Ian Rosenstein, Chair
(315) 859-4730

Chemistry Department
Hamilton College
198 College Hill Road
Clinton, NY 13323


Max Majireck, Organic Chemistry

Assistant Professor                             

Office: Science Center 1073
Phone: 315-859-4742
Email: mmajirec@hamilton.edu

At Hamilton since 2013

EDUCATION

B.S. in Biochemistry, Grove City College (Charles E. Kriley)

Ph.D. in Organic Chemistry, Pennsylvania State University (Steven M. Weinreb)

Postdoctoral Research in Chemical Biology, Harvard University / Broad Institute (Stuart L. Schreiber)

 

COURSES

Chem 190 - Organic Chemistry I

Chem 255 - Organic Chemistry II

Chem 360 - Organic Synthesis Towards Improved Human Health

Chem 371 - Research Methods in Chemistry

 

RESEARCH

Research Interests:  Organic synthesis, medicinal chemistry, natural products, chemical biology.

Research in the Majireck group aims to (1) develop new methodologies for synthesis of biologically interesting small molecules and (2) openly collaborate with the biomedical research community to identify small molecule probes of human disease biology.

Toward our first aim, we have recently identified a rapid approach to biologically active dihydropyrimidines (DHPs).  Similar compounds (mainly pyrimidines) are known to exhibit anti-cancer and/or anti-infective properties, often by acting as cytotoxic anti-metabolites within pathogenic cells.  Our strategy enables access to the structurally-related, but synthetically challenging DHP scaffolds which we intend to evaluate for their activity in relevant biological assays.

A second project utilizes recently developed transition-metal catalysis to synthesize a collection of N-(2-alkoxyvinyl)sulfonamides.  We hypothesize that derivatives of such compounds may serve as useful biological probes of metal-binding proteins such as histone deacetylases, an essential family of chromatin-modifying enzyme involved in epigenetic regulation.

In other work, our lab is developing a general approach for the synthesis of neuroactive alkaloids related to indolizidine.  Using structure-activity relationships, we hope to identify critical factors that enable blood-brain-barrier penetrance within this class of compound.  As probes, these alkaloids may be useful for studying the role(s) of key nodes (e.g. G-protein-coupled receptors or ion-channels) within the complex cell circuitry of the brain.

Compounds synthesized by our lab will be screened for biological activity, both at Hamilton College and at non-profit biomedical research institutes such as the Broad Institute of Harvard & MIT and MIT’s Koch Institute for Integrative Cancer Research.

 

AWARDS AND HONORS

2017  New York Six (NY6) New Academic Working Group Seed Grant

2015  Class of 1963 Excellence in Teaching Award; Hamilton College

2015  Sigma Xi Grants-in-Aid of Research (Awarded to group member Ben Wesley)

2015  Social Innovation and Transformational Leadership Grant; Sponsored by the Levitt Center & DOF at Hamilton College

2014  Class of 1966 Career Development Award; Hamilton College

2013  Leukemia & Lymphoma Society Postdoctoral Fellowship (Declined to accept tenure track position at Hamilton College)

2013  American Chemical Society CIBA/YCC Young Scientist Travel Award

2012  Broad Institute Spot Award; Employee/Student Recognition Program

2012  American Chemical Society Travel Award for Postdoc to Faculty Workshop

2010  Braucher Research Award; Pennsylvania State University

2007  Dan Waugh Memorial Teaching Award; Pennsylvania State University

2005  First Year Graduate Student Fellowship; Pennsylvania State University

2005  Swezey-Janicki Research Award; Grove City College

2004  Sigma Xi Induction, The Scientific Research Society

2003  Kemikos Honor Society; Grove City College

2004  Marie C. Lush Scholarship; Grove City College

2001 – 2005  CONSOL Energy College Scholarship; selected by the National Merit Scholarship Corporation

 

PUBLICATIONS

11. Bennett, J. B.; Shapiro, J. D.; Choinski, K. N.; Mei, Y.; Aulita, S. M.; Dominguez, G. M.; Majireck, M. M. "Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and subsequent conversion to substituted phthalans and phenethylamines" J. Vis. Exp. 2017, accepted, in press.

