One-pot relay catalysis: divergent synthesis of furo[3,4-b]indoles and cyclopenta[b]indoles from 3-(2-aminophenyl)-1,4-enynols.

Described herein is an efficient divergent strategy for the synthesis of furo[3,4-b]indoles via a sequential Ag(i)/Bi(iii)/Pd(ii) catalysis and cyclopenta[b]indoles via a one-pot Ag(i)/Brønsted acid relay catalysis from 3-(2-aminophenyl)-4-pentenyn-3-ols, accessible in three simple steps from 2-aminobenzaldehydes.

Tuning aminopolycarboxylate chelators for efficient complexation of trivalent actinides.

The complexation of trivalent lanthanides and minor actinides (Am3+, Cm3+, and Cf3+) by the acyclic aminopolycarboxylate chelators 6,6'-((ethane-1,2-diylbis-((carboxymethyl)azanediyl))bis-(methylene))dipicolinic acid (H4octapa) and 6,6'-((((4-(1-(2-(2-(2-hydroxyethoxy)ethoxy)ethyl)-1H-1,2,3-triazol-4-yl)pyridine-2,6-diyl)bis-(methylene))bis-((carboxymethyl)azanediyl))bis-(methylene)) dipicolinic acid (H4pypa-peg) were studied using potentiometry, spectroscopy, competitive complexation liquid-liquid extraction, and ab initio molecular dynamics simulations. Two studied reagents are strong multidentate chelators, well-suited for applications seeking radiometal coordination for in-vivo delivery and f-element isolation. The previously reported H4octapa forms a compact coordination packet, while H4pypa-peg is less sterically constrained due to the presence of central pyridine ring. The solubility of H4octapa is limited in a non-complexing high ionic strength perchlorate media. However, the introduction of a polyethylene glycol group in H4pypa-peg increased the solubility without influencing its ability to complex the lanthanides and minor actinides in solution.

Malaria Box-Inspired Discovery of N-Aminoalkyl-ß-carboline-3-carboxamides, a Novel Orally Active Class of Antimalarials.

Virtual ligand screening of a publicly available database of antimalarial hits using a pharmacophore derived from antimalarial MMV008138 identified TCMDC-140230, a tetrahydro-ß-carboline amide, as worthy of exploration. All four stereoisomers of this structure were synthesized, but none potently inhibited growth of the malaria parasite Plasmodium falciparum. Interestingly, 7e, a minor byproduct of these syntheses, proved to be potent in vitro against P. falciparum and was orally efficacious (40 mg/kg) in an in vivo mouse model of malaria.

Synthesis of benzofurans via an acid catalysed transacetalisation/Fries-type O → C rearrangement/Michael addition/ring-opening aromatisation cascade of ß-pyrones.

An unusual and facile approach for the synthesis of 2-benzofuranyl-3-hydroxyacetones from 6-acetoxy-ß-pyrones and phenols is presented. The synthetic sequence involves a cascade transacetalisation, Fries-type O → C rearrangement followed by Michael addition and ring-opening aromatisation. The versatility of this method was further demonstrated via the synthesis of 4,4a-dihydropyrano[3,2-b]benzofuran-3-ones, furo[3,2-c]coumarins, and spiro[benzofuran-2,2'-furan]-4'-ones. The unexpected cascade event would also provide new possible considerations in the ß-pyrone-involved organic synthesis.