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4 H ‐1‐benzothiopyran‐4‐one‐3‐carboxylic acids and 3,4‐dihydro‐2 H ‐isothiazolo[5,4‐ b benzothiopyran‐3,4‐diones as quinolone antibacterial analogs
Author(s) -
Cecchetti Violetta,
Fravolini Arnaldo,
Fringuelli Renata,
Schiaffella Fausto,
Lorenzini Maria Cristina,
Tabarrini Oriana
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300455
Subject(s) - chemistry , nitrogen atom , quinolone , antibacterial activity , nalidixic acid , sulfur , stereochemistry , medicinal chemistry , carboxylic acid , bacteria , organic chemistry , antibiotics , ciprofloxacin , group (periodic table) , biochemistry , biology , genetics
The endocyclic replacement of a nitrogen atom at the 1‐position of quinolone antibacterial nucleus with a sulfur atom was investigated. A series of 1‐benzothiopyran‐4‐one‐3‐carboxylic acids 14–16 and isothiazolo‐[5,4‐ b ][1]benzothiopyran‐3,4‐diones 22–24 , suitably functionalized with a fluorine atom at C‐6 and heterocyclic base at C‐7, were prepared. The antibacterial evaluation of the target compounds showed an activity comparable to that of nalidixic acid for compounds 14–16 , while an increased activity against gram‐positive bacteria was observed for compounds 22–24 .