You wish to test 9 esters for antitumor activity. Assume that one and only one o

Question

You wish to test 9 esters for antitumor activity. Assume that one and only one of the 9 esters will actually have antitumor activity. You will prepare the esters from an alcohol and an acid as was done in the lab. However, you will prepare the mixtures containing one alcohol and 3 acids or mixtures containing 1 acid and 3 alcohols. How many mixtures will you need to prepare to find the 1 antitumor compound? How many of these mixtures will exhibit antitumor activity? If the experiment gave exactly 3 mixtures with antitumor activity, how many of the 9 esters would be antitumor agents?

Explanation / Answer

Structure-activity relationship studies for caffeic acid derivatives suggest that catechol ring is essential for cytotoxicity of CAPE (caffeic acid phenethyl ester ) and it has been proven that part of its anticancer effect is due to antioxidant mechanism of catechol ring. Moreover metylation of hydroxyl groups reduces the activity of CAPE. Conjugated double bond is also required for inhibition of cell growth

Aliphatic esters of caffeic acid with 2, 5- or 3, 5- or 2, 3- dihydroxy benzene rings had comparable cytotoxicity to doxorubicin.

Replacement of the ester by amide or hydroxy groups substantially decreased or abolished cytotoxicity QSAR studies on aliphatic esters of CA showed the dependence of cytotoxicity of this compound on hydrophobicity and steric factors

. Based on the previous studies on CAPE analogues, it has been discovered that replacing phenyl with cyclohexyl increases the cytotoxic activity.

Elongation of alkyl chain of phenethyl up to eight carbons, increases strength of compound.

Furthermore in aliphatic esters, elongation of the chain up to 17 carbons enhances potency

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