PMID- 35542496 OWN - NLM STAT- PubMed-not-MEDLINE LR - 20220615 IS - 2046-2069 (Electronic) IS - 2046-2069 (Linking) VI - 8 IP - 50 DP - 2018 Aug 7 TI - Expedient synthesis of eumelanin-inspired 5,6-dihydroxyindole-2-carboxylate ethyl ester derivatives. PG - 28323-28328 LID - 10.1039/c8ra06148c [doi] AB - Dihydroxyindoles such as 5,6-dihydroxyindole-2-carboxylic acid (DHICA) are the main monomer units of eumelanin, the black to brown pigment in humans, and have emerging biological roles beyond melanin. Elaboration of commercially available 5,6-dimethoxy-2-carboxylate ethyl ester provides ready access to DHICA-inspired small molecules, including 3-(hetero)aryl-indoles and 4,7-di-(hetero)aryl-indoles. CI - This journal is (c) The Royal Society of Chemistry. FAU - Aebly, Andrew H AU - Aebly AH AD - Department of Chemistry and Biochemistry, Oberlin College 119 Woodland St. Oberlin OH 44074 USA Jason.Belitsky@Oberlin.edu. FAU - Levy, Jeffrey N AU - Levy JN AD - Department of Chemistry and Biochemistry, Oberlin College 119 Woodland St. Oberlin OH 44074 USA Jason.Belitsky@Oberlin.edu. FAU - Steger, Benjamin J AU - Steger BJ AD - Department of Chemistry and Biochemistry, Oberlin College 119 Woodland St. Oberlin OH 44074 USA Jason.Belitsky@Oberlin.edu. FAU - Quirke, Jonathan C AU - Quirke JC AD - Department of Chemistry and Biochemistry, Oberlin College 119 Woodland St. Oberlin OH 44074 USA Jason.Belitsky@Oberlin.edu. FAU - Belitsky, Jason M AU - Belitsky JM AUID- ORCID: 0000-0002-7998-3892 AD - Department of Chemistry and Biochemistry, Oberlin College 119 Woodland St. Oberlin OH 44074 USA Jason.Belitsky@Oberlin.edu. LA - eng PT - Journal Article DEP - 20180807 PL - England TA - RSC Adv JT - RSC advances JID - 101581657 EIN - RSC Adv. 2019 Sep 3;9(48):27754. PMID: 35532451 PMC - PMC9083952 COIS- There are no conflicts of interest to declare. EDAT- 2018/08/07 00:00 MHDA- 2018/08/07 00:01 PMCR- 2018/08/07 CRDT- 2022/05/11 04:09 PHST- 2018/07/20 00:00 [received] PHST- 2019/09/03 00:00 [revised] PHST- 2018/07/28 00:00 [accepted] PHST- 2022/05/11 04:09 [entrez] PHST- 2018/08/07 00:00 [pubmed] PHST- 2018/08/07 00:01 [medline] PHST- 2018/08/07 00:00 [pmc-release] AID - c8ra06148c [pii] AID - 10.1039/c8ra06148c [doi] PST - epublish SO - RSC Adv. 2018 Aug 7;8(50):28323-28328. doi: 10.1039/c8ra06148c. eCollection 2018 Aug 7.