On molecular complexes derived from amino acids and nicotinamides in combination with boronic acids

摘要: Cocrystallization experiments of three representative aromatic boronic acids, namely phenylboronic acid (PBA), 1,4-benzenediboronic (BDBA) and 4-iodophenylboronic (IPBA), with a series essential amino nicotinamide (NA) isonicotinamide (INA) gave total nine molecular complexes the compositions: PBA–PRO (1 : 1), PBA–PRO–H2O (1 : 1 : 1), α-BDBA–PRO (1 : 2), β-BDBA–PRO α-IPBA–PRO β-IPBA–PRO BDBA–INA IPBA–INA (1 : 1) IPBA–NA where PRO = L-proline. Of these, α-BDBA–PRO/β-BDBA–PRO α-IPBA–PRO/β-IPBA–PRO were true polymorphs. Experiments varying solvent in screening process showed that formation polymorphs is influenced strongly by presence/absence water. For cocrystalline phases L-proline, structural characterization revealed components connected into high-dimensional hydrogen bonded networks. As expected, charge-assisted –B(OH)2⋯carboxylate heterosynthon dominant was found to display degrees distortion from planarity. The displayed similar crystal packing, differences only one direction lattice (AAAA versus ABAB stacking). cocrystals exhibited 1D or 2D layers, which formed through (B)O–H⋯pyridine, B(OH)2⋯amide, amide⋯amide and/or single-bridged (B)O–H⋯O(H)B interactions. Comparison between structures position heteroatom (iso)nicotinamide not controlled final crystalline form but also produced different bonding In vitro toxicology studies cell viability conserved when human kidney hepatic cells are treated even high concentrations acids examined herein. However, some teratogenicity chicken embryos.