Home

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
1. [1]
  H P Singh, I Kaur, G Sharma. Int. J. Pharm. Sci. Rev. Res., 2015, 33(1):40~47.
2. [2]
  J S Wu, Y H Peng, J M Wu et al. J. Med. Chem., 2010, 53(24):8770~8774.
3. [3]
  P Malla, R Kumar, M KMahapatra et al. Med. Res. Rev., 2014, 34(6):1146~1167.
4. [4]
  Y Ohtake, T Sato, T Kobayashi et al. J. Med. Chem., 2012, 55(17):7828~7840.
5. [5]
  A B Hughes, A J Rudge. Nat. Prod. Rep., 1994, 11(2):135~162.
6. [6]
7. [7]
  Y Tsuda, M Hanajima, N Matsuhira et al. Chem. Pharm. Bull., 1989, 37(9):2344~2350.
8. [8]
  S P Han, D L Hagan, J R Taylor et al. Diabetes, 2008, 57(6):1723~1729.
9. [9]
  Z J Xin, Z Jia, D He et al. Adv. Mat. Res., 2013, 634:1371~1375.
10. [10]
  W Meng, A E Bruce, A N Alexandra et al. J. Med. Chem., 2008, 51(5):1145~1149.
11. [11]
  T Hirashima, O Manabe. Chem. Lett., 1975, 259~260.
12. [12]
  J M Riordan, P E Morris, D E Kiely. J. Carbohyd. Chem., 1993, 12(7):865~879.
13. [13]
  E W Baxter, A B Reitz. J. Org. Chem., 1994, 59:3175~3185.
14. [14]
  A F Abdel-Magid, M Chisholm, S Mehrman. WO:2009035969 A1, 2009.
1. [1]
  Peiling Li , Qing Feng , Hongling Yuan , Qin Wang . Live Interview Recording about the Penicillin Family. University Chemistry, 2024, 39(9): 122-127. doi: 10.3866/PKU.DXHX202311022
2. [2]
  Feiya Cao , Qixin Wang , Pu Li , Zhirong Xing , Ziyu Song , Heng Zhang , Zhibin Zhou , Wenfang Feng . Magnesium-Ion Conducting Electrolyte Based on Grignard Reaction: Synthesis and Properties. University Chemistry, 2024, 39(3): 359-368. doi: 10.3866/PKU.DXHX202308094
3. [3]
  Shuixing Dai , Jilei Jiang , Yuxiao Wang , Jinqi Hu , Minghua Huang . Application of Knoevenagel Reaction in Organic Chemistry Teaching. University Chemistry, 2025, 40(5): 334-341. doi: 10.12461/PKU.DXHX202405208
4. [4]
  Zhongxin YU , Wei SONG , Yang LIU , Yuxue DING , Fanhao MENG , Shuju WANG , Lixin YOU . Fluorescence sensing on chlortetracycline of a Zn-coordination polymer based on mixed ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2415-2421. doi: 10.11862/CJIC.20240304
5. [5]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
6. [6]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
7. [7]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
8. [8]
  Jiarong Feng , Yejie Duan , Chu Chu , Dezhen Xie , Qiu'e Cao , Peng Liu . Preparation and Application of a Streptomycin Molecularly Imprinted Electrochemical Sensor: A Suggested Comprehensive Analytical Chemical Experiment. University Chemistry, 2024, 39(8): 295-305. doi: 10.3866/PKU.DXHX202401016
9. [9]
  Guodong Xu , Chengcai Sheng , Xiaomeng Zhao , Tuojiang Zhang , Zongtang Liu , Jun Dong . Reform of Comprehensive Organic Chemistry Experiments in the Context of Emerging Engineering Education: A Case Study on the Improved Preparation of Benzocaine. University Chemistry, 2024, 39(11): 286-295. doi: 10.12461/PKU.DXHX202403094
10. [10]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(1400)
HTML views(632)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return