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Page 1
9-Azahomocubane.
Fahrenhorst-Jones T, Marshall DL, Burns JM, Pierens GK, Van Meurs DP, Kong D, Bernhardt PV, Blanksby SJ, Savage GP, Eaton PE, Williams CM. Fahrenhorst-Jones T, et al. Chemistry. 2024 Jan 11;30(3):e202303133. doi: 10.1002/chem.202303133. Epub 2023 Nov 20. Chemistry. 2024. PMID: 37823679
Cubane: 50 years later.
Biegasiewicz KF, Griffiths JR, Savage GP, Tsanaktsidis J, Priefer R. Biegasiewicz KF, et al. Chem Rev. 2015 Jul 22;115(14):6719-45. doi: 10.1021/cr500523x. Epub 2015 Jun 23. Chem Rev. 2015. PMID: 26102302 Review. No abstract available.
Cyclooctatetraene: A Bioactive Cubane Paradigm Complement.
Xing H, Houston SD, Chen X, Ghassabian S, Fahrenhorst-Jones T, Kuo A, Murray CP, Conn KA, Jaeschke KN, Jin DY, Pasay C, Bernhardt PV, Burns JM, Tsanaktsidis J, Savage GP, Boyle GM, De Voss JJ, McCarthy J, Walter GH, Burne THJ, Smith MT, Tie JK, Williams CM. Xing H, et al. Chemistry. 2019 Feb 21;25(11):2729-2734. doi: 10.1002/chem.201806277. Epub 2019 Jan 25. Chemistry. 2019. PMID: 30681236 Free PMC article.
Cubane was recently validated as a phenyl ring (bio)isostere, but highly strained caged carbocyclic systems lack pi character, which is often critical for mediating key biological interactions. ...COT either outperformed or matched cubane in multiple cases suggestin …
Cubane was recently validated as a phenyl ring (bio)isostere, but highly strained caged carbocyclic systems lack pi character, which …
The cubane paradigm in bioactive molecule discovery: further scope, limitations and the cyclooctatetraene complement.
Houston SD, Fahrenhorst-Jones T, Xing H, Chalmers BA, Sykes ML, Stok JE, Farfan Soto C, Burns JM, Bernhardt PV, De Voss JJ, Boyle GM, Smith MT, Tsanaktsidis J, Savage GP, Avery VM, Williams CM. Houston SD, et al. Org Biomol Chem. 2019 Jul 17;17(28):6790-6798. doi: 10.1039/c9ob01238a. Org Biomol Chem. 2019. PMID: 31241113
This investigation highlights the scope and limitations of incorporating cubane into bioactive molecule discovery, both in terms of synthetic compatibility and physical property matching. Cubane maintained bioisosterism in the case of the Chagas disease antiparasiti …
This investigation highlights the scope and limitations of incorporating cubane into bioactive molecule discovery, both in terms of s …
Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere.
Chalmers BA, Xing H, Houston S, Clark C, Ghassabian S, Kuo A, Cao B, Reitsma A, Murray CE, Stok JE, Boyle GM, Pierce CJ, Littler SW, Winkler DA, Bernhardt PV, Pasay C, De Voss JJ, McCarthy J, Parsons PG, Walter GH, Smith MT, Cooper HM, Nilsson SK, Tsanaktsidis J, Savage GP, Williams CM. Chalmers BA, et al. Angew Chem Int Ed Engl. 2016 Mar 7;55(11):3580-5. doi: 10.1002/anie.201510675. Epub 2016 Feb 5. Angew Chem Int Ed Engl. 2016. PMID: 26846616
Herein, we report the validation of Eaton's hypothesis with cubane derivatives of five molecules that are used clinically or as agrochemicals. Two cubane analogues showed increased bioactivity compared to their benzene counterparts whereas two further analogues disp …
Herein, we report the validation of Eaton's hypothesis with cubane derivatives of five molecules that are used clinically or as agroc …
Electrochemical investigation of Mn4O4-cubane water-oxidizing clusters.
