title: Facile synthesis, structural evaluation, antimicrobial activity and synergistic effects of novel imidazo[1,2-a]pyridine based organoselenium compounds.
abstract: A simple and efficient method has been described to synthesize the hitherto unknown imidazo[1,2-a]pyridine selenides (5a-l) by reaction of 2-chloroimidazo [1,2-a]pyridines with aryl/heteroaryl selenols, generated in situ by reduction of various diselenides with hypophosphorous acid. The crystal structures of 3-nitro-2-(phenylselanyl)-imidazo[1,2-a]pyridine (5a), 2-(mesitylselanyl)-3-nitro-imidazo[1,2-a]pyridine (5d) and 3-nitro-2-(pyridin-2-ylselanyl)-imidazo[1,2-a]pyridine (5e) were confirmed by X-ray crystallography and the DFT calculations were performed to determine various structural parameters which were correlated with the X-ray crystal structures. The synthesized compounds were subjected to antimicrobial evaluation and it was found that compounds 5a and 5j were active against gram negative bacterium Escherichia coli whereas compound 5e was active against different fungal strains. Time kill assay was performed to understand the microbial activity of synthesized organoselenium compounds and the toxicity of these compounds was evaluated against human cell lines. Synergistic effects of active compounds 5a and 5e were tested with existing antibiotic drugs which exhibited that the antibiotic combination with synthesized organoselenium compounds efficiently enhanced the antimicrobial activity.
authors: Department of Chemistry & Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh, 160014, India.
authors: Sanjeev
authors: S
authors: Kumar
authors: Department of Chemistry & Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh, 160014, India.
authors: Nidhi
authors: N
authors: Sharma
authors: Department of Microbial Biotechnology, Panjab University, Chandigarh, 160014, India.
authors: Indresh K
authors: IK
authors: Maurya
authors: Department of Chemistry & Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh, 160014, India.
authors: Aman K K
authors: AKK
authors: Bhasin
authors: Department of Applied Sciences, University Institute of Engineering & Technology (U.I.E.T), Panjab University, Chandigarh, 160014, India.
authors: Nishima
authors: N
authors: Wangoo
authors: Department of Chemistry, CICECO - Aveiro Institute of Materials, University of Aveiro, 3810-193 Aveiro, Portugal.
authors: Paula
authors: P
authors: Brandão
authors: Department of Chemistry, CICECO - Aveiro Institute of Materials, University of Aveiro, 3810-193 Aveiro, Portugal; Department of Medical Sciences, iBiMED - Institute of Biomedicine, University of Aveiro, 3810-193 Aveiro, Portugal.
authors: Vítor
authors: V
authors: Félix
authors: Department of Chemistry & Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh, 160014, India. Electronic address: kkbhasin@pu.ac.in.
authors: K K
authors: KK
authors: Bhasin
authors: Department of Chemistry & Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh, 160014, India. Electronic address: rohitksg@pu.ac.in.
authors: Rohit K
authors: RK
authors: Sharma
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D060326:Chemistry Techniques, Synthetic; D004357:Drug Synergism; D004926:Escherichia coli / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D057809:HEK293 Cells; D006367:HeLa Cells; D006801:Humans; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D011725:Pyridines / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000890:Anti-Infective Agents; D016566:Organoselenium Compounds; D011725:Pyridines