Ryan Murelli
Department Chairperson and Professor
Chemistry and Biochemistry
Location: 437 Ingersoll Hall Extension
Phone: 718.951.5000 x2821
Fax: 718.951.4607
Email:
Ryan Murelli's Web site
Ryan Murelli joined the Brooklyn College faculty in September 2010. He teaches organic chemistry in addition to conducting research at the college, and holds a joint appointment with the CUNY Graduate Center. His research interests are broad but are based around synthetic organic chemistry. He worked on total synthesis and synthetic methods development while earning his Ph.D. Following the completion of his thesis work, he began postdoctoral research at Yale University, where he worked on several projects spanning bacteriology, immunology and cancer research. His research at Brooklyn College is aimed at developing new synthetic methods and employing them toward the study and development of biologically active small molecules.
Education:
Postdoctoral Training, Yale University - 2010 (Chemical Biology)
Ph.D., Boston College - 2007 (Organic Chemistry)
B.A., Hamilton College - 2002 (Chemistry)
Areas of Expertise:
Ryan Murelli's lab is interested in developing and using the tools of chemistry and biology to meet current challenges in medicine. A major driving force behind the lab's work is the development of new synthetic methods that enable rapid access to known but underexplored small molecules. These routes are then applied to studying and understanding the target's function, and developing improved analogs that could serve as therapeutics.
Books and Publications
Bejcek, L. P.; Murelli, R. P. "Synthesis of Aryl-Substituted 2-Methoxyphenol Derivatives from Maltol-Derived Oxidopyrylium Cycloadducts through an Acid-Mediated Ring-Contraction Cascade" Chem. Comm. 2020, Accepted, doi: 10.1039/C9CC09213G. (Books and Publications: Forthcoming Publications) 2020
Lanave, G.; Martella, V.; Tempesta, M.; Catella, C.; Murelli, R. P.; Morrison, L. A.; Lucenta, M. S.; Buinavoglia, C.; Camero, M. "Antiviral Activity of α-Hydroxytropolones on Caprine Alphaherpesvoris 1 in Vitro" Res. Vet. Sci. 2020, 129, 99-102. (Books and Publications: Article (Peer-reviewed)) 2020
Agyemang, N. B.; Kukla, C. R.; Edwards, T. C.; Li, Q.; Langen, M. K.; Schaal, A.; Franson, A. D.; Gazquez Casals, A.; Donald, K. A.; Yu, A. J.; Donlin, M. J.; Morrison, L. A.; Tavis, J. E.; Murelli, R. P. "Divergent Synthesis of a Thiolate-Based α-Hydroxytropolone Library with a Dynamic Bioactivity Profile" RSC Advances, 9, 34227-34234. (Books and Publications: Article (Peer-reviewed)) 2019
Agyemang, N. B.; Murelli, R. P. "Synthesis of 5-Hydroxy-4-methoxy-2-methylpyrylium Trifluoromethanesulfonate from Kojic Acid" Org. Synth. 96, 494-510. (Books and Publications: Article (Peer-reviewed)) 2019
Bejcek, L. P.; Garimallaprabhakaran, A. K.; Suyabatmaz, D. M.; Greer, A.; Hersh, W. H.; Greer, E. M.; Murelli, R. P. "Maltol- and Allomaltol-Derived Oxidopyrylium Ylides: Methyl Substitution Pattern Kinetically Influences [5+3] Dimerization versus [5+2] Cycloaddition Reactions" J. Org. Chem., 84, 14670-14678. (Books and Publications: Article (Peer-reviewed)) 2019
