Cyclooctatetraene: A Bioactive Cubane Paradigm Complement.

Authors :: 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
Source :: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2019 Feb 21; Vol. 25 (11), pp. 2729-2734. Date of Electronic Publication: 2019 Jan 25.
Publication Year :: 2019
Abstract: 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.<br /> (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)