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. Author manuscript; available in PMC: 2012 Aug 21.
Published in final edited form as: Drug Dev Res. 1998 Dec 21;45(2):52–66. doi: 10.1002/(SICI)1098-2299(199810)45:2<52::AID-DDR2>3.0.CO;2-V

TABLE 2.

Structures of Pyridoxal-6-azoaryl-5-phosphate Derivatives Examined as Antagonists at P2 Receptors

graphic file with name nihms-385205-t0001.jpg
Compounda 2′ 3′ 4′ 5′ X
2 H H H H CH2O
3 SO3H H H H CH2O
4 H SO3H H H CH2O
5 H H SO3H H CH2O
6 (PPADS) SO3H H SO3H H CH2O
7 (IsoPPADS) SO3H H H SO3H CH2O
8 OCH3 H H SO3H CH2O
9 H COOH H H CH2O
10 H H COOH H CH2O
11 COOH Cl H H CH2O
12 Cl H H H CH2O
13 Cl H H SO3H CH2O
14 Cl H H COOH CH2O
15 H Cl COOH H CH2O
16 Cl H H NO2 CH2O
17 NO2 H H NO2 CH2O
18 H H NO2 H CH2O
20 SO3H H H SO3H CH2
21 Cl H H SO3H CH2
23 SO3H H H SO3H CH2CH2
24 Cl H H SO3H CH2CH2
25 H H COOH H CH2CH2
27 SO3H H H SO3H CH=CH
29 SO3H H H SO3H CH2CH2CH2
30 Cl H H SO3H CH2CH2CH2
graphic file with name nihms-385205-t0002.jpg
R1 R2 R3 R4 R5
32 H SO3H H SO3H H
33 SO3H H SO3H H H
34 H SO3H H SO3H SO3H
a

Compounds 1 (X=CH2O), 19 (X=CH2), 22 (X=CH2CH2), 26 (X=CH=CH), and 28 (X=CH2CH2CH2), and 31 (X=CH=CHCH2) are non–azo-linked precursors (see Schemes 1 and 2). Compounds 1, 2, 3, 5, 6, 17, and 18 were reported by Lambrecht etal., 1996.