Novel flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents

A method for synthesizing a flavanone having the structure of formula (II)

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• wherein
• R1, R2 and R3 are independently selected from the group consisting of hydroxyl, halo, C1-C6 alkoxy, C5-C12 aryloxy, and C5-C12 aralkyloxy, and further wherein either R1 and R2 or R2 and R3 can be joined to form a two-atom or three-atom linkage selected from alkylene, substituted alkylene, and heteroalkylene,
• R6, R7, R8 and R9 are independently selected from the group consisting of hydrogen, C1-C6 alkoxy, C5-C12 aryloxy, and C5-C12 aralkyloxy, or R6 and R7 are linked together to form a cyclohexyl, cyclopentyl, or phenyl ring, and R8 and R9 are hydrogen, or R8 and R9 are linked together to form a cyclohexyl, cyclopentyl, or phenyl ring, and R6 and R7 are hydrogen, and
• R10 and R11 are independently selected from the group consisting of hydrogen, hydroxyl, C1-C6 alkyl, C1-C6 alkoxy, and halo,
• the method comprising condensing the ketone (X)
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• with the aromatic aldehyde (XI)
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• in the presence of a nitrogenous organic base.

A method for synthesizing a flavanol having the structure of formula (III)

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• wherein
• R1, R2 and R3 are independently selected from the group consisting of hydroxyl, halo, C1-C6 alkoxy, C5-C12 aryloxy, and C5-C12 aralkyloxy, and further wherein either R1 and R2 or R2 and R3 can be joined to form a two-atom or three-atom linkage selected from alkylene, substituted alkylene, and heteroalkylene,
• R6, R7, R8 and R9 are independently selected from the group consisting of hydrogen, C1-C6 alkoxy, C5-C12 aryloxy, and C5-C12 aralkyloxy, or R6 and R7 are linked together to form a cyclohexyl, cyclopentyl, or phenyl ring, and R8 and R9 are hydrogen, or R8 and R9 are linked together to form a cyclohexyl, cyclopentyl, or phenyl ring, and R6 and R7 are hydrogen, and
• R10 and R11 are independently selected from the group consisting of hydrogen, hydroxyl, C1-C6 alkyl, C1-C6 alkoxy, and halo,
• the method comprising contacting a flavanone having the structure (II)
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• with a reducing agent under reaction conditions effective to convert the 4-oxo moiety to a hydroxyl group.

A method for synthesizing a chalcone having the structure of formula (IV)

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• wherein
• R1, R2 and R3 are independently selected from the group consisting of hydroxyl, halo, C1-C6 alkoxy, C5-C12 aryloxy, and C5-C12 aralkyloxy, and further wherein either R1 and R2 or R2 and R3 can be joined to form a two-atom or three-atom linkage selected from alkylene, substituted alkylene, and heteroalkylene,
• R6, R7, R8 and R9 are independently selected from the group consisting of hydrogen, C1-C6 alkoxy, C5-C12 aryloxy, and C5-C12 aralkyloxy, or R6 and R7 are linked together to form a cyclohexyl, cyclopentyl, or phenyl ring, and R8 and R9 are hydrogen, or R8 and R9 are linked together to form a cyclohexyl, cyclopentyl, or phenyl ring, and R6 and R7 are hydrogen, and
• R10 and R11 are independently selected from the group consisting of hydrogen, hydroxyl, C1-C6 alkyl, C1-C6 alkoxy, and halo,
• the method comprising reacting the ketone (X)
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• with the aromatic aldehyde (XI)
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• in the presence of an aqueous inorganic base.