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. Author manuscript; available in PMC: 2015 Jun 1.
Published in final edited form as: Bioorg Med Chem Lett. 2014 Apr 13;24(11):2473–2476. doi: 10.1016/j.bmcl.2014.04.013

Table 2.

SAR study of the A-ring of 1,2,4-bis-aryloxadiazole. Expression of an AHR response gene, Cyp1a1, was measured in HC11 MECs treated with 10 μM compound for 48 hours.

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Compound X R1 R2 R3 R4 Relative Cyp1a1
11 CH o-Cl p-Cl H m-CF3 1.84 +/− 0.28
12 CH o-Cl p-Cl H m-CO2Me 0.18 +/− 0.49
13 CH o-F H H m-CO2Me 0.29 +/− 0.74
14 CH o-F H H m-CO2H 3.71 +/− 0.22
15 CH o-Cl p-Cl H o-Cl 5.91 +/− 0.18
16 CH o-Cl p-Cl H m-Cl 1.59 +/− 0.30
17 CH o-Cl p-Cl H p-Cl 8.15 +/− 0.14
18 CH o-Cl p-Cl H p-O-propargyl 0.66 +/− 0.26
19 CH o-NO2 p-Cl H p-O-propargyl 0.29 +/− 0.35
20 CH o-NH2 p-Cl H p-O-allyl 0.62 +/− 0.16
21 CH o-NH2 p-Cl H p-O-propargyl 0.38 +/− 0.42
22 N o-Cl m-Cl p-Cl H 0.53 +/− 0.28
23 N o-Cl p-Cl H H 0.37 +/− 0.13
24 N o-NO2 p-Cl H H 8.25 +/− 0.13
25 N o-NO2 p-OAc H H 0.35 +/− 0.41