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. Author manuscript; available in PMC: 2008 Feb 8.
Published in final edited form as: Bioorg Med Chem. 2006 Jul 7;14(19):6525–6538. doi: 10.1016/j.bmc.2006.06.019

Table 1.

Structures and pharmacological activities of arylisothiocyanato SARMs against prostate cancer cell lines (LNCaP, DU145, PC-3, and PPC-1), bladder cancer cell line (TSU-Pr1), and normal monkey kidney cell line (CV-1) (IC50 in µM)

graphic file with name nihms32200t1.jpg
  R1 X R2 R3 IC50(µM)
 Ki (nM) on hAR
          LNCaP DU145 PC-3 PPC-1 TSU-Pr1 CV-1  
DHT                     0.43 ± 0.01
R-bicalutamidea         45.9 ± 8.8 74.7 ± 12.2 71.6 ± 6.7 39.3 ± 1.8 8.3 ± 1.6 38.1± 9.2 11.0 ± 2.0
S-23 NO2 O H H 17.4 ± 4.9 74.7 ± 5.9 59.1 ± 3.3 74.7 ± 5.9 57.1 ± 2.3 >100 4.6 ± 0.310
R-23b NO2 O H H 24.9 ± 1.7 28.7 ± 1.7 15.7 ± 1.4 22.3 ± 0.1 28.7 ± 1.7 44.3 ± 1.1 36.2 ± 2.8
S-24 CN O H H 17.8 ± 12.8 76.8 ± 8.2 69.5 ± 4.8 43.2 ± 14.4 54.8 ± 3.1 N.D. 8.1 ± 0.3
S-25 NO2 O H F 13.9 ± 2.9 50.8 ± 6.0 47.2 ± 2.9 34.3 ± 5.1 45.3 ± 6.1 N.D. 12.6 ± 1.1
S-26 CN O H F 66.3 ± 14.9 76.0 ± 6.9 62.1 ± 12.2 56.9 ± 5.1 54.8 ± 3.9 N.D. 6.3 ± 1.0
S-27 NO2 O H Cl 30.6 ± 11.0 72.1 ± 3.3 41.2 ± 8.2 43.5 ± 7.4 39.8 ± 7.3 N.D. 11.9 ± 2.7
S-28 CN O H Cl 52.0 ± 15.3 55.0 ± 6.1 48.6 ± 2.5 53.0 ± 10.7 51.1 ± 6.7 N.D. 8.6 ± 0.9
S-29 NO2 O F H 23.8 ± 2.0 47.9 ± 3.9 39.5 ± 1.4 31.8 ± 1.3 49.0 ± 1.0 N.D. 34.6 ± 6.5
S-30 NO2 O Cl H 20.3 ± 1.4 29.4 ± 2.9 26.8 ± 1.6 22.2 ± 1.2 26.9 ± 1.1 N.D. 31.1 ± 1.8
31c NO2 CH2 H H 20.6 ± 3.8 23.4 ± 1.3 21.1 ± 2.7 20.7 ± 0.9 23.8 ± 3.0 N.D. 31.8 ± 1.8
S-32 NO2 NH H H 21.5 ± 0.7 29.4 ± 2.9 32.4 ± 2.1 26.5 ± 1.3 38.3 ± 1.0 N.D. 21.4 ± 7.0
S-33 NO2 NCH3 H H 13.8 ± 0.4 N.D. 27.8 ± 1.8 21.9 ± 1.2 14.7 ± 0.3 N.D. 41.2 ± 5.9
R-34 NO2 S H H N.D. N.D. N.D. N.D. N.D. N.D. 54.8 ± 3.0
R-35 CN S H H 10.6 ± 7.1 88.3 ± 8.2 91.1 ± 6.3 86.9 ± 4.1 65.6 ± 4.2 >100 0.6 ± 0.111
S-35b CN S H H 64.0 ± 5.9 >100 >100 >100 >100 >100 430 ± 13
R-36 NO2 SO2 H H 29.4 ± 1.6 59.3 ± 1.9 58.9 ± 4.1 43.9 ± 3.1 43.3 ± 3.7 N.D. 14.4 ± 4.4
R-37 CN SO2 H H 42.7 ± 5.3 81.5 ± 28.7 70.1 ± 7.6 69.4 ± 1.8 59.2 ± 6.7 >100 41.0 ± 2.011

N.D., not determined.

a

Reversible ligand; tested on above cell lines and AR binding affinity determined.

b

Opposite enantiomeric (inactive) isomers synthesized using the chiral auxiliary starting from l-proline (vs d-proline for the other compounds via the same synthetic procedure as S-23 and R-35).

c

Racemic mixture.