Table I.
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compd | R = | R′ = | mp, °C | Anal. | m1 | m2 | m3 | m4 |
1 | CH3 | H | 0.029 | 0.61 ± 0.05 | 0.24 | 0.33 | ||
3 | 0.0018 | 0.0503 | 0.0069 | 0.0174 | ||||
11a | CH3 | 8-SCH3 | >205dec | C20H23N5O2S·1HCl·1.5H2O | 4.66 ± 1.02 | 11.0 | 3.62 ± 0.14 | n.d.l |
11b | CH3 | 8-SO2NH2 | C19H22N6O4S·0.5H2Oa | >30 | >30 | >30 | n.d. | |
11c | CH3 | 8-SO2NH(CH2)2NHBoc | 210–213 dec | C26H35N7O6S·3oxalate·0.25H2O | >30 | n.d. | >30 | n.d. |
11d | CH3 | 8-SO2NH(CH2)2NH2 | 155–158 | C21H27N7O4S·1.5oxalate·0.5H2O | >30 | n.d. | >30 | n.d. |
11e | CH3 | 8-SO2NH(CH2)2NHAc | 190–193 | C23H29N7O5S·2oxalate·0.5H2O | >30 | n.d. | >30 | n.d. |
15 | CH3 | 9-CH2OSi(CH3)2-t-Bu | 245–248 | C26H37N5O3Si·0.25H2O | >30 | 4.4 ± 0.3 | >30 | n.d. |
16 | CH3 | 9-CH2OH | C20H23N5O3·1.5H2O | 4.4 | n.d. | 4.4 | n.d. | |
17aj | CH3 | H | 108–111 | C21H25N5O2·1HCl·1.75H2O | 7.7 ± 2.1 | 8.00 | n.d. | n.d. |
17bk | CH3 | H | oil | C26H32N6O2·0.5H2O | 8.9 ± 4.7 | n.d. | n.d. | n.d. |
18 | H | H | >230 | 0.37 | 3.34 | 1.31 | 1.67 | |
19a | COCH3 | H | >290 | C20H21N5O3·0.25H2O | >100 | >100 | >100 | >100 |
19b | COC6H5 | H | 202–205 | C25H23N5O3·HCl·0.75H2O | >100 | >100 | >100 | >100 |
20 | SO2CH3 | H | 180–183 | C19H21N5O4S·HCl | >100 | >100 | >100 | >100 |
21 | CSNHC6H5 | H | 204–206 | C25H24N6O2S·0.75H2O | >100 | >100 | >100 | >100 |
22 | CH2≡CH | H | 249–251 | C21H21N5O2 | 1.67 ± 0.06 | 1.37 ± 0.06 | n.d. | n.d. |
23 | CH2C6H5 | H | 145–148 | C25H25N5O2·oxalate·H2Ob | 0.33 | 0.24 ± 0.10 | 0.24 | 0.22 |
24a | CH2C6H4-p-CONHCH3 | H | 191–193 | C27H28N6O3·oxalate·0.5H2O | 2.84 | 2.65 | 4.02 | 2.94 |
24b | CH2C6H4-p-CONH(CH2)2NHBoc | H | 155–158 | C33H39N7O5·oxalate·H2Oc | n.d. | 2.50 | n.d. | n.d. |
24c | CH2C6H4-p-CONH(CH2)2NH2 | H | 208–212 | C26H31N7O3·oxalate·5H2Od | 1.39 | 0.96 | 3.65 | 1.04 |
24d | CH2C6H4-p-CONH(CH2)4NHBoc | H | 173–175 | C35H43N7O5·oxalate·0.5H2O | 1.68 | 1.09 | 3.47 | n.d. |
25 | (CH2)2OH | H | 197–200 | C20H23N5O3 | 5.8 ± 1.0 | 3.2 | 9.5 | n.d. |
26 | (CH2)2Cl | H | 188–190 | C20H22N5O2Cl·2HCl·1.5H2O | 0.052 | 0.21 | 0.078 | 0.13 |
27 | (CH2)2NH2 | H | 190–193 | C20H24N6O2·1H2O | 1.19 | 3.04 | 1.97 | 2.84 |
28 | (CH2)2NHAc | H | 93–95 | C22H26N6O3·0.75H2O | 0.67 | 2.52 | 0.97 | 2.57 |
29a | (CH2)2NHCO(CH2)2NHBoc | H | 112–115 | C28H37N7O5·1CHCl3·0.5H2O | 13.3 ± 5.95 | 6.06 | 6.19 ± 0.28 | n.d. |
29b | (CH2)2NHCO(CH2)3NHBoc | H | 130–133 | C29H39N7O5e | 4.80 ± 1.36 | 3.34 | 4.10 ± 0.52 | n.d. |
