Abstract
Three novel L-histidine amide derivatives were synthesized and the corresponding chemical structures were characterized by means of melting point analysis, IR, MS, 1H NMR as well as 13C NMR. The coagulation activities of the compounds were evaluated by an MOE(molecular operating environment) docking technique and coagulation test. The results obtained from molecular docking show that the interactions between the compounds and thrombin exhibit procoagulant activity in combination with an improved combinatory effect. Moreover, the results of in vitro coagulation tests show that the L-histidine amide derivatives feature coagulant activities in common coagulation pathways. Compared with the blank control group, the optimal shortening rates of compounds 1―3 were 39.08%(0.5 mmol/L), 22.94%(1.0 mmol/L) and 15.38%(0.0625 mmol/L), respectively.
Similar content being viewed by others
References
Bunev A. S., Vasiliev M. A., Statsyuk V. E., Ostapenko G. I., Pere-gudov A. S., Journal of Fluorine Chemistry, 2014, 163, 34
Xue W. J., Li H. Z., Gao F. F., Wu A. X., Tetrahedron, 2014, 70(2), 239
Wei J. R., Liu K., Lin F. Q., He C. P., Luo X., Zou J. J., He W., Nong W. Q., Lin C. W., Applied Biological Chemistry, 2016, 59(2), 271
Dong W. B., Mao X. M., Guan Y., Kang Y., Shang D. J., Scientific Reports, 2017, 7, 40228
Ramadhan U. H., Al-Salihi N. J., Journal of Chemistry, 2011, 8(4), 1832
Garza-Ortiz A., Camacho-Camacho C., Sainz-Espuñes T., Rojas I., Gutiérrez-Lucas L. R., Gutierrez C. A., Vera R., Marco A., Bioinor-ganic Chemistry and Applications, 2013, 13, 502713
Luo B., Chen F. Y., Hebei Medicine, 2008, 4, 455
Costanzo M. J., Almond H. R., Hecker L. R., Schott M. R., Yabut S. C., Zhang H. C., Andrade-Gordon P., Corcoran T. W., Giardino E. C., Kauffman J. A., Journal of Medicinal Chemistry, 2005, 48(6), 1984
Anas A. R. J., Kisugi T., Umezawa T., Matsuda F., Campitelli M. R., Quinn R. J., Okino T., Journal of Natural Products, 2012, 75(9), 1546
Dong Z. X., Shi Z. H., Li N. G., Zhang W., Gu T., Zhang P. X., Wu W. Y., Tang Y. P., Fang F., Xue X., Chemical Biology & Drug Design, 2016, 87(6), 946
Jasmine F., Gerhard K., Angewandte Chemie International Edition, 2006, 45(6), 985
Handley L. D., Treuheit N. A., Venkatesh V. J., Komives E. A., Bio-chemistry, 2015, 54(43), 6650
Debbabi K. F., Bashandy M. S., Al-Harbi S. A., Aljuhani E. H., Al-Saidi H. M., Journal of Molecular Structure, 2017, 1131, 124
Jiang L. G., Yuan C., Chen H. W., Wang Y., Zhao B. Y., Zhang X., Huang M. D., Chinese J. Struct. Chem., 2011, 30(7), 1021
Zaki I., Ramadan M., Abdelrahman M. H., Aly Omar M., Monat-shefte füer Chemie, 2017, 148(8), 1483
Kheder N. A., Molecules, 2016, 21(3), 326
Subramanian V., Ain Q. U., Henno H., Pietilä Lars O., Fuchs J., Pru-sis P., Bender A., Wohlfahrt G., Med. Chem. Comm., 2017, 8(5), 1037
Zhang E., Feng S., Materials Science & Engineering C Materials for Biological Applications, 2015, 52, 37
Acknowledgements
We would like to thank the Sun Yat-sen University for providing the MOE(2008.09) software used throughout this study.
Author information
Authors and Affiliations
Corresponding author
Additional information
Supported by the National Natural Science Foundation of China(No.21362001), the Guangxi Key Laboratory of Traditional Chinese Medicine Quality Standards, China(No.guizhongzhongkai201104) and the High Level Innovation Team and Outstanding Scholar Project of Guangxi Institutions of Higher Education, China(No.guijiaoren [2014] 49).
Rights and permissions
About this article
Cite this article
He, W., Zhao, A., Zou, J. et al. Synthesis, in vitro coagulation activities and molecular docking studies on three L-histidine amide derivatives. Chem. Res. Chin. Univ. 34, 90–94 (2018). https://doi.org/10.1007/s40242-018-7184-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s40242-018-7184-4