Table 1.

In vitro affinities (Ki, μM) of α-truxillic acid and its congeners

Entry	Compound	Ar	X	R	FABP3 Ki	FABP5 Ki	FABP7 Ki	cLogP
1	1a	Ph	O	H	>10	>10	>10	3.07
2	1g	3,4-(MeO)2Ph	O	H	>10	>10	>10	2.38
3	1i	3-OH-4-(MeO)Ph	O	H	>10	>10	>10	1.43
4	3 (racemic)	Ph	O	1-naphthyl	2.70 ± 0.42	0.81 ± 0.09	0.45 ± 0.07	6.97
5	(R,R,R,R)-3	Ph	O	1-naphthyl	3.26 ± 0.70	0.78 ± 0.14	0.89 ± 0.24	6.97
6	(S,S,S,S)- 3	Ph	O	1-naphthyl	2.82 ± 0.10	0.80 ± 0.14	0.66 ± 0.16	6.97
7	3a	Ph	O	benzyl	>10	3.81 ± 0.53	0.53 ± 0.12	5.28
8	3b	Ph	O	4-MeO-benzyl	>10	2.15 ± 0.10	1.14 ± 0.06	5.20
9	3c	Ph	O	4-F-benzyl	>10	2.42 ± 0.18	1.65 ± 0.21	5.42
10	3d	Ph	O	4-Br-benzyl	>10	1.58 ± 0.16	1.25 ± 0.03	6.13
11	3e	Ph	O	2-iodophenyl	1.18 ± 0.10	1.34 ± 0.21	0.94 ± 0.34	5.77
12	3f	Ph	O	3-ethynylphenyl	>10	0.89 ± 0.15	0.78 ± 0.12	5.06
13	3g	Ph	O	biphenyl-2-yl	0.70 ± 0.42	0.77 ± 0.08	0.35 ± 0.12	6.12
14	3h	Ph	O	biphenyl-3-yl	9.75 ± 0.79	0.85 ± 0.22	0.74 ± 0.17	6.68
15	3i	Ph	O	biphenyl-4-yl	3.93 ± 0.16	2.52 ± 0.36	2.27 ± 0.03	6.68
16	3j	Ph	O	2′-HO-biphenyl-2-yl	3.52 ± 0.53	1.59 ± 0.43	0.54 ± 0.18	5.19
17	3k	Ph	O	2,4,5-trichlorophenyl	2.98 ± 0.85	0.80 ± 0.11	0.54 ± 0.02	6.67
18	3l	Ph	O	trans-2-phenylcyclohex-1-yl	1.08 ± 0.37	0.21 ± 0.02	0.40 ± 0.03	7.17
19	3l-A	Ph	O	(1R,2S)-2-phenylcyclohex-1-yl	0.83 ± 0.15	0.21 ± 0.02	0.33 ± 0.05	7.17
20	3l-B	Ph	O	(1S,2R)-2-phenylcyclohex-1-yl	0.88 ± 0.14	0.20 ± 0.03	0.25 ± 0.12	7.17
21	3l-A/C	Ph	O	(1R,2S)-2-phenylcyclohex-1-yl	0.64 ± 0.16	0.18 ± 0.03	0.33 ± 0.15	7.17
22	3l-B/D	Ph	O	(1S,2R)-2-phenylcyclohex-1-yl	0.82 ± 0.09	0.21 ± 0.02	0.15 ± 0.02	7.17
23	3m	Ph	O	Indan-2-yl	>10	1.57 ± 0.15	2.41 ± 0.09	5.56
24	3n	Ph	O	CF3CH2-	>10	>10	1.59 ± 0.24	3.87
25	3o	Ph	O	6-acetamidonaphth-1-yl	2.82 ± 0.18	0.97 ± 0.18	1.12 ± 0.45	5.10
26	3o-γ	Ph	O	5-ethynylnaphth-1-yl	3.56 ± 0.58	7.08 ± 0.44	7.43 ± 1.11	6.23
27	3p	Ph	O	9-fluorenylmethyl	4.94 ± 0.31	3.92 ± 0.75	1.03 ± 0.22	7.10
28	3q	Ph	O	cyclohexyl	>10	2.56 ± 0.16	2.70 ± 0.62	5.61
29	3r	Ph	O	3-[1-(3,6,9-trioxadodecanyl)-1,2,3- triazol-4-yl]phenyl	>10	2.17 ± 0.32	0.50 ± 0.11	4.49
30	3s	Ph	O	6-acetamidonaphth-1-yl	>10	>10	1.06 ± 0.07	5.10
31	4a	3-MeO-4-HO-Ph	O	1-naphthyl	1.06 ± 0.19	>10	2.12 ± 0.19	4.33
32	4b	2-MeO-Ph	O	1-naphthyl	0.69 ± 0.17	0.55 ± 0.05	0.67 ± 0.04	5.00
33	4c	2-O2N-Ph	O	1-naphthyl	>10	>10	>10	5.29
34	4d	4-HO-Ph	O	1-naphthyl	2.30 ± 0.47	>10	1.06 ± 0.34	4.63
35	4e	2-MeO-Ph	O	(1R,2S)-2-phenylcyclohex-1-yl	0.40 ± 0.08	0.68 ± 0.06	0.40 ± 0.03	6.20
36	4f	2-Cl-Ph	O	(1R,2S)-2-phenylcyclohex-1-yl	>10	1.70 ± 0.33	>10	8.59
37	4g	2,6-Cl2−Ph	O	(1R,2S)-2-phenylcyclohex-1-yl	>10	1.23 ± 0.18	6.32 ± 0.96	10.01
38	4h	2-Br-Ph	O	(1R,2S)-2-phenylcyclohex-1-yl	>10	2.76 ± 0.16	>10	8.89
39	4i	2-O2N-Ph	O	(1R,2S)-2-phenylcyclohex-1-yl	>10	>10	>10	6.49
40	4j	2-MeO-Ph	O	9-fluorenylmethyl	>10	1.72 ± 0.12	>10	6.14
41	4k	2-Cl-Ph	O	9-fluorenylmethyl	>10	0.89 ± 0.05	3.54 ± 0.77	8.52
42	4l	2-MeO-Ph	O	quinolin-5-yl	>10	3.93±0.51	>10	4.89
43	5a	Ph	O	benzyl	>10	>10	>10	7.50
44	5b	Ph	O	4-MeO-benzyl	>10	>10	>10	7.33
45	5c	Ph	O	4-F-benzyl	>10	>10	>10	7.78
46	5d	Ph	O	tetrahydropyran-4-ylmethyl	>10	>10	>10	3.97
47	5e	Ph	O	biphenyl-3-yl	N.D.**	N.D.**	N.D.**	10.29
48	6a	Ph	NH	4-(5,6,7,8-tetrahydronaphth-2-yl)thiazol-2-yl	>10	>10	>10	7.48
49	6a-γ	Ph	NH	biphenyl-4-yl	>10	>10	>10	7.48
50	6b	Ph	NH	4-(5,6,7,8-tetrahydronaphth-2-yl)thiazol-2-yl	>10	>10	>10	6.46

Ki values represent an average ± S.E. of at least three independent experiments. ^** No data were obtained due to poor solubility.