Table 1.

Inhibitor activity of the test compounds (1–38) in the enol-keto and keto-enol tautomeric conversion of phenylpyruvate.

Compounds	X	Ar	Inhibition of ketonase (IC50, μM)	Inhibition of enolase (IC50, μM)
1	–	Phenyl	82.8 ± 16.5	20.2 ± 3.9
2	CH2	Phenyl	127 ± 20	113 ± 16
3	(CH2)2	Phenyl	84.0 ± 15.3	129 ± 19
4	CH2	4′- CH3-phenyl	16.5 ± 3.4	2290 ± 343
5	CH2	4′-OCH3-phenyl	57.0 ± 14.1	33.4 ± 8.8
6	CH2	4′-Cl-phenyl	59.1 ± 9.7	42.8 ± 3.1
7	CH2	2′-Cl-phenyl	2640 ± 406	458 ± 73
8	CH2	4′-Br-phenyl	52.2 ± 11.5	232 ± 54
9	CH2	3′-Br-phenyl	7340 ± 1024	3350 ± 424
10	CH2	4′-F-phenyl	72.4 ± 3.4	42.1 ± 4.3
11	CH2	2′,6′-(Cl)2-phenyl	58.9 ± 10.3	35.5 ± 5.9
12	CH2	3′,4′-(Cl)2-phenyl	2620 ± 696	91.5 ± 9.0
13	CH2	2′,4′-(Cl)2-phenyl	16.9 ± 4.2	301 ± 42
14	CH2	4′-COOH-phenyl	187 ± 32	37.7 ± 16.3
15	CH2	4′-(NCH3)2--phenyl	90.2 ± 15.1	495 ± 101
16	CH2	4′-CN-phenyl	146 ± 17	43.2 ± 12.4
17	CH2	3′,4′-(OCH3)2 -phenyl	585 ± 94	302 ± 63
18	CH2	3′,4′-(OCH2O)-phenyl	50.7 ± 6.0	213 ± 31
19	CH2	2′-Furyl	57.7 ± 12.6	25.4 ± 4.7
20	CH2	2′-Thienyl	54.0 ± 5.5	52.3 ± 7.6
21	CH2	2′-Pyrrolyl	142 ± 31	125 ± 39
22	CH2	N-Methyl-2′-pyrrolyl	23.8 ± 3.8	27.8 ± 5.6
23	CH2	3′-Indolyl	58.8 ± 10.6	2.89 ± 0.75
24	CH2	2′-Pyridyl	5.63 ± 0.94	28.6 ± 7.4
25	CH2	3′-Pyridyl	20.3 ± 5.5	28.6 ± 6.0
26	CH2	4′-Pyridyl	21.0 ± 6.9	209 ± 77
27	O	Phenyl	267 ± 59	1740 ± 483
28	O	4′- CH3-phenyl	102 ± 19	3620 ± 829
29	O	3′- CH3-phenyl	56.1 ± 8.8	443 ± 112
30	O	4′-OCH3-phenyl	96.0 ± 29.9	425 ± 70
31	O	3′-OCH3-phenyl	97.0 ± 20.7	205 ± 32
32	O	2′-OCH3-phenyl	4.31 ± 1.34	1260 ± 159
33	O	4′-Br-phenyl	311 ± 77	1890 ± 438
34	O	2′-Br-phenyl	98.3 ± 16.0	3200 ± 887
35			419 ± 113	– (Because of low solubility data are not available)
36	S	Phenyl	208 ± 42	633 ± 108
37	SO	Phenyl	94.6 ± 25.4	193 ± 59
38	SO2	Phenyl	160 ± 38	151 ± 27