24539-28-4Relevant articles and documents
Systematic Substitution on the Cubane Nucleus: Steric and Electronic Effects
Eaton, Philip E.,Xiong, Yusheng,Zhou, Jian Ping
, p. 4277 - 4281 (1992)
Effective methodology for the synthesis of cubanes with novel substitution patterns is presented.The use of an electron-withdrawing group to accelerate ortho-metalation of amide-activated cubanes is described, as is the effect of the steric bulk of the activating group on the degree of ortho-metalation.
Thermo-cage opening of 4-iodo-1-vinylcubane to a novel styrene derivative
Carroll, Vincent M.,Harpp, David N.,Priefer, Ronny
, p. 2677 - 2680 (2008)
Cubane (1) and its derivatives have been cited for exhibiting unusual properties, including explosive and antiviral activity. An additional characteristic of these compounds is their tendency to undergo cage opening under certain conditions. In our attempt to polymerize 4-iodo-1-vinylcubane (4), 4-vinyl-trans-β-iodostyrene (10) was formed quantitatively. By examining both the thermolytic and Lewis acid-assisted rates, a possible mechanism for the rearrangement of 4→10 has been proposed.
Determining the necessity of phenyl ring π-character in warfarin
Xing, Hui,Houston, Sevan D.,Chen, Xuejie,Jin, Da-Yun,Savage, G. Paul,Tie, Jian-Ke,Williams, Craig M.
, p. 1954 - 1956 (2019)
Despite the difficulty in administering a safe dose regimen and reports of emerging resistance, warfarin (1) remains the most widely-used oral anticoagulant for the prevention and treatment of thrombosis in humans globally. 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 steric and electronic properties of the phenyl pharmacophore. The tolerance of VKOR to further functional group modification (carboxylate 14, PTAD adduct 15) was also investigated. The results demonstrate the importance of both annulene conferred π-interactions and ring size in the activity of warfarin.
Indoleamine 2,3-dioxygenase inhibitor
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Paragraph 0217-0220, (2020/12/30)
The invention provides a novel compound capable of inhibiting activity of indoleamine 2,3-dioxygenase (IDO), a pharmaceutical composition containing the compound, a preparation method of the compoundand application of the compound in preparation of drugs for treating proliferative diseases, infectious diseases, immune-related diseases and/or inflammatory diseases.
Cyclooctatetraene: A Bioactive Cubane Paradigm Complement
Xing, Hui,Houston, Sevan D.,Chen, Xuejie,Ghassabian, Sussan,Fahrenhorst-Jones, Tyler,Kuo, Andy,Murray, Cody-Ellen P.,Conn, Kyna-Anne,Jaeschke, Kara N.,Jin, Da-Yun,Pasay, Cielo,Bernhardt, Paul V.,Burns, Jed M.,Tsanaktsidis, John,Savage, G. Paul,Boyle, Glen M.,De Voss, James J.,McCarthy, James,Walter, Gimme H.,Burne, Thomas H. J.,Smith, Maree T.,Tie, Jian-Ke,Williams, Craig M.
supporting information, p. 2729 - 2734 (2019/02/03)
Cubane was recently validated as a phenyl ring (bio)isostere, but highly strained caged carbocyclic systems lack π character, which is often critical for mediating key biological interactions. This electronic property restriction associated with cubane has been addressed herein with cyclooctatetraene (COT), using known pharmaceutical and agrochemical compounds as templates. COT either outperformed or matched cubane in multiple cases suggesting that versatile complementarity exists between the two systems for enhanced bioactive molecule discovery.
Enantioselective synthesis of (: R)-2-cubylglycine including unprecedented rhodium mediated C-H insertion of cubane
Houston, Sevan D.,Chalmers, Benjamin A.,Savage, G. Paul,Williams, Craig M.
supporting information, p. 1067 - 1070 (2019/02/07)
The first enantioselective synthesis of (R)-2-cubylglycine, an analogue of (R)-2-phenylglycine in which the phenyl ring has been replaced by cubane, is disclosed. The key step was a telescoped Strecker reaction using (S)-2-amino-2-phenylethanol as a chiral auxiliary. Exploration of an alternative synthetic approach resulted in unprecedented cubane C-H insertion.