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. Author manuscript; available in PMC: 2013 Apr 1.
Published in final edited form as: Bioorg Med Chem Lett. 2012 Jan 4;22(7):2635–2639. doi: 10.1016/j.bmcl.2011.12.123

Table 1.

C(2)/C(5)/C(6) amidine analogs and cytotoxicity graphic file with name nihms-348084-t0001.jpg

Compound 2R 5R X uPA IC50 μM tPA IC50 μM Plasmin IC50 μM Trypsin IC50 μM Cytoxicity
amiloride acylguanidine (H2N)2C=NC(O)– NH2 Cl 7 220 >250 >250 50% cytotoxic at 250μM by 24h
7 amidox-Am-C(5)-Gly-OBn amidoxime H2NC(NOH)- -NHCH2CO2Bn Cl 74 200 >250 >250 Not cytotoxic
8 amidox-Am-C(5)-Gly-OH amidoxime H2NC(NOH)- -NHCH2CO2H Cl 231 >250 >250 >250 Not cytotoxic
8-H dechloro-amidox-Am-C(5)-Gly-OH amidoxime H2NC(NOH)- -NHCH2CO2H H 279 >250 230 >250 Not cytotoxic
11 amidine-Am-C(5)-Gly-OBn amidine H2NC(NH)- -NHCH2CO2Bn Cl 4 200 >250 >250 50% cytotoxic at 250μM by 72h
2 amidine-Am-C(5)-Gly-OH amidine H2NC(NH)- -NHCH2CO2H Cl 237 >250 >250 >250 Not cytotoxic
2-H dechloro- amidine-Am-C(5)-Gly-OH amidine H2NC(NH)- -NHCH2CO2H H 212 >250 >250 >250 Not cytotoxic
12 amide-Am-C(5)-Gly-OBn carboxamide H2NC(O)- -NHCH2CO2Bn Cl 69 >250 >150 >250 Not cytotoxic
14 Am-C(5)-Gly-OBn acyl guanidine (H2N)2C=NC(O)- -NHCH2CO2Bn Cl 3 >190 >250 >250 50% cytotoxic at 100μM by 24h
1 Am-C(5)-Gly-OH acyl guanidine (H2N)2C=NC(O)- -NHCH2CO2H Cl 17 >250 >250 >250 Not cytotoxic
1-H dechloro-Am-C(5)-Gly-0H acyl guanidine (H2N)2C=NC(O)- -NHCH2CO2H H 47 >250 >250 >250 Not cytotoxic