Design, Synthesis, and Testing of a Molecular Truck for Colonic Delivery of 5-Aminosalicylic Acid

A molecular scaffold bearing eight terminal alkyne groups was synthesized from sucrose. Eight copies of an azide-terminated, azo-linked precursor to 5-aminosalicylic acid were attached to the scaffold via copper(I)-catalyzed azide–alkyne cycloaddition. The resulting compound was evaluated in a DSS model of colitis in BALB/c mice against sulfasalazine as a control. Two independent studies verified that the novel pro-drug, administered in a dose calculated to result in an equimolar 5-ASA yield, outperformed sulfasalazine in terms of protection from mucosal inflammation and T cell activation. A separate study established that 5-ASA appeared in feces produced 24–48 h following administration of the pro-drug. Thus, a new, orally administered pro-drug form of 5-aminosalicylic acid has been developed and successfully demonstrated

Palladium-catalyzed hydrogenations in dichloromethane

Dichloromethane is shown to be a useful solvent in catalytic hydrogenation reactions of easily reduced functional groups (alkenes, alkynes, imines, and nitroarenes) using palladium on carbon as the catalyst under mild conditions (ambient pressure and temperature).Petroleum Research Fund12 month embargo; published online: 01 September 2022This item from the UA Faculty Publications collection is made available by the University of Arizona with support from the University of Arizona Libraries. If you have questions, please contact us at [email protected]

Solvent-free nitration of electron-rich arenes

<p>Nitration of relatively electron-rich arenes does not require an additive or a solvent. For example, reaction on a gram scale of anisole with acetyl nitrate, generated <i>in situ</i> by mixing 100% HNO₃ with acetic anhydride, produced 2,4-dinitroanisole in 82% yield after crystallization of the crude product. Results with five additional monosubstituted benzene derivatives possessing highly activated, weakly activated, or weakly deactivated rings are reported.</p