Design, synthesis, and biological evaluation of simplified α-keto heterocycle, trifluoromethyl ketone, and formyl substituted folate analogues as potential inhibitors of GAR transformylase and AICAR transformylase

Thomas H. Marsilje; Michael P. Hedrick; Joel Desharnais; Ali Tavassoli; Yan Zhang; Ian A. Wilson; Stephen J. Benkovic; Dale L. Boger

doi:10.1016/S0968-0896(03)00456-5

Design, synthesis, and biological evaluation of simplified α-keto heterocycle, trifluoromethyl ketone, and formyl substituted folate analogues as potential inhibitors of GAR transformylase and AICAR transformylase

Thomas H. Marsilje, Michael P. Hedrick, Joel Desharnais, Ali Tavassoli, Yan Zhang, Ian A. Wilson, Stephen J. Benkovic, Dale L. Boger

Chemistry

Research output: Contribution to journal › Article › peer-review

36 Scopus citations

Abstract

A series of simplified α-keto heterocycle, trifluoromethyl ketone, and formyl substituted folate analogues lacking the benzoylglutamate subunit were prepared and examined as potential inhibitors of glycinamide ribonucleotide transformylase (GAR Tfase) and aminoimidazole carboxamide transformylase (AICAR Tfase).

Original language	English (US)
Pages (from-to)	4487-4501
Number of pages	15
Journal	Bioorganic and Medicinal Chemistry
Volume	11
Issue number	20
DOIs	https://doi.org/10.1016/S0968-0896(03)00456-5
State	Published - Oct 1 2003

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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Marsilje, T. H., Hedrick, M. P., Desharnais, J., Tavassoli, A., Zhang, Y., Wilson, I. A., Benkovic, S. J., & Boger, D. L. (2003). Design, synthesis, and biological evaluation of simplified α-keto heterocycle, trifluoromethyl ketone, and formyl substituted folate analogues as potential inhibitors of GAR transformylase and AICAR transformylase. Bioorganic and Medicinal Chemistry, 11(20), 4487-4501. https://doi.org/10.1016/S0968-0896(03)00456-5

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title = "Design, synthesis, and biological evaluation of simplified α-keto heterocycle, trifluoromethyl ketone, and formyl substituted folate analogues as potential inhibitors of GAR transformylase and AICAR transformylase",

abstract = "A series of simplified α-keto heterocycle, trifluoromethyl ketone, and formyl substituted folate analogues lacking the benzoylglutamate subunit were prepared and examined as potential inhibitors of glycinamide ribonucleotide transformylase (GAR Tfase) and aminoimidazole carboxamide transformylase (AICAR Tfase).",

author = "Marsilje, {Thomas H.} and Hedrick, {Michael P.} and Joel Desharnais and Ali Tavassoli and Yan Zhang and Wilson, {Ian A.} and Benkovic, {Stephen J.} and Boger, {Dale L.}",

note = "Funding Information: We gratefully acknowledge the financial support of the National Institutes of Health (CA 63536 to D.L.B., I.A.W., S.J.B.), the Skaggs Institute for Chemical Biology, and a Skaggs predoctoral fellowship (Y.Z.). ",

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Marsilje, TH, Hedrick, MP, Desharnais, J, Tavassoli, A, Zhang, Y, Wilson, IA, Benkovic, SJ & Boger, DL 2003, 'Design, synthesis, and biological evaluation of simplified α-keto heterocycle, trifluoromethyl ketone, and formyl substituted folate analogues as potential inhibitors of GAR transformylase and AICAR transformylase', Bioorganic and Medicinal Chemistry, vol. 11, no. 20, pp. 4487-4501. https://doi.org/10.1016/S0968-0896(03)00456-5

Design, synthesis, and biological evaluation of simplified α-keto heterocycle, trifluoromethyl ketone, and formyl substituted folate analogues as potential inhibitors of GAR transformylase and AICAR transformylase. / Marsilje, Thomas H.; Hedrick, Michael P.; Desharnais, Joel et al.
In: Bioorganic and Medicinal Chemistry, Vol. 11, No. 20, 01.10.2003, p. 4487-4501.

Research output: Contribution to journal › Article › peer-review

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T1 - Design, synthesis, and biological evaluation of simplified α-keto heterocycle, trifluoromethyl ketone, and formyl substituted folate analogues as potential inhibitors of GAR transformylase and AICAR transformylase

AU - Marsilje, Thomas H.

AU - Hedrick, Michael P.

AU - Desharnais, Joel

AU - Tavassoli, Ali

AU - Zhang, Yan

AU - Wilson, Ian A.

AU - Benkovic, Stephen J.

AU - Boger, Dale L.

N1 - Funding Information: We gratefully acknowledge the financial support of the National Institutes of Health (CA 63536 to D.L.B., I.A.W., S.J.B.), the Skaggs Institute for Chemical Biology, and a Skaggs predoctoral fellowship (Y.Z.).

PY - 2003/10/1

Y1 - 2003/10/1

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Marsilje TH, Hedrick MP, Desharnais J, Tavassoli A, Zhang Y, Wilson IA et al. Design, synthesis, and biological evaluation of simplified α-keto heterocycle, trifluoromethyl ketone, and formyl substituted folate analogues as potential inhibitors of GAR transformylase and AICAR transformylase. Bioorganic and Medicinal Chemistry. 2003 Oct 1;11(20):4487-4501. doi: 10.1016/S0968-0896(03)00456-5

Design, synthesis, and biological evaluation of simplified α-keto heterocycle, trifluoromethyl ketone, and formyl substituted folate analogues as potential inhibitors of GAR transformylase and AICAR transformylase

Abstract

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