Preparation and testing of homocubyl amines as therapeutic NMDA receptor antagonists

Pharmaceuticals that contain polycyclic hydrocarbon scaffolds

“…15). 353 Evaluation of cubanes 139-142 in the hydrochloride form showed pronounced affinity suggesting these systems would act as efficient voltage-dependent NMDA receptor antagonists.…”

Molecular Acrobatics in Polycyclic Frames: Synthesis of Functionalized D3-Trishomocubanes via the Rearrangement Approach

“…Functionalized trishomocubanes , have attracted the attention of synthetic chemists because of their significant biological activities. For example, amino-substituted trishomocubane derivatives show prominent pharmacological properties against tuberculosis and neurodegenerative and antiviral diseases. , Moreover, amino derivatives, such as trishomocubyl-4-amine ( 2 ) acts as an NMDA receptor antagonist, trishomocubyl derivative 3 shows potent anti-TB activity, D 3 -trishomocubylbenzamide 4 acts as a P2X7 receptor antagonist, and substituted trishomocubylamine 5 exhibits anti-Parkinson activity (Figure ).…”

Prying open a Thiele cage: discovery of an unprecedented extended pinacol rearrangement

“…Nevertheless, Dunn and Donohue showed many years ago that exposure of Thiele's ester to ultraviolet light results in an efficient intramolecular [2+2] reaction that transforms the 'open' Thiele's ester into a 'closed' 1,3-bishomocubane structure that we shall refer to here as a Thiele cage (Figure 2A). 8 Marchand and others have exploited this reaction to make a wide variety of structures incorporating the 1,3-bishomocubane motif, 4,5,[9][10][11][12] but here too, deep-seated structural changes for cages derived from Thiele's acid or ester are exceedingly rare.…”

“…In an effort to further increase the steric demands for the system, we next reacted ester 2b with phenyl lithium to afford the very hindered diol 3 (Scheme 2). 22 The constrained nature of this molecule is highlighted by the fact that the ß-proton at C10 of the pentacyclo [5.3.0.0 2,5 .0 3,9 .0 4,8 ]decane core appears at -0.65 ppm in the 1 H NMR spectrum-evidence of substantial magnetic shielding by the phenyl groups on C11. Diol 3 also did not react under photochemical conditions, or upon heating in aprotic solvents.…”

“…(5) 0.0298(5) 0.0237(5) 0.0061(4) -0.0023(4) 0.0026(4)C(35) 0.0272(5) 0.0224(5) 0.0221(5) 0.0046(4) 0.0055(4) 0.0021(4)C(36) 0.0197(4) 0.0191(4) 0.0218(5) 0.0019(4) 0.0055(4) 0.0002(3) S94…”