Synthesis of isoprenoid bisphosphonate ethers through C–P bond formations: Potential inhibitors of geranylgeranyl diphosphate synthase

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• Pham, A. C.; Holstein, S. A.; Borgstahl, G. E. O. Structural Insight into Geranylgeranyl Diphosphate Synthase (GGDPS) for Cancer Therapy. Molecular cancer therapeutics 2023, 23, 14–23. doi:10.1158/1535-7163.mct-23-0358
• Ebetino, F. H.; Sun, S.; Cherian, P.; Roshandel, S.; Neighbors, J. D.; Hu, E.; Dunford, J. E.; Sedghizadeh, P. P.; McKenna, C. E.; Srinivasan, V.; Boeckman, R. K.; Russell, R. G. G. Bisphosphonates: The role of chemistry in understanding their biological actions and structure-activity relationships, and new directions for their therapeutic use. Bone 2021, 156, 116289. doi:10.1016/j.bone.2021.116289
• Gendaszewska-Darmach, E.; Garstka, M. A.; Błażewska, K. M. Targeting Small GTPases and Their Prenylation in Diabetes Mellitus. Journal of medicinal chemistry 2021, 64, 9677–9710. doi:10.1021/acs.jmedchem.1c00410
• Ambrosi, A.; Bringley, D.; Calimsiz, S.; Garber, J. A. O.; Huynh, H. V.; Mohan, S.; Sarma, K.; Shen, J.; Curl, J. W.; Kwong, B.; Lapina, O.; Leung, E.; Lin, L.; Martins, A. A.; McGinitie, T. M.; Phull, J.; Roberts, B.; Rosario, M.; Shi, B.; Standley, E. A.; Wang, L.; Wang, X.; Yu, G. Synthesis of Rovafovir Etalafenamide (Part III): Evolution of the Synthetic Process to the Phosphonamidate Fragment. Organic Process Research & Development 2021, 25, 1247–1262. doi:10.1021/acs.oprd.0c00428
• Goetz, D. B.; Varney, M. L.; Wiemer, D. F.; Holstein, S. A. Amides as bioisosteres of triazole-based geranylgeranyl diphosphate synthase inhibitors. Bioorganic & medicinal chemistry 2020, 28, 115604. doi:10.1016/j.bmc.2020.115604
• Manaswiyoungkul, P.; de Araujo, E. D.; Gunning, P. T. Targeting prenylation inhibition through the mevalonate pathway. RSC medicinal chemistry 2020, 11, 51–71. doi:10.1039/c9md00442d
• Abdelmagid, W. M.; Adak, T.; Freeman, J. O.; Tanner, M. E. Studies with Guanidinium- and Amidinium-Based Inhibitors Suggest Minimal Stabilization of Allylic Carbocation Intermediates by Dehydrosqualene and Squalene Synthases. Biochemistry 2018, 57, 5591–5601. doi:10.1021/acs.biochem.8b00731
• Abdou, W. M.; Ganoub, N. A. F.; Ismail, M.; Sabry, E.; Barghash, R. F.; Geronikaki, A. Developing efficient protocols for synthesis, antiosteoarthritic, antiinflammatory assessments and docking studies of nitrogen-containing bisphosphonate derivatives. Arabian Journal of Chemistry 2017, 10, 1084–1097. doi:10.1016/j.arabjc.2016.02.019
• Sevrain, C. M.; Berchel, M.; Couthon, H.; Jaffrès, P.-A. Phosphonic acid: Preparation and applications. Beilstein journal of organic chemistry 2017, 13, 2186–2213. doi:10.3762/bjoc.13.219
• Khomich, O. A.; Yanvarev, D. V.; Novikov, R. A.; Kornev, A. B.; Puljulla, E.; Vepsäläinen, J.; Khomutov, A. R.; Kochetkov, S. N. On the Reaction of Carbonyl Diphosphonic Acid with Hydroxylamine and O-alkylhydroxylamines: Unexpected Degradation of P-C-P Bridge. Molecules (Basel, Switzerland) 2017, 22, 1040. doi:10.3390/molecules22071040
• Haney, S. L.; Wills, V. S.; Wiemer, D. F.; Holstein, S. A. Recent Advances in the Development of Mammalian Geranylgeranyl Diphosphate Synthase Inhibitors. Molecules (Basel, Switzerland) 2017, 22, 886. doi:10.3390/molecules22060886
• De Luca, L.; Chiminazzo, A.; Sperni, L.; Strukul, G.; Scarso, A. Pyrrolidine-Containing Bisphosphonates as Potential Anti-Resorption Bone Drugs. Chemistry (Weinheim an der Bergstrasse, Germany) 2017, 23, 3474–3478. doi:10.1002/chem.201605878
• Allen, C.; Kortagere, S.; Tong, H.; Matthiesen, R. A.; Metzger, J. I.; Wiemer, D. F.; Holstein, S. A. Olefin Isomers of a Triazole Bisphosphonate Synergistically Inhibit Geranylgeranyl Diphosphate Synthase. Molecular pharmacology 2017, 91, 229–236. doi:10.1124/mol.116.107326
• Matthiesen, R. A.; Wills, V. S.; Metzger, J. I.; Holstein, S. A.; Wiemer, D. F. Stereoselective Synthesis of Homoneryl and Homogeranyl Triazole Bisphosphonates. The Journal of organic chemistry 2016, 81, 9438–9442. doi:10.1021/acs.joc.6b01693
• Foust, B. J.; Allen, C.; Holstein, S. A.; Wiemer, D. F. A new motif for inhibitors of geranylgeranyl diphosphate synthase. Bioorganic & medicinal chemistry 2016, 24, 3734–3741. doi:10.1016/j.bmc.2016.06.019
• Teixeira, F. C.; Lucas, C.; Curto, M. J. M.; Teixeira, A. P. S.; Duarte, M. T.; André, V. Novel Bisphosphonates Derived from 1H‐Indazole, 1H‐Pyrazolo[3,4‐b]Pyridine, and 1H‐Pyrazolo[3,4‐b]Quinoline. Heteroatom Chemistry 2015, 27, 3–11. doi:10.1002/hc.21282
• Reilly, J. E.; Neighbors, J. D.; Tong, H.; Henry, M. D.; Hohl, R. J. Targeting geranylgeranylation reduces adrenal gland tumor burden in a murine model of prostate cancer metastasis. Clinical & experimental metastasis 2015, 32, 555–566. doi:10.1007/s10585-015-9727-0
• Reilly, J. E.; Zhou, X.; Tong, H.; Kuder, C. H.; Wiemer, D. F.; Hohl, R. J. In vitro studies in a myelogenous leukemia cell line suggest an organized binding of geranylgeranyl diphosphate synthase inhibitors. Biochemical pharmacology 2015, 96, 83–92. doi:10.1016/j.bcp.2015.04.009
• Reilly, J. E. Ph.D. Thesis, The University of Iowa, . doi:10.17077/etd.31qmwi51

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