. Author manuscript; available in PMC: 2016 Apr 12.

Published in final edited form as: J Med Chem. 2016 Jan 29;59(3):1207–1216. doi: 10.1021/acs.jmedchem.5b01910

Table 3.

Exploring Aromatic Substitutions of Isoxazole and 1,2,4-Oxadiazole^b

Z	Compound ID	%S31N inhibition^*	%WT inhibition^*	% plaque formation at 1 uM(A/WSN/33)^**
C	4^a	90/63	11	32±2
N	18f^a	83/N.T.	11	66±3
C	14i	90/N.T.	28	47±5
N	18g	81/N.T.	3	74±10
C	14j	84/N.T.	12	47±1
N	18h	73/N.T.	24	N.T.
C	14k	90/87	27	39±3
C	141^a	91/N.T.	20	26±3
N	18i^a	75/N.T.	8	N.T.
C	14m	87/65	14	84±6
N	181	86/72	16	88±1
C	14n	77/N.T.	12	N.T.
C	14o	78/N.T.	23	N.T.
C	14p	85/68	8	56±7
C	14q^a	87/N.T.	13	59±9
N	18k^a	86/N.T.	18	92±7
C	14r	87/73	12	39±1
C	14s	79/N.T.	8	N.T.
C	8a	79/N.T.	5	N.T.
N	181	90/77	7	66±3
C	14t	62/N.T.	10	N.T.
N	18m	82/N.T.	18	76±5
N	20a	39/N.T.	18	N.T.
N	20b	58/N.T.	13	N.T.
C	20c	67/N.T.	27	N.T.

Percent inhibition in TEVC assays was previously reported.

^b*

Values represent the mean of three independent measurements. We typically see no more than 5% variation in the percent inhibition on a given day, or 10% error for measurements made on different days with different batches of oocytes. The data are presented as percent inhibition at 100 µM/percent inhibition at 30 µM. N.T. = not tested.

^**

Plaque reduction assays were performed against the M2-S31N containing A/WSN/33 virus in duplicates. The percent of plaque formation is defined as the ratio of plaque numbers in the presence of compounds divided by the plaque numbers in the absence of compounds.