Douglas Stack, Ph.D.
- Professor
- 351 DSC
- Organic Chemistry
Additional Information
Research Interests
My current research involves the chemistry of o-quinones as both toxic metabolites and synthetic precursors to produce novel organic structures. In addition, our lab uses computational methods to gain insights into the chemistry of a variety of organic reactions.Publications
Leas, D. A.; Dong, Y.; Garrison, J. C.; Wang, X.; Ezell, E. L.; Stack, D. E.; Vennerstrom, J. L., Tricyclic Imidazolidin-4-ones by Witkop Oxidation of Tetrahydro-β-carbolines. The Journal of Organic Chemistry 2020, in press.
Stack, D. E.; Mahmud, B., Efficient access to bisphenol A metabolites: synthesis of monocatechol, mono-o-quinone, dicatechol, and di-o-quinone of bisphenol A. Synth. Commun. 2018, 48 (2), 161-167.
Stack, D. E.; Conrad, J. A.; Mahmud, B., Structural Identification and Kinetic Analysis of the in Vitro Products Formed by Reaction of Bisphenol A-3,4-quinone with N-Acetylcysteine and Glutathione. Chem. Res. Toxicol. 2018, 31 (2), 81-87.
Wu, J.; Leas, D. A.; Dong, Y.; Wang, X.; Ezell, E. L.; Vennerstrom, J. L.; Stack, D. E., Synthesis of 2-Azaadamantan-6-one: A Missing Isomer. ACS Omega 2018, 3 (9), 11362-11367.
Leas, D. A.; Dong, Y.; Vennerstrom, J. L.; Stack, D. E., One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides. Organic Letters 2017, 19 (10), 2518-2521.
Stack, D. E.; Eastman, R., NMR analysis of t-butyl-catalyzed deuterium exchange at unactivated arene localities. Journal of Labelled Compounds and Radiopharmaceuticals 2016, 59 (12), 500-505.
Stack, D., Identifying the Tautomeric Form of a Deoxyguanosine-Estrogen Quinone Intermediate. Metabolites 2015, 5 (3), 475.
Stack, D. E.; Ritonya, J.; Jakopovic, S.; Maloley-Lewis, B., Regioselective deuterium labeling of estrone and catechol estrogen metabolites. Steroids 2014, 92 (0), 32-38.
Stack, D. E.; Li, G.; Hill, A.; Hoffman, N., Mechanistic Insights into the Michael Addition of Deoxyguanosine to Catechol Estrogen-3,4-quinones. Chem. Res. Toxicol. 2008, 21 (7), 1415-1425.
Stack, D. E.; Hill, A. L.; Diffendaffer, C. B.; Burns, N. M., Synthesis of a New Fluorescent Probe Specific for Catechols. Organic Letters 2002, 4 (25), 4487-4490.
Jankowiak, R.; Zamzow, D.; Stack, D. E.; Todorovic, R.; Cavalieri, E. L.; Small, G. J., Spectral Characterization of Fluorescently Labeled Catechol Estrogen 3,4-Quinone-Derived N7 Guanine Adducts and Their Identification in Rat Mammary Gland Tissue. Chem. Res. Toxicol. 1998, 11 (11), 1339-1345.
Cao, K.; Stack, D. E.; Ramanathan, R.; Gross, M. L.; Rogan, E. G.; Cavalieri, E. L., Synthesis and Structure Elucidation of Estrogen Quinones Conjugated with Cysteine, N-Acetylcysteine, and Glutathione. Chem. Res. Toxicol. 1998, 11 (8), 909-916.
Jan, S.-T.; Devanesan, P. D.; Stack, D. E.; Ramanathan, R.; Byun, J.; Gross, M. L.; Rogan, E. G.; Cavalieri, E. L., Metabolic Activation and Formation of DNA Adducts of Hexestrol, a Synthetic Nonsteroidal Carcinogenic Estrogen. Chem. Res. Toxicol. 1998, 11 (5), 412-419.
Stack, D. E.; Cavalieri, E. L.; Rogan, E. G., Catecholestrogens as procarcinogens: depurinating adducts and tumor initiation. Advances in Pharmacology (San Diego) 1998, 42 (Catecholamines), 833-836.
