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. Author manuscript; available in PMC: 2014 Aug 16.
Published in final edited form as: J Org Chem. 2013 Aug 1;78(16):7859–7884. doi: 10.1021/jo401027r

Table 2.

Anti-proliferative activities produced by 3,5-dihydroxychroman-3-ol esters.

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Entry R1 R2 R3 R4 R5 MCF-7 (IC50, μM) SKBr3 (IC50, μM)
23a OH OH H H H 98.24 ± 1.76 >100
23b OH OH OMe H H 57.75 ± 3.12 50
23c OH OH H OMe H >100 >100
23d OH OH OMe OMe H >100 >100
23e OH OH OMe H OMe 96.50 ± 3.51 >50
23f OH OH OH H H 61.94 ± 6.85 85.30 ± 5.36
23g OH OH H OH H >100 >100
23h OH OH m OMePh OMe H 21.93 ± 2.27 34.84 ± 16.29
23i OH OH Prenyl OAc H 10.66 ± 1.09 23.15 ± 0.25
23j OH H H H H >100 >100
23k OH H OMe H H >100 >100
22l OH H H OMe H >100 >100
23m OH H m-OMePh OMe H 55.09 ± 5.53 57.73 ± 4.28
23n OH H Prenyl OAc H 15.94 ± 1.86 25.25 ± 4.05
23o H OH H H H >100 >100
23p H OH OMe H H >100 >100
22q H OH H OMe H >100 >100
23r H OH m-OMePh OMe H 21.6 ± 2.55 41.72 ± 0.34
23s H OH Prenyl OAc H 60 ± 7.38 >100