TY - JOUR
T1 - Erratum
T2 - 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)
AU - Doering, Skye R
AU - Freeman, Katie
AU - Debevec, Ginamarie
AU - Geer, Phaedra
AU - Santos, Radleigh G.
AU - Lavoi, Travis M.
AU - Giulianotti, Marc A.
AU - Pinilla, Clemencia
AU - Appel, Jon R.
AU - Houghten, Richard A.
AU - Ericson, Mark D.
AU - Haskell-Luevano, Carrie
N1 - Publisher Copyright:
© 2023 American Chemical Society.
PY - 2023/5/25
Y1 - 2023/5/25
N2 - 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}.
AB - 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}.
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U2 - 10.1021/acs.jmedchem.3c00588
DO - 10.1021/acs.jmedchem.3c00588
M3 - Comment/debate
C2 - 37155917
AN - SCOPUS:85159607380
SN - 0022-2623
VL - 66
SP - 7063
EP - 7065
JO - Journal of medicinal chemistry
JF - Journal of medicinal chemistry
IS - 10
ER -