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Citation: Cui Yi, Li Xiabing, Wang Wei, Li Baolin. Synthesis and Hypoglycemic Effect of N-[(3-(4-ethoxybenzyl)-4-chlorophenyl]-1-deoxynojirimycin[J]. Chemistry, ;2017, 80(7): 661-666, 687. shu

Synthesis and Hypoglycemic Effect of N-[(3-(4-ethoxybenzyl)-4-chlorophenyl]-1-deoxynojirimycin

Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry; National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China; School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi'an, 710062

Corresponding author: Li Xiabing, xiabingli@snnu.edu.cn
Received Date: 10 January 2017
Accepted Date: 6 March 2017

Figures(2)

By using hypoglycemic drugs dapagliflozin, canagliflozin and 1-deoxynojirimycin as reference, the target compound N-[(3-(4-ethoxybenzyl)-4-chlorophenyl]-1-deoxynojirimycin(A) was firstly designed and synthesized. Herein, the intermediate 2-chloro-5-amino-4'-ethoxy diphenyl methane was prepared from 2-chloro-5-nitro benzoic acid through a synthetic route including chlorination of carboxylic acid, Friedel-Crafts acylation, reduction of carbonyl and reduction of nitro. On the other hand, 5-keto-D-glucose was gotten from 1, 2-O-isopropylidene-D-glucofuranose by selective oxidation and hydrolysis. The crude A was obtained by the double reductive amination of 2-chloro-5-amino-4'-ethoxy diphenyl methane and 5-keto-D-glucose. The crude A was treated with acetic anhydride to yield tetraacetyl N-[(3-(4-ethoxybenzyl)-4-chlorophenyl]-1-deoxynojirinmycin(B). B was purified by column chromatography. Then the hydrolyzation of B gave the pure compound A. It was found that the compound A can effectively decrease the SD rats' blood glucose, increase urine volume and the excretion of urine glucose after dosing orally the compound A to SD rats.
- 1-Deoxynojirimycin,
- Canagliflozin,
- Blood glucose,
- Urine glucose,
- Hypoglycemic action
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