Anti‐fungal and anti‐bacterial activities of some pyrrole, furan‐and thiophen‐sulphonamides and sulphonanilides

Abstract

The anti-fungal and anti-bacterial activities and phytotoxicity of pyrrole-and 5-nitropyrrole-2-sulphonamides are compared with furan and thiophen analogues. Certain compounds of the group have appreciable anti-bacterial activity consistent with structure-activity investigations of other anti-bacterials derived from these heterocycles.2.1.1.1. Sodium pyrrole-2-sulphonate Pyrrole (30.0 g), pyridine-sulphur trioxide' (75 g) and 1,2-dichloroethane (250 ml) were refluxed 16 h. The solvent was decanted from the solid which was treated with water and the boiling solution neutralised with sodium carbonate. After evaporation, the residue was extracted with boiling ethanol-water (9 : 1 ; 500 ml) for 1 h; the filtered solution yielded sodium pyrrole-2-sulphonate (17.3 g) on cooling. 43

Tuning Side Arm Electronics in Unsymmetrical Cyclotriazadisulfonamide (CADA) Endoplasmic Reticulum (ER) Translocation Inhibitors to Improve their Human Cluster of Differentiation 4 (CD4) Receptor Down-Modulating Potencies

“…A mixture of 0.13 g (0.72 mmol) of 3- N -methylpyrrole-1-sulfonyl chloride, − 0.30 g (0.80 mmol) of 7 , and 5 mL of DCM was stirred vigorously at room temperature for 24 h. Concentration by rotary evaporation and drying in vacuo gave 0.41 g (91%) of crude product, which was partially purified by silica column chromatography and then by chromatotron (70:30 (v/v) ethyl acetate/hexane), yielding 113 mg (27%) of product. After many unsuccessful purification attempts, this impure material was used in the next step.…”

Studies of heterocyclic compounds. 8. The synthesis and some reactions of 4-bromoimidazole-5-sulfonyl derivatives

“…The synthesis and reactions of the 4-bromoimidazole-5sulfonyl chloride (2) and its corresponding azide, 3, are shown in Scheme I, following known procedures, while the properties of the sulfonamides (5-20, 27, 28) are given in Table I. In the infrared spectra of the compounds, the NH2 stretching of the 5-imidazolesulfonamlde (5) is split into two bands located at 3345 and 3270 cm-1, as usually observed for a sulfonamides (4), while in the secondary sulfonamides, 7-20, the SO2N-H stretching vibrations (associated form) showed In the range 3340-3220 cm"1.…”

“…General Procedure of the Cycloaddltlon of the Nttronea (1a-e) and N-Phenylmalelmlde (2). A solution of 1 mmol of nitrone (1a-e) In 3 mL of dry benzene was added to a solution of 173 mg (1 mmol) of W-phenylmaleimide in 2 mL of dry benzene.…”

“…4-Bromo-S-Imldazolesulfonyl Chloride (2). A mixture of 4-bromoimidazole (10.0 g, 68 mol), chlorosulfonlc acid (14.0 mL), and thionyl chloride (5.0 mL) was heated at 200 °C for 2 h and then poured into crushed ice when the 4-bromo-5imidazolesulfonyl chloride precipitated out.…”

Novel Imides Amino Acids and Dipeptide Derivatives

“…Sulfonamides are well-established antibactrial agents (15) , and several are also fungicidal (16) , several cyclic imides display antifungal properties, probably associated with their ability to acylate enzymes by nucleophilic ring-opening (17) .…”