Synthesis, structure and biological activity of four new picolinohydrazonamide derivatives

Abstract

Four new picolinohydrazonamide derivatives, namely, 6-methyl-N'-(morpholine-4-carbonothioyl)picolinohydrazonamide, C₁₂H₁₇N₅OS, 6-chloro-N'-(morpholine-4-carbonothioyl)picolinohydrazonamide methanol monosolvate, C₁₁H₁₄ClN₅OS·CH₃OH, 6-chloro-N'-(4-phenylpiperazine-1-carbonothioyl)picolinohydrazonamide, C₁₇H₁₉ClN₆S, and 6-chloropicolinohydrazonamide, C₆H₇ClN₄, have been synthesized and characterized by NMR spectroscopy and single-crystal low-temperature X-ray diffraction. In addition, their antibacterial and anti-yeast activities have been determined. The first three compounds adopt the zwitterionic form in the crystal structure regardless of the presence or absence of solvent molecules in the structure. They also adopt the same symmetry, i.e. P2₁/c (P2₁/n), unlike the fourth structure which is chiral and has the space group P2₁2₁2₁. For all the studied cases, intermolecular N-H...O and N-H...N hydrogen bonds play an essential role in the formation of the structures.

Keywords: biological activity; computational chemistry; crystal structure; picolinohydrazonamide.