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. Author manuscript; available in PMC: 2024 Jan 17.
Published in final edited form as: J Med Chem. 2002 Aug 1;45(16):3440–3450. doi: 10.1021/jm011093d

Table 2.

Synthesized Tricyclic Purinone Derivatives: Substitution Pattern, Method of Preparation, Yields, and Analytical Data1

compda stereo-
chemistry		 n R1 R2 R4 R7 R8 method yield
(%)		 formula analyses mp
(°C)		 [α]D20 b
15 0 CH3 H H H H A 49 C8H9N5O•HCl•0.7H2O C, H, N >250
16 0 CH3 H benzyl H H A 41 C15H15N5O•2HCl C, H, Nc 235
17 0 CH3 H CH3 H H A 75 C9H11N5O•2HCl•0.2H2O C, H, N >250
R-18 R 0 CH3 H CH3 H CH3 C 35 C10H13N5O•2HCl•0.3H2O C, H, N >250 2.3
S-18 S 0 CH3 H CH3 H CH3 C 39 C10H13N5O•2HCl•0.5H2O C, H, N >250 −2.8
RS-19 rac 0 CH3 H CH3 H C2H5 B 45 C11H15N5O•2HCl•0.25H2O C, H, N >250 0
R-19 R 0 CH3 H CH3 H C2H5 B 42 C11H15N5O•2HCl•0.1H2O C, H, N >250 4.2
S-19 S 0 CH3 H CH3 H C2H5 B 32 C11H15N5O•2HCl•0.1H2O C, H, N >250 −3.9
RS-20 rac 0 CH3 H CH3 CH3 H B 48 C10H13N5O•2HCl•0.1H2O C, H, N 175 0
R-20 R 0 CH3 H CH3 CH3 H B 52 C10H13N5O•2HCl•0.5H2O C, H, N 200 −3.4
S-20 S 0 CH3 H CH3 CH3 H B 54 C10H13N5O•2HCl•H2O C, H, N 200 3.3
21 0 CH3 phenyl H H H A 38 C14H13N5O•HCl•0.6H2O Cd, H, N >250
22 0 CH3 phenyl CH3 H H A 45 C15H15N5O•HCl•H2O C, H, N >250
RS-23 rac 0 CH3 phenyl CH3 H C2H5 D 29 C17H19N5O•HCl•0.3H2O C, H, N >250 0
R-23 R 0 CH3 phenyl CH3 H C2H5 D 27 C17H19N5O•HCl•0.5H2O C, H, N >250 2.4
S-23 S 0 CH3 phenyl CH3 H C2H5 D 28 C17H19N5O•HCl•0.3H2O C, H, N >250 −2.6
RS-24 rac 0 H phenyl CH3 H C2H5 D 36 C16H17N5O•HCl•3H2O C, H, N >250 0
R-24 R 0 H phenyl CH3 H C2H5 D 35 C16H17N5O•HCl•2H2O C, H, Ne >250 4.5
S-24 S 0 H phenyl CH3 H C2H5 D 35 C16H17N5O•HCl•2H2O C, H, N >250 −4.8
R-25 R 0 CH3 styryl CH3 H C2H5 D 16 C19H21N5O 335.174f >250 3.3
S-25 S 0 CH3 styryl CH3 H C2H5 D 14 C19H21N5O 335.175f >250 −3.2
R-26 R 0 H styryl CH3 H C2H5 D 32 C18H19N5O•HCl•0.6H2O C, H, N >250 3.2
S-26 S 0 H styryl CH3 H C2H5 D 28 C18H19N5O•HCl•0.7H2O C, H, N >250 −3.1
27 1 CH3 H CH3 - - A 52 C10H13N5O•2HCl•0.2H2O C, H, N >250
28 1 CH3 Cl CH3 - - A 30 C10H12N5OCl•HCl•0.1H2O C, H, N 261
29 2 CH3 H CH3 - - A 27 C11H15N5O•2HCl•0.1H2O C, H, Ng 198
30 3 CH3 H CH3 - - A 14 C12H17N5O•2HCl C, H, N 210
a

Hydrochlorides of imidazopurinones.

b

Solvent, methanol; concentration, 1.00 g/100 mL.

c

N: calcd, 18.81; found, 18.35.

d

C: calcd, 53.46; found, 53.04.

e

N: calcd, 19.04; found, 18.52.

f

Determined by high-resolution mass spectroscopy.

g

N: calcd, 22.74; found, 22.24.