{"doi":"10.1002/cbdv.202200327","title":"Cu‐Catalyzed Chan–Evans–Lam Coupling Reactions of 2‐Nitroimidazole with Aryl Boronic Acids: An Effort toward New Bioactive Agents against <i>S. pneumoniae</i>","abstract":"The coupling of phenylboronic acids with poorly-activated imidazoles is studied as a model system to explore the use of copper-catalyzed Chan-Evans-Lam (CEL) coupling for targeted C-N bond forming reactions. Optimized CEL reaction conditions are reported for four phenanthroline-based ligand systems, where the ligand 4,5-diazafluoren-9-one (dafo, L2) with 1 molar equivalent of potassium carbonate yielded the highest reactivity. The substrate 2-nitroimidazole (also known as azomycin) has documented antimicrobial activity against a range of microbes. Here N-arylation of 2-nitroimidazole with a range of aryl boronic acids has been successfully developed by copper(II)-catalyzed CEL reactions. Azomycin and a range of newly arylated azomycin derivatives were screened against S. pneumoniae, where 1-(4-(benzyloxy)phenyl)-2-nitro-1H-imidazole (3d) was demonstrated to have a minimal inhibition concentration value of 3.3 μg/mL.","journal":"Chemistry & Biodiversity","year":2022,"id":264283,"datarank":0.0,"base_score":0.0,"endowment":0.0,"self_citation_contribution":0.0,"citation_network_contribution":0.0,"self_endowment_contribution":0.0,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":12,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9493,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2022-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":922344,"name":"Patrick E. Sheridan","orcid":null,"position":1,"is_corresponding":false},{"id":922345,"name":"Alanna K. Hauer","orcid":null,"position":2,"is_corresponding":false},{"id":922346,"name":"Allyn E. Garrett","orcid":null,"position":3,"is_corresponding":false},{"id":922347,"name":"Danielle E. McConnell","orcid":null,"position":4,"is_corresponding":false},{"id":440669,"name":"Justin A. Thornton","orcid":null,"position":5,"is_corresponding":false},{"id":340419,"name":"Sean L. Stokes","orcid":"0000-0001-6093-5172","position":6,"is_corresponding":false},{"id":340420,"name":"Joseph P. Emerson","orcid":"0000-0002-7556-1393","position":7,"is_corresponding":false},{"id":921896,"name":"Selvam Raju","orcid":"0000-0001-8003-8794","position":0,"is_corresponding":true}],"reference_count":58,"raw_metadata":null,"created_at":"2026-07-19T00:26:37.567338Z","pmid":"35819995","pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}