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3-deoxy-5-hydroxy-1-amino carbohydrate compound and application thereof

A technology for aminocarbon sugars and compounds, which is applied in the preparation of aminohydroxy compounds, carbon-based compounds, amino sugars, etc., to achieve good inhibitory activity.

Active Publication Date: 2020-10-09
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-hydroxy-1-amino carbohydrate compound and application thereof
  • 3-deoxy-5-hydroxy-1-amino carbohydrate compound and application thereof
  • 3-deoxy-5-hydroxy-1-amino carbohydrate compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1a

[0032] Example 1a: Under ice water bath, compound 14 totals 4.88g (11.0mmol), 10% Pd / C 0.20g, Na 2 CO 3 0.24 g and 100 mL of MeOH were vigorously stirred to carry out atmospheric catalytic hydrogenation for 2.0 h. Filter, the filtrate is 1.0M NaH 2 PO 4 / Na 2 HPO 4 The buffer was diluted with 100 mL, and then 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] D 20 = +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 ): δ206.19,137.95,137.79,137.68,128....

Embodiment 1b

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

Embodiment 1c

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

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Abstract

The invention belongs to the field of pharmacy, and particularly relates to a 3-deoxy-5-hydroxy-1-amino carbohydrate compound with a general formula shown in the specification and an application of the 3-deoxy-5-hydroxy-1-amino carbohydrate compound, and R is described in the claims and the specification. The protected 3-deoxy-5-hydroxycyclohexanone is synthesized through a stereoselective reduction method and a position selective reduction method, and the compound has a novel carbohydrate skeleton. The preparation method comprises the following steps: enabling a compound to react with small molecular amines by virtue of a reductive amination method, so as to obtain a corresponding target object protected by a protecting group, and finally, carrying out a deprotecting group reaction, so asto obtain an amino carbohydrate target object with 3-deoxy-5-hydroxyl structural characteristics. The target object has good inhibitory activity on alpha-glycosidase, and has a significant inhibitoryeffect on blood glucose rise of normal ICR mice after sucrose loading, and the target object 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-hydroxy-5-amino carbon sugar compounds and uses thereof. Background technique [0002] The oxygen atom (-O-) in the molecular ring of the carbon sugar system is methine (-CH 2 -) Replacement product. After replacement, it still retains the basic skeleton or structural characteristics of the original sugar and has similar biological activity, but has a more stable chemical structure and more stable biological characteristics (McCasland GE, et al., J . Org. Chem., 1966, 31, 1516). As carbon sugar mimetics (mimetics), it has been widely researched and reported as a compound with hypoglycemic activity, etc.; it can also be used as a skeleton of sugar in nucleoside or nucleotide molecules, showing antibacterial, antitumor or antiviral activities (Lahiri R., et al., Chem. Soc. Rev., 2013, 42, 5102). [0003] Commercial drugs acarbose (1) and voglibose (2) are used as sugar mimics and are α-g...

Claims

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Application Information

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Patent Type & Authority Applications(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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