Table 1.

Opioid and benzodiazepine receptor binding of 2′-fluorophenyl substituted imidazodiazepines.

Entry	Compound	R1	R2	R3 CH3	KOR % 1	MOR % 1	DOR % 1	BZR % 1	KOR (Ki, nM)	BZR (Ki, nM)
1	GL-I-30	HC≡C	t-BuO	(S)	95	54	7	96	27	177
2	GL-I-33	HC≡C	t-PenO	(S)	94	30	25	96	34	117
3	GL-I-41	HC≡C	t-Bu(H)N	(S)	97	40	10	90	39	140
4	GL-I-78	c-Pr	EtO	(S)	96	32	41	76	48	352
5	SH-I-048B	Br	EtO	(S)	95	0	0	61	63	96
6	GL-I-32	HC≡C	PrO	(S)	95	9	14	98	64	148
7	GL-I-31	HC≡C	i-PrO	(S)	94	32	8	97	65	245
8	GL-I-38	HC≡C	c-PrO	(S)	95	18	16	96	68	127
9	SH-I-047	Br	EtO	(R)	82	16	0	84	86	238
10	SH-053-2′F-S-CH3	HC≡C	EtO	(S)	93	7	36	92	90	111
11	GL-I-43	HC≡C	Et(H)N	(S)	95	22	3	94	102	44
12	MP-III-023	HC≡C	Me(H)N	(S)	91	0	16	97	119	37
13	MP-III-021	HC≡C	MeO	(S)	93	0	22	88	122	219
14	GL-I-77	HC≡C	EtS	(S)	95	41	4	92	125	124
15	GL-I-55	HC≡C	c-Pr(H)N	(S)	93	17	24	95	150	20
16	GL-III-68	c-Pr	Et(H)N	(R)	88	0	10	100	150	452
17	GL-III-42	c-Pr	EtO	(R)	86	0	13	62	174	726
18	GL-II-74	HC≡C	Et(H)N	(R)	86	10	0	84	194	68
19	GL-III-66	HC≡C	i-Pr(H)N	(R)	63	0	0	88	233	271
20	MP-III-058	Br	MeO	(R)	84	0	4	86	237	290
21	SH-053-2′F-R-CH3	HC≡C	EtO	(R)	89	28	32	85	240	379
22	GL-II-75	HC≡C	c-Pr(H)N	(R)	81	0	3	85	278	93
23	GL-II-76	HC≡C	Pyrrolidine	(R)	80	0	0	43	371	- 2
24	MP-III-022	HC≡C	Me(H)N	(R)	80	3	22	95	381	83
25	GL-I-36	HC≡C	F3CCH2O	(S)	85	8	0	77	411	418
26	GL-III-69	Br	Me2N	(R)	75	0	10	100	511	446
27	MP-II-075	HC≡C	BzO	H	84	0	16	98	547	21
28	MP-III-004	HC≡C	MeO	(R)	76	0	24	78	599	445
29	GL-I-54	HC≡C	Me2N	(S)	78	18	11	94	788	90
30	GL-III-70	c-Pr	Me2N	(R)	68	0	50	100	800	3395
31	GL-II-73	HC≡C	Me2N	(R)	58	6	0	75	1189	506
32	MP-III-019.B	HC≡C	H2N	(R)	62	2	0	94	1534	54
33	MP-III-018.B	HC≡C	H2N	(S)	51	2	10	97	2782	17
34	GL-III-54	Cl	HO	(R)	22	0	0	100	- 2	42
35	SH-053-2′F-S-CH3-Acid	HC≡C	HO	(S)	20	0	18	93	- 2	29
36	SH-053-2′F-R-CH3-Acid	HC≡C	HO	(R)	16	0	0	93	- 2	37
37	GL-II-93	Br	HO	(R)	0	0	0	73	- 2	86

¹ Percent inhibition at 10,000 nM; ² dose response was carried out only for compounds with an inhibition of >50%.