10-(2-benzoxazolcarbonyl)-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic acid: A potential inhibitor of GAR transformylase and AICAR transformylase
10-(2-benzoxazolcarbonyl)-5,10-dideaza-acyclic-5,6,7,8-tetrahydrofolic acid: A potential inhibitor of GAR transformylase and AICAR transformylase
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).
binding sites
cell line
cell survival/drug effects
drug design
enzyme inhibitors/chemical synthesis/pharmacology
humans
hydroxymethyl and formyl transferases, antagonists & inhibitors
inhibitory concentration 50
phosphoribosylaminoimidazolecarboxamide formyltransferase
phosphoribosylglycinamide formyltransferase
purines/antagonists & inhibitors, biosynthesis
structure-activity relationship
tetrahydrofolates, chemistry/pharmacology
4503-4509
Marsilje, Thomas H.
2d64bf3a-143b-4a00-8b9c-825beceb810e
Hedrick, Michael P.
ba690321-bfda-496d-98de-c3d383497035
Desharnais, Joel
f4d5b1db-e99b-4487-b37a-f64f24c7914a
Capps, Kevin
da71a039-199b-46d7-8b70-a84bf948e8d8
Tavassoli, Ali
d561cf8f-2669-46b5-b6e1-2016c85d63b2
Zhang, Yan
8552a39d-0c4d-4712-8ad8-d0d5cc9d1779
Wilson, Ian A.
7865d500-d638-4a67-ad6d-fefad0ae83bb
Benkovic, Stephen J.
f85498a5-27fc-4a22-9069-ff61a4297520
Boger, Dale L.
d81e0270-0561-47df-8904-85718bd462ff
October 2003
Marsilje, Thomas H.
2d64bf3a-143b-4a00-8b9c-825beceb810e
Hedrick, Michael P.
ba690321-bfda-496d-98de-c3d383497035
Desharnais, Joel
f4d5b1db-e99b-4487-b37a-f64f24c7914a
Capps, Kevin
da71a039-199b-46d7-8b70-a84bf948e8d8
Tavassoli, Ali
d561cf8f-2669-46b5-b6e1-2016c85d63b2
Zhang, Yan
8552a39d-0c4d-4712-8ad8-d0d5cc9d1779
Wilson, Ian A.
7865d500-d638-4a67-ad6d-fefad0ae83bb
Benkovic, Stephen J.
f85498a5-27fc-4a22-9069-ff61a4297520
Boger, Dale L.
d81e0270-0561-47df-8904-85718bd462ff
Marsilje, Thomas H., Hedrick, Michael P., Desharnais, Joel, Capps, Kevin, Tavassoli, Ali, Zhang, Yan, Wilson, Ian A., Benkovic, Stephen J. and Boger, Dale 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 & Medicinal Chemistry, 11 (20), .
(doi:10.1016/S0968-0896(03)00457-7).
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).
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More information
Published date: October 2003
Keywords:
binding sites
cell line
cell survival/drug effects
drug design
enzyme inhibitors/chemical synthesis/pharmacology
humans
hydroxymethyl and formyl transferases, antagonists & inhibitors
inhibitory concentration 50
phosphoribosylaminoimidazolecarboxamide formyltransferase
phosphoribosylglycinamide formyltransferase
purines/antagonists & inhibitors, biosynthesis
structure-activity relationship
tetrahydrofolates, chemistry/pharmacology
Organisations:
Chemistry
Identifiers
Local EPrints ID: 45312
URI: http://eprints.soton.ac.uk/id/eprint/45312
ISSN: 0968-0896
PURE UUID: 073af4e2-806b-44ee-9af3-962327096a7e
Catalogue record
Date deposited: 21 Mar 2007
Last modified: 16 Mar 2024 03:51
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Contributors
Author:
Thomas H. Marsilje
Author:
Michael P. Hedrick
Author:
Joel Desharnais
Author:
Kevin Capps
Author:
Yan Zhang
Author:
Ian A. Wilson
Author:
Stephen J. Benkovic
Author:
Dale L. Boger
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