Pier Cirillo - University of New Haven

Education

Ph.D. in Synthetic Organic Chemistry, Boston University, 1995
B.Sc. Hons. in Chemistry, University of the Witwatersrand, 1987

Doctoral Dissertation

Chiral Allylic Silanes in Organic Synthesis: Formal Synthesis of (+)-Sesbanimide A. Doctorate in Philosophy. Boston University, 1995

Research Interests

Before joining the faculty at the University of New Haven, I spent twelve years in medicinal chemistry research at a pharmaceutical company, designing and synthesizing kinase inhibitors and receptor modulators that have the potential to treat inflammatory diseases. My current research interest is the laboratory synthesis of: natural products and their analogs, polyoxygenated compounds, and heterocyclic compounds. The motivation is to discover, in collaboration with biochemists, new compounds of potential medicinal interest such as antibiotics and anti-cancer chemotherapeutic agents. Special consideration is given to new, efficient, and green methods of synthesis.

Selected Scholarly Publications

Bartolozzi, A.; Cirillo, P.F.; Berry, A.K.; Hickey, E.R.; Thomson, D.S.; Wu, L.; Zindell, R.; Albrecht, C.; Ceci, A.; Gemkow, M.J.; Nagaraja, N.V.; Romig, H.; Sauer, A.; Riether, D. Selective CB2 Receptor Agonists, Part 3: The Optimization of a Piperidine-Based Series that Demonstrated Efficacy in an In Vivo Neuropathic Pain Model. Bioorg. Med. Chem. Lett. 201525(3): 587-592.
Hickey, E.R.; Zindell R.; Cirillo, P.F.; Wu, L.; Ermann, M.; Berry, A.K.; Thomson, D.S.; Albrecht, C.; Gemkow, M.J.; Riether, D. Selective CB2 Receptor Agonists, Part 1: The Identification of Novel Ligands Through Computer Aided Drug Design (CADD) Approaches. Bioorg. Med. Chem. Lett. 201525(3): 575-580.

