Novel cyclam multicomponent crystal forms: synthesis, characterization and antimicrobial activity

• Published in: CrystEngComm 2023-10, Vol.25 (41), p.5787-5795
• Main Authors: Saied, Rajaa, Alves, Paula C, Rijo, Patrícia, André, Vânia, Alves, Luis G
• Format: Article
• Language: English
• Subjects: Salicylic acid; Synergistic effect
• ISSN: 1466-8033; 1466-8033
• DOI: 10.1039/d3ce00354j

Novel multicomponent crystal forms were obtained from reactions of trans -disubstituted cyclam derivatives with flufenamic and salicylic acids. The reactions of H 2 ( 4-CF3 PhCH 2 ) 2 cyclam with those acids led to the formation of salts of the formulae [H 2 {H 2 ( 4-CF3 PhCH 2 ) 2 cyclam}]( 3-CF3 PhNHC 6 H 4 COO) 2 and [H 2 {H 2 ( 4-CF3 PhCH 2 ) 2 cyclam}](HOC 6 H 4 COO) 2 , respectively. The reaction of H 2 (PhCH 2 ) 2 cyclam with flufenamic acid led to the formation of the salt [H 2 {H 2 (PhCH 2 ) 2 cyclam}]( 3-CF3 PhNHC 6 H 4 COO) 2 , whereas its reaction with salicylic acid afforded the ionic cocrystal [H 2 (PhCH 2 ) 2 cyclam](HOC 6 H 4 COOH) 2 ·[H 2 {H 2 (PhCH 2 ) 2 cyclam}](HOC 6 H 4 COO) 2 . The compounds obtained were fully characterized and tested against several yeasts as well as Gram-positive and Gram-negative bacterial strains. The results have shown that the new multicomponent forms display relevant antimicrobial activity when compared to their parent cyclam derivatives, highlighting the importance of exploring synergistic effects to unveil new and efficient antimicrobial agents. Novel multicomponent crystal forms were obtained from reactions of trans -disubstituted cyclam derivatives with flufenamic and salicylic acids.