The synthesis and matrix metalloproteinase (MMP) inhibitory activity of a cyclam-marimastat conjugate and its metal complexes are described. The conjugate, synthesized with a copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition ("click" reaction), contains two zinc-binding groups (ZBGs). The metal complexation behavior with copper(II) and zinc(II) was investigated using UV/Vis spectrophotometr...

A novel primary amine-containing monomer, 1-(30-aminopropyl)-4-acrylamido-1,2,3-triazole hydrochloride (APAT), was prepared from N-propargylacrylamide and 3-azidopropylamine hydrochloride via copper-catalyzed Huisgen 1,3-dipolar cycloaddition (click reaction). Poly(N-isopropylacrylamide)-b-poly(1-(30-aminopropyl)-4acrylamido-1,2,3-triazole hydrochloride), PNIPAM-b-PAPAT, was then synthesized vi...

Over a number of years work in our laboratory has been developing new chemistry for the use of cellulose nanocrystals (CNCs) as scaffolds for the creation of nanomaterials with novel, stimuli responsive characteristics. Our work takes advantage of the rigid nature of CNCs, the unique nanopattern etched on their surface in the form of regularly spaced primary OH groups, and the fact that these m...

An efficient and operationally simple synthesis of 7-deuteropyrazolo[1,5-a]pyridine and 7-deutero-1,2,4-triazolo[1,5-a]pyridine derivatives using α-H/D exchange of 1-aminopyridinium cations in basic D2O followed by a 1,3-cycloaddition of acetylenes and nitriles is presented. A high regioselectivity and a high degree of deuterium incorporation were achieved. The procedure was applied for several...

The Rh(II)-catalyzed formal [3+2] and [3+3] cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines have been developed, which enable the efficient synthesis of polysubstituted 3-aminopyrroles and 1,2-dihydropyrazines, respectively. The reported [3+2] cycloaddition represents the first application of 1-sulfonyl 1,2,3-triazole as a [2C]-component in relevant cycloaddition reactions.

7-Aryl-1,3,5-cycloheptatrienes react intermolecularly with methylenecyclopropanes in a triple gold(I)-catalyzed reaction to form cyclopentenes. The same formal (4+1) cycloaddition occurs with cyclobutenes. Other precursors of gold(I) carbenes can also be used as the C1 component of the cycloaddition.

Nickel(0) catalyzed [4+2] cycloaddition of electron-deficient dienes to alkynes and subsequent aromatization gave highly substituted arenes. This formal inverse electron-demand Diels-Alder cycloaddition is attributed to the formation of a seven-membered nickelacycle from a diene and an alkyne.

Yb(NTf(2))(3)-catalyzed [3 + 3] cycloaddition between isatin ketonitrones and cyclopropanes is described. A variety of spiro[tetrahydro-1,2-oxazine]oxindoles were obtained in moderate to good yields along with good regioselectivities. This is the first example of the intermolecular [3 + 3] cycloaddition between ketone-derived nitrones and cyclopropanes.

Copper-catalyzed, thermal or microwave promoted 1,3-dipolar cycloaddition (Click Reaction) of 2-propynyl and 3-butynyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-glycopyranosides in the D-gluco, D-galacto and D-manno series afford the corresponding dimeric cycloaddition products.

The biosynthesis of dimeric pyrrole-imidazole alkaloids is likely mediated by enzyme-catalyzed reversible single-electron transfer (SET) cycloaddition. We now show that Ir(ppy)3 can promote SET-mediated formal [2+2] and [4+2] cycloaddition reactions of pyrrole-imidazole alkaloids-related substrates under photolytic conditions. This biomimetic approach is useful for the construction of the core ...