Synthesis, X-ray structural determination and biological evaluation of novel ferrocene grafted spiroquinoxalinopyrrolidine

Arumugam N., Almansour A. I., Kumar R. S., Soliman S. M., Viswanathan E., DEGE N., ...Daha Fazla

JOURNAL OF MOLECULAR STRUCTURE, cilt.1226, 2021 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1226
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1016/j.molstruc.2020.129348
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Anahtar Kelimeler: 1,3-Dipolar cycloaddition, Spiropyrrolidines, X-ray diffraction study DFT calculation, Food borne bacterial inhibitory activity, Antioxidant activity, ANTIMALARIAL ACTIVITY, IN-VITRO, DERIVATIVES, ANTIOXIDANT, ANIONS
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

Synthesis of a hybrid heterocycle comprising ferrocene, spiropyrrolidine and quinoxaline structural moieties have been achieved in good yield via ionic liquid expedited multicomponent 1,3-dipolar cycloaddition reaction. Structural properties of the synthesized compound were exploited using single crystal X- ray crystallographic studies. Hirshfeld analysis revealed the importance of H center dot center dot center dot H (59.6%), C-H center dot center dot center dot pi (22.4%) and N center dot center dot center dot H (3.5%) contacts within the molecular packing. The Fe-C interactions around ferrocenyl moiety were investigated using Natural Bond Orbital (NBO) and Atoms In Molecules (AIM) calculations. A predominant covalent character of interactions between Fe-C were been accessed from AIM calculation. A weaker extend of pi-back donation appeared in cyclopentadienyl moiety carrying the substituent instead of unsubstituted one. Further, the in vitro antimicrobial potential of the synthesized compound against five food borne bacterial pathogens reveals its significant activity against E. coli and S. enterica with MIC values 6.00 mu g/mL and 8.00 mu g/mL, respectively. The antioxidant activity of compound 5 was found to be 84.37 +/- 0.55 at 250 mu g/mL concentration with an IC50 value = 33.80 mu g/mL. (C) 2020 Elsevier B.V. All rights reserved.