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Sulfonium salt derivative as well as preparation method and medical application thereof

A derivative and sulfonium technology, applied in the field of chemical synthesis, can solve the problems of inability to reach the small intestine in form, and the compound is not acid-resistant, and achieve the effect of ingenious design, good tolerance, and cheap and easy-to-obtain raw materials

Active Publication Date: 2022-03-29
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the target of this type of drug is α-glucosidase located at the brush border of the small intestine cavity, which means that this type of compound must pass through the extremely acidic stomach before reaching the small intestine to play a role, and the above-mentioned compounds are not acid-resistant. So it can't all reach the small intestine in prototype form

Method used

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  • Sulfonium salt derivative as well as preparation method and medical application thereof
  • Sulfonium salt derivative as well as preparation method and medical application thereof
  • Sulfonium salt derivative as well as preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Preparation of 4,6,7-tri-O-benzyl-phenylheptenyl-3,5-diol

[0061]

[0062] Dissolve 1,2-O-isopropylidene-furan-D-glucose 9 (10g, 45.4mmol) in DMF (150mL), add NaH (3.6g, 149.9mmol) in batches under ice-water bath, and Stirring at low temperature for 30 min, BnBr (17.8 mL, 149.9 mmol) was added dropwise, and stirring was continued at room temperature for 2 hours after the addition was complete. After the completion of the reaction was monitored by a thin-layer silica gel plate, ice water was slowly added in an ice-water bath to quench. EA extraction, washing with water and saturated NaCl solution. Combined organic layers, anhydrous Na 2 SO 4 Dry, concentrate under reduced pressure, make 100-200 mesh silica gel sand, separate and purify by chromatography column, PE:EA=50:1 and collect compound 10 (19.6 g, 40.4 mmol, 89%) as a yellow oil.

[0063] Compound 10 (12g, 24.5mmol), dissolved in 50mL of water, was stirred at room temperature and added to CF 3 COOH (50mL)...

Embodiment 2

[0067] Preparation of 2-I-4,6,7-tri-O-benzyl-1-C-phenylpyranoside

[0068]

[0069] Compound 12 (625 mg, 1.2 mmol) was dissolved in MeCN solution (10 mL), and NaHCO was added at -25°C 3 Powder (490mg, 3.6mmol), I 2 (910mg, 3.6mmol), continue to stir overnight at this temperature, after the completion of the TLC detection reaction, EA extracted 3 times, washed with water, washed with saturated NaCl, combined organic layers, anhydrous NaCl 2 SO 4 Drying, concentration under reduced pressure, 100-200 mesh silica gel sand, separation and purification by chromatography column, PE: EA = 15: 1 was collected to obtain compound 13 (511 mg, 0.8 mmol, 79%), a brown oily substance, namely 2-I- 4,6,7-Tri-O-benzyl-1-C-phenylpyranoside.

[0070] 1 H NMR (300MHz, CDCl 3)δ7.36–7.20(m,20H),4.80(d,J=10.4Hz,2H),4.72(dd,J=11.0,2.3Hz,1H),4.58–4.48(m,3H),4.46–4.40 (m,2H),4.24(d,J=9.1Hz,2H),3.95(dd,J=11.6,2.5Hz,2H),3.75(dd,J=10.7,2.0Hz,1H),3.59(dd, J=10.7,4.8Hz,1H). 13 CNMR (75MHz, CDCl 3...

Embodiment 3

[0072] Preparation of 2-deoxy-4,6,7-tri-O-benzyl-1-C-phenylpyranoside

[0073]

[0074] Compound 13 (378 mg, 0.6 mmol) was dissolved in THF (20 mL), added dry 10% Pd / C (30 mg), Et 3 N (100uL, 0.7mmol), oil bath 60°C in H 2 React in the environment for 3 hours, after the reaction is detected by TLC, filter out Pd / C with diatomaceous earth, spin dry the mother liquor, make sand with 100-200 mesh silica gel, separate and purify by chromatography column, PE:EA=10:1 and collect the compound 14 (300mg, 0.58mmol, 96%), yellow oily substance, namely 2-deoxy-4,6,7-tri-O-benzyl-1-C-phenylpyranoside.

[0075] 1 H NMR (300MHz, CDCl 3 )δ7.35–7.22(m, 20H), 4.82(t, J=10.6Hz, 2H), 4.59– 4.44(m, 5H), 4.23–4.00(m, 3H), 3.91(d, J=10.7Hz ,1H),3.73(dd,J=10.6,4.7Hz,1H), 3.65(s,1H),2.12(t,J=13.1Hz,1H),1.83(d,J=13.5Hz,1H). 13 C NMR (75MHz, CDCl 3 ) δ142.6, 138.8, 138.6, 134.0, 128.39, 128.36, 128.3, 128.2, 127.8, 127.63, 127.59, 127.5, 127.4, 127.2, 126.0, 76.6, 74.3, 73.5, 56.3, 73.3, 93.3 ...

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Abstract

The invention discloses sulfonium salt derivatives as well as a preparation method and medical application thereof, and particularly relates to a compound as shown in a formula I. The sulfonium salt derivatives with brand new structures are designed according to a bioisostere principle, and the compounds have good tolerance to gastric acid; compared with a natural product, the sulfonium salt compound provided by the invention has stronger alpha-glucosidase inhibitory activity, can be used as an onium salt type alpha-glucosidase inhibitor, and is mainly prepared from 1, 2-O-isopropylidene furan D-glucose as a raw material through a one-pot method. The onium salt derivative molecule with alpha-glucosidase inhibitory activity is obtained through multi-step reaction, and the molecule has hypoglycemic activity.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a class of sulfonium salt derivatives, a preparation method and a medical application thereof. Background technique [0002] The Salacia plant Salacia is derived from a compound with a sulfonium salt structure. The structural formula is as follows. It has a hypoglycemic activity comparable to that of commercially available α-glucosidase inhibitors. The researchers studied its structure-activity relationship to determine It is expected to discover a class of candidate hypoglycemic agents with a completely new structure. [0003] [0004] The researchers conducted a structure-activity relationship study on the structure of this type of sulfonium salt with hypoglycemic effect. Enzyme activity experiments showed that the compound with desulfurization at the C-3' position of the acyclic side chain was more sensitive to α- The inhibitory activity of glucosidase was enhanced. Nakam...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/06A61P3/10
CPCC07D409/06A61P3/10
Inventor 谢唯佳陶文祥丁莹
Owner CHINA PHARM UNIV
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