Synthesis and evaluation of cytotoxic activity of arylfurans

Ru‐ and Pd‐Catalysed Synthesis of 2‐Arylfurans by One‐Flask Heck Arylation/Oxidation

“…For certain substrates, the Ti III -mediated arylation of furans with diazonium salts might have potential as a useful alternative. [14] It has been reported, though, that Meerwein-type arylation reactions cannot be applied to the synthesis of 2,5-diarylfurans such as 6 or 9, [7] which have instead been synthesized from symmetrical 2,5-distannylfurans [15] in double Stille couplings. The disadvantages of this method include potential contamination of the products with organostannane residues, as well as selectivity issues arising when the method is adopted for the synthesis of unsymmetrical 2,5-diarylfurans.…”

“…[6] Apart from these clinically approved drugs, numerous other 2-aryl-, 2-alkyl-5-aryl-and 2,5-diarylfurans have been investigated as drug candidates in medicinal chemistry studies over the past decade. These compounds ( Figure 2) were tested for diverse applications, such as activity against several cancer cell lines (compounds 5 and 6), [7] cardioprotective activity through inhibition of Na + /H + exchangers (7), [8,9] activity as an HIV-integrase inhibitor (8), [10,11] activity against Mycobacterium tuberculosis (9) [12] or as potential therapeutics for smoking cessation (10). [13] [a] Universität Potsdam, Institut für Chemie (Organische Synthesechemie Because of the low to moderate yields normally observed for Meerwein arylation reactions of furans, this method is restricted to cheap or conveniently available starting materials.…”

Antileishmanial Activity and Structure-Activity Relationship of Triazolic Compounds Derived from the Neolignans Grandisin, Veraguensin, and Machilin G

“…These compounds have been considered important scaffolds in molecular modification studies due to their antileishmanial and antichagasic activities [13][14][15][16]. Cassamale et al [12] demonstrated the antileishmanial activity of these triazole derivatives on promastigote forms; now the present work shows their activity on L. (L.) amazonensis intracellular amastigotes, searching for structure-activity relationship information to support the development of new drug candidates for CL.…”

Cross‐Coupling of Heteroarenes by CH Functionalization: Recent Progress towards Direct Arylation and Heteroarylation Reactions Involving Heteroarenes Containing One Heteroatom

“…arylfurans include numerous compounds exhibiting interesting biological and pharmacological activities. [13] For instance, the 2-arylfuran derivative 1 (dantrolene) ( Figure 1) is a muscle relaxant commonly used for the treatment of life-threatening complications during anesthesia; [14] compound 2 ( Figure 1) effectively inhibits infection by both laboratory-adapted and primary HIV-1 strains and blocks HIV-1 mediated cell-cell fusion and gp41 six-helix bundle formation; [15] azofuran 3 ( Figure 1) possesses significant activity against cancer cells without affecting the lymphocyte proliferation in human peripheral blood mononuclear cells; [16] the 3-substituted (5-arylfuran-2-ylcarbonyl)-guanidine 4 ( Figure 1) exhibits high Na + /H + exchange isoform-1 inhibitory activity; [17] and bioymifi (5) (Figure 1) is a compound that binds to the extracellular domain of the DR 5 receptors and induces their aggregation. [18] In 2009, Doucet and co-workers reported that 2-butyl-5-arylfurans could be selectively prepared by the reaction of 2 equiv.…”