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Chinese Journal of Organic Chemistry >

2015 , Vol. 35 >Issue 5: 1161 - 1165

DOI: https://doi.org/10.6023/cjoc201410026

Notes

Optimization of the Synthetic Process of Antineoplastic Drug Dacarbazine

  • Xiao Shengwei ,
  • Liu Zhijun ,
  • Liu Yang ,
  • Chen Heru
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  • a Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632;
    b Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632

Received date: 2014-10-18

  Revised date: 2014-12-19

  Online published: 2015-01-07

Supported by

Project supported by the National Natural Science Foundation of China (No.81172982).

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Abstract

Dacarbazine has been prepared started from glycine, which was carried on firstly through a four-step process including esterification, formylation, dehydration, amidation to give 2-isocyanoacetamide with a total yield of 42.9%. 2-Isocyanoacetamide was then cyclized with cyanamide under basic condition to afford the important intermediate 5-amino-1H-imidazole-4-carboxamide with yield of 68.2%. This intermediate undergoing diazotization and following coupling reaction with dimethylamine led to the target compound. The overall yield was 22.3%. All the intermediates and the target products dacarbazine were confirmed by 1H NMR, 13C NMR and ESI-MS. The current process is economic efficient charac-terized by applied cheap materials, mild conditions, and good overall yield.

Key words： dacarbazine; process optimization; drug synthesis; anticancer

Cite this article

Xiao Shengwei , Liu Zhijun , Liu Yang , Chen Heru . Optimization of the Synthetic Process of Antineoplastic Drug Dacarbazine[J]. Chinese Journal of Organic Chemistry, 2015 , 35(5) : 1161 -1165 . DOI: 10.6023/cjoc201410026

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