Berkowitz, A. J.; Franson, A. D.; Gazquez Cassals, A.; Donald, K. A.; Yu, A. J.; Garimallaprabhakaran, A. K.; Morrison, L. A.; Murelli, R. P. "Importance of Lipophilicity for Potent Anti-Herpes Simplex Virus-1 Activity of α-Hydroxytropolones" Med. Chem. Commun., 2019, 10, 1173-1176. (Books and Publications: Article (Peer-reviewed)) 2019
Hirsch, D. R.; Metrano, A. J.; Stone, E. A.; Storch, G.; Miller, S. J.; Murelli, R. P. "Troponoid Atropisomerism: Studies on the Configurational Stability of Tropone-Amide Chiral Axes" Org. Lett. 2019, 21, 2412-2415 (Books and Publications: Article (Peer-reviewed)) 2019
Stasiak, J. P.; Grigoryan, A.; Murelli, R. P. "Spectrophotometric Determination of α-Hydroxytropolone pKa values" Tetrahedron Lett. 2019, 60, 1643-5 (Books and Publications: Article (Peer-reviewed)) 2019
Tavis, J. E.; Zoidis, G.; Meyers, M. J.; Murelli, R. P. "Chemical Approaches to Inhibiting the Hepatitis B Virus Ribonuclease H" ACS. Infect. Dis. 2019, 5, 655-8 (Books and Publications: Forthcoming Publications) 2019
Long, K. R.; Lomonosova, E.; Li, W.; Ponzar, N. L.; Villa, J. A.; Touchette, E.; Rapp, S.; Liley, R. M.; Murelli, R. P.; Grigoryan, A.; Buller, R. M.; Wilson, L.; Bial, J.; Sagartz, J. E.; Tavis, J. E. "Efficacy of Hepatitis B Virus Ribonuclease H Inhibitors, a New Class of Replication Antagonists, in FRG Human Liver Chimeric Mice" Antiviral Res. 2018, 149, 41-47. (Books and Publications: Article (Peer-reviewed)) 2018
Bejcek, L. P.; Murelli, R. P. "Oxidopyrylium [5+2] Cycloaddition Chemistry: Historical Perspective and Recent Advances (2008-2018)" Tetrahedron, 2018, 74, 2501-2521. (Books and Publications: Article (Peer-reviewed)) 2018
Berkowitz, A. J.; Abdelmessih, R. G.; Murelli, R. P. "Amidation Strategy for Final-Step α-Hydroxytropolone Diversification" Tetrahedron Lett. 2018, 59, 3026-8. (Books and Publications: Article (Peer-reviewed)) 2018
Cao, F.; Orth, C.; Donlin, M. J.; Adegboyega, P.; Meyers, M. J.; Murelli, R. P.; Elagawany, M.; Elgendy, B.; Tavis, J. E. "Synthesis and evaluation of troponoids as a new class of antibiotics" ACS Omega, 2018, 3, 15125-33. (Books and Publications: Article (Peer-reviewed)) 2018
D'Erasmo, M. P.; Murelli, R. P. "Fluorous-Phase Approach to α-Hydroxtropolone Synthesis" J. Org. Chem. 2018, 83, 1478-1485. (Books and Publications: Article (Peer-reviewed)) 2018
Dehghanpir, S. D.; Birkenheuer, C. H.; Yang, K.; Murelli, R. P.; Morrison, L. A.; Le Grice, S. F. J.; Baines, J. D. "Broad Anti-Herpesviral Activity of α-Hydroxtropolones" Vet. Microbiol. 2018 214, 125-131. (Books and Publications: Article (Peer-reviewed)) 2018
Hirsch, D. R.; Schiavone, D. V.; Berkowitz, A. J.; Morrison, L. A.; Masaoka, T.; Wilson, J. A.; Lomonosova, E.; Zhao, H.; Patel, B. S.; Dalta, S. H.; Majidi, S. J.; Pal, R.; K.; Gallicchio, E.; Tang, L.; Tavis, J. E.; Le Grice, S. F. J.; Beutler, J. A.; Murelli, R. P. "Synthesis and Biological Assessment of 3,7-Dihydroxytropolones" Org. Biomol. Chem. 2018, 16, 62-69. (Books and Publications: Article (Peer-reviewed)) 2018
Miller, J. T.; Zhao, H.; Masaoka, T.; Varnado, B.; Cornejo Castro, E. M.; Marshall, V. A.; Kouhestani, K.; Lynn, A. Y.; Aron, K. E.; Xia, A.; Beutler, J. A.; Hirsch, D. R.; Tang, L.; Whitby, D.; Murelli, R. P.; Le Grice, S. F. J. "Sensitivity of the C-Terminal Nuclease Domain of Kaposi's Sarcoma-Associated Herpesvirus ORF29 to Two Classes of Active Site Ligands" Antimicrob. Agents. Chemother. 2018, 62, e00233-18. (Books and Publications: Article (Peer-reviewed)) 2018