30a | (CH2)2NHCO(CH2)2NH2 | H | 85–88 | C23H29N7O3·2.67TFA·1.55H2O | 4.34 ± 0.26 | 5.84 | 6.65 ± 0.43 | n.d. |
30b | (CH2)2NHCO(CH2)3NH2 | H | C24H31N7O3·3TFA | 9.53 ± 2.46 | 6.34 | 11.5 ± 1.98 | n.d. | |
31a | (CH2)2NHCO(CH2)2NHAc | H | 180–183 | C25H31N7O4·0.75H2O | 39.4 ± 16.6 | 34.5 | >100 | n.d. |
31b | (CH2)2NHCO(CH2)3NHAc | H | 162–165 | C26H33N7O4·2.75H2Of | 9.65 ± 2.98 | 8.82 | 10.8 ± 0.45 | n.d. |
32d | (CH2)6NHBoc | H | C29H40N6O4·oxalate·H2Og | 0.0371 ± 0.0017 | 0.0214 ± 0.0039 | 0.0460 ± 0.0155 | 0.0232 ± 0.0053 | |
33a | (CH2)3NPth | H | 202–204 | C29H28N6O4·0.75H2O | 1.81 ± 0.40 | 0.84 ± 0.35 | n.d. | n.d. |
33b | (CH2)4NPth | H | 195–196 | C30H30N6O4·oxalate·0.5H2O | 0.17 ± 0.006 | 0.089 ± 0.005 | 0.12 | 0.21 |
33c | (CH2)5NPth | H | 120–122 | C30H32N6O4 | 0.060 ± 0.001 | 0.020 ± 0.001 | n.d. | n.d. |
33d | (CH2)6NPth | H | 157–158 | C32H34N6O4·1DMF | 0.018 ± 0.008 | 0.018 ± 0.003 | n.d. | n.d. |
34a | (CH2)3NH2 | H | 111–113 | C21H26N6O2·1.5H2O | 3.87 ± 0.12 | 5.12 ± 0.93 | n.d. | n.d. |
34b | (CH2)4NH2 | H | 121–123 | C22H28N6O2·1H2O | 3.08 ± 0.22 | 1.74 ± 0.03 | n.d. | n.d. |
34c | (CH2)5NH2 | H | 200–202 | C23H30N6O2·1H2O | 1.17 ± 0.01 | 5.89 ± 0.13 | n.d. | n.d. |
34d | (CH2)6NH2 | H | 138–140 | C24H32N6O2·0.5CHCl3·0.67H2Oh | 1.31 ± 0.02 | 1.34 ± 0.12 | n.d. | n.d. |
34e | (CH2)7NH2 | H | 72–75 | C25H34N6O2·1.5-H2O | 0.066 | 0.057 | n.d. | n.d. |
34f | (CH2)8NH2 | H | 65–68 | C26H36N6O2·H2O | 0.020 ± 0.001 | 0.026 ± 0.0005 | n.d. | n.d. |
34g | (CH2)9NH2 | H | 140–143 | C27H38N6O2 | 0.024 ± 0.001 | 0.024 ± 0.007 | n.d. | n.d. |
34h | (CH2)10NH2 | H | 95–97 | C28H40N6O2·1.5H2O | 0.0158 ± 0.0009 | 0.0117 ± 0.0007 | n.d. | n.d. |
35g | (CH2)9NHAc | H | 170–173 | C29H40N6O3·2oxalate | 0.052 ± 0.001 | 0.050 ± 0.018 | n.d. | n.d. |
35h | (CH2)10NHAc | H | 87–90 | C30H48N6O3·0.5H2O | 0.075 ± 0.013 | 0.043 ± 0.025 | n.d. | n.d. |
36 | (CH2)10NEt2 | H | 168–171 | C32H48N6O2·4oxalate·3H2O | 0.0030 ± 0.0004 | 0.0135 ± 0.0009 | n.d. | n.d. |
37 | (CH2)10NHCH2-(o-MeO)Ph | H | 153–156 | C36H48N6O3· 4oxalate·4H2Oi | 0.0033 ± 0.0006 | 0.022 ± 0.0012 | n.d. | n.d. |
Calcd 5.28 H, found 5.87.
Calcd 13.08 N, found 11.93.
Calcd 13.58 N, found 12.58.
Calcd 6.25 H, found 5.45.
Calcd 17.33 N, found 16.73.
Calcd 6.97 H, found 6.17.
Calcd 13.04 N, found 12.26.
Calcd 16.53 N, found 18.01.
Calcd 8.04 N, found 6.84.
R″ = Et.
R″ = (CH2)6CN.
n.d. = not determined.