10. Bennett, J. B.; Shapiro, J. D.; Choinski, K. N.; Mei, Y.; Aulita, S. M.; Reinheimer, E. W.; Majireck, M. M. "Synthesis of phthalan and phenethylamine derivatives via addition of alcohols to rhodium(II)-azavinyl carbenoids" Tetrahedron Lett. 2017, 58, 1117.

9. Chattopadhyay, S.; Stewart, A. L.; Mukherjee, S.; Huang, C.; Hartwell, K. A.; Miller, P. G.; Subramanian, R.; Carmody, L.; Yusuf, R. Z.; Sykes, D. B.; Paulk, J.; Vetere, A.; Vallet, S.; Santo, L.; Cirstea, D.; Hideshima, T.; Dancik, V.; Majireck, M. M.; Hussain, M. M.; Singh, S.; Quiroz, R.; Iaconelli, J.; Karmacharya, R.; Tolliday, N. J.; Clemons, P. A.; Kapoor, T. M.; Moore, M. A. S.; Stern, A. M.; Shamji, A. F.; Ebert, B. L.; Golub, T. R.; Raje, N. S.; Scadden, D. T.; Schreiber, S. L. “Niche-Based Screening in Multiple Myeloma Identifies a Novel Kinesin-5 Inhibitor with Improved Selectivity over Hematopoietic Progenitors” Cell Reports, 201510,  755.

8. Feng, Y.; Majireck, M. M.; Weinreb, S. M. “Total Syntheses of the Monoterpene Indole Alkaloids (±)-Alstilobanine A and E and (±)-Angustilodine” J. Org. Chem. 2014, 79, 7. [Featured Article]

7. Feng, Y.; Majireck, M. M.; Weinreb, S. M. “Total Synthesis of the Unusual Monoterpenoid Indole Alkaloid (±)-Alstilobanine A” Angew. Chem. Int. Ed. 2012, 51, 12846; Angew. Chem. 2012, 124, 13018.

6. Chauhan, P. S.; Majireck, M. M.; Weinreb, S. M. “Regioselective alpha-monochlorination of N-protected-3-piperidones” Heterocycles 2011, 84, 577.

5. Majireck, M. M.; Witek, J. A.; Weinreb, S. M.  “An expedient reductive method for conversion of ketoximes to the corresponding carbonyl compounds” Tetrahedron Lett. 2010, 51, 3555.

4. Li, P.; Majireck, M. M.; Witek, J. A.; Weinreb, S. M.  “Efficient methodology for alkylation of vinylnitroso compounds with carbon nucleophiles” Tetrahedron Lett. 2010, 51, 2032.

3. Li, P.; Majireck, M. M.; Korboukh, I.; Weinreb, S. M.  “A mild, efficient method for the oxidation of alpha-diazo-beta-hydroxyesters to alpha-diazo-beta-ketoesters” Tetrahedron Lett. 2008, 49, 3162.

2. Majireck, M. M.; Weinreb, S. M.   “A study of the scope and regioselectivity of the ruthenium-catalyzed [3 + 2]-cycloaddition of azides with internal alkynes” J. Org. Chem. 2006, 71, 8680.  [Over 170 citations]

1. Kriley, C. E.; Majireck, M. M.; Tobolewski, J. M.; Kelvington, L. E.; Cummings, S. H.; Hershberger, S. J.; Link, J. D.; Silverio, A. L.; Fanwick, P. E.; Rothwell, I. P.  “Synthesis and characterization of two novel cobalt (II) phosphine complexes: crystal structures of [CoCl3(Cy2PCH2PCy2H)] and [Co(NO3)2(Cy2PCH2PCy2O)]. Cy = cyclohexyl, C6H11”  Inorg. Chim. Acta  2005, 358,  57.