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Synthesis and characterisation of 5-acyl-6,7-dihydrothieno[3,2-c]pyridine inhibitors of Hedgehog acyltransferase.

Lanyon-Hogg T, Masumoto N, Bodakh G, Konitsiotis AD, Thinon E, Rodgers UR, Owens RJ, Magee AI, Tate EW - Data Brief (2016)

Bottom Line: In this data article we describe synthetic and characterisation data for four members of the 5-acyl-6,7-dihydrothieno[3,2-c]pyridine (termed "RU-SKI") class of inhibitors of Hedgehog acyltransferase, including associated NMR spectra for final compounds.RU-SKI 41 (9a), RU-SKI 43 (9b), RU-SKI 101 (9c), and RU-SKI 201 (9d) were profiled for activity in the related article "Click chemistry armed enzyme linked immunosorbent assay to measure palmitoylation by Hedgehog acyltransferase" (Lanyon-Hogg et al., 2015) [1]. (1)H NMR spectral data indicate different amide conformational ratios between the RU-SKI inhibitors, as has been observed in other 5-acyl-6,7-dihydrothieno[3,2-c]pyridines.The synthetic and characterisation data supplied in the current article provide validated access to the class of RU-SKI inhibitors.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Imperial College London, SW7 2AZ, UK; Institute of Chemical Biology, Imperial College London, SW72AZ, UK.

ABSTRACT
In this data article we describe synthetic and characterisation data for four members of the 5-acyl-6,7-dihydrothieno[3,2-c]pyridine (termed "RU-SKI") class of inhibitors of Hedgehog acyltransferase, including associated NMR spectra for final compounds. RU-SKI compounds were selected for synthesis based on their published high potencies against the enzyme target. RU-SKI 41 (9a), RU-SKI 43 (9b), RU-SKI 101 (9c), and RU-SKI 201 (9d) were profiled for activity in the related article "Click chemistry armed enzyme linked immunosorbent assay to measure palmitoylation by Hedgehog acyltransferase" (Lanyon-Hogg et al., 2015) [1]. (1)H NMR spectral data indicate different amide conformational ratios between the RU-SKI inhibitors, as has been observed in other 5-acyl-6,7-dihydrothieno[3,2-c]pyridines. The synthetic and characterisation data supplied in the current article provide validated access to the class of RU-SKI inhibitors.

No MeSH data available.


1H NMR (400 MHz, CDCl3) of RU-SKI 43(9b).
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f0030: 1H NMR (400 MHz, CDCl3) of RU-SKI 43(9b).

Mentions: As demonstrated in our previous study of the5-acyl-6,7-dihydrothieno[3,2-c]pyridine core[4], the amide in theRU-SKI compounds also adopts two conformations (Fig. 1). Theconformational preference is affected by non-covalent interactions between theamide carbonyl and neighbouring substituents [4]. Altered conformational ratios are observedin the 1H NMR data of the RU-SKI compounds(Table 1, Fig. 2, Fig. 6, Fig. 10, Fig. 14). Thesynthetic, characterisation and conformational data of compounds9a–9d is reported here, along with NMRspectra of final RU-SKI inhibitors.


Synthesis and characterisation of 5-acyl-6,7-dihydrothieno[3,2-c]pyridine inhibitors of Hedgehog acyltransferase.

Lanyon-Hogg T, Masumoto N, Bodakh G, Konitsiotis AD, Thinon E, Rodgers UR, Owens RJ, Magee AI, Tate EW - Data Brief (2016)

1H NMR (400 MHz, CDCl3) of RU-SKI 43(9b).
© Copyright Policy - CC BY
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4816282&req=5

f0030: 1H NMR (400 MHz, CDCl3) of RU-SKI 43(9b).
Mentions: As demonstrated in our previous study of the5-acyl-6,7-dihydrothieno[3,2-c]pyridine core[4], the amide in theRU-SKI compounds also adopts two conformations (Fig. 1). Theconformational preference is affected by non-covalent interactions between theamide carbonyl and neighbouring substituents [4]. Altered conformational ratios are observedin the 1H NMR data of the RU-SKI compounds(Table 1, Fig. 2, Fig. 6, Fig. 10, Fig. 14). Thesynthetic, characterisation and conformational data of compounds9a–9d is reported here, along with NMRspectra of final RU-SKI inhibitors.

Bottom Line: In this data article we describe synthetic and characterisation data for four members of the 5-acyl-6,7-dihydrothieno[3,2-c]pyridine (termed "RU-SKI") class of inhibitors of Hedgehog acyltransferase, including associated NMR spectra for final compounds.RU-SKI 41 (9a), RU-SKI 43 (9b), RU-SKI 101 (9c), and RU-SKI 201 (9d) were profiled for activity in the related article "Click chemistry armed enzyme linked immunosorbent assay to measure palmitoylation by Hedgehog acyltransferase" (Lanyon-Hogg et al., 2015) [1]. (1)H NMR spectral data indicate different amide conformational ratios between the RU-SKI inhibitors, as has been observed in other 5-acyl-6,7-dihydrothieno[3,2-c]pyridines.The synthetic and characterisation data supplied in the current article provide validated access to the class of RU-SKI inhibitors.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Imperial College London, SW7 2AZ, UK; Institute of Chemical Biology, Imperial College London, SW72AZ, UK.

ABSTRACT
In this data article we describe synthetic and characterisation data for four members of the 5-acyl-6,7-dihydrothieno[3,2-c]pyridine (termed "RU-SKI") class of inhibitors of Hedgehog acyltransferase, including associated NMR spectra for final compounds. RU-SKI compounds were selected for synthesis based on their published high potencies against the enzyme target. RU-SKI 41 (9a), RU-SKI 43 (9b), RU-SKI 101 (9c), and RU-SKI 201 (9d) were profiled for activity in the related article "Click chemistry armed enzyme linked immunosorbent assay to measure palmitoylation by Hedgehog acyltransferase" (Lanyon-Hogg et al., 2015) [1]. (1)H NMR spectral data indicate different amide conformational ratios between the RU-SKI inhibitors, as has been observed in other 5-acyl-6,7-dihydrothieno[3,2-c]pyridines. The synthetic and characterisation data supplied in the current article provide validated access to the class of RU-SKI inhibitors.

No MeSH data available.