Medicinal & Synthetic Organic Chemistry
Snowden Research Group
Medicinal Chemistry
Our group is involved in the rational design, synthesis, and physicochemical properties determination of small molecule, occupancy-based protein methyl transferase inhibitors (e.g., DOT1L and PRMT3 inhibitors) and anti-microbial targeted protein degraders. We closely collaborate with computational and biology partners who help identify, screen, and decipher mechanisms of action of novel inhibitors and protein degraders. Collectively, we then optimize the pharmacodynamic performance and the pharmacokinetic properties of the most potent and target-selective “drug-like” leads.
Research
Organic Synthesis
We develop and study new methods and synthesis applications involving latent di-electrophiles such as gem-dihaloepoxide intermediates (e.g., extensions and variations of the Jocic-Reeve reaction). These methods and strategies furnish convenient and affordable functional group transformations (e.g., one-carbon homologation—functionalization of alcohols and aldehydes) and potentially powerful tools to generate complex, chiral target molecules including deoxy-C-glycosides, which are prevalent in biologically active natural products.
Representative Publications
Identification of DOT1L inhibitors by
structure-based virtual screening adapted
from a nucleoside-focused library
Parallel Solution Phase Synthesis and Preliminary Biological Activity of a 5′-Substituted Cytidine Analog Library
Small Diversity Library of 𝛼-Methyl Amide Analogs of Sulindac for Probing Anticancer Structure-Activity Relationships
One-Carbon Homologation of Primary Alcohols and Reductive Homologation of Aldehydes
Palladium-Catalyzed ortho-Halogenation
of Diaryl Oxime Ethers
Preparation of One-Carbon Homologated Amides from Aldehydes or Primary Alcohols
Synthesis of Potent CERT Inhibitor HPA-12 Featuring a Tandem Corey-Link and Intramolecular Nucleophilic Acyl Substitution Reaction
Stereospecific Suzuki, Sonogashira, and Negishi Coupling Reactions of N-Alkoxyimidoyl Iodides and Bromides
Stereoselective Synthesis of cis- or trans-2,4-Disubstituted Butyrolactones from Wynberg Lactone
One-Pot Synthesis of Trichloromethyl
Carbinols from Primary Alcohols
Recent Synthetic Applications
Involving gem-Dichloroepoxides
Carbocupration-Functionalization of Arynes – Rapid Access to Variably ortho-Substituted ((E)-3-Phenylprop-1-enyl)silanes
General and Practical Conversion of Aldehydes to Homologated Carboxylic Acids
tert-Butyldimethylsilyloxytrichloromethyl-methane – readily accessible and robust protecting group for (hetero)aryl aldehydes
Comparative Reductive Desymmetrization of Cyclic 2,2-Disubstituted-1,3-Diones
Facile Preparation of 2-Iodoaryl Trifluoromethanesulfonates:
Superior Aryne Precursors
Convergent synthesis of potent
COX-2 inhibitor inotilone
Practical Approach to 𝛼- or
𝛾-Heterosubstituted Enoic Acids
Group Members
Dr. Snowden
Timothy S.
Snowden
Associate Professor
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NIH Postdoctoral Fellow, The University of Pennsylvania, 2001-2003, Gary Molander
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PhD, The University of Texas at Austin, 2001, Eric Anslyn
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BS, Clemson University, 1994
Recent
Graduates
Amarraj
Chakraborty
PhD Candidate
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MS, Mississippi State University, 2015, Keith Mead
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MS, CSJM University, India, 2007
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BS, The University of Calcutta, 2004
Graduate Students
Anna F.
Howard
1st Year Graduate Student
• BS, St. Olaf College, 2020
Garrett D.
Clements
2nd Year Graduate Student
-
BS, The University of Alabama, 2019
Diana M. Soto Martinez
1st Year Graduate Student
• MS, Universidad del Valle 2017
• BS, Universidad del Valle 2013
Undergraduate Students
Thomas A.
Cope
Undergraduate
Jeremy M.
Jones
Undergraduate
CONTACT US
Mailing Address
Department of Chemistry and Biochemistry
The University of Alabama – Box 870336
Tuscaloosa, AL 35487-0336
Phone
(205) 348-8550
