Cody Timmons

Vicinal Diamino Functionalities as Privileged Structural Elements in Biologically Active Compounds and Exploitation of their Synthetic Chemistry

The chemistry, synthetic routes and medicinal properties of vicinal diamines and imidazolines are discussed. Synthetic routes towards chemically and pharmaceutically important molecules containing vicinal diamine functionality are discussed in detail. This mini review article covers the new developments of diamine chemistry between 2000 and 2005.

Density Functional Theory Calculation of 13C NMR Shifts of Diazaphenanthrene Alkaloids: Reinvestigation of the Structure of Samoquasine A

The (13)C NMR shifts of 48 diazaphenanthrene-type alkaloids have been calculated at the B3LYP/6-311+G(2d,p) level of theory. The results support the structural reassignment of samoquasine A as 2.

Novel imidazolination reaction of alkenes provides an easy access to new α,β-differentiated 1,2-vicinal diamines

α,β-Differentiated 1,2-vicinal diamines have been efficiently synthesized by using new electrophilic imidazolination reaction of alkenes. The hydrolysis of imidazolines was performed by treatment with 6 M HCl in THF at 70 °C without epimerization. Eight examples were examined to give good to excellent yields (87–96%).

Construction of a bacterial autoinducer detection system in mammalian cells

Quorum sensing (QS) is a cell density-dependent signaling system used by bacteria to coordinate gene expression within a population. QS systems in Gram negative bacteria consist of transcription factors of the LuxR family and their acyl homoserine lactone (AHL) ligands. We describe here a method for examining QS signaling systems in mammalian cells that uses engineered LuxR-type proteins from the opportunistic pathogen, Pseudomonas aeruginosa, which can function as AHL-dependent transcription factors. The engineered proteins respond to their cognate ligands and display sequence specific DNA binding properties. This system has several potential biotechnological and biological applications. It may be used to characterize any LuxR-type protein, screen animal and plant cell extracts or exudates for compounds that mimic or interfere with AHL signaling or to screen different cell types for AHL inactivating activities.

MgI2-catalyzed halo aldol reaction: a practical approach to (E)-β-iodovinyl-β′-hydroxyketones

A novel generation of 1-iodo-3-siloxy-1,3-butadienes has been developed by reacting trimethylsilyl iodide (TMS-I) with α,β-unsaturated ketones in dichloromethane at 0 °C without the use of any catalyst. The halo aldol reaction of these butadiene intermediates with aldehydes was efficiently carried out by using magnesium iodide as the catalyst. Twelve β-iodo-α,β-unsaturated-β′-hydroxyketones (halo aldols) have been synthesized under the new condition with excellent geometric selectivity and good chemical yields (>80% chemical yields for 11 examples).