Lee, Y.; Mootien, S.; Shoen, C.; Destefano, M.; Cirillo, P.; Asojo, O.A.; Yeung, K.R.; Ledizet, M.; Cynamon, M.H.; Aristoff, P.A.; Koski, R.A.; Kaplan, P.A.; Anthony, K.G. Inhibition of Mycobacterial Alanine Racemase Activity and Growth by Thiadiazolidinones. Biochem. Pharmacol. 201386(2):222-230.
Bai, F.; Asojo, O.A.; Ciustea, M.; Ledizet, M.; Cirillo, P.; Aristoff, P.A.; Leng, L.; Bucala, R.; Koski, R.A., Anthony, K.G. Chicago Sky Blue 6B, A Novel Allosteric Inhibitor for Macrophage Migration Inhibitory Factor. J. Biol. Chem.2012 287: 30653-30663.
Ciustea, M.; Mootien, S.; Rosato, A.E.; Perez, O.; Cirillo, P.; Yeung, K.R.; Ledizet, M.; Cynamon, M.H.; Aristoff, P.A.; Koski, R.A.; Kaplan, P.A.; Anthony, K.G. Thiazolidinones: A New Class of Alanine Racemase Inhibitors With Antimicrobial Activity Against Methicillin-Resistant Staphylococcus aureus. Biochem. Pharmacol.201283: 368-377.
Riether, D.; Wu, L.; Cirillo, P.F.; Berry, A.; Walker, E.R.; Ermann, M.; Noya-Marino, B.; Jenkins, J.E.; Albaugh, D.; Albrecht, C.; Fisher, M.; Gemkow, M.J.; Grbic, H.; Löbbe, S.; Möller, C.; O’Shea, K.; Sauer, A.; Shih D.-T.; Thomson, D.S. 1,4-Diazepane Compounds as Potent and Selective CB2 Agonists: Optimization of Metabolic Stability. Bioorg. Med. Chem. Lett. 201121(7): 2011-2016.
Cirillo, Pier F.; Hickey, Eugene; Breitfelder, Steffen; Betageri, Raj; Fadra, Tazmeen; Gaenzler, Faith; Gilmore, Thomas; Goldberg, Daniel; Kamhi, Victor; Kirrane, Thomas; Kroe, Rachel R.; Madwed, Jeffrey; Moriak, Monica; Netherton, Matthew; Pargellis, Christopher A.; Patel, Usha; Qian, Kevin C.; Regan, John R.; Sharma, Rajiv; Sun, Sanxing; Swinamer, Alan; Torcellini, Carol; Takahashi, Hidenori; Tsang, Michele, Xiong, Zhaoming; Moss, Neil Discovery and Characterization of the N-Phenyl-N’-Naphthylurea Class of p38 MAP Kinase Inhibitors. Bioorg. Med. Chem. Lett.200919(9): 2386-2391.
Regan, John; Capolino, Alison; Cirillo, Pier F.; Gilmore, Thomas; Graham, Anne G.; Hickey, Eugene; Kroe, Rachel R.; Madwed, Jeffrey; Moriak, Monica; Nelson, Richard; Pargellis, Christopher A.; Swinamer, Alan; Torcellini, Carol; Tsang, Michele; Moss, Neil. Structure-Activity Relationships of the p38a MAP Kinase Inhibitor 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[4-(2-morpholin-4-yl-ethoxy)naphthalen-1-yl]urea (BIRB 796). J. Med. Chem.200346(22): 4676-4686.
Cirillo, Pier F.; Pargellis, Christopher; Regan, John. The non-diaryl heterocycle classes of p38 MAP kinase inhibitors. Curr. Top. Med. Chem.20022(9): 1021-1035.
Regan, John; Breitfelder, Steffen; Cirillo, Pier; Gilmore, Thomas; Graham, Anne G.; Hickey, Eugene; Klaus, Bernhard; Madwed, Jeffrey; Moriak, Monica; Moss, Neil; Pargellis, Chris; Pav, Sue; Proto, Alfred; Swinamer, Alan; Tong, Liang; Torcellini, Carol. Pyrazole Urea-Based Inhibitors of p38 MAP Kinase: From Lead Compound to Clinical Candidate. J. Med. Chem. 200245(14): 2994-3008.
Pargellis, Christopher; Tong, Liang; Churchill, Laurie; Cirillo, Pier F.; Gilmore, Thomas; Graham, Anne G.; Grob, Peter M.; Hickey, Eugene R.; Moss, Neil; Pav, Susan; Regan, John. Inhibition of p38 MAP kinase by utilizing a novel allosteric binding site. Nature Struct. Biol.20029(4): 268-272.
Cirillo, Pier F.; Danishefsky, Samuel J. The glycal assembly method on solid supports: synthesis of oligosaccharides and glycoconjugates. Solid Support Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries2001 15-40. P.H. Seeberger Ed., Wiley, New York.
Danishefsky, Samuel J.; Hu, Shuanghua; Cirillo, Pier F.; Eckhardt, Matthias; Seeberger, Peter H. A highly convergent total synthetic route to glycopeptides carrying a high-mannose core pentasaccharide domain N-linked to a natural peptide motif. Chemistry-A European Journal 19973(10): 1617-1628.
Seeberger, Peter H.; Cirillo, Pier F.; Hu, Shuanghua; Beebe, Xenia; Bilodeau, Mark T.; Danishefsky, Samuel J. Synthesis of the pentasaccharide core structure of asparagine-linked glycoprotein oligosaccharides by the glycal assembly method. Enantiomer 19961(4-6): 311-323.
Jain, Nareshkumar F.; Cirillo, Pier F.; Pelletier, Roberta; Panek, James S. Double stereodifferentiation in the Lewis acid promoted crotylation of (S)-2-alkoxypropanal with chiral b-alkyl (E)-crotylsilanes. Tet. Lett. 199536(48): 8727-30.
Cirillo, Pier F.; Panek, James S. Studies directed toward the synthesis of (+)-sesbanimide A: construction of the AB-ring system (a formal total synthesis). J. Org. Chem.199459(11): 3055-63.
Panek, James S.; Cirillo, Pier F. Acyclic diastereoselectivity in the Lewis acid promoted additions of chiral, b-methyl-substituted (E)-crotylsilanes with achiral aldehydes. J. Org. Chem. 199358(5): 999-1002.
Cirillo, Pier F.; Panek, James S. Recent progress in the chemistry of acylsilanes. A review. Org. Prep. Proc. Intl.199224(5): 553-82.
Cirillo, Pier F.; Panek, James S. Diastereoselectivity in nucleophilic addition reactions to (a,b-dialkoxyacyl) silanes: an operationally useful route to optically active 1,2,3-syn-triols. J. Org. Chem.1990 55(25): 6071-3.
Panek, James S.; Cirillo, Pier F. p-Facial selectivity in catalytic osmylation reactions of chiral C1-oxygenated allylic silanes. J. Am. Chem. Soc.1990 112(12): 4873-8.

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Recent Professional Activities

Medicinal Chemistry Consultant – L2 Diagnostics, since 2011
Senior Lecturer – The University of New Haven - 2013-2016
Lecturer – The University of New Haven - 2009-2013
Principal Scientist – Boehringer Ingelheim Pharmaceuticals, Inc. - 2003-2008
Senior Scientist – Boehringer Ingelheim Pharmaceuticals, Inc. - 1997-2002
Post-Doctoral Research Fellow – Memorial Sloan-Kettering Cancer Center - 1995-1996

Professional Memberships

Member, American Chemical Society

Courses Taught

CHEM 4501 Advanced Organic Chemistry
CHEM 4550 /6650 Medicinal Chemistry
CHEM 3341 Synthetic Methods
CHEM 2201/2203 Organic Chemistry I with Lab
CHEM 2202/2204 Organic Chemistry II with Lab
CHEM 1115/1117 General Chemistry I with Lab
CHEM 1105 Intro General and Organic Chemistry with Lab

Pier Cirillo, Ph.D.