Synthesis and Biological Activity of a New Class of Sulfone-Linked Pyrrolylpyrazoles and Pyrrolylisoxazoles from Methyl-3-aryl-2-(E-arylethenesulfonyl)acrylate

Abstract

A new class of sulfone-linked bis heterocycles, methyl-3-(4 -aryl-1 H-pyrazol-3 -ylsulfonyl)-4-aryl-3H-pyrrole-3-carboxylate (8), methyl-3-(1 -phenyl-3 ,5 -diaryl-1 H-pyrazol-4 -ylsulfonyl)-4-aryl-3H-pyrrole-3-carboxylate (9) and methyl-3-(3 ,5 -diarylisoxazol-4 -ylsulfonyl)-4-aryl-3H-pyrrole-3-carboxylate (10) were prepared by the regioselective reaction of methyl-3-aryl-2-(E-arylethenesulfonyl)acrylate (2) with tosylmethyl isocyanide followed by fuctionalization of olefin moiety with 1,3-dipolar reagents. The lead compounds were tested for their antimicrobial activity.

Synthesis of 3H-pyrroles (microreview)

“…18 Another method for the synthesis of 3H-pyrroles exhibiting antimicrobial activity that uses isonitriles has been described. 9 This method of obtaining 3H-pyrroles involves a reaction of p-toluenesulfonylmethyl isocyanide with unsaturated sulfones.…”

Organokatalytische Synthese von enantiomerenreinen 2H‐ und 3H‐Pyrrolen: Inhibitoren des Hedgehog‐Signalwegs

“…Wie bereits erwähnt, weisen zahlreiche 2 H ‐– und 3 H ‐Pyrrole– interessante biologische Eigenschaften auf, was uns dazu ermutigte, unsere neuen Strukturmotive auf potentielle Bioaktivitäten zu untersuchen. Wir waren speziell an möglichen Anti‐Tumor‐Aktivitäten dieser neuartigen Verbindungen interessiert und fokussierten uns zu Beginn unserer Untersuchungen auf Inhibitoren des Hh‐Signalwegs .…”

Synthesis and antimicrobial activity of 3-aroyl-4-heteroaryl pyrroles and pyrazoles

“…The olefin moiety present in 3 was exploited to develop five membered heterocycles (Scheme 1). In fact, we have extensively used ethereal diazomethane as 1,3-dipolar reagent to prepare pyrazolines (Padmavathi et al, 2009). In fact, we have extensively used ethereal diazomethane as 1,3-dipolar reagent to prepare pyrazolines (Padmavathi et al, 2009).…”