Synthesis of New Matrine Derivatives in Aqueous Phase and Their Crystal Structures

Thirteen matrine derivatives were synthesized with high yield with one step in aqueous phase. The chemical structures of the synthesized compounds were characterized by H-1 NMR, C-13 NMR and HRMS. Three crystals of compound 13-(piperidin-1-yl)matrine (a), 13-(piperidin-1-yl)carbodithioate matrine (k) and 13-(morpholin-4-yl) carbodithioate matrine (m) were obtained and X-ray diffraction data showed that their structures included five chiral carbon atoms with the absolute configuration of 5(S), 6(S), 7(R), 11(R) and 13(S). Meanwhile, there were three classical hydrogen bonds: O(2)-H(21B)center dot center dot center dot N(2), O(2)-H(21A)center dot center dot center dot O(1) and C(9)-H(9A)center dot center dot center dot O(1) by analyzing the data of compound 13-(piperidin-1-yl)matrine (a). These strong hydrogen bonds can play a key role in the accumulation of crystals. Biological studies indicated that the synthetic derivatives had some inhibitory effect against SW480, A549 and A431 cells. The introduction of N or S atom at C-13 position of matrine could improve the antitumor activity.