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. Author manuscript; available in PMC: 2017 Apr 28.
Published in final edited form as: J Med Chem. 2015 Nov 9;59(8):3609–3634. doi: 10.1021/acs.jmedchem.5b01457

Table 15. Rigidification of the cis-amide into five-membered heterocyclic rings.

graphic file with name nihms-735690-t0166.jpg
Compd R X IC50a (nM) EC50b (nM)
123 Cl graphic file with name nihms-735690-t0167.jpg 50 6700
124 Cl graphic file with name nihms-735690-t0168.jpg 30 3000
125 Cl graphic file with name nihms-735690-t0169.jpg 50
126 Cl graphic file with name nihms-735690-t0170.jpg 30 2700
127 Cl graphic file with name nihms-735690-t0171.jpg 60 3700
128 Cl graphic file with name nihms-735690-t0172.jpg 60
129 Cl graphic file with name nihms-735690-t0173.jpg 70
130 Cl graphic file with name nihms-735690-t0174.jpg 70 2400
131 Cl graphic file with name nihms-735690-t0175.jpg 40 730
132 F graphic file with name nihms-735690-t0176.jpg 50 760
133 CN graphic file with name nihms-735690-t0177.jpg 8 1200
134 7.7
a

Measured in a IMAP assay.

b

Cellular activity is expressed as inhibition of LPS-induced Hsp27 Ser78 phosphorylation in THP-1 cells.