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3-deoxy-5-hydroxyl-1-amino carbon sugar compound and its application

A technology of amino carbon sugars and compounds, applied in the preparation of amino hydroxyl compounds, carbon-based compounds, amino sugars, etc., to achieve obvious hypoglycemic activity and significant α-glucosidase inhibitory activity

Active Publication Date: 2022-05-20
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although carbon sugars or carbon sugar analogs have a wide range of biological activities, the synthesis of multiple chiral centers and multifunctional structural features in their molecules is still a challenge in the chemical community, especially for compounds with new skeleton types

Method used

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  • 3-deoxy-5-hydroxyl-1-amino carbon sugar compound and its application
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  • 3-deoxy-5-hydroxyl-1-amino carbon sugar compound and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1a

[0032] Embodiment 1a: under ice-water bath, compound 14 counts 4.88g (11.0mmol), 10%Pd / C 0.20g, Na 2 CO 3 0.24g and MeOH 100mL were vigorously stirred for atmospheric catalytic hydrogenation for 2.0h. Filtration, the filtrate was washed with 1.0M NaH 2 PO 4 / Na 2 HPO 4 The buffer solution was diluted with 100 mL, and concentrated under reduced pressure to recover methanol. The residue was extracted with ethyl acetate and dried over anhydrous sodium sulfate. After concentration, the crude product was separated by column chromatography to obtain 3.04 g of white solid 12 with a yield of 62.0%. m.p 104~106℃,[α] D20 =+82.88(c 1.0, CHCl 3 ).

[0033] 1 H NMR (600MHz, CDCl 3 ):δ7.29–7.17(m,15H),4.80(d,J=11.9Hz,1H),4.57(d,J=11.5Hz,1H),4.41–4.38(m,4H),3.94(dd, J=11.6Hz, 4.7Hz, 1H), 3.83(dd, J=12.7Hz, 6.1Hz, 1H), 3.56(d, J=8.7Hz, 1H), 3.10(d, J=8.7Hz, 1H), 2.65(d,J=14.7,1H),2.42-2.39(m,1H),2.36(d,J=14.6,1H),2.07(q,J=12.2Hz,1H).

[0034] 13 C NMR (150MHz, CDCl 3 ): δ206.1...

Embodiment 1b

[0036] Example 1b: Under similar conditions, 10% Ru / C 0.25g was used instead of Pd / C in Example 1a, and 2.89g of 12 was obtained after similar post-treatment, with a yield of 59.0%.

Embodiment 1c

[0037] Example 1c: Under similar conditions, 0.40 g of Raney / Ni(W–2) was used instead of Pd / C in Example 1a. After similar post-treatment, 2.40 g of 12 was obtained, with a yield of 49.0%.

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PUM

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Abstract

The present invention belongs to the field of pharmacy, and specifically relates to 3-deoxy-5-hydroxyl-1-amino carbon sugar compounds with the following general formula and uses thereof, wherein R is as described in the claims and description. The invention synthesizes protected 3-deoxy-5-hydroxycyclohexanone through a stereo and position selective reduction method, and the compound has a novel carbon sugar skeleton. The compound is reacted with small molecule amines by reductive amination method to obtain the target object protected by the corresponding protecting group, and finally the aminocarbon sugar target object with 3-deoxy-5-hydroxyl structural characteristics is obtained through deprotection group reaction. The target substance has good inhibitory activity on α-glucosidase, and has a significant inhibitory effect on the blood sugar rise after sucrose loading in normal ICR mice, suggesting that it can be used for further development of hypoglycemic drugs.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to 3-deoxy-1-hydroxyl-5-amino carbon sugar compounds and applications thereof. Background technique [0002] The oxygen atom (-O-) in the carbon sugar molecular ring is replaced by the methine group (-CH 2 -) The replacement product, after the replacement, it still retains the basic skeleton or structural characteristics of the original sugar, has similar biological activity, but has a more stable chemical structure and more stable biological characteristics (McCasland G.E., et al., J . Org. Chem., 1966, 31, 1516). As carbon sugar mimetics (mimetics) have been widely researched and reported compounds, with hypoglycemic activity, etc.; can also be used as the backbone of sugar in nucleoside or nucleotide molecules, showing antibacterial, antitumor or antiviral activities (Lahiri R., et al., Chem. Soc. Rev., 2013, 42, 5102). [0003] Commercially available drugs acarbose (acarbose, 1) and vog...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H5/06C07H1/00C07C215/44C07C213/08C07C45/69C07C49/517A61P3/10A61K31/7008A61K31/133
CPCC07H5/06C07H1/00C07C215/44C07C49/517A61P3/10C07C2601/14Y02P20/55
Inventor 许佑君姜春风刘佳明刘凯旋段明飞
Owner SHENYANG PHARMA UNIVERSITY
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