We specialize in hit-to-lead medicinal chemistry which is a key part of the complex and interdisciplinary process of discovery and development of new medicines. We synthesize small organic molecules with drug-like structural features including natural products and their derivatives. Working closely with biologists who evaluate these new compounds, we refine their chemical structures to achieve optimal biological properties and pharmaceutical potential, ultimately aiming to advance promising "drug candidates" into clinical trials.
We develop new reactions and synthetic strategies that enhance the capacity of chemists to produce valuable speciality compounds from simpler inexpensive building blocks. We focus mainly on three areas: 1) using sulfoxides and vinyl sulfides as versatile synthetic intermediates, 2) using environmentally benign heterogeneous reagents to simplify reactions and 3) efficiently preparing nitrogen-rich heterocyclic scaffolds with drug-like structural properties.
Our work at McMaster University
Efficient Synthesis of Cannabigerol, Grifolin, and Piperogalin via Alumina-Promoted Allylation
N. G. Jentsch, X. Zhang, J. Magolan
J. Nat. Prod 2020, in press
Genetic and chemical screening in human blood serum reveals unique antibacterial targets and compounds against Klebsiella pneumoniae
B. S. Weber, A. M. De Jong, A. B. Y. Guo, S. Dharavath, S. French, A. A. Fiebig-Comyn, B. K. Coombes, J. Magolan, E. D. Brown
Cell Reports 2020, 32(3), 107927
Magolan Lab member Dr. Srinivas Dharavath made synthetic chemistry contributions to this collaborative investigation led by the lab of Prof. Eric Brown.
Targeting two-component systems uncovers a small molecule inhibitor of Salmonella virulence.
C. N. Tsai, C. R. MacNair, M. P. T. Cao, J. N. Perry, J. Magolan, E. D. Brown, B. K. Coombes
Cell Chem. Bio. 2020, 27(7), 793-805
Magolan Lab member Dr. My Cao made synthetic chemistry contributions to this collaborative investigation led by the lab of Prof. Brian Coombes.
Mechanism of Action of an EPAC1-Selective Competitive Partial Agonist
H. Shao, H. Mohamed, S. Boulton, J. Huang, P. Wang, H. Chen, J. Zhou, U. Luchowska-Stańska, N. Jentsch, A. Armstrong, J. Magolan, Y. Stephen, G. Melacini
J. Med. Chem. 2020, 63(9), 4762-4775
Magolan Lab members Dr. Nick Jentsch and Alison Armstrong made synthetic chemistry contributions to this collaborative protein NMR-based investigation led by the lab of Prof. Giuseppe Melacini.
Isolation and Synthesis of Veranamine, an Antidepressant Lead from the Marine Sponge Verongida rigida
A. J. Kochanowska-Karamyan, H. C. Araujo, X. Zhang, A. El-Alfy, P. Carvalho, M. A. Avery, S. Holmbo, J. Magolan, M. T. Hamann
J. Nat. Prod. 2020, 83(4), 1902-1098
Magolan Lab members Hugo Araujo, Xiong Zhang, and Steven Holmbo completed the first gram scale total synthesis of veranamine as part of this international collaboration co-led by Dr. Magolan and Dr. Hamann.
Uncovering the hidden antibiotic potential of Cannabis
M. A. Farha, O. M. El-Halfawy, R.T. Gale, C. R. MacNair, L. A. Carfrae, X. Zhang, N. G. Jentsch, J. Magolan, E. D. Brown
ACS Infec. Dis. 2020, 6(3), 338-346
Magolan Lab members Xiong Zhang and Dr. Nick Jentsch made synthetic chemistry contributions to this collaborative investigation led by Prof. Eric Brown's lab.
Alkylation of indoles with α,β-unsaturated ketones using alumina in hexanes
Zhang, X., Jones-Mensah, E., Deobald J., Magolan J.
Advanced Synthesis and Catalysis 2019, 361, 5548-5551.
A macrophage-based screen identifies antibacterial compounds selective for intracellular Salmonella Typhimurium
Ellis, M.J., Tsai, C.N., Johnson, J.W., French, S., Elhenawy, W., Porwollik, S., Andrews-Polymenis, H., McClelland, M., Magolan, J., Coombes, B.K., Brown, E.D
Nature Communications 2019, 10(1), 197
Magolan Lab member Dr. Jarrod Johnson made synthetic chemistry contributions to this collaborative investigation led by the labs of Prof. Eric Brown and Prof. Brian Coombes.
