Polycyclic carbogenic molecules and uses thereof as anti-cancer agents
AssigneeNorthwestern University
InventorsRegan James Thomson, Emily E. Robinson
Life of this patent
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Abstract
Disclosed are new polycyclic carbogenic molecules and their methods of synthesis. The new polycyclic carbogenic molecules may be utilized in anti-cancer therapies. In particular, the polycyclic carbogenic molecules may be formulated as pharmaceutical compositions that comprise the small molecules, which compositions may be administered in methods of treating and/or preventing cell proliferative diseases and disorders such as cancer. The new polycyclic carbogenic molecules may be prepared from vinyl- or allyl-substituted cyclohexenone precursors via preparation of a silyl bis-enol ether intermediate.
Claims24
A compound or a salt, solvate, epoxide, or spirocyclic derivative thereof having a Formula I:
- wherein:
- m and n are selected from 0 or 1;
- and
- each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from hydrogen, alkyl, dialkyl, hydroxyl, protected hydroxyl, alkoxy, alkyl-alkoxy, alkyl-dialkoxy, and acetyl;
- or R3 and R5 together form an epoxide;
- or R4 and R6 together from an epoxide;
- or R7 and R8 together from an epoxide.
A compound or a salt, solvate, or epoxide thereof having a Formula VII:
- wherein:
- m and n are selected from 0 or 1;
- and
- each occurrence of R1, R3, R5, R7, R8, and R10 is independently selected from hydrogen, alkyl, dialkyl, hydroxyl, protected hydroxyl, alkoxy, alkyl-alkoxy, alkyl-dialkoxy, and acetyl;
- or R3 and R5 together form an epoxide;
- or R7 and R8 together from an epoxide.
A compound or a salt, solvate, or epoxide thereof having Formula VIII:
- wherein:
- m and n are selected from 0 or 1;
- and
- each occurrence of R1, R2, R3, R4, R5, and R6 is independently selected from hydrogen, alkyl, and dialkyl.
A compound or a salt, solvate, or spirocyclic derivative thereof having a Formula IX:
- wherein:
- m and n are selected from 0 or 1;
- and
- each occurrence of R1, R2, R3, R4, R5, R6, R7, and R8 is independently selected from hydrogen, alkyl, and dialkyl;
- or R5 from a keto group with the ring carbon to which it is attached;
- or R6 forms a keto group with the ring carbon to which it is attached.
A compound or a salt, solvate, epoxide, or spirocyclic derivative thereof having a Formula XI:
- wherein:
- m and n are selected from 0 or 1;
- and
- each occurrence of R1, R2, R3, R4, R7, and R8 is independently selected from hydrogen, alkyl, and dialkyl.
A synthesis method for a polycyclic molecule comprising:
- (a) reacting a:
- (i) first precursor comprising a cyclohexanone substituted at the 5-position or the 6-position with a vinyl group or an allyl group,
- (ii) a second precursor which is a cyclohexanone substituted at the 5-position or the 6-position with a vinyl group or an allyl group, or a second precursor which is an alkyl vinyl ketone;
- and
- (iii) a dialkyl silyl dihalide to form a symmetrical or unsymmetrical silyl bis-enol ether;
- and
- (b) performing oxidative coupling and ring-closing metathesis of the symmetrical or unsymmetrical silyl bis-enol ether to provide the polycyclic molecule.
Dependencies are inferred from the claim text.