Dinuclear zinc(II) complexes of symmetric Schiff-base ligands with extended quinoline sidearms.

The synthesis of two 2-formylquinolines is reported via the Skraup method followed by SeO(2) oxidation. Each aldehyde is condensed with (1R,2R)-diaminocyclohexane and (R)-BINAM, yielding four enantiomerically-pure bis(imine-quinoline) ligands. The neutral ligands are reacted with ZnCl(2) to give complexes with bis(bidentate) coordination of ZnCl(2) units.

Iron(II) and zinc(II) monohelical binaphthyl-salen complexes with overlapping benz[a]anthryl sidearms.

The synthesis of the polyaromatic aldehyde 1-hydroxybenz[a]anthracene-2-carboxaldehyde is reported via a seven step protocol from 9,10-dihydroanthracene, with an overall yield of 30%. Two equivalents of the aldehyde are condensed with (R)-1,1'-binaphthyl-2,2'-diamine to produce a new binaphthyl-salen ligand, which is subsequently complexed to iron(II) and zinc(II) ions. The ligand and complexes are characterized by single-crystal X-ray crystallography.

Monohelical Iron(II) and Zinc(II) complexes of a (1R,2R)-cyclohexyl salen ligand with benz[a]anthryl sidearms.

An enantiomerically pure C2-symmetric salen ligand with benz[a]anthracene siderams produces M helical complexes (FeII and ZnII) in solution. Interconversion to produce a 1:1 mixture of helical conformers in the solid state is possible, despite overlapped sidearms.

Iron(II) and zinc(II) monohelical binaphthyl salen complexes.

A new chiral binaphthyl salen ligand with rigid polyaromatic sidearms gives monohelical complexes (Fe(II) and Zn(II)) of predetermined handedness.

Synthesis of symmetric bis(imidazole-4,5-dicarboxamides) substituted with amino acids.

A series of symmetric bis(imidazole-4,5-dicarboxamides) (bis-I45DCs) were prepared with amino acid esters and a variety of linker groups. The critical pyrazine intermediates, substituted with amino acid esters, were synthesized by stoichiometric control of the amino acid ester, even though primary alkanamines, in comparison, generally offer less selectivity for this reaction. Diamines are added to subsequently react with and open the remaining acyl imidazole bonds in the pyrazine intermediates and thereby yield the bis-I45DCs.

Small molecule inhibition of hepatitis C virus E2 binding to CD81.

The hepatitis C virus (HCV) is a causal agent of chronic liver infection, cirrhosis, and hepatocellular carcinoma infecting more than 170 million people. CD81 is a receptor for HCV envelope glycoprotein E2. Although the binding of HCV-E2 with CD81 is well documented the role of this interaction in the viral life cycle remains unclear.

An improved method for the synthesis of dissymmetric N,N'-disubstituted imidazole-4,5-dicarboxamides.

Symmetrically and dissymmetrically disubstituted imidazole-4,5-dicarboxamides (I45DCs) have diverse bioactivities and therefore represent useful small molecules for lead structure identification in drug discovery. For this reason, an improved synthesis was developed as a first step in the preparation of greater numbers of analogues. The method involves the transformation of imidazole-4,5-dicarboxylic acid into dissymmetrically disubstituted I45DCs in four steps and in a minimum yield of 51%.