Crystal Structures, ct-DNA/BSA Binding Properties and Antibacterial Activities of Halogenated Pyridyl Hydrazones  

作　　者：LIAO Geng-Hui LIU Xiang-Rong ZHAO Shun-Sheng YANG Zai-Wen YANG Zheng 廖庚晖;刘向荣;赵顺省;杨再文;杨征(College of Chemistry and Chemical Engineering,Xi'an University of Science and Technology,Xi'an 710054,China)

机构地区：[1]College of Chemistry and Chemical Engineering,Xi'an University of Science and Technology,Xi'an 710054,China

出　　处：《Chinese Journal of Structural Chemistry》2020年第3期467-484,377,共19页结构化学（英文）

基　　金：supported by the National Natural Science Foundation of China(Nos.21073139 and 21373158);Science and Technology on Combustion and Explosion Laboratory Foundation of Shaanxi(No.6142603010301)。

摘　　要：Three new halogenated pyridyl hydrazones, namely 4-chlorobenzaldehyde-4-chloropyridine-2-formyl acylhydrazone(C(13)H9Cl2N3O, 3 a), 4-bromobenzaldehyde-4-chloropyridine-2-formyl acylhydrazone(C(13)H9BrClN3O, 3 b) and 4-iodobenzaldehyde-4-chloropyridine-2-formyl acylhydrazone(C(13)H9ClIN3O, 3 c), have been synthesized and characterized by elemental analysis, IR, 1 H NMR, and single-crystal X-ray diffraction. The X-ray diffraction analysis revealed that 3 a^3 c crystallize in monoclinic with space group Cc. The units of 3 a ~ 3 c were linked by intermolecular N–H...X(X = Cl, Br, I) hydrogen bonds into 2 D layered structures, which were further extended into 3 D networks by a series of π-π stacking interactions. Thermogravimetric analysis showed that all of them possessed higher thermal stabilities. The reactivities toward calf thymus DNA(ct-DNA) and bovine serum albumin(BSA) of 3 a^3 c were investigated by UV-vis and fluorescent spectroscopy as well as molecular docking simulation. Both theoretical and experimental results indicated that 3 a^3 c bound to ct-DNA in the mode of minor groove binding, and interacted with BSA through the hydrophobic cavity near TRP213. Besides, the orders of binding affinities of 3 a^3 c to ct-DNA and BSA were both 3 c > 3 b > 3 a, which were the same as that of antibacterial activities. Thus, the interactions of iodinated acylhydrazone with biological targets were stronger than that of chlorinated and brominated acylhydrazones, which provided a representative case for halogenation of lead compounds in rational drug design.

关 键 词：ACYLHYDRAZONE crystal structure thermal stability CT-DNA BSA antibacterial activity 

分 类 号：O626.32[理学—有机化学] TQ463.54[理学—化学]