Cavalieri, E. L.; Stack, D. E.; Devanesan, P. D.; Todorovic, R.; Dwivedy, I.; Higginbotham, S.; Johansson, S. L.; Patil, K. D.; Gross, M. L.; et al., Molecular origin of cancer: catechol estrogen-3,4-quinones as endogenous tumor initiators. Proc. Natl. Acad. Sci. U. S. A. 1997, 94 (20), 10937-10942.
Casale, G.; Rogan, E.; Stack, D.; Devanesan, P.; Cavalieri, E., Production and immunochemical characterization of a high-affinity monoclonal antibody specific for 7-(benzo[a]pyren-6-yl)guanine (BP-6-N7Gua), a depurinating DNA adduct of benzo[a]pyrene. Polycyclic Aromatic Compounds 1996, 10 (1-4), 195-201.
Casale, G. P.; Rogan, E. G.; Stack, D.; Devanesan, P.; Cavalieri, E. L., Production of a High-Affinity Monoclonal Antibody Specific for 7-(Benzo[a]pyren-6-yl)guanine and Its Application in a Competitive Enzyme-Linked Immunosorbent Assay. Chem. Res. Toxicol. 1996, 9 (6), 1037-1043.
Stack, D. E.; Byun, J.; Gross, M. L.; Rogan, E. G.; Cavalieri, E. L., Molecular Characteristics of Catechol Estrogen Quinones in Reactions with Deoxyribonucleosides. Chem. Res. Toxicol. 1996, 9 (5), 851-859.
Stack, D. E.; Cremonesi, P.; Hanson, A.; Rogan, E. G.; Cavalieri, E. L., Radical cations of benzo[a]pyrene and 6-substituted derivatives: reaction with nucleophiles and DNA. Xenobiotica 1995, 25 (7), 755-60.
Cremonesi, P.; Stack, D. E.; Rogan, E. G.; Cavalieri, E. L., Radical Cations of Benzo[a]pyrene and 6-Substituted Derivatives: Synthesis and Reaction with Nucleophiles. J. Org. Chem. 1994, 59 (25), 7683-7.
Stack, D. E. Advancements in active copper chemistry. 1993 (Ph.D. Thesis).
Stack, D. E.; Klein, W. R.; Rieke, R. D., Preparation of higher order cyano and non-ate allyl copper reagents from the reaction of allyl chlorides with a formal copper anion. Tetrahedron Lett. 1993, 34 (19), 3063-6.
Rieke, R. D.; Stack, D. E.; Dawson, B. T.; Wu, T. C., Preparation and chemistry of the active copper species derived from CuI.cntdot.PBu3, CuI.cntdot.PPh3, and CuCN.cntdot.nLiX complexes. J. Org. Chem. 1993, 58 (9), 2483-91.
Stack, D. E.; Rieke, R. D., Formation of a new bis-organocopper reagent from the reaction of 2,3-dichloropropene and highly active zero valent copper derived from a CuCN.cntdot.2LiCl complex. Tetrahedron Lett. 1992, 33 (44), 6575-8.
Stack, D. E.; Dawson, B. T.; Rieke, R. D., Direct formation of highly functionalized allylic organocopper reagents from allylic chlorides and acetates. J. Am. Chem. Soc. 1992, 114 (13), 5110-16.
Stack, D. E.; Dawson, B. T.; Rieke, R. D., Direct formation of functionalized and allylic organocopper reagents derived from a cuprous cyanide lithium bromide complex. J. Am. Chem. Soc. 1991, 113 (12), 4672-3.
Rieke, R. D.; Dawson, B. T.; Stack, D. E.; Stinn, D. E., Two-equivalent reduction of copper(I) complexes; evidence of an anionic copper species. Synth. Commun. 1990, 20 (17), 2711-21.
Patents
Cavalieri, E. L.; Casale, G. P.; Rogan, E. G.; Stack, D. E. Preparation of estrogen-purine base and estrogen-mercaptate adducts for use as fluorescent probes and monoclonal antibodies. 97-US67179740061, 19970421., 1997.
