Synthesis of Key Impurities as Quality Control Standards of Oxfendazole

doi:10.11944/j.issn.1000-0518.2016.09.150434

Chinese Journal of Applied Chemistry ›› 2016, Vol. 33 ›› Issue (9): 1061-1066.DOI: 10.11944/j.issn.1000-0518.2016.09.150434

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Synthesis of Key Impurities as Quality Control Standards of Oxfendazole

LI Zhao^a^b,FENG Jia^b^c,GAO Yuanyuan^a^b,LI Bo^b^*(),ZHU Weiliang^b^*(),CHEN Kaixian^a^b

^aShanghai University of Traditional Chinese Medicine,Shanghai 201203,China
^bShanghai Institute of Materia Medica,Chinese Academy of Sciences,Shanghai 201203,China
^cNano Science and Technology Institute,University of Science and Technology of China,Suzhou,Jiangsu 215123,China

Received:2015-12-08 Accepted:2016-03-08 Published:2016-08-23 Online:2016-08-23
Contact: LI Bo,ZHU Weiliang
Supported by:
Supported by the National Natural Science Foundation of China(No.81273435, No.81302699), the Natural Science Foundation of Shanghai(No.14ZR1447800)

Abstract

Abstract:

Oxfendazole, a benzimidazolecarbamate(BZC) compound, is a broad-spectrum antihelmintic and antimicrobial agent. The insufficient sources of its impurities affected the quality control of the product. Herein, a simple and efficient method for synthesis of four impurities, fenbendazole, methyl (5-(phenylsulfonyl)-1H-benzo[d]imidazol-2-yl)carbamate, 5-(phenylsulfinyl)-1H-benzo[d]imidazol-2-amine and 1,3-bis(5-(phenylsulfinyl)-1H-benzo[d]imidazol-2-yl)urea, is revealed. Especially, the key imidazole ring was constructed efficiently via two different strategies. Furthermore, oxidative products of sulfur ether, sulphone and sulfoxide were obtained by controlling oxidative conditions. This method not only increases the source of the standard substances for quality control of oxfendazole, but also provides an efficient synthetic strategy to prepare the novel antihelmintic, antimicrobial and antitumor agents based on oxfendazol.

Key words: oxfendazole, impurity, standard substances, synthesis

LI Zhao, FENG Jia, GAO Yuanyuan, LI Bo, ZHU Weiliang, CHEN Kaixian. Synthesis of Key Impurities as Quality Control Standards of Oxfendazole[J]. Chinese Journal of Applied Chemistry, 2016, 33(9): 1061-1066.

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Synthesis of Key Impurities as Quality Control Standards of Oxfendazole

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