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The antiprotozoal drug 3a,4,5,6,7,7a-hexahydro-3-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,2-benzisoxazole (I), which exhibits activity against trypanosomiasis, is also antibacterial in vivo. Since the urine from a dog dosed with I showed a broader spectrum of antibacterial activity than I itself, metabolites from this urine were isolated and partially characterized. The metabolites were mono- and dihydroxy-substituted species with the hydroxyl groups on carbons 4--7 of the hexahydrobenzisoxazole ring. These observations led to the synthesis of several such hydroxy derivatives of I, and their properties fully supported the proposed positions of metabolic hydroxylation. One synthetic compound, the 6,7-cis-dihydroxy compound, exhibited higher antibacterial activity against Salmonella schottmuelleri in mice and greater trypanocidal activity in vivo against Trypanosoma cruzi (Brazil strain) than I.
W J Vandenheuvel, and
B H Arison, and
T W Miller, and
P Kulsa, and
P Eskola, and
H Mrozik, and
A K Miller, and
H Skeggs, and
S B Zimmerman, and
B M Miller
April 1984,
Mutation research,
W J Vandenheuvel, and
B H Arison, and
T W Miller, and
P Kulsa, and
P Eskola, and
H Mrozik, and
A K Miller, and
H Skeggs, and
S B Zimmerman, and
B M Miller
April 2013,
Acta crystallographica. Section E, Structure reports online,
W J Vandenheuvel, and
B H Arison, and
T W Miller, and
P Kulsa, and
P Eskola, and
H Mrozik, and
A K Miller, and
H Skeggs, and
S B Zimmerman, and
B M Miller
April 2009,
Acta crystallographica. Section E, Structure reports online,
W J Vandenheuvel, and
B H Arison, and
T W Miller, and
P Kulsa, and
P Eskola, and
H Mrozik, and
A K Miller, and
H Skeggs, and
S B Zimmerman, and
B M Miller
March 2014,
Acta crystallographica. Section E, Structure reports online,
W J Vandenheuvel, and
B H Arison, and
T W Miller, and
P Kulsa, and
P Eskola, and
H Mrozik, and
A K Miller, and
H Skeggs, and
S B Zimmerman, and
B M Miller
February 2010,
Acta crystallographica. Section E, Structure reports online,
W J Vandenheuvel, and
B H Arison, and
T W Miller, and
P Kulsa, and
P Eskola, and
H Mrozik, and
A K Miller, and
H Skeggs, and
S B Zimmerman, and
B M Miller
December 2008,
Acta crystallographica. Section E, Structure reports online,
W J Vandenheuvel, and
B H Arison, and
T W Miller, and
P Kulsa, and
P Eskola, and
H Mrozik, and
A K Miller, and
H Skeggs, and
S B Zimmerman, and
B M Miller
September 2012,
Acta crystallographica. Section E, Structure reports online,
W J Vandenheuvel, and
B H Arison, and
T W Miller, and
P Kulsa, and
P Eskola, and
H Mrozik, and
A K Miller, and
H Skeggs, and
S B Zimmerman, and
B M Miller
April 2012,
Acta crystallographica. Section E, Structure reports online,
W J Vandenheuvel, and
B H Arison, and
T W Miller, and
P Kulsa, and
P Eskola, and
H Mrozik, and
A K Miller, and
H Skeggs, and
S B Zimmerman, and
B M Miller
June 2013,
Acta crystallographica. Section E, Structure reports online,
W J Vandenheuvel, and
B H Arison, and
T W Miller, and
P Kulsa, and
P Eskola, and
H Mrozik, and
A K Miller, and
H Skeggs, and
S B Zimmerman, and
B M Miller
January 2008,
Acta crystallographica. Section E, Structure reports online,
