Synthesis and Carbonic Anhydrase Inhibitory Activity of 4-Substituted 2-Thiophenesulfonamides

Abstract

A series of 4-substituted 2-thiophenesulfonamides was prepared from 3-thiophenecarboxaldehyde using metalation chemistry developed for 3-furaldehyde. Several of these compounds inhibit carbonic anhydrase II in vitro at concentrations of less than 10 nM. In addition, none of these compounds exhibit sensitization potential as determined from in vitro measurement of cysteine reactivity.

Direct Preparation of 3-Thienyl Organometallic Reagents: 3-Thienylzinc and 3-Thienylmagnesium Iodides and 3-Thienylmanganese Bromides and Their Coupling Reactions

“…The properties of these polymers are strongly dependent upon the substutents of the thiophene ring. More interestingly, 3-substituted thiophene derivatives have been found to be topical carbonic anhydrase inhibitors …”

Arylglyoxals in Synthesis of Heterocyclic Compounds

“…Thiophenes and their polycyclic derivatives comprise an important heterocyclic class that exhibit remarkable electrochemical, optical, physical, and biological properties. Also, thiophenes have wide range of applications in advanced materials such as conjugated polymers, , organic conductors, semiconductors, and light emitting devices and in treatment of various diseases as pharmaceuticals . Thiophene derivatives have been prepared by various methods, such as Gewald , and Paal–Knorr , reactions.…”

Synthesis and structure elucidation of some novel thiophene and benzothiophene derivatives as cytotoxic agents

“…The mixture was then boiled in ethanol for a few minutes, poured onto an acidifi ed ice/water mixture and the product was crystallized from ethanol to give 4 (Table I). (6). General procedure.…”

“…H NMR and 13 C NMR spectra were recorded with Varian Gemini-200 (200 MHz, Varian UK) and Jeol AS 500 MHz (Jeol, Japan) instruments in DMSO-d 6 as a solvent, using TMS as internal standard. Chemical shift s are expressed as d ppm.…”