Additional Information
Research Interests
My current research involves the chemistry of o-quinones as both toxic metabolites and synthetic precursors to produce novel organic structures. In addition, our lab uses computational methods to gain insights into the chemistry of a variety of organic reactions.Publications
Leas, D. A.; Dong, Y.; Garrison, J. C.; Wang, X.; Ezell, E. L.; Stack, D. E.; Vennerstrom, J. L., Tricyclic Imidazolidin-4-ones by Witkop Oxidation of Tetrahydro-β-carbolines. The Journal of Organic Chemistry 2020, in press.
Stack, D. E.; Mahmud, B., Efficient access to bisphenol A metabolites: synthesis of monocatechol, mono-o-quinone, dicatechol, and di-o-quinone of bisphenol A. Synth. Commun. 2018, 48 (2), 161-167.
Stack, D. E.; Conrad, J. A.; Mahmud, B., Structural Identification and Kinetic Analysis of the in Vitro Products Formed by Reaction of Bisphenol A-3,4-quinone with N-Acetylcysteine and Glutathione. Chem. Res. Toxicol. 2018, 31 (2), 81-87.
Wu, J.; Leas, D. A.; Dong, Y.; Wang, X.; Ezell, E. L.; Vennerstrom, J. L.; Stack, D. E., Synthesis of 2-Azaadamantan-6-one: A Missing Isomer. ACS Omega 2018, 3 (9), 11362-11367.
Leas, D. A.; Dong, Y.; Vennerstrom, J. L.; Stack, D. E., One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides. Organic Letters 2017, 19 (10), 2518-2521.
Stack, D. E.; Eastman, R., NMR analysis of t-butyl-catalyzed deuterium exchange at unactivated arene localities. Journal of Labelled Compounds and Radiopharmaceuticals 2016, 59 (12), 500-505.
Stack, D., Identifying the Tautomeric Form of a Deoxyguanosine-Estrogen Quinone Intermediate. Metabolites 2015, 5 (3), 475.
Stack, D. E.; Ritonya, J.; Jakopovic, S.; Maloley-Lewis, B., Regioselective deuterium labeling of estrone and catechol estrogen metabolites. Steroids 2014, 92 (0), 32-38.
Stack, D. E.; Li, G.; Hill, A.; Hoffman, N., Mechanistic Insights into the Michael Addition of Deoxyguanosine to Catechol Estrogen-3,4-quinones. Chem. Res. Toxicol. 2008, 21 (7), 1415-1425.
Stack, D. E.; Hill, A. L.; Diffendaffer, C. B.; Burns, N. M., Synthesis of a New Fluorescent Probe Specific for Catechols. Organic Letters 2002, 4 (25), 4487-4490.
Jankowiak, R.; Zamzow, D.; Stack, D. E.; Todorovic, R.; Cavalieri, E. L.; Small, G. J., Spectral Characterization of Fluorescently Labeled Catechol Estrogen 3,4-Quinone-Derived N7 Guanine Adducts and Their Identification in Rat Mammary Gland Tissue. Chem. Res. Toxicol. 1998, 11 (11), 1339-1345.
Cao, K.; Stack, D. E.; Ramanathan, R.; Gross, M. L.; Rogan, E. G.; Cavalieri, E. L., Synthesis and Structure Elucidation of Estrogen Quinones Conjugated with Cysteine, N-Acetylcysteine, and Glutathione. Chem. Res. Toxicol. 1998, 11 (8), 909-916.
Jan, S.-T.; Devanesan, P. D.; Stack, D. E.; Ramanathan, R.; Byun, J.; Gross, M. L.; Rogan, E. G.; Cavalieri, E. L., Metabolic Activation and Formation of DNA Adducts of Hexestrol, a Synthetic Nonsteroidal Carcinogenic Estrogen. Chem. Res. Toxicol. 1998, 11 (5), 412-419.
Stack, D. E.; Cavalieri, E. L.; Rogan, E. G., Catecholestrogens as procarcinogens: depurinating adducts and tumor initiation. Advances in Pharmacology (San Diego) 1998, 42 (Catecholamines), 833-836.
