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@article{Lanyon-Hogg:2015:10.1021/acs.joc.5b00205,
author = {Lanyon-Hogg, T and Ritzefeld, M and Masumoto, N and Magee, AI and Rzepa, HS and Tate, EW},
doi = {10.1021/acs.joc.5b00205},
journal = {Journal of Organic Chemistry},
pages = {4370--4377},
title = {Modulation of Amide Bond Rotamers in 5-Acyl-6,7-dihydrothieno[3,2-c]pyridines},
url = {http://dx.doi.org/10.1021/acs.joc.5b00205},
volume = {80},
year = {2015}
}
TY - JOUR
AB - 2-Substituted N-acyl-piperidine is a widespread and important structuralmotif, found in approximately 500 currently available structures, and present in nearly30 pharmaceutically active compounds. Restricted rotation of the acyl substituent insuch molecules can give rise to two distinct chemical environments. Here wedemonstrate, using NMR studies and density functional theory modeling of the lowestenergy structures of 5-acyl-6,7-dihydrothieno[3,2-c]pyridine derivatives, that the amideE:Z equilibrium is affected by non-covalent interactions between the amide oxygen andadjacent aromatic protons. Structural predictions were used to design molecules that promote either the E- or Z-amideconformation, enabling preparation of compounds with a tailored conformational ratio, as proven by NMR studies. Analysis ofthe available X-ray data of a variety of published N-acyl-piperidine-containing compounds further indicates that these moleculesare also clustered in the two observed conformations. This finding emphasizes that directed conformational isomerism hassignificant implications for the design of both small molecules and larger amide-containing molecular architectures.
AU - Lanyon-Hogg,T
AU - Ritzefeld,M
AU - Masumoto,N
AU - Magee,AI
AU - Rzepa,HS
AU - Tate,EW
DO - 10.1021/acs.joc.5b00205
EP - 4377
PY - 2015///
SN - 1520-6904
SP - 4370
TI - Modulation of Amide Bond Rotamers in 5-Acyl-6,7-dihydrothieno[3,2-c]pyridines
T2 - Journal of Organic Chemistry
UR - http://dx.doi.org/10.1021/acs.joc.5b00205
UR - http://hdl.handle.net/10044/1/26518
VL - 80
ER -
Prof. Ed Tate
GSK Chair in Chemical Biology
Department of Chemistry
Molecular Sciences Research Hub, White City Campus,
82 Wood Lane, London, W12 0BZ
e.tate@imperial.ac.uk
Tel: +44 (0)20 759 + ext 43752 or 45821