56061-32-6Relevant academic research and scientific papers
The first cns-active carborane: A novel p2x7 receptor antagonist with antidepressant activity
Wilkinson, Shane M.,Gunosewoyo, Hendra,Barron, Melissa L.,Boucher, Aurelie,McDonnell, Michelle,Turner, Peter,Morrison, Daniel E.,Bennett, Maxwell R.,McGregor, Iain S.,Rendina, Louis M.,Kassiou, Michael
, p. 335 - 339 (2014/06/09)
Relative to other polycyclic frameworks (1-3), a carborane cage (4 and Cs·5) exerts a significant biological effect as an inhibitor of the purinergic P2X7 receptor (P2X7R) which allows one to target depression in vivo and thus demonstrate, for the first time, that a carborane has the capacity to modify CNS activity.
Stereoselective preparation of mono- and bis-derivatives of pentacyclo[6.3.0.02,6.03,10.05,9] undecane (D 3-trishomocubane)
Mishura, Anastasiia M.,Sklyarova, Anna S.,Sharapa, Dmitriy I.,Levandovsky, Igor A.,Serafin, Michael,Fokin, Andrey A.,Rodionov, Vladimir N.
, p. 2144 - 2150 (2013/10/22)
The rearrangement of easily accessible Cookson's diketone with chlorosulfonic acid in chloroform followed by the acidic hydrolysis gave 6-chloro-7-hydroxy-dichloropentacyclo[6.3.0.02,6.0 3,10.05,9]undecane-4-one, whose syn-stereochemistry was assigned through the X-ray crystal structure analysis. This key structure was used for the stereoselective synthesis of the D 3-trishomocubane derivatives as well as for the preparation of potential drugs bearing hydroxy- and amino-functional groups. A new multigram preparative synthesis of D 3-trishomocubane was developed.
Preparation and testing of homocubyl amines as therapeutic NMDA receptor antagonists
Sklyarova, Anna S.,Rodionov, Vladimir N.,Parsons, Christopher G.,Quack, Guenter,Schreiner, Peter R.,Fokin, Andrey A.
, p. 360 - 366 (2013/03/29)
Computational modeling demonstrates that the van-der-Waals surfaces of homocubyl amines are similar to that of the neuroprotector Memantine . Utilizing readily available precursors we report the preparation of a series of homological cubylamines, namely pentacyclo[6.3.0. 02,6.03,10.05,9]undecyl-4-amine (trishomocubyl-4-amine, 2), pentacyclo[5.3.0.02,5.0 3,9.04,8]decyl-10-amine (bishomocubyl-10-amine, 3), pentacyclo[4.3.0.02,5.03,8.04,7]nonyl-9-amine (homocubyl-9-amine, 4), and pentacyclo[4.2.0.02,5.0 3,8.04,7]octyl-1-amine (cubylamine, 5). The hydrochlorides of amines 2-5 show pronounced affinity for the (+)MK-801 channel binding site, and it seems likely that these compounds would act as very fast voltage-dependent NMDA receptor antagonists.
Novel polycyclic 'cage'-1,2-diamines as potential anti-tuberculosis agents
Onajole, Oluseye K.,Coovadia, Yacoob,Kruger, Hendrik G.,Maguire, Glenn E.M.,Pillay, Melendhran,Govender, Thavendran
, p. 1 - 9 (2012/09/08)
A series of polycyclic 'cage' derivatives of N-geranyl-1,2 diamines were synthesized and screened for their anti-mycobacterial activity against H 37Rv, multidrug resistant (MDR) and extensively drug-resistant (XDR) strains of tuberculosis. By substituting the adamantyl skeleton of SQ109 with trishomocubanyl (9), oxa-pentacycloundecyl (14, 16), pentacycloundecyl, PCU, (10, 15) and azapentacycloundecyl (22, 23), the effect of other polycyclic "cage" skeletons could be investigated. Compound 9 (trishomocubanyl moiety) proved to be the most active (MICs: 0.5-2 μg/mL) while PCU hydroxyl derivatives (15 and 23), oxa-pentacycloundecyl and azapentacycloundecyl derivatives displayed similar activity to SQ109 (MICs: 0.5-4 μg/mL) against all three strains of TB used in this study.
D3-trishomocubane-4-carboxylic acid as a new chiral building block: Synthesis and absolute configuration
Gaidai, Alexandr V.,Volochnyuk, Dmitriy M.,Shishkin, Oleg V.,Fokin, Andrey A.,Levandovskiy, Igor A.,Shubina, Tatyana E.
, p. 810 - 816 (2012/05/07)
The preparation of (±)-D3-trishomocubanone on a multigram scale from 1,4-benzoquinone and cyclopentadiene was optimized to give the target product in 39% overall yield, that was transformed to (±)-D 3-trishomocubane-4-carboxylic acid via a three-step procedure involving the Corey-Chaykovsky reaction followed by boron trifluoride-diethyl ether catalyzed epoxide ring opening and further oxidation. Optically active (+)-D3-trishomocubane-4-carboxylic acid was prepared through the resolution of the racemate by crystallization of its salt with (R)-phenylethylamine; the absolute configuration was assigned by X-ray crystal structure analysis. Georg Thieme Verlag Stuttgart · New York.
REACTIONS OF TETRACYCLO4,11.05,9>UNDECANE-2,7-DIONE WITH ELECTROPHILIC HALOGENATING REAGENTS
Petrenko, A. E.,Aleksandrov, A. M.,Sorochinskii, A. E.,Kukhar, V. P.
, p. 2038 - 2041 (2007/10/02)
The reaction of tetracyclo4,11.05,9>undecan-2,7-dione with boron tribromide leads to the formation of derivatives of pentacyclo3,6.02,10.05,9>undecane.In the reactions with phosphorus pentachloride and sulfur tetrafluoride the main products are 1,7-dichloro- and 1,7-difluoro-12-oxapentacyclo2,6.03.10.05.9>undecanes.
Carbonylation and Valence Isomerization of 1,3-Dihomocubane Derivatives by Chlorodicarbonylrhodium Dimer
Zlotogorski, Changa,Blum, Jochanan,Osawa, Eiji,Schwartz, Helmut,Hoehne, Gerhard
, p. 971 - 976 (2007/10/02)
1,3-Dihomocubane and several analogous cage compounds react with Rh2(CO)4Cl2 to give dinuclear acyl-rhodium complexes.These complexes are transformed into dicyclopentadiene and/or D3-trihomocubanone derivatives either upon heating or by treatment with triphenylphosphine. 1,3-Ethanomethanocubane reacts analogously.The kinetics of these metal-induced transformations follow the second-order rate law.A linear relationship exists between the constants and the calculated strain energies of the starting cage compounds.