Donlin, M. J.; Zunica, A.; Lipnicky, A; Garimallaprabhakaran, A. K.; Berkowitz, A. J.; Grigoryan, A.; Meyers, M. J.; Tavis, J. E.; Murelli, R. P. "Troponoids can inhibit growth of the human fungal pathogen Cryptococcus neoformans" Antimicrob. Agents Chemother., 2017, 61, e02574-16. (Books and Publications: Article (Peer-reviewed)) 2017
Fuhr, K. N.; Hirsch, D. R.; Murelli, R. P.; Brenner-Moyer, S. E. "Catalytic Enantioselective Intermolecular [5+2] Dipolar Cycloadditions of a 3-Hydroxy-4-Pyrone-Derived Oxidopyrylium Ylide", Org. Lett., 2017, 19, 6356-9. (Books and Publications: Article (Peer-reviewed)) 2017
Grady, L. M.; Szczepaniak, R.; Murelli, R. P.; Masaoka, T.; Le Grice, S. F. J.; Wright, D. L.; Weller, S. K. "The exonuclease activity of HSV-1 UL12 is required for the production of viral DNA that can be packaged to produce infectious virus" J. Virol. 2017, 91, e01380-17 (Books and Publications: Article (Peer-reviewed)) 2017
Lomonosova, E.; Daw, J.; Garimallaprabhakaran, A. K.; Agyemang N. A.; Ashani, Y.; Murelli, R. P.; Tavis, J. E. "Efficacy and cytotoxicity in cell culture of novel α-hydroxytropolone inhibitors of hepatitis B virus ribonuclease H" Antiviral Res. 2017, 144, 164-172. (Books and Publications: Article (Peer-reviewed)) 2017
D'Erasmo, M. P.; Masaoka, T.; Wilson, J. A.; Hunte, E. M. Jr.; Beutler, J. A.; Le Grice, S. F. J.; Murelli, R. P. 'Traceless Solid-Phase α-Hydroxtropolone Synthesis' Medicinal Chemistry Communication, Accepted. (Books and Publications: Article (Peer-reviewed)) 2016
D'Erasmo, M. P.; Meck, C.; Lewis, C. A.; Murelli, R. P. "Discovery and Development of a 3-Component Oxidopyrylium [5+2] Cycloaddition Reaction" Journal of Organic Chemistry, 81, 3744-51. (Books and Publications: Article (Peer-reviewed)) 2016
Ireland, P. J.; Tavis, J. E.; D'Erasmo, M. P.; Hirsch, D. R.; Murelli, R. P.; Cadiz, M. M.; Patel, B. S.; Gupta, A. K.; Edwards, T. C.; Korom, M.; Moran, E. A.; Morrison, L. A. "Synthetic α-hydroxytropolones inhibit replication of wild-type and acyclovir-resistant herpes simplex viruses" Antimicrobial Agents Chemotherapeutics, 60, 2140-9. (Books and Publications: Article (Peer-reviewed)) 2016
Masaoka, T.; Zhao, H.; Hirsch, D. R.; D'Erasmo, M. P.; Meck, C.; Varnado, B.; Gupta, A.; Meyers, M. J.; Baines, J. D.; Beutler, J. A.; Murelli, R. P.; Tang,L.; Le Grice, S. F. J. "Characterization the C-terminal nuclease domain of herpes simplex virus pUL15 as a target of nucleotidyltransferase inhibitors." Biochemistry, 55, 809-19. (Books and Publications: Article (Peer-reviewed)) 2016
Murelli, R. P.; D'Erasmo, M. P.; Hirsch, D. R.; Meck, C.; Masaoka, T.; Wilson, J. A.; Zhang, B.; Pal, R. K.; Gallicchio, E.; Beutler, J. A.; Le Grice, S. F. J. 'Synthetic α-Hydroxytropolones as Inhibitors of HIV Reverse Transcriptase Ribonuclease H Activity' Medicinial Chemistry Communication, 9, 1783-8. (Books and Publications: Article (Peer-reviewed)) 2016
Zhang, B.; D'Erasmo, M. P.; Murelli, R. P. Gallicchio, E. "Free Energy-Based Virtual Screening and Optimization of RNase H Inhibitors of HIV-1 Reverse Transcriptase" ACS Omega, 1, 435-47. (Books and Publications: Article (Peer-reviewed)) 2016