Cavalieri, E. L.; Stack, D. E.; Devanesan, P. D.; Todorovic, R.; Dwivedy, I.; Higginbotham, S.; Johansson, S. L.; Patil, K. D.; Gross, M. L.; et al., Molecular origin of cancer: catechol estrogen-3,4-quinones as endogenous tumor initiators. Proc. Natl. Acad. Sci. U. S. A. 1997, 94 (20), 10937-10942.
Casale, G.; Rogan, E.; Stack, D.; Devanesan, P.; Cavalieri, E., Production and immunochemical characterization of a high-affinity monoclonal antibody specific for 7-(benzo[a]pyren-6-yl)guanine (BP-6-N7Gua), a depurinating DNA adduct of benzo[a]pyrene. Polycyclic Aromatic Compounds 1996, 10 (1-4), 195-201.
Casale, G. P.; Rogan, E. G.; Stack, D.; Devanesan, P.; Cavalieri, E. L., Production of a High-Affinity Monoclonal Antibody Specific for 7-(Benzo[a]pyren-6-yl)guanine and Its Application in a Competitive Enzyme-Linked Immunosorbent Assay. Chem. Res. Toxicol. 1996, 9 (6), 1037-1043.
Stack, D. E.; Byun, J.; Gross, M. L.; Rogan, E. G.; Cavalieri, E. L., Molecular Characteristics of Catechol Estrogen Quinones in Reactions with Deoxyribonucleosides. Chem. Res. Toxicol. 1996, 9 (5), 851-859.
Stack, D. E.; Cremonesi, P.; Hanson, A.; Rogan, E. G.; Cavalieri, E. L., Radical cations of benzo[a]pyrene and 6-substituted derivatives: reaction with nucleophiles and DNA. Xenobiotica 1995, 25 (7), 755-60.
Cremonesi, P.; Stack, D. E.; Rogan, E. G.; Cavalieri, E. L., Radical Cations of Benzo[a]pyrene and 6-Substituted Derivatives: Synthesis and Reaction with Nucleophiles. J. Org. Chem. 1994, 59 (25), 7683-7.
Stack, D. E. Advancements in active copper chemistry. 1993 (Ph.D. Thesis).
Stack, D. E.; Klein, W. R.; Rieke, R. D., Preparation of higher order cyano and non-ate allyl copper reagents from the reaction of allyl chlorides with a formal copper anion. Tetrahedron Lett. 1993, 34 (19), 3063-6.
Rieke, R. D.; Stack, D. E.; Dawson, B. T.; Wu, T. C., Preparation and chemistry of the active copper species derived from CuI.cntdot.PBu3, CuI.cntdot.PPh3, and CuCN.cntdot.nLiX complexes. J. Org. Chem. 1993, 58 (9), 2483-91.
Stack, D. E.; Rieke, R. D., Formation of a new bis-organocopper reagent from the reaction of 2,3-dichloropropene and highly active zero valent copper derived from a CuCN.cntdot.2LiCl complex. Tetrahedron Lett. 1992, 33 (44), 6575-8.
Stack, D. E.; Dawson, B. T.; Rieke, R. D., Direct formation of highly functionalized allylic organocopper reagents from allylic chlorides and acetates. J. Am. Chem. Soc. 1992, 114 (13), 5110-16.
Stack, D. E.; Dawson, B. T.; Rieke, R. D., Direct formation of functionalized and allylic organocopper reagents derived from a cuprous cyanide lithium bromide complex. J. Am. Chem. Soc. 1991, 113 (12), 4672-3.
Rieke, R. D.; Dawson, B. T.; Stack, D. E.; Stinn, D. E., Two-equivalent reduction of copper(I) complexes; evidence of an anionic copper species. Synth. Commun. 1990, 20 (17), 2711-21.
Patents
Cavalieri, E. L.; Casale, G. P.; Rogan, E. G.; Stack, D. E. Preparation of estrogen-purine base and estrogen-mercaptate adducts for use as fluorescent probes and monoclonal antibodies. 97-US67179740061, 19970421., 1997.