafluoroisopropanol (v:v = 4: 2) Dissolving, using a carbon rod as an anode and a platinum sheet as a cathode, stirring and reacting for 3 hours at a constant current of 10 mA at room temperature, and monitoring the reaction process by TLC;

[0027] After the reaction was complete, the mixture was extracted with ethyl acetate (10 mL). Anhydrous Na for organic layer 2 SO 4 Dry, spin the solvent under reduced pressure, and purify the residue by column chromatography (silica gel, petroleum ether / ethyl acetate = 1:20 elution) to obtain a white solid 3aa;

[0028] White solid (75%, 72.5 mg). mp: 193.8-194.6 o C, 1 H NMR (400 MHz, CDCl 3 ) δ 7.57-7.49 (m, 3H)...

Embodiment 2

[0030] 9-(o-toluenesulfonyl)-9 H - Synthesis and characterization of xanthene (3ba):

[0031]

[0032] 0.6 mmol 2-methylbenzenesulfonyl hydrazide, 0.3 mmol 9 H -Xanthene, 0.06 mmol potassium iodide and 0.6 mmol cesium carbonate were added to a 25 mL three-necked flask, and 6 mL of a mixture of 1,2-dichloroethane and hexafluoroisopropanol (v:v = 4:2) was added Dissolve, use a carbon rod as an anode, and a platinum sheet as a cathode, carry out a stirring reaction for 4 hours at a constant current of 12 mA at room temperature, and monitor the reaction process by TLC;

[0033] After the reaction was complete, the mixture was extracted with ethyl acetate (10 mL). Anhydrous Na for organic layer 2 SO 4 Dry, spin the solvent under reduced pressure, and purify the residue by column chromatography (silica gel, petroleum ether / ethyl acetate = 1:30 elution) to obtain a white solid 3ba;

[0034] White solid (44%, 44.4 mg). mp: 216.7-217.8 o C, 1 H NMR (600 MHz, CDCl 3 ) δ 7.57-...

Embodiment 3

[0036] 9-(m-toluenesulfonyl)-9 H - Synthesis and characterization of xanthene (3ca):

[0037]

[0038] 0.6 mmol 3-methylbenzenesulfonyl hydrazide, 0.3 mmol 9 H -Xanthene, 0.06 mmol tetrabutylammonium iodide and 0.6 mmol sodium methoxide were added to a 25 mL three-necked flask, and 6 mL of a mixture of 1,2-dichloroethane and hexafluoroisopropanol (v:v = 4:2) dissolving, using a carbon rod as an anode, and a platinum sheet as a cathode, at a constant current of 15 mA, stirring and reacting for 5 hours under normal temperature conditions, TLC monitoring reaction process;

[0039] After the reaction was complete, the mixture was extracted with ethyl acetate (10 mL). Anhydrous Na for organic layer 2 SO 4After drying, the solvent was spin-dried under reduced pressure, and the residue was purified by column chromatography (silica gel, petroleum ether / ethyl acetate = 1:40 elution) to obtain a white solid 3ca;

[0040] White solid (70%, 70.6 mg). mp: 169.5-170.2 o C, 1 H NMR...

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Abstract

The invention discloses a method for electrochemical synthesis of alkyl sulfone compounds. Sulfohydrazide is used as a sulfonylation reagent, xanthene and sulfonyl hydrazine are subjected to a cross dehydrogenation coupling reaction under efficient and environment-friendly electrochemical conditions, direct sulfonylation of xanthene C (sp3)-H bonds is achieved, and a series of alkyl sulfone compounds are synthesized. In-vitro antitumor activity screening finds that the synthesized compounds have high anti-tumor activity. The method does not need pre-functionalization of a substrate, and has the advantages of high atom economy, no transition metal and oxidant conditions, good functional group tolerance and the like. In addition, the anti-tumor activity of the alkyl sulfone compounds is screened by utilizing an MTT (Methyl Thiazolyl Tetrazolium) method. The result shows that the compounds 3da and 3af have good inhibitory activity on HeLa and Bel-7402 cells.

Description

technical field [0001] The invention relates to an alkyl sulfone compound, and specifically discloses a method for synthesizing an alkyl sulfone compound by coupling an xanthene and a sulfonyl hydrazide under electrochemical conditions, and the application of the alkyl sulfone compound. Background technique [0002] Alkyl sulfones are widely found in nature, have a wide range of biological activities, and are essential structural motifs in medicine and pesticides. For example, Eletriptan can be used clinically to treat acute migraine; Sulbactam Sodium is an antibiotic that can be used clinically to treat diseases such as respiratory tract infection and urinary tract infection ; Bicalutamide (Bicalutamide, AstraZeneca's best-selling drug) is an oral active non-steroidal anti-androgen, which can be used to treat prostate cancer. [0003] At the same time, alkyl sulfones are also commonly used synthetic intermediates in organic chemistry. Therefore, the synthesis of alkyl sul...

Claims

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Application Information

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IPC IPC(8): C25B3/05C25B3/07C25B3/23A61K31/352A61P35/00
CPCC25B3/05C25B3/07C25B3/23A61K31/352A61P35/00
Inventor 莫祖煜马献力高雷魏琬絜潘英明唐海涛
Owner GUILIN MEDICAL UNIVERSITY
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