Lu, G., E. Lomonosova, X. Cheng, E.A. Moran, M.J. Meyers, S.F.J. Le Grice, C.J. Thomas, J.-K. Jiang, C. Meck, D.R. Hirsch, M.P. D'Erasemo, D.M. Suyabatmaz, R.P. Murelli and J.E. Tavis. "Hydroxylated tropolones inhibit hepatitis B virus replication by blocking the viral ribonuclease H activity." Antimicrobial Agents Chemotherapy 59: 1070-79. (Books and Publications: Article (Peer-reviewed)) 2015
Zhao, H.; Lin, Z.; Lynn, A. Y.; Varnado, B.; Beutler, J. A.; Murelli, R. P.; Le Grice, S. F. J.; Tang, L. "Two distinct modes of metal ion binding in the nuclease active site of a viral DNA-packaging terminase: insight into the two-metal-ion catalytic mechanism" Nucleic Acids Res., 43, 11003-16. (Books and Publications: Article (Peer-reviewed)) 2015
D'Erasmo, M.P., W.B. Smith, A. Munoz, P. Mohandas, A.S. Au, J.J. Marineau, L.E.N. Quadri, J.E. Bradner and R.P. Murelli. "7,9-Diaryl-1,6,8-trioxaspiro[4.5]dec-3-e-2-ones: Readily Accessible and Highly Potent Anticancer Compounds." Bioorganic and Medicinal Chemistry Letters 24: 4035-38. (Books and Publications: Article (Peer-reviewed)) 2014
Hirsch, D.R., G.C. Cox, M.P. D'Erasmo, T. Shakya, C. Meck, N. Mohd, G.D. Wright and R.P. Murelli. "Inhibition of ANT(2")-Ia resistance enzyme and rescue of aminoglycoside antibiotic activity by synthetic α-hydroxytropolones." Bioorganic and Medicinal Chemistry Letters 24: 4943-47. (Books and Publications: Article (Peer-reviewed)) 2014
Meck, C., M.P. D' Erasmo, D.R. Hirsch and R.P. Murelli. "The Biology and Synthesis of α-hydroxytropolones." Medicinal Chemistry Communications 5: 842-52. (Books and Publications: Article (Peer-reviewed)) 2014
Williams, Y.D., C. Meck, N. Mohd and R.P. Murelli "Triflic Acid Mediated Rearrangements of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones: Synthesis of Methoxytropolones and Furans." Journal of Organic Chemistry 78: 11707-13. (Books and Publications: Article (Peer-reviewed)) 2013
Meck, C., N. Mohd and R.P. Murelli. "An oxidopyrylium cyclization/ring-opening route to polysubstituted alpha‑hydroxytropolones." Organic Letters 14: 5988-91. (Books and Publications: Article (Peer-reviewed)) 2012
Munoz, A. and R.P. Murelli. "Acid-mediated coupling of gamma-hydroxybutenolides and aldehydes: Synthesis of a new class of spirocyclic ketal-lactones." Tetrahedron Letters 53: 6779-81. (Books and Publications: Article (Peer-reviewed)) 2012
Nelson, J.W., A.G. Chamessian, P.J. McEnany, R.P. Murelli, B.I. Kazmiercak and D.A. Spiegel. "A Biosynthetic Strategy for Re-engineering the Staphylococcus Aureus Cell Wall With Non-native Small Molecules." ACS Chemical Biology 5: 1147-55. (Books and Publications: Article (Peer-reviewed)) 2010
Zhang, A.X., R.P. Murelli, C. Barinka, J. Michel, A. Cocleaza, W.L. Jorgensen, J. Lubkowski and D.A. Spiegel. "A Remote Arene Binding Site of Prostate Specific Membrane Antigen Revealed by Antibody-Recruiting Small Molecules." Journal of the American Chemical Society 132: 12711-16. (Books and Publications: Article (Peer-reviewed)) 2010
Murelli, R.P., A.X. Zhang, J. Michel, W.L. Jorgensen and D.A. Spiegel. "Chemical Control Over Immune Recognition: A Class of Antibody-Recruiting Small Molecules (ARMs) That Target Prostate Cancer." Journal of the American Chemical Society 131: 17090-92. (Books and Publications: Article (Peer-reviewed)) 2009
