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. Author manuscript; available in PMC: 2016 Aug 1.
Published in final edited form as: Curr Med Chem. 2016;23(3):201–241. doi: 10.2174/0929867323666151127201829

Table 5.

Structure and cytotoxicity of benzothiazole PAC-1 derivatives.

graphic file with name nihms801440u4.jpg
72h IC50 (μM)
Compound R1 R2 HT-29 MDA-MB-231 MKN-45 NCI-H226 SK-N-SH
26a NMe2 3-All N.D. 3.55 ± 0.17 1.01 ± 0.15 N.D. 1.68 ± 0.11
26b NMe2 3,5-(t-Bu)2 N.D. 13.9 ± 0.24 2.48 ± 0.08 N.D. 2.28 ± 0.04
26c NEt2 3-All N.D. 5.25 ± 0.19 1.80 ± 0.12 N.D. 2.10 ± 0.09
26d NEt2 3,5-(t-Bu)2 N.D. 7.23 ± 1.01 4.06 ± 1.26 N.D. 2.46 ± 0.21
26e 4-Me-1-Pip 3-All N.D. 3.11 ± 0.31 1.31 ± 0.22 N.D. 2.58 ± 0.12
26f 4-Me-1-Pip 3,5-(t-Bu)2 N.D. 12.1 ± 0.15 9.70 ± 0.26 N.D. 2.79 ± 0.13
26g NMe2 4-OBn 2.19 ± 0.17 1.34 ± 0.11 1.06 ± 0.10 0.91 ± 0.03 1.14 ± 0.11
26h NMe2 4-OCH2(4-F-Ph) 1.32 ± 0.07 2.02 ± 0.01 1.72 ± 0.04 0.42 ± 0.05 0.88 ± 0.03
26i NMe2 4-OCH2(3-F-Ph) 1.03 ± 0.12 2.02 ± 0.12 1.35 ± 0.04 0.51 ± 0.03 1.29 ± 0.08
26j NMe2 4-OCH2(2-F-Ph) 1.51 ± 0.04 0.66 ± 0.02 0.35 ± 0.03 0.59 ± 0.01 1.94 ± 0.15
26k NMe2 4-OCH2(4-CF3-Ph) 0.92 ± 0.08 0.63 ± 0.03 0.29 ± 0.01 0.24 ± 0.02 0.60 ± 0.02
26l NMe2 4-OCH2(2,4-Cl2-Ph) N.D. 2.02 ± 0.13 1.38 ± 0.05 0.50 ± 0.04 0.59 ± 0.01
26m NMe2 4-OCH2(2,3-Cl2-Ph) N.D. 2.94 ± 0.08 1.45 ± 0.03 0.81 ± 0.01 0.87 ± 0.02
26n NEt2 4-OCH2(4-F-Ph) 1.47 ± 0.03 0.97 ± 0.08 0.31 ± 0.07 0.57 ± 0.07 0.71 ± 0.06
26o NEt2 4-OCH2(3-F-Ph) 0.76 ± 0.02 1.12 ± 0.11 0.63 ± 0.10 1.05 ± 0.03 1.34 ± 0.05
26p NEt2 4-OCH2(2-F-Ph) 1.06 ± 0.12 0.88 ± 0.02 0.55 ± 0.02 0.62 ± 0.06 0.91 ± 0.15
26q NEt2 4-OCH2(4-CF3-Ph) 1.59 ± 0.14 1.06 ± 0.05 0.57 ± 0.01 0.54 ± 0.04 0.85 ± 0.02
26r NEt2 4-OCH2(2,3-Cl2-Ph) 4.01 ± 0.27 1.74 ± 0.02 0.71 ± 0.05 0.95 ± 0.02 1.41 ± 0.13
26s 4-Me-1-Pip 4-OCH2(4-F-Ph) 4.01 ± 0.18 2.37 ± 0.04 0.79 ± 0.12 0.31 ± 0.03 0.40 ± 0.01
26t 4-Me-1-Pip 4-OCH2(3-F-Ph) 1.02 ± 0.11 0.83 ± 0.05 0.38 ± 0.01 0.36 ± 0.04 0.56 ± 0.09
26u 4-Me-1-Pip 4-OCH2(2-F-Ph) 1.65 ± 0.13 0.42 ± 0.01 0.40 ± 0.02 0.45 ± 0.05 1.38 ± 0.11
26v 4-Me-1-Pip 4-OCH2(4-CF3-Ph) 1.12 ± 0.06 0.58 ± 0.03 0.31 ± 0.02 0.65 ± 0.11 0.75 ± 0.08
26w 4-Me-1-Pip 4-OCH2(2,3-Cl2-Ph) 3.34 ± 0.18 1.00 ± 0.11 0.45 ± 0.07 0.33 ± 0.05 0.55 ± 0.09
26x NMe2 - N.D. 16.18 ± 0.55 5.32 ± 0.12 N.D. 6.12 ± 1.12
26y NEt2 - N.D. 12.7 ± 0.36 5.83 ± 0.48 N.D. 4.37 ± 0.69
26z 4-Me-1-Pip - N.D. 10.49 ± 1.05 4.35 ± 1.08 N.D. 2.72 ± 0.15
PAC-1 - - 1.36 ± 0.02 4.58 ± 0.05 3.56 ± 0.05 1.02 ± 0.08 3.06 ± 0.16

Pip = piperidinyl; N.D. = not determined. [57]