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. Author manuscript; available in PMC: 2016 Jan 27.
Published in final edited form as: Eur J Med Chem. 2014 Nov 20;90:315–331. doi: 10.1016/j.ejmech.2014.11.035

Table 1.

Potential sites amenable for optimization and ELISA results of marinopyrroles.

graphic file with name nihms-643927-f0010.jpg
ID R1 R2 Mcl-1/Bima Bcl-xL/Bima
1b 2-OH 2′-OH 8.9 ± 1.0 16.4 ± 3.3
23c 2-OH-4-CF3 2′-OH-4′-CF3 8.1 ± 0.9 9.7 ± 1.3
24 2-OH-5-Cl-4-Me 2′-OH-5′-Cl-4′-Me 2.6 ± 0.6 2.5 ± 0.4
25 2-OH-4-C=CH 2′-OH-4′-C=CH 3.9 ± 0.2 5.6 ± 0.5
26 2-OH-4-CH=CH2 2′-OH-4′-CH=CH2 3.7 ± 0.5 3.5 ± 0.7
27 2-OH-4-Et 2′-OH-4′-Et 2.1 ± 0.5 3.9 ± 1.3
28c 2-OH-4-OSO2CF3 2′-OH-4′-OSO2CF3 1.0 ± 0.3 2.1 ± 0.7
29c 2-OH-4-OH 2′-OH-4′-OH 39.5 ± 6.2 >50
30c 2-OH-5-Cl-4-OH 2′-OH-5′-Cl-4′-OH 10.7 ± 0.2 >50
31d 2-OH-4-SCH2CO2Et 2′-OH-4′-SCH2CO2Et 1.8 ± 0.3 1.2 ± 0.2
32d 2-OH-4-SCH2Ph 2′-OH-4′-SCH2Ph 0.7 ± 0.2 0.6 ± 0.2
33d 2-OH-4-SCH2(p-MeOPh) 2′-OH-4′-SCH2(p-MeOPh) 0.7 ± 0.1 0.6 ± 0.1
34d 2-OH-4-SCH2CO2H 2′-OH-4′-SCH2CO2H 6.1 ± 1.3 >100
35e 2-OH-4-PO(OH)2 2′-OH-4′-PO(OH)2 10.9 ± 3.1 27.3 ± 7.2
36 graphic file with name nihms-643927-t0011.jpg graphic file with name nihms-643927-t0012.jpg 7.8 ± 1.5 >100
37 graphic file with name nihms-643927-t0013.jpg graphic file with name nihms-643927-t0014.jpg 1.6 ± 0.6 14.0 ± 4.7
38 graphic file with name nihms-643927-t0015.jpg graphic file with name nihms-643927-t0016.jpg 5.2 ± 0.8 >50
39 graphic file with name nihms-643927-t0017.jpg graphic file with name nihms-643927-t0018.jpg 3.3 ± 0.9 1.6 ± 0.3
40 graphic file with name nihms-643927-t0019.jpg graphic file with name nihms-643927-t0020.jpg 1.5 ± 0.2 0.8 ± 0.2
41 graphic file with name nihms-643927-t0021.jpg graphic file with name nihms-643927-t0022.jpg 1.4 ± 0.5 3.8 ± 1.3
42 graphic file with name nihms-643927-t0023.jpg graphic file with name nihms-643927-t0024.jpg 0.6 ± 0.3 0.5 ± 0.1
43 graphic file with name nihms-643927-t0025.jpg graphic file with name nihms-643927-t0026.jpg 18.4 ± 0.3 >100
44 graphic file with name nihms-643927-t0027.jpg graphic file with name nihms-643927-t0028.jpg 5.1 ± 0.4 8.1 ± 2.5
45 graphic file with name nihms-643927-t0029.jpg graphic file with name nihms-643927-t0030.jpg 16.5 ± 1.9 >50
46f 2-OMe 2′-OMe-4′-Cl 8.0 ± 1.6 9.5 ± 2.2
47f 2-OH 2′-OH-3′-Cl 4.1 ± 1.4 10.1 ± 2.2
48f 2-OH 2′-OH-5′-Cl 3.9 ± 1.1 18.3 ± 3.0
49f 2-OH 2′-OH-4′-Cl 6.5 ± 1.3 9.2 ± 2.3
50g 2-OH 2′-OH-5′-F 8.9 ± 0.9 13.3 ± 3.3
51g 2-OH 2′-OH-4′-F 9.6 ± 0.4 21.3 ± 5.6
52g 2-OH 2′-OH-6′-F 13.1 ± 0.3 43.7 ± 10.0
53 2-OMe 2′-OMe and N-Meh 15.5 ± 3.3 64.9 ± 15.5
54 2-OH 2′-OH and N-Meh > 100 7.9 ± 1.8
ABT-263 4.3 ± 0.4 nM
a

IC50 in μM (average ± SEM, n ≥ 3) unless specified

b

Activity as disruptors of Mcl-1 and Bc1-xl reported previously and here for SAR discussion [13]

c

Chemistry, anti-MRSA activity was reported previously [12]

d

Chemistry and activity as disruptors of Mcl-1 and Bcl-xL reported previously and here for SAR discussion [15]

e

Chemistry and activity as disruptors of Mcl-1 and Bcl-xL reported previously and here for SAR discussion [13]

f

Chemistry and anti-MRSA activity were reported previously [5]

g

Chemistry and anti-MRSA activity were reported previously [14]

h

N-Methyl analogue.