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. Author manuscript; available in PMC: 2012 May 22.
Published in final edited form as: J Med Chem. 2012 Apr 23;55(9):4526. doi: 10.1021/jm300471g

Correction to Synthesis, Structure-Affinity Relationships, and Radiolabeling of Selective High-Affinity 5-HT4 Receptor Ligands as Prospective Imaging Probes for Positron Emission Tomography

PMCID: PMC3356876  NIHMSID: NIHMS372644  PMID: 22524275

Manuscript number of paper to be corrected: jm100668r Reference citation of paper to be corrected: J. Med. Chem. 2010, 53, 7035-7047. Rong Xu, Jinsoo Hong, Cheryl L. Morse, and Victor W. Pike*: Structure-Affinity Relationships, and Radiolabeling of Selective High-Affinity 5-HT4 Receptor Ligands as Prospective Imaging Probes for Positron Emission Tomography

Dr. John E. Campbell (Sunovion Pharmaceuticals Inc.) kindly brought to the authors attention the possibility that the nitration of compound 17c (methyl 7-fluoro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylate) may actually have proceeded selectively in 6-position rather than in 8-position, and therefore that compound 17d, the derived amine 17e and the 5-HT4 ligand 17 may have been misidentified. Accordingly, we performed X-ray crystallography on compounds 17d and 17. The determined X-ray structures confirm the misidentification of 17d and 17, which are in fact the corresponding 6-isomers, methyl 7-fluoro-6-nitro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylate and 6-amino-7-fluoro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid. The intermediate 17e is therefore 6-amino-7-fluoro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid. This correction reveals 17 to be unique among reported high-affinity selective 5-HT4 receptor ligands, belonging to the amino dihydrobenzo[b][1,4]dioxine-5-carboxylic ester structural class, in having an amino group in ortho rather than para position to the ester functionality.

Specific corrections to the published manuscript are as follows:

  • Page 7036, 2nd column, 2nd paragraph, line 3 should be “6-amino-7-fluoro” instead of “7-fluoro”.

  • Page 7037, Scheme 4. Compound 17d has the nitro group in 6 position not the 8-position, and compounds 17e and 17 have the amino groups in 6-position not 8-position.

  • Page 7038, Table 1: structure 17 has the amino group in 6-position not 8-position. In the final column of this table the cLogD value for this compound should be “2.69' instead of “2.42”.

  • Page 7044, 1st column, line 32 should be “-6-nitro-” instead of “-8-nitro-”.

  • Page 7044, 1st column, line 45 should be “6-Amino-” instead of “8-Amino-”.

  • Page 7044, 1st column, line 60 should be “6-Amino-” instead of “8-Amino-”.

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