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 | Zendy

Cecchetti Violetta | Zendy; Fravolini Arnaldo | Zendy; Fringuelli Renata | Zendy; Schiaffella Fausto | Zendy; Lorenzini Maria Cristina | Zendy; Tabarrini Oriana | Zendy

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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 .

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