{"doi":"10.1021/acs.joc.4c01028","title":"Syntheses of 3-(2-Nitrovinyl)-indoles, Benzo[<i>a</i>]carbazoles, Naphtho[2,1-<i>a</i>]carbazoles, and 1-Hydroxy-β-carbolines Lead to Identification of Antiproliferative Compounds Active under Hypoxia","abstract":"Herein, we describe a novel reaction between C-2-substituted indoles and 2-nitroacetophenones leading to a variety of indole-containing heterocyclic scaffolds. At 60 °C in AcOH with H 2 SO 4 as catalyst, C-2 aryl indoles give 3-(2-nitrovinyl)-indoles with high Z or E geometric selectivity depending on the type of substrate utilized. These compounds undergo an electrocyclization process in a sealed vial in a microwave apparatus in DMF at 250 °C to give benzo[ a ]carbazoles and naphtho[2,1- a ]carbazoles depending on whether the C-2 aromatic moiety is phenyl or naphthyl. Utilization of 2-methylindoles in the reaction with 2-nitroacetophenones and performing the reaction in a sealed vial in a microwave apparatus in AcOH at 200 °C leads to 1-hydroxy-β-carbolines. Selected compounds from each scaffold were tested for antiproliferative activities against MDA-MB-231 triple-negative breast cancer cells under normoxic and hypoxic conditions, and three compounds belonging to the 3-(2-nitrovinyl)-indole and 1-hydroxy-β-carboline series were identified to have single-digit micromolar IC 50 values.","journal":"The Journal of Organic Chemistry","year":2024,"id":451753,"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":3,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9528,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2024-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1273149,"name":"Connor Edvall","orcid":"0000-0002-1268-8055","position":1,"is_corresponding":false},{"id":709126,"name":"А. В. Аксенов","orcid":"0000-0002-6644-9949","position":2,"is_corresponding":false},{"id":709129,"name":"Дмитрий А. Аксенов","orcid":"0000-0002-0727-9652","position":3,"is_corresponding":false},{"id":1273150,"name":"Igor A. Kurenkov","orcid":"0000-0002-0911-4093","position":4,"is_corresponding":false},{"id":1273151,"name":"И. В. Аксенова","orcid":"0000-0002-8083-1407","position":5,"is_corresponding":false},{"id":1273152,"name":"Anna M. Zatsepilina","orcid":"0000-0001-9053-592X","position":6,"is_corresponding":false},{"id":709131,"name":"Nicolai A. Aksenov","orcid":"0000-0002-7125-9066","position":7,"is_corresponding":false},{"id":288432,"name":"Sanku Mallik","orcid":"0000-0003-4236-2512","position":8,"is_corresponding":false},{"id":526597,"name":"Alexander Kornienko","orcid":"0000-0003-2041-7367","position":9,"is_corresponding":false},{"id":709127,"name":"Nikolai A. Arutiunov","orcid":"0000-0003-2675-9093","position":0,"is_corresponding":true}],"reference_count":21,"raw_metadata":null,"created_at":"2026-07-19T02:02:45.951080Z","pmid":"39284576","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":[]}