{"doi":"10.1021/acsomega.2c08184","title":"Synthesis and Photoreactivity of 7-Nitroindoline-<i>S</i>-thiocarbamates","abstract":"High Resolution Image Download MS PowerPoint Slide The photolytic properties of N -acyl-7-nitroindolines make these compounds attractive as photocleavable protecting groups and “caged” compounds for the light-induced release (“uncaging”) of biologically active compounds and as acylating reagents under neutral conditions. However, the synthesis of N -acyl-7-nitroindolines usually requires multiple steps, and the direct acylation of 7-nitroindolines can be quite challenging. 7-Nitroindolines with other types of N -carbonyl-containing groups may also be photoreactive and could potentially be better accessible. Here we demonstrate the short and efficient synthesis of 5-bromo-7-nitroindoline- S -thiocarbamates, a new class of photoreactive compounds, and the study of some of their photochemical and photophysical properties. Using 5-bromo-7-nitroindoline- S -ethylthiocarbamate as a model compound, we show that it can undergo one-photon and two-photon photolysis at 350 and 710 nm, respectively. Our experimental data and quantum chemistry calculations support a photolysis pathway that differs from photolysis pathways previously reported for N -acyl-7-nitroindolines. The photolysis with 350 nm light results in 5-bromo-7-nitrosoindoline, which is in equilibrium with its dimeric form(s), as supported by experiment and theory. This study expands the scope of photoreactive 7-nitroindoline derivatives and informs the development of novel photocleavable compounds.","journal":"ACS Omega","year":2023,"id":385950,"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":1,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9501,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2023-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1154658,"name":"H. Patricio Del Castillo","orcid":null,"position":1,"is_corresponding":false},{"id":1154299,"name":"Irodiel Vinales","orcid":"0000-0002-4544-9587","position":2,"is_corresponding":false},{"id":1154659,"name":"Juan E. M. Urbay","orcid":null,"position":3,"is_corresponding":false},{"id":1154660,"name":"Aurelio Paez","orcid":null,"position":4,"is_corresponding":false},{"id":1154661,"name":"Matthew R. Weaver","orcid":null,"position":5,"is_corresponding":false},{"id":1154662,"name":"Roberto Iturralde","orcid":null,"position":6,"is_corresponding":false},{"id":482878,"name":"Igor L. Estevao","orcid":"0000-0003-3946-8375","position":7,"is_corresponding":false},{"id":961216,"name":"Sohan R. Jankuru","orcid":"0000-0002-3905-6488","position":8,"is_corresponding":false},{"id":353857,"name":"Igor C. Almeida","orcid":"0000-0002-2443-8213","position":9,"is_corresponding":false},{"id":262775,"name":"Chunqiang Li","orcid":"0000-0003-1220-1611","position":10,"is_corresponding":false},{"id":1154663,"name":"Carl W. Dirk","orcid":null,"position":11,"is_corresponding":false},{"id":686919,"name":"Katja Michael","orcid":"0000-0001-6754-3702","position":12,"is_corresponding":false},{"id":1154657,"name":"Philip T. Baily","orcid":null,"position":0,"is_corresponding":true}],"reference_count":30,"raw_metadata":null,"created_at":"2026-07-19T01:17:56.803401Z","pmid":"36936343","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":[]}