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

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

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
Organic Chemistry
Clinical Biochemistry

Access to Document

10.1016/S0968-0896(03)00457-7

Cite this

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

@article{6b5d8f9b37b248a494534a4555b657d0,

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",

month = oct,

day = "1",

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

language = "English (US)",

volume = "11",

pages = "4503--4509",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Ltd",

number = "20",

}

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).

UR - https://www.scopus.com/pages/publications/0042835693

UR - https://www.scopus.com/pages/publications/0042835693#tab=citedBy

U2 - 10.1016/S0968-0896(03)00457-7

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

M3 - Article

C2 - 13129586

AN - SCOPUS:0042835693

SN - 0968-0896

VL - 11

SP - 4503

EP - 4509

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 20

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this