Stern, E., S.M. Jay, S.L. Demento, R.P. Murelli, M.A. Reed, T. Malinski, D.A. Spiegel, D.J. Mooney and T.M. Fahmy. "Spatiotemporal Control Over Molecular Delivery and Cellular Encapsulation From Electropolymerized Micro and Nanopatterned Surfaces." Advanced Functional Materials 19: 2888-95. (Books and Publications: Article (Peer-reviewed)) 2009
Murelli, R.P., S. Catalán, M.P. Gannon and M.L. Snapper. "Ruthenium-Catalyzed Enyne Cross-Metathesis-Cyclopropanation: Three Component Access to Vinyl Cyclopropanes." Tetrahedron Letters 49: 5714-17. (Books and Publications: Article (Peer-reviewed)) 2008
Murelli, R.P. and M.L. Snapper. "Ruthenium-Catalyzed Tandem Cross-Metathesis/Wittig Olefination: Generation of Conjugated Dienoic Esters From Terminal Olefins." Organic Letters 9: 1749-52. (Books and Publications: Article (Peer-reviewed)) 2007
Murelli, R.P., A.K. Cheung and M.L. Snapper. "Conformationally Restricted (+)-Cacospongionolide B Analogues: Influence on Secretory Phospholipase A2 Inhibition." Journal of Organic Chemistry 72: 1545-52. (Books and Publications: Article (Peer-reviewed)) 2007
Cheung, A.K., R. Murelli and M.L. Snapper. "Total Syntheses of (+)- and (-)-Cacospongionolide B, Cacospongionolide E, and Related Analogues. Preliminary Study of Structural Features Required for Phospholipase A2 Inhibition." Journal of Organic Chemistry 69: 5712-19. (Books and Publications: Article (Peer-reviewed)) 2004
Creative Work
Le Grice, Stuart F. J.; Sztuba-Solinska, Joanna; Murelli, Ryan P. "Chemical entities for lytic activation of Kaposi's sarcoma herpesvirus (KSHV) and therapeutic targeting of viral enzymes/proteins" PCT Int. Appl. No. WO 2019118803 A1 (Filed: Jun 20, 2019). 2019
Donlin, M. J.; Tavis, J. E.; Murelli, R.; Meyers, M. J. "Preparation of substituted cycloheptatrienones as antifungal compounds" PCT Int. Appli. No. WO 2017-184752. (Filed Oct. 2017) 2017
Tavis, J. E.; Morrison, L. A.; Murelli, R. P. "Preparation of hydroxylated tropolone inhibitors of nucleotidyl transferases in treatment of herpesvirus and Hepatitis B" PCT Int. Appl. No. WO 2016-US36914. Patent No. WO 2016201243. (Filed: Dec 15, 2016). 2016
Spiegel, D.; Murelli, R.; Zhang, A. "Chimeric Small Molecules that Recruit Antibodies to Cancer Cells" PCT Int. Appl. No. WO 2009-US2857. Patent No. WO 2009139863. (Filed: Nov. 11, 2009). 2009
Awards, Honors and Fellowships
Alfred P. Sloan Foundation CUNY Junior Faculty Award in Science and Engineering ($50,000) (Grants and Fellowships) 2015
National Institutes of Health (RO1) "Optimization of alpha-hydroxytropolones as novel inhibitors of the HBV RNaseH" ($658,553 of $2,740,000) [PI, John E. Tavis] Role: Collaborator (Grants and Fellowships) 2015
National Institutes of Health (SCORE) "Synthetic and biological studies of α-Hydroxytropolones" ($1,558,600) (Grants and Fellowships) 2015
National Institutes of Health SCORE Grant (SC2GM099596) "Synthetic and biological studies of antitubercular natural products" ($471,000) (Grants and Fellowships) 2012
PSC CUNY Program (65420-00 42) "Synthesis of 7-hydroxytropolones" ($3,500) (Grants and Fellowships) 2012