Our work at the University of Idaho
One-pot carbonyl reduction and carbonate formation using sodium borohydride in dialkyl carbonate solvents
Osumah, A., Magolan J., Waynant, K.
Tetrahedron Letters. 2019, 60(44), 151203
Biaryl Ketones via Suzuki-Miyaura Cross-Coupling of Organotrifluoroborates and Acid Chlorides.
Frobes, A. M.; Meier, G. P.; Jones-Mensah, E.; Magolan J.
Eur. J. Org. Chem. 2016, 17, 2983-2987.
Dimethylsulfoxide as a Synthon in Organic Chemistry.
Jones-Mensah, E.; Karki, M.; Magolan, J.
Synthesis 2016, 48(10), 1421-1436.
Cerium-Free Luche Reduction Directed by Rehydrated Alumina.
Jones-Mensah, E.; Nickerson, L. A.; Deobald, J. L.; Ertel, A. B.; Knox, H. L.; Magolan. J.
Tetrahedron 2016, 72(26) 3748-3753.
Evaluation of Synthetic Coumarins for Antiausterity Cytotoxicity against Pancreatic Cancers.
Farley, C. M.; Dibwe, D.F.; Ueda, J.; Hall, E.A.; Awale, S. Magolan, J.
Bioorg. Chem. Med. Lett. 2016, 26(5), 1471-1474.
Bromination of Olefins with HBr and DMSO.
Karki, M.; Magolan, J.
J. Org. Chem. 2015, 80(7) 3701-3707.
Aryl methyl sulfides via SNAr using DMSO as the source of the thiomethyl moiety.
Jones-Mensah, E.; Magolan, J.
Tetrahedron Lett. 2014, 55(38), 5323-5326.
Dehydroaromatization with V2O5.
Karki, M.; Araujo, H. C.; Magolan, J.
Synlett 2013, 24(13), 1675-1678.
Combined Pd/C and Montmorillonite Catalysis for Efficient One-Pot Synthesis of Benzimidazoles.
Weires, N.A.; Boster, J.; Magolan, J.
Eur. J. Org. Chem. 2012, 33, 6508-6512
highlighted: Snieckus V.; Singh S.P. SYNFACTS 2013, 9(3), 254
Publications from Dr. Magolan's graduate and postdoctoral research
Tilly, D.; Magolan, J.; Mortier, J.
Directed Remote Aromatic Metalations: Mechanisms and Driving Forces.
Chemistry a European Journal 2012, 18(13), 3804-3820. (link)
Magolan, J.; Adams, N.B.P.; Onozuka, H.; Esumi, H.; Hugerford, N.L.; Coster, M.J.
Synthesis and biological evaluation of analogues of the natural product angelmarin for anti-pancreatic cancer activity.
ChemMedChem 2012, 7(5), 766-770. (link)
Magolan, J.; Coster, M.J.
Targeting the resistance of pancreatic cancer cells to nutrient deprivation: anti-austerity compounds.
Current Drug Delivery 2010, 7(5), 355-369. (link)
Magolan, J.; Coster M.J.
Total Synthesis of (+)-Angelmarin.
Journal of Organic Chemistry 2009, 74(14), 5083–5086. (link)
Magolan, J.; Carson, C.; Kerr, M.A.
Total Synthesis of (±)-Mersicarpine.
Organic Letters 2008, 10(7), 1437-1440. (link)
Li, L.; Jones, C.D.; Magolan, J.; Lemieux, R.P.
Siloxane-terminated phenylpyrimidine liquid hosts.
Journal of Materials Chemistry 2007, 17, 2313-2319. (link)
Magolan, J.; Kerr, M.A.
Expanding the Scope of Mn(OAc)3-Mediated Cyclizations: Synthesis of the Tetracyclic Core of Tronocarpine.
Organic Letters 2006, 8(17), 3777-3779. (Link)
England, D.B.; Magolan, J.; Kerr, M.A.
Synthesis of the Western Half of the Lolicines and the Lolitrems.
Organic Letters 2006, 8(11), 2209-2212. (link)