-transparent.png){kind=logo}
N10-Propargylfolic acid (2), which is the closest pteridine analogue of the thymidylate synthase inhibitor N10-propargyl-5,8-dideazafolic acid (PDDF), was synthesized starting from diethyl [p-(N-propargylamino)benzoyl]-L-glutamate (5) and N-(3-bromo-2-oxopropyl)phthalimide (8). The 7,8-dihydro derivative of propargylfolic acid served as a synthetic substrate of Lactobacillus casei dihydrofolate reductase. Propargylfolic acid and its reduced derivatives were weak inhibitors of L. casei thymidylate synthase compared to PDDF. All derivatives of propargylfolate were active against the growth of Streptococcus faecium, but with the exception of 7,8-dihydropropargylfolic acid, all were inactive against L. casei. Although less potent than PDDF, marked inhibition of thymidylate synthase by 2 was observed in permeabilized L1210 cells.
M Ghazala, and
M G Nair, and
T R Toghiyani, and
R L Kisliuk, and
Y Gaumont, and
T I Kalman
September 1991,
Journal of medicinal chemistry,
M Ghazala, and
M G Nair, and
T R Toghiyani, and
R L Kisliuk, and
Y Gaumont, and
T I Kalman
June 1989,
Journal of medicinal chemistry,
M Ghazala, and
M G Nair, and
T R Toghiyani, and
R L Kisliuk, and
Y Gaumont, and
T I Kalman
July 1978,
Journal of medicinal chemistry,
M Ghazala, and
M G Nair, and
T R Toghiyani, and
R L Kisliuk, and
Y Gaumont, and
T I Kalman
April 1983,
Journal of medicinal chemistry,
M Ghazala, and
M G Nair, and
T R Toghiyani, and
R L Kisliuk, and
Y Gaumont, and
T I Kalman
April 2013,
Chemistry (Weinheim an der Bergstrasse, Germany),
M Ghazala, and
M G Nair, and
T R Toghiyani, and
R L Kisliuk, and
Y Gaumont, and
T I Kalman
July 1979,
Journal of medicinal chemistry,
M Ghazala, and
M G Nair, and
T R Toghiyani, and
R L Kisliuk, and
Y Gaumont, and
T I Kalman
July 1989,
Journal of medicinal chemistry,
M Ghazala, and
M G Nair, and
T R Toghiyani, and
R L Kisliuk, and
Y Gaumont, and
T I Kalman
June 1989,
Journal of medicinal chemistry,
M Ghazala, and
M G Nair, and
T R Toghiyani, and
R L Kisliuk, and
Y Gaumont, and
T I Kalman
December 2015,
Chemistry (Weinheim an der Bergstrasse, Germany),
M Ghazala, and
M G Nair, and
T R Toghiyani, and
R L Kisliuk, and
Y Gaumont, and
T I Kalman
November 2014,
The Journal of organic chemistry,
