Catalyzed syntheses of novel series of spiro thiazolidinone derivatives with nano Fe2O3: spectroscopic, X-ray, Hirshfeld surface, DFT, biological and docking evaluations

• Published in: Scientific reports 2024-08, Vol.14 (1), p.18773-25, Article 18773
• Main Authors: Abbass, Eslam M., El-Rayyes, Ali, Khalil Ali, Ali, El-Farargy, Ahmed F., Kozakiewicz-Piekarz, Anna, Ramadan, Ramadan M.
• Format: Article
• Language: English
• Subjects: 639/638; 639/638/403; 639/638/549; Antimicrobial; Biological properties; Catalysts; DFT; DNA structure; Docking; Ferric oxide; Hirshfeld surface; Humanities and Social Sciences; Hydrogen bonding; multidisciplinary; Nanoparticles; Science; Science (multidisciplinary); Spiro thiazolidinone; X-ray; X-ray diffraction
• ISSN: 2045-2322; 2045-2322
• DOI: 10.1038/s41598-024-65282-z

Twelve spiro thiazolidinone compounds ( A–L ) were synthesized via either conventional thermal or ultrasonication techniques using Fe 2 O 3 nanoparticles. The modification of the traditional procedure by using Fe 2 O 3 nanoparticles led to enhancement of the yield of the desired candidates to 78–93% in approximately half reaction time compared with 58–79% without catalyst. The products were fully characterized using different analytical and spectroscopic techniques. The structure of the two derivatives 4-phenyl-1-thia-4-azaspirodecan-3-one ( A ) and 4-(p-tolyl)-1-thia-4-azaspirodecan-3-one ( B ) were also determined using single crystal X-ray diffraction and Hirshfeld surface analysis. The two compounds ( A and B ) were crystallized in the orthorhombic system with Pbca and P2 1 2 1 2 1 space groups, respectively. In addition, the crystal packing of compounds revealed the formation of supramolecular array with a net of intermolecular hydrogen bonding interactions. The energy optimized geometries of some selected derivatives were performed by density functional theory (DFT/B3LYP). The reactivity descriptors were also calculated and correlated with their biological properties. All the reported compounds were screened for antimicrobial inhibitions. The two derivatives, F and J , exhibited the highest levels of bacterial inhibition with an inhibition zone of 10–17 mm. Also, the two derivatives, F and J , displayed the most potent fungal inhibition with an inhibition zone of 15–23 mm. Molecular docking investigations of some selected derivatives were performed using a B-DNA (PDB: 1BNA) as a macromolecular target. Structure and activity relationship of the reported compounds were correlated with the data of antimicrobial activities and the computed reactivity parameters.