α-葡萄糖苷酶抑制剂c -6- o -甲基-1-脱氧诺吉霉素的化学合成及初步生物学评价

IF 1.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Carbohydrate Chemistry Pub Date : 2020-01-01 DOI:10.1080/07328303.2019.1700995

Lin Wang , Tingting Liang , Zhijie Fang

{"title":"α-葡萄糖苷酶抑制剂c -6- o -甲基-1-脱氧诺吉霉素的化学合成及初步生物学评价","authors":"Lin Wang , Tingting Liang , Zhijie Fang","doi":"10.1080/07328303.2019.1700995","DOIUrl":null,"url":null,"abstract":"<div>A facile and efficient synthesis of 6-O-methyl-1-deoxynojirimycin 4 from commercially available methyl α-D-glucopyranoside in 10 steps and 25% overall yield was reported. The synthetic strategy was based on the regioselective protection/deprotection at 6-O-position and cyclization as the main reaction steps. Compound 4 was evaluated for its inhibitory effect (IC50) on α-glucosidase using an in vitro assay. It showed improved inhibitory activity compared to 1-deoxynojirimycin and acarbose.</div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 1","pages":"Pages 36-49"},"PeriodicalIF":1.2000,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2019.1700995","citationCount":"1","resultStr":"{\"title\":\"Chemical synthesis and preliminary biological evaluation of C-6-O-methyl-1-deoxynojirimycin as a potent α-glucosidase inhibitor\",\"authors\":\"Lin Wang , Tingting Liang , Zhijie Fang\",\"doi\":\"10.1080/07328303.2019.1700995\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div>A facile and efficient synthesis of 6-O-methyl-1-deoxynojirimycin 4 from commercially available methyl α-D-glucopyranoside in 10 steps and 25% overall yield was reported. The synthetic strategy was based on the regioselective protection/deprotection at 6-O-position and cyclization as the main reaction steps. Compound 4 was evaluated for its inhibitory effect (IC50) on α-glucosidase using an in vitro assay. It showed improved inhibitory activity compared to 1-deoxynojirimycin and acarbose.</div>\",\"PeriodicalId\":15311,\"journal\":{\"name\":\"Journal of Carbohydrate Chemistry\",\"volume\":\"39 1\",\"pages\":\"Pages 36-49\"},\"PeriodicalIF\":1.2000,\"publicationDate\":\"2020-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1080/07328303.2019.1700995\",\"citationCount\":\"1\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Carbohydrate Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S0732830322001148\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Carbohydrate Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S0732830322001148","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}

引用次数: 1

摘要

以市售α- d -葡萄糖吡喃苷甲酯为原料，经10步合成6- o -甲基-1-脱氧诺吉霉素4，总收率为25%。该合成策略以6- o位区域选择性保护/去保护和环化为主要反应步骤。体外实验评价化合物4对α-葡萄糖苷酶的抑制作用(IC50)。与1-脱氧诺吉霉素和阿卡波糖相比，其抑制活性有所提高。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Chemical synthesis and preliminary biological evaluation of C-6-O-methyl-1-deoxynojirimycin as a potent α-glucosidase inhibitor

A facile and efficient synthesis of 6-O-methyl-1-deoxynojirimycin 4 from commercially available methyl α-D-glucopyranoside in 10 steps and 25% overall yield was reported. The synthetic strategy was based on the regioselective protection/deprotection at 6-O-position and cyclization as the main reaction steps. Compound 4 was evaluated for its inhibitory effect (IC₅₀) on α-glucosidase using an in vitro assay. It showed improved inhibitory activity compared to 1-deoxynojirimycin and acarbose.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Journal of Carbohydrate Chemistry 化学-生化与分子生物学

CiteScore

2.10

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： The Journal of Carbohydrate Chemistry serves as an international forum for research advances involving the chemistry and biology of carbohydrates. The following aspects are considered to fall within the scope of this journal: -novel synthetic methods involving carbohydrates, oligosaccharides, and glycoconjugates- the use of chemical methods to address aspects of glycobiology- spectroscopic and crystallographic structure studies of carbohydrates- computational and molecular modeling studies- physicochemical studies involving carbohydrates and the chemistry and biochemistry of carbohydrate polymers.