Brimblecombe R, Bond AM, Dismukes GC, Swiegers GF, Spiccia L. Brimblecombe R, et al. Phys Chem Chem Phys. 2009 Aug 14;11(30):6441-9. doi: 10.1039/b901419e. Epub 2009 May 26. Phys Chem Chem Phys. 2009. PMID: 19809676
A comparison of catalytic photocurrent generated by films deposited by two methods of electrode immobilization reveals that doping of the catalyst in Nafion results in higher photocurrent than was observed for a solid layer of cubane on an electrode surface. In dichloromet …
A comparison of catalytic photocurrent generated by films deposited by two methods of electrode immobilization reveals that doping of the ca …
Determining the necessity of phenyl ring π-character in warfarin.
Xing H, Houston SD, Chen X, Jin DY, Savage GP, Tie JK, Williams CM. Xing H, et al. Bioorg Med Chem Lett. 2019 Aug 1;29(15):1954-1956. doi: 10.1016/j.bmcl.2019.05.039. Epub 2019 May 23. Bioorg Med Chem Lett. 2019. PMID: 31147103 Free PMC article.
Systematic substitution of the warfarin phenyl ring with either 1,3,5,7-cyclooctatetraene (COT) (2), cubane (3), cyclohexane (4) or cyclooctane (5) and subsequent evaluation against the target enzyme, vitamin K epoxide reductase (VKOR), facilitated interrogation of both st …
Systematic substitution of the warfarin phenyl ring with either 1,3,5,7-cyclooctatetraene (COT) (2), cubane (3), cyclohexane (4) or c …
Cyclooctatetraenes through Valence Isomerization of Cubanes: Scope and Limitations.
Houston SD, Xing H, Bernhardt PV, Vanden Berg TJ, Tsanaktsidis J, Savage GP, Williams CM. Houston SD, et al. Chemistry. 2019 Feb 21;25(11):2735-2739. doi: 10.1002/chem.201805124. Epub 2019 Jan 29. Chemistry. 2019. PMID: 30693963
The scope and limitations of Eaton's rhodium(I)-catalyzed valence isomerization of cubane to cyclooctatetraene (COT) were investigated in the context of functional group tolerability, multiple substitution modes and the ability of cubane-alcohols to undergo one-pot …
The scope and limitations of Eaton's rhodium(I)-catalyzed valence isomerization of cubane to cyclooctatetraene (COT) were investigate …
Cage hydrocarbons as linkers in dimeric drug design: Case studies with trimethoprim and tedizolid.
Vujcic B, Wyllie J, Tania, Burns J, White KF, Cromwell S, Lupton DW, Dutton JL, Soares da Costa TP, Houston SD. Vujcic B, et al. Bioorg Med Chem Lett. 2023 Jan 15;80:129086. doi: 10.1016/j.bmcl.2022.129086. Epub 2022 Nov 21. Bioorg Med Chem Lett. 2023. PMID: 36423825
This is exemplified by dimerization, a design concept in which two pharmacophores are covalently linked to form a new chemical entity. The cage hydrocarbons cubane (1), bicyclo[2.2.2]octane (BCO) (2), adamantane (3), and bicyclo[1.1.1]pentane (BCP) (4) present themselves a …
This is exemplified by dimerization, a design concept in which two pharmacophores are covalently linked to form a new chemical entity. The c …
Nonclassical Phenyl Bioisosteres as Effective Replacements in a Series of Novel Open-Source Antimalarials.
Tse EG, Houston SD, Williams CM, Savage GP, Rendina LM, Hallyburton I, Anderson M, Sharma R, Walker GS, Obach RS, Todd MH. Tse EG, et al. J Med Chem. 2020 Oct 22;63(20):11585-11601. doi: 10.1021/acs.jmedchem.0c00746. Epub 2020 Sep 30. J Med Chem. 2020. PMID: 32678591
The replacement of one chemical motif with another that is broadly similar is a common method in medicinal chemistry to modulate the physical and biological properties of a molecule (i.e., bioisosterism). In recent years, bioisosteres such as cubane and bicyclo[1.1.1]penta …
The replacement of one chemical motif with another that is broadly similar is a common method in medicinal chemistry to modulate the physica …
21 results