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. Author manuscript; available in PMC: 2016 Apr 15.
Published in final edited form as: ACS Chem Neurosci. 2015 Feb 12;6(4):599–614. doi: 10.1021/cn500330v

Table 2.

Mono-substituted benzylic substituents at the 1-position and their effect on OX antagonism

graphic file with name nihms-678114-f0010.jpg
Number R1 R2 Ke (OX1, nM)b Ke (OX2, nM)c OX2/OX1
11 OMe OMe 199± 47 >10,000 >50.3
41 O-Isopropyl H 1470± 70 >10,000 >6.8
42 NO2 H >10,000 1200± 160 <0.12
43 NH2 H 1310± 90 a
44 NMe2 H 75.3± 1.3 660±160 8.8
45 H O-n-Propyl 370± 50 >10,000 >27
46 H O-Isopropyl 489± 68 >10,000 >20
47 H NH2 >10,000d a
48 H NMe2 253± 85 >10,000 >40
49 H NHAc >10,000d a
50 H NHCONH-n-hexyl >10,000d a
51 H Isopropyl 85± 21 >10,000 >118
a

< 35% inhibition at 10 μM

b

Values are the mean ± SEM of at least three independent experiments performed in duplicate

c

Values are the mean ± SEM of at least two independent experiments in performed duplicate; for compounds with Ke < 100 nM at OX1 at least three independent experiments in duplicate were performed.

d

Values are the mean ± SEM of two independent experiments performed in duplicate.