Abstract

Chalcones and pyrazolines are reported to exhibit anti-cancer properties. To continue this research, successful synthesis schemes starting with chalcone derivatives were discovered that would lead to synthesis of pyrazoline prodrugs. Prodrugs are non-toxic until they are activated once the compound enters the oxygen depleted environment of a hypoxic tumor cell. Activated by the cleaving of the promoiety, a sulfate group, of the molecule and resulting in the death of the cancer cell by inhibiting the production of tubulin. To achieve the synthesis of the desired pyrazoline derivative, 3-(4-fluorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one was synthesized as a necessary precursor using a base-promoted reaction of 4-fluorobenzaldehyde and 4-methoxyacetophenone. It was determined that synthesizing a pyrazoline in a one-pot reaction with the chalcone was not favorable and resulted in hydrazone. Therefore, 3- (benzylamino)-1-phenyl-3-(2,4,6-trimethoxyphenyl)propan-1-one intermediate was synthesized along with 3- (benzylamino)-3-(2,5-dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)propan-1-one to determine that the reaction would be successful with another chalcone derivative. 3-(benzylamino)-1-phenyl-3-(2,4,6-trimethoxyphenyl)propan- 1-one was used to synthesis 3-(benzylamino)-1-phenyl-3-(2,4,6-trimethoxyphenyl)propan-1-one oxime. Which then will be reacted to close the nitrogen ring to produce the pyrazoline. This methodology allows for pyrazolines derivatives to be synthesized from varying chalcones derivatives. Then to be synthesized further into a prodrug that is designed to target hypoxic tumor cells to cause apoptosis.

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