10-(2-Benzoxazolcarbonyl)-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic acid: A potential inhibitor of GAR transformylase and AICAR transformylase

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

doi:10.1016/S0968-0896(03)00457-7

10-(2-Benzoxazolcarbonyl)-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic acid: A potential inhibitor of GAR transformylase and AICAR transformylase

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

Chemistry

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5 Scopus citations

Abstract

The design and synthesis of 10-(2-benzoxazolcarbonyl)-DDACTHF (1) as an inhibitor of glycinamide ribonucleotide transformylase (GAR Tfase) and aminoimidazole carboxamide transformylase (AICAR Tfase) are reported. Ketone 1 and the corresponding alcohol 13 were evaluated for inhibition of GAR Tfase and AICAR Tfase and the former was found to be a potent inhibitor of recombinant human (rh) GAR Tfase (K_i=600 nM).

Original language	English (US)
Pages (from-to)	4503-4509
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	11
Issue number	20
DOIs	https://doi.org/10.1016/S0968-0896(03)00457-7
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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10.1016/S0968-0896(03)00457-7

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Marsilje, T. H., Hedrick, M. P., Desharnais, J., Capps, K., Tavassoli, A., Zhang, Y., Wilson, I. A., Benkovic, S. J., & Boger, D. L. (2003). 10-(2-Benzoxazolcarbonyl)-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic acid: A potential inhibitor of GAR transformylase and AICAR transformylase. Bioorganic and Medicinal Chemistry, 11(20), 4503-4509. https://doi.org/10.1016/S0968-0896(03)00457-7

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title = "10-(2-Benzoxazolcarbonyl)-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic acid: A potential inhibitor of GAR transformylase and AICAR transformylase",

abstract = "The design and synthesis of 10-(2-benzoxazolcarbonyl)-DDACTHF (1) as an inhibitor of glycinamide ribonucleotide transformylase (GAR Tfase) and aminoimidazole carboxamide transformylase (AICAR Tfase) are reported. Ketone 1 and the corresponding alcohol 13 were evaluated for inhibition of GAR Tfase and AICAR Tfase and the former was found to be a potent inhibitor of recombinant human (rh) GAR Tfase (Ki=600 nM).",

author = "Marsilje, {Thomas H.} and Hedrick, {Michael P.} and Joel Desharnais and Kevin Capps 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., and S.J.B.), the Skaggs Institute for Chemical Biology, and a Skaggs predoctoral fellowship (Y.Z., K.C.).",

year = "2003",

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doi = "10.1016/S0968-0896(03)00457-7",

language = "English (US)",

volume = "11",

pages = "4503--4509",

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Marsilje, TH, Hedrick, MP, Desharnais, J, Capps, K, Tavassoli, A, Zhang, Y, Wilson, IA, Benkovic, SJ & Boger, DL 2003, '10-(2-Benzoxazolcarbonyl)-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic acid: A potential inhibitor of GAR transformylase and AICAR transformylase', Bioorganic and Medicinal Chemistry, vol. 11, no. 20, pp. 4503-4509. https://doi.org/10.1016/S0968-0896(03)00457-7

TY - JOUR

T1 - 10-(2-Benzoxazolcarbonyl)-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic acid

T2 - A potential inhibitor of GAR transformylase and AICAR transformylase

AU - Marsilje, Thomas H.

AU - Hedrick, Michael P.

AU - Desharnais, Joel

AU - Capps, Kevin

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., and S.J.B.), the Skaggs Institute for Chemical Biology, and a Skaggs predoctoral fellowship (Y.Z., K.C.).

PY - 2003/10/1

Y1 - 2003/10/1

N2 - The design and synthesis of 10-(2-benzoxazolcarbonyl)-DDACTHF (1) as an inhibitor of glycinamide ribonucleotide transformylase (GAR Tfase) and aminoimidazole carboxamide transformylase (AICAR Tfase) are reported. Ketone 1 and the corresponding alcohol 13 were evaluated for inhibition of GAR Tfase and AICAR Tfase and the former was found to be a potent inhibitor of recombinant human (rh) GAR Tfase (Ki=600 nM).

AB - The design and synthesis of 10-(2-benzoxazolcarbonyl)-DDACTHF (1) as an inhibitor of glycinamide ribonucleotide transformylase (GAR Tfase) and aminoimidazole carboxamide transformylase (AICAR Tfase) are reported. Ketone 1 and the corresponding alcohol 13 were evaluated for inhibition of GAR Tfase and AICAR Tfase and the former was found to be a potent inhibitor of recombinant human (rh) GAR Tfase (Ki=600 nM).

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DO - 10.1016/S0968-0896(03)00457-7

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AN - SCOPUS:0042835693

SN - 0968-0896

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EP - 4509

JO - Bioorganic and Medicinal Chemistry

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ER -

10-(2-Benzoxazolcarbonyl)-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic acid: A potential inhibitor of GAR transformylase and AICAR transformylase

Abstract

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