Synthesis and evaluation of new amidrazone-derived hydrazides as a potential anti-inflammatory agents

• Published in: Monatshefte für Chemie Vol. 149; no. 8; pp. 1493 - 1500
• Main Authors: Paprocka, Renata, Wiese-Szadkowska, Małgorzata, Helmin-Basa, Anna, Mazur, Liliana, Kutkowska, Jolanta, Michałkiewicz, Jacek, Modzelewska-Banachiewicz, Bożena, Pazderski, Leszek
• Format: Journal Article
• Language: English
• Published: Vienna Springer Vienna 2018; Springer Nature; Springer Nature B.V
• Subjects: Analytical Chemistry; Anhydrides; Antibacterial materials; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry, Multidisciplinary; Chemistry/Food Science; Crystal structure; Hydrazides; Ibuprofen; Inorganic Chemistry; Molecular chains; Molecular structure; NMR; Nuclear magnetic resonance; Organic Chemistry; Original Paper; Physical Chemistry; Physical Sciences; Science & Technology; Single crystals; Theoretical and Computational Chemistry; Toxicity; X-ray diffraction; Anti-inflammatory activity; Antiproliferative agents; Drug research; Acylation; Crystal structure; IBUPROFEN; CELLS; ACID; ANTIBACTERIAL; DERIVATIVES; ANTIMICROBIAL ACTIVITY
• ISSN: 0026-9247; 1434-4475
• DOI: 10.1007/s00706-018-2197-8

The series of new hydrazide derivatives were synthesized in reactions of N 3 -substituted amidrazones with cyclic anhydrides as potential anti-inflammatory and antibacterial agents. The compounds were characterized by 1 H- 13 C two-dimensional NMR techniques, which revealed the presence of two tautomeric forms in DMSO- d 6 solutions, while the molecular structure of one species was confirmed by single-crystal X-ray diffraction. The anti-inflammatory effects of hydrazides on peripheral blood mononuclear cells were experimentally evaluated. Three compounds showed antiproliferative activity comparable to ibuprofen. One derivative demonstrated strong reduction of lymphocyte proliferation stimulated by anti-CD3 antibody (by 90%) and PHA, as well as low cell toxicity. The obtained compounds exhibited relatively weak antibacterial activity; they were more effective against Gram-positive bacterial strains. Graphical abstract