Crystal structural and in silico studies of Schiff bases derived from 4-aminoantipyrine

• Published in: Solid state sciences 2020-08, Vol.106, p.106293, Article 106293
• Main Authors: Ossai, Valentine, Obiefuna, Ayogu Patrick, Laraps, Bulus Caleb, Okenyeka, Obinna Ugochukwu, Ezeorah, Julius Chigozie, Dege, Necmi, Ibezim, Akachukwu, Lutter, Michael, Jurkschat, Klaus, Obasi, Nnamdi Lawrence
• Format: Article
• Language: English
• Subjects: 4-Aminoantipyrine; DNA; In silico; Schiff base; X-ray crystallography
• ISSN: 1293-2558; 1873-3085
• DOI: 10.1016/j.solidstatesciences.2020.106293

Two Schiff bases, 4-[(2-hydroxynaphthalen-1-yl)methylidene]amino}-1,5,-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one (APNA) and 4-[(2,3-Dihydroxybenzylidene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one (SBAP) derived from 4-aminoantipyrine are reported. The compounds were recrystallized in methanol and characterized using spectroscopic techniques (IR, NMR) and single-crystal X-ray diffraction analysis. The XRD structure shows that APNA and SBAP crystallize respectively in the orthorhombic and monoclinic crystal systems, space groups of Pna2(1) and C2/c, and both has Z = 8 in the unit cells. SBAP has all trans configuration around its central C=N double bond. It is stabilized by C18–H18⋯N2 and C7–H7⋯O3 intramolecular hydrogen bonds. The presence of distinctive bond length of N3–C12 in APNA and C=N (1451 cm−1) stretching vibration in the IR spectrum of SBAP are evidence that the Schiff bases formed. Additional hydroxyl group in SBAP raised the TPSA (146.478 Å2) more than APNA's (83.087 Å2) which had more aromatic ring (increased conjugation) and lesser number of hydroxyl group. The computed molecular descriptors of APNA and SBAP suggest that pyrazolones will have no pharmacokinetic challenge if developed as drug. [Display omitted] •The crystal systems and space groups obtained from the crystals gave APNA (orthorhombic, Pna2(1)) and SBAP (monoclinic, C2/c).•Additional hydroxyl group in SBAP raised the TPSA more than APNA which had more aromatic ring.•The biological activity of the compounds against the tested bacterial is moderate.•The compounds were able to cleave DNA.