PMID- 9354237
OWN - NLM
STAT- MEDLINE
DCOM- 19971219
LR  - 20190831
IS  - 0968-0896 (Print)
IS  - 0968-0896 (Linking)
VI  - 5
IP  - 9
DP  - 1997 Sep
TI  - 10-Formyl-5,8,10-trideazafolic acid (10-formyl-TDAF): a potent inhibitor of 
      glycinamide ribonucleotide transformylase.
PG  - 1817-30
AB  - The synthesis of 10-formyl-5,8,10-trideazafolic acid (3) as a potential inhibitor 
      of glycinamide ribonucleotide transformylase (GAR Tfase) is reported. The target 
      compound was prepared by a convergent synthesis utilizing the alkylation of 
      hydrazone 5 with benzylic bromide 6 to construct the core heterocycle 7. The 
      aldehyde 3 and related agents were evaluated as inhibitors of purN GAR Tfase and 
      avian AICAR Tfase. Compound 3 exhibited potent inhibition of GAR Tfase with a Ki 
      of 0.26 +/- 0.05 microM. In contrast, 3 exhibited more moderate inhibition of 
      aminoimidazole carboxamide ribonucleotide transformylase (AICAR Tfase), with Ki 
      of 7.6 +/- 1.5 microM.
FAU - Boger, D L
AU  - Boger DL
AD  - Department of Chemistry, Scripps Research Institute, La Jolla, CA 92037, USA.
FAU - Haynes, N E
AU  - Haynes NE
FAU - Kitos, P A
AU  - Kitos PA
FAU - Warren, M S
AU  - Warren MS
FAU - Ramcharan, J
AU  - Ramcharan J
FAU - Marolewski, A E
AU  - Marolewski AE
FAU - Benkovic, S J
AU  - Benkovic SJ
LA  - eng
GR  - CA63536/CA/NCI NIH HHS/United States
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PT  - Research Support, U.S. Gov't, P.H.S.
PL  - England
TA  - Bioorg Med Chem
JT  - Bioorganic & medicinal chemistry
JID - 9413298
RN  - 0 (Enzyme Inhibitors)
RN  - EC 2.1.2.- (Hydroxymethyl and Formyl Transferases)
RN  - EC 2.1.2.2 (Phosphoribosylglycinamide Formyltransferase)
SB  - IM
MH  - Cell Division/drug effects
MH  - Drug Design
MH  - Enzyme Inhibitors/chemical synthesis/chemistry/*pharmacology
MH  - Humans
MH  - Hydroxymethyl and Formyl Transferases/*antagonists & inhibitors
MH  - Kinetics
MH  - Magnetic Resonance Spectroscopy
MH  - Molecular Structure
MH  - Phosphoribosylglycinamide Formyltransferase
MH  - Spectrometry, Mass, Fast Atom Bombardment
MH  - Tumor Cells, Cultured
EDAT- 1997/11/14 00:00
MHDA- 1997/11/14 00:01
CRDT- 1997/11/14 00:00
PHST- 1997/11/14 00:00 [pubmed]
PHST- 1997/11/14 00:01 [medline]
PHST- 1997/11/14 00:00 [entrez]
AID - S0968-0896(97)00120-X [pii]
AID - 10.1016/s0968-0896(97)00120-x [doi]
PST - ppublish
SO  - Bioorg Med Chem. 1997 Sep;5(9):1817-30. doi: 10.1016/s0968-0896(97)00120-x.