The Green Chemistry and Sustainable Materials program at UMASS

Adrian Huang, Ph. D.
Department of Chemistry
Wellesley College
[email protected]
Ph. D. in Organic Chemistry
Department of Chemistry and Biochemistry, UCLA (Los Angeles, CA)
Advisor: Professor Michael E. Jung, Ph. D.
Thesis titles: “Toward the Total Synthesis of Eleutherobin” and
“Asymmetric Induction Utilizing Chiral Imidazolidines”
M. S. in Organic Chemistry
Duquesne University, Pittsburgh, PA
Advisor: Professor Fraser F. Fleming, Ph. D.
Thesis title: “The Syntheses of Cyanocycloalkenones”
M. S. E. in Polymer Science Engineering
Da Lian University of Technology, China
Thesis title: “Improving Mechanic Properties of Polyethylene/Nylon-6 With Maleic
B. S. in Chemistry
Department of Chemistry, Xian Tang University, China
Research on Liquid Crystals
Medicinal Chemist
Pfizer/Wyeth R&D (Cambridge, MA)
Research Scientist, Organometallic Chemistry and Polymer Material
DuPont Central R&D (Wilmington, DE)
Selected Accomplishments As a Medicinal Chemist
BTK Project for Rheumatoid Arthritis
 Identified safe and efficacious covalent inhibitors
 Improved kinome selectivities, blood activity, and exposure
 Designed irreversible and reversible inhibitors via computational chemistry
 Designed and developed asymmetric syntheses to the lead compounds
 Performed thorough patent analyses
HSD-1 Project for Type II Diabetes
 Entered clinical trial
 Solved poor microsomal stability and high CYP450 activity problems
 Designed and developed new catalysts for asymmetric syntheses of the lead compound
Adrian Huang, Ph.D.
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 Developed a methodology yielding novel 1,1,1,3,3,3-hexafluoro-amines, resulting in one
patent (US 2008188659) and one paper (Synlett, 2009, 15, 2518.)
P-Selectin Project for Atherosclerosis
 Entered clinical trial
 Resolved low aqueous solubility and poor oral exposure issues
 Designed and synthesized the second generation lead compound, PSI-421, which
demonstrated oral efficacy in two animal models with improved bioavailability
 Oral presentation in 238th ACS National Meeting, Washington, D. C., August 18, 2009
CRTH2 Project for Asthma
 Solved low permeability, efflux, and poor bioavailability problems
 Designed the key synthetic routes for the team
 Prepared many synthetically challenging compounds
 Presented a poster in Gordon Conference, Heterocyclic Compounds, June 26, 2011
TACE Project for Rheumatoid Arthritis
 Focused on improving selectivity over the clinical candidate TMI-001
 Computer-aided design and synthesis of selective and potent compounds to TACE
Chemistry Instructor
Department of Chemistry, Wellesley College (Wellesley, MA)
Teach organic chemistry and introductory laboratory classes; Supervise
undergraduate research projects on medicinal chemistry, organic chemistry, and
material science
Undergraduate Research Advisor
Pfizer/Wyeth Research (Cambridge, MA)
Guided two undergraduate interns in developing asymmetric synthesis of tertiary
alcohols and preparing chiral catalysts
Teaching Assistant
Department of Chemistry and Biochemistry, UCLA (Los Angeles, CA)
Served as an organic chemistry laboratory teaching assistant; recognized for
exceptional teaching abilities
Teaching Assistant
Da Lian University of Technology, China
Supervised three undergraduate students for their research theses on polymer
Kaila, N.; Huang, A.; Moretto, A.; Follows, B.; Janz, K.; Lowe, M.; Thomason, J.; Mansour, T.;
Hubeau, C.; Page, K.; Morgan, P.; Fish, S.; Xu, X.; Williams, C.; and Saiah, E. “Diazine Indole
Acetic Acids as Potent, Selective, and Orally Bioavailable Antagonists of Chemoattractant
Receptor Homologous Molecule Expressed on Th2 Cells (CRTH2) for the Treatment of Allergic
Inflammatory Diseases” J. Med. Chem. 2012, 55(11), 5088.
Huang, A.; Moretto, A.; Janz, K.; Lowe, M.; Bedard, P.W.; Tam, S.; Di, L.; Clerin, V.; Sushkov,
N.; Tchemychev, B.; Tsao, D. H. H.; Keith Jr., J. C.; Shaw, G.; Schaub, R. G.; Wang, Q.; Kaila,
N. “Discovery of 2-[1-(4-Chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-
Adrian Huang, Ph.D.
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carboxylic Acid (PSI-421), a P-Selectin Inhibitor with Improved Pharmacokinetic Properties and
Oral Efficacy in Models of Vascular Injury” J. Med. Chem. 2010, 53(16), 6003.
Huang, A.; Li, H. Q.; Massefski, W.; Saiah, E. “Direct Trifluoromethylation of Nitriles Promoted
by Tetrabutylammonium Bifluoride.” Synlett, 2009, 15, 2518.
Wu, J.J.; Green, N.; Hotchandani, R.; Hu, Y., Condon, J.; Huang, A.; Kaila, N.; Li, H. Q.; Guler,
S.; Li, W.; Tam, S.; Wang, Q.; Pelker, J.; Marusic, S.; Hus, S.; Hall, J. P.; Telliez, J. B.; Cui, J.;
Li, L.L. “Selective Inhibitors of Tumor Progression Loci-2 (Tpl2) Kinase with Potent Inhibition
of TNF- Production in Human Whole Blood.” Bioorg. Med. Chem. Lett. 2009, 19(13), 3485.
