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The synthesis and antimicrobial activity of the methylenedioxy positional isomers, 1-ethyl-1,4-dihydro-5,6-methylenedioxy-4-oxo-3-quinolinecarboxylic acid (9) and 1-ethyl-1,4-dihydro-7,8-methylenedioxy-4-oxo-3-quinolinecarboxylic acid (17), of oxolinic acid (18) have been accomplished. Isomer 9 was prepared by the reaction of N-ethyl-6,7-methylenedioxyisatoic anhydride with sodioethyl formylacetate [L. A. Mitscher, H. E. Gracey, G. W. Clark III, and T. Suzuki, J. Med. Chem., 21, 485 (1978)], while isomer 17 was prepared by thermal cyclization of diethyl 2-[(2,3-methylenedioxyanilino)methylene]malonate [D. Kaminsky and R. I. Meltzer, J. Med. Chem., 11, 160 (1968)]. Both of the new isomers are less active in vitro when compared to oxolinic acid (18) itself.
L A Mitscher, and
D L Flynn, and
H E Gracey, and
S D Drake
January 1968,
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L A Mitscher, and
D L Flynn, and
H E Gracey, and
S D Drake
April 2013,
Journal of inorganic biochemistry,
L A Mitscher, and
D L Flynn, and
H E Gracey, and
S D Drake
September 1968,
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L A Mitscher, and
D L Flynn, and
H E Gracey, and
S D Drake
January 1992,
Annual review of medicine,
L A Mitscher, and
D L Flynn, and
H E Gracey, and
S D Drake
March 2021,
ACS medicinal chemistry letters,
L A Mitscher, and
D L Flynn, and
H E Gracey, and
S D Drake
May 1995,
Journal of toxicology and environmental health,
L A Mitscher, and
D L Flynn, and
H E Gracey, and
S D Drake
March 1992,
Chest,
L A Mitscher, and
D L Flynn, and
H E Gracey, and
S D Drake
October 1991,
Die Pharmazie,
L A Mitscher, and
D L Flynn, and
H E Gracey, and
S D Drake
December 1989,
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L A Mitscher, and
D L Flynn, and
H E Gracey, and
S D Drake
October 1967,
The Journal of organic chemistry,
