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An overview on structural modifications of ligustrazine and biological evaluation of its synthetic derivatives

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Abstract

Ligustrazine, a natural product from Rhizoma Chuanxiong containing a pyrazine ring, has been widely used in China for treatment of heart diseases. Because of its remarkable effects but rapid metabolism, studies on structural modification of ligustrazine have attracted much attention. Ligustrazine synthetic derivatives reported in recent decades can be divided into ethers, esters, amides and piperazines, olefins, and others. These derivatives are mainly derived from four primary intermediates. The lack of a comprehensive and recent review on this topic prompted us to gather more new information. This paper is a compilation of almost all of the 304 synthetic ligustrazine derivatives we encountered; the information included is expected to be of benefit to further studies of ligustrazine.

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Abbreviations

TMP:

Ligustrazine

TMP-Br:

2-Bromomethyl-3,5,6-trimethylpyrazine

TMP-Cl:

2-Chloromethyl-3,5,6-trimethylpyrazine

TMP-NH2 :

(3,5,6-Trimethylpyrazin-2-yl)methanamine

TMP-OH:

(3,5,6-Trimethylpyrazin-2-yl)methanol

TMP-COOH:

3,5,6-Trimethylpyrazine-2-carboxylic acid

OH-TMP-OH:

2,5-Dimethylol-3,6-dimethylpyrazine

HUVECs:

Human umbilical vein endothelial cells

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Acknowledgments

This work was supported by the National Natural Science Foundation of China (NO. 81173519) and the Innovation Team Project Foundation of Beijing University of Chinese Medicine named “Lead Compound Discovering and Developing Innovation Team Project Foundation” (NO. 2011-CXTD-15).

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Authors and Affiliations

  1. School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing, 100102, China

    Kuo Xu, Penglong Wang, Xin Xu, Fuhao Chu & Haimin Lei

  2. School of Basic Medicine, Beijing University of Chinese Medicine, Beijing, 100029, China

    Jinxuan Lin & Yuzhong Zhang

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  1. Kuo Xu
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  2. Penglong Wang
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  3. Xin Xu
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Correspondence to Haimin Lei.

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Xu, K., Wang, P., Xu, X. et al. An overview on structural modifications of ligustrazine and biological evaluation of its synthetic derivatives. Res Chem Intermed 41, 1385–1411 (2015). https://doi.org/10.1007/s11164-013-1281-2

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