Synthesis of combretastatin A-2 prodrugs

Details Synthesis of combretastatin A-2 prodrugs Synthesis of combretastatin A-2 prodrugs

2006-09-12

2006-09-12

Solola, Taofiq (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Phosphorus esters

Reexamination Certificate

active

07105695

ABSTRACT:
The original synthesis of combretastatin A-2 (1a) was modified to provide an efficient scale-up procedure for obtaining this antineoplastic stilbene. Subsequent conversion to a useful prodrug was accomplished by phosphorylation employing in situ formation of dibenzylchlorophosphite followed by cleavage of the benzyl ester protective groups with bromotrimethylsilane to afford phosphoric acid intermediate 11. The latter was immediately treated with sodium methoxide to complete a practical route to the disodium phosphate prodrug (2a). The phosphoric acid precursor (11) of phosphate 2a was employed in a parallel series of reactions to produce a selection of metal and ammonium cation prodrug candidates. Each of the phosphate salts (2a–q) was evaluated with respect to relative solubility behavior, cancer cell growth inhibition, and antimicrobial activity.

REFERENCES:
patent: WO 99/35150 (1999-07-01), None
patent: WO 02/006279 (2002-01-01), None

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