Medicinal chemistry of polycyclic cage compounds in drug discovery research

Conformationally Preorganized Diastereomeric Norbornane-Based Maltosides for Membrane Protein Study: Implications of Detergent Kink for Micellar Properties

“…Of the facial agents developed for membrane protein study, the current agents contain systematic chiral variation only in the lipophilic region. The distinct features of the norbornane scaffold are widely exploited where conformational preorganization is paramount: in peptidomimetics 24 and medicinal chemistry, 25 in supramolecular chemistry as photo-switchable ion carriers, 26a,b and as chiral auxiliaries for asymmetric synthesis. 26c–g However, they have not so far been applied to membrane protein research.…”

Hexacyclo[7.5.1.01,6.06,13.08,12.010,14]pentadecane-7,15-dione

“…Several cage systems can undergo rearrangements to generate intricate polycycles (Hopf, 2000;Osawa & Yonemitsu, 1992). Polycyclic cage compounds have applications in medicinal chemistry for drug discovery research (Oliver & Malan, 2008;Geldenhuys et al 2005).…”

Structural elucidation of dioxa‐cage compounds from tetrahydroisobenzofuran‐1(3H)‐one: analysis of NMR data and GIAO chemical shifts calculations

“…[1][2][3][4] Their rigid, strained and often symmetric structure provides singular physicochemical properties [5] and bioactivities. [6,7] Besides of being potential substrates for studies of molecular rearrangements [8][9][10] and other reaction mechanisms, [11][12][13] the cage compounds are useful intermediates for the synthesis of more complex molecules, including natural products. [14][15][16][17] In this paper, the synthesis and characterisation of dioxa-cage compounds with 3-oxo-4,11-dioxatetracyclo[5.2.1.1 5,8 .0 2,6 ] undecane skeleton is on focus, because our attempt to functionalize the tetrahydroisobenzofuran-1(3H)-one 1 resulted in isolation of compounds 2, 3 and 4 ( Fig.…”