Erratum: Discovery of Nanomolar Melanocortin-3 Receptor (MC3R)-Selective Small Molecule Pyrrolidine Bis-Cyclic Guanidine Agonist Compounds Via a High Throughput 'Unbiased' Screening Campaign (J. Med. Chem. (2021) 64:9 (5577−5592) DOI: 10.1021/acs.jmedchem.0c02041)

Skye R Doering, Katie Freeman, Ginamarie Debevec, Phaedra Geer, Radleigh G. Santos, Travis M. Lavoi, Marc A. Giulianotti, Clemencia Pinilla, Jon R. Appel, Richard A. Houghten, Mark D. Ericson, Carrie Haskell-Luevano

Research output: Contribution to journalComment/debatepeer-review

Abstract

For the described pyrrolidine bis-cyclic guanidine compounds, the correct starting reagents and synthetic methodologies were described. During the reduction of the amide moieties to amines (see Scheme 1 as a representative example), Cahn-Ingold- Prolog sequence rules dictate that the a-carbon of R3 DThr residues (found in compounds 1, 2, 3, 10, 11, 12, 19, 20, 21, 28, 29, and 30) switches from R to S. The -carbon on the side chain is not reprioritized following the reduction and remains S. While the a-carbon was correctly labeled in the publication, the -carbon was inadvertently switched to R. Therefore, the R3 position of compounds 1, 2, 3, 10, 11, 12, 19, 20, 21, 28, 29, and 30 should read (S,S)-1-hydroxyethyl, not (S,R)-. A complete, corrected Table 1 is presented below. In the Supporting Information, the compound titles in the compound characterization section and SMILES structures for 1, 2, 3, 10, 11, 12, 19, 20, 21, 28, 29, and 30 are incorrect. As an example, the title for 1 should be (S)-1-((S)-3-(adamantan-1-ylmethyl)-1- ((R)-1-cyclohexyl-3-((S)-2-(((R)-2-imino-5-isobutylimidazolidin-1-yl)methyl)pyrrolidin-1-yl)propan-2-yl)-2-iminoimidazolidin-4- yl)ethanol, not the reported (R)-1-((S)-3-(adamantan-1-ylmethyl)- 1-((R)-1-cyclohexyl-3-((S)-2-(((R)-2-imino-5-isobutylimidazoli-din-1-yl)methyl)pyrrolidin-1-yl)propan-2-yl)-2-iminoimidazolidin-4-yl)ethanol. The authors apologize for the error. {table presented} {figure presented}.

Original languageEnglish (US)
Pages (from-to)7063-7065
Number of pages3
JournalJournal of medicinal chemistry
Volume66
Issue number10
DOIs
StatePublished - May 25 2023

Bibliographical note

Publisher Copyright:
© 2023 American Chemical Society.

PubMed: MeSH publication types

  • Published Erratum

Fingerprint

Dive into the research topics of 'Erratum: Discovery of Nanomolar Melanocortin-3 Receptor (MC3R)-Selective Small Molecule Pyrrolidine Bis-Cyclic Guanidine Agonist Compounds Via a High Throughput 'Unbiased' Screening Campaign (J. Med. Chem. (2021) 64:9 (5577−5592) DOI: 10.1021/acs.jmedchem.0c02041)'. Together they form a unique fingerprint.

Cite this