Table II.
Characterization of Compounds Synthesized
compde | formula |
Rf
|
low resolutiona | high resolutiona
|
||
---|---|---|---|---|---|---|
Ad | Bd | calcd | found | |||
3 | C28H39BrN4O2S | 0.66 | 577,b 575,b 497, 317, 185 | 575.2055 | 575.2027 | |
577.2038 | 577.2029 | |||||
4 | C28H41N5O2S | 0.15 | 0 | 512,b M+ (511),c 368,c 327,c 314,c 254c | 512.3059 | 512.3073 |
5 | C37H49N5O4S | 0.51 | 0.53 | 660,b 402, 277,185 | 660.3584 | 660.3607 |
6 | C36H48N6O3S | 0.41 | 0.32 | 645,b 387, 318, 229 | 645.3584 | 645.3608 |
8 | C35H44N8O4S | 0.69 | 0.75 | 674,b 647, 553, 461, 369, 277 | 673.3284 | 673.3344 |
9 | C38H55N7O4S2 | 0.39 | 0.26 | 738,b 468, 342, 227 | 738.3835 | 738.3848 |
10 | C36H45N7O2S3 | 0.83 | 0.93 | 704,b 688, 307, 242 | 704.2875 | 704.2894 |
11 | C37H46N8O3S3 | 0.58 | 747,b 461, 369, 277 | 747.2933 | 747.2964 | |
12 | C37H44N8O2S4 | 0.85 | 0.9 | 761,b 729, 553, 461, 369 | 761.2548 | 761.2570 |
13 | C36H45N7O2S3 | 0.89 | 0.94 | 704, 553, 461, 369, 277 | 704.2875 | 704.2891 |
14 | C49H51N5O8S | 0 | 0.31 | 870,b 613, 461, 309 | 870.3534 | 870.3535 |
15 | C49H48Br4N6O7S2 | 0.30 | 1217b | 1212.9838 | 1212.984 |
Unless noted, by fast atom bombardment mass spectroscopy, using glycerol matrix, in the positive ion mode.
M + 1.
EI mass spectroscopy.
Solvent A = chloroform/methanol/ammonia, 90:10:1; solvent B = chloroform/methanol/acetic acid, 85:10:5.
Refer to Table I for structures. Yields for conjugates of TAC (compounds 5 and 7–13) were generally in the range of 50–80%.