Huang, A.; Joseph-McCarthy, D.; Lovering, F.; Sun, L.; Wang, W.; Xu, W.; Zhu, Y.; Cui, J.;
Zhang, Y.; Levin, J. “Structure-based design of TACE selective inhibitors: Manipulations in the
S1'-S3' pocket.” Bioorg. Med. Chem. 2007, 15(18), 6170.
Green, N.; Hu, Y.; Janz, K.; Li, H.; Kaila, N.; Guler, S.; Thomason, J.; Joseph-McCarthy, D.;
Tam, S.; Hotchandani, R.; Huang, A.; Wang, Q.; Leung, L.; Pelker, J.; Marusic, S.; Hsu, S.;
Telliez, J.; Hall, P.; Cuozzo, J.; Lin, L. “Inhibitors of Tpl2 Kinase and TNF- Production:
Selectivity and In Vivo Anti-inflammatory Activity of Novel 8-substituted-4-anilino-6aminoquinoline-3-carbonitriles.” J. Med. Chem. 2007, 50(19), 4728.
Kaila, N.; Janz, K.; Huang, A.; Moretto, A.; DeBernardo, S.; Bedard, P.W.; Tam, S.; Clerin, V.;
Keith Jr.; J. C.; Tsao, D. H. H.; Sushkova, N.; Shaw, G.; Camphausen, R. T.; Schaub, R. G.;
Wang, Q. “2-(4-Chlorobenzyl)-3-Hydroxy-7,8,9,10-Tetrahydrobenzo[H]Quinoline-4-Carboxylic
Acid (PSI-697): Identification Of A Clinical Candidate From The Quinoline Salicylic Acid Series
Of P-Selectin Antagonists.” J. Med. Chem. 2007, 50(1), 40.
Lombart, H.; Feyfant, E.; Joseph-McCarthy, D.; Huang, A.; Lovering, F.; Sun, L.; Zhu, Y.; Zeng,
C.; Zhang, Y.; Levin, J. “Design and Synthesis of 3,3-Piperidine Hydroxamate Analogs as
Selective TACE Inhibitors.” Bioorg. Med. Chem. Lett. 2007, 17, 4333.
Joseph-McCarthy, D.; Parris, K.; Huang, A.; Failli, A.; Quagliato, D.; Dushin, E. G.; Novikova,
E.; Severina, E.; Tuckman, M.; Petersen, P. J.; Dean, C.; Fritz, C. C.; Meshulam, T.; DeCenzo,
M.; Dick, L.; McFadyen, I. J.; Somers, W. S.; Lovering, F.; Gilbert, A. M. “Use of StructureBased Drug Design Approaches to Obtain Novel Anthranilic Acid Acyl Carrier Protein Synthase
Inhibitors.” J. Med. Chem., 2005, 48(25), 7960.
Jung, M. E.; Huang, A.; Johnson, T. “Unusual Diastereoselectivity in Intramolecular DielsAlder Reactions of Substituted 3, 5-Hexadienyl Acrylates. Preference for a Boat-like Structure of
the Six-Atom Tether due to Ester Overlap.” Org. Lett. 2000, 2(13), 1835.
Jung, M. E.; Huang A. “Use of Optically Active Imidazolidines in Asymmetric Induction.” Org.
Lett. 2000, 2(17), 2659.
Fleming, F.; Huang, A.; Sharuef, V.; Pu, Y. “Unsaturated nitriles: Procedures for a Domino
Ozonolysis-Aldol Syntheses of Oxonitriles.” J. Org. Chem., 1999, 64, 2830.
Huang, A.; Marcone, J.; Mason, K.; Marshall, W.; Moloy, K. “N-Pyrrolyl Phosphines: Enhanced
π-Acceptor Character via Carboalkoxy-Substitution.” Organometallics, 1997, 16, 3377.
Fleming, F.; Huang, A.; Sharief, V.; Pu, Y. “Unsaturated Nitriles: A Domino Ozonolysis-Aldol
Syntheses of Highly Reactive Oxonitriles.” J. Org. Chem. 1997, 62, 3036.
Tzou, J.; Huang, A.; Fleming , F.; Norman, R.; Chang, S. Acta Crystallogr. Sect. C. 1996, C52,
Book Title: Anti-Inflammatory Drug Discovery. Chapter 10 “Bruton’s Tyrosine Kinase
(BTK)” by Mark Schnute, Adrian Huang, and Eddine Saiah. Editors: J. I. Levin; S. Laufer.
ISBN: 978-1-84973-534-6, DOI:10.1039/9781849735346. Publisher: Royal Society of
Adrian Huang, Ph.D.
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Chemistry Royal Society of Chemistry, Thomas Graham House, Science Park, Cambridge, CB4
0WF, UK, 2012.
Saiah, E.; Li, H.; Huang, A. “Method for Preparing Halogenated Amines” US Patent Application
No. 2008/188659.
Kaila, N.; Huang, A.; Bedard, P. “Preparation of substituted 3-hydroxy-4-quinolinecarboxylic
acids as selectin inhibitors.” US Patent Application No. 2008/0242700.
Kaila, N.; Janz, K.; Huang, A.; Moretto, A.; Janz, K.; Bedard, P. “Preparation of quinoline
compounds as selectin inhibitors for disease treatment.” International Patent Application
Publication No. WO/2008/121817.
Kaila, N.; Debernardo, S.; Janz, K.; Camphausen, R.; Bedard, P.; Huang, A. “Preparation of
fused quinoline derivatives as selectin inhibitors.” US Patent Application No. 2005/101569.