Synthesis, X-ray crystallography and antimicrobial activity of 2-cyanoguanidinophenytoin

Synthesis, X-ray crystallography and antimicrobial activity of 2-cyanoguanidinophenytoin

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Abstract The optimized synthesis of [5-oxo-4,4-diphenylimidazolidin-2-ylidene]cyanamide, which is known as 2-cyanoguanidinophenytoin (CNG-DPH) (3), and (imidazo[4,5-d]imidazole-2,5-diylidine)dicyanamide (4) has been reported in the present work.Furthermore, new Mannich bases derived from CNG-DPH were synthesized via its reaction with formaldehyde and using the corresponding amines, piperidine (base redken shades 9gi 5), and morpholine (base 6).Also, the antimicrobial activity and X-ray crystal structures for CNG-DPH and their Mannich bases were studied.The bases 3 and 6 crystallized in a monoclinic system; the crystal structure of 3 tech lighting tellium containing four molecules in the unit cell with a P21/c space group.The unit cell of 6 has eight molecules with a C2/c space group.

The inter and intra hydrogen bond contacts packed and stabilized both of the structures.The morpholine ring of base 6 demonstrated a distinctive chair configuration.Mannich bases 5 and 6 showed promising antimicrobial effects.base 4 has a greater percentage for in vitro cytotoxicity (IC50) against normal cells, whereas 3 has the lowest ratio.