HCID 11442519, compound → HCID 45263211, compound
Reaction equation
[ClH:1].Cl.Cl.NCCC[N:8]([CH2:14][C:15]1[C:16]2[C:21]([CH:22]=[C:23]3[C:28]=1[CH:27]=[CH:26][CH:25]=[CH:24]3)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9][CH2:10][CH2:11][CH2:12][NH2:13].Cl.Cl.Cl.NCCCCN(CC1C2C(C=C3C=1C=CC=C3)=CC=CC=2)CCCCN.Cl.Cl.Cl.NCCCCN(CC1C2C(C=C3C=1C=CC=C3)=CC=CC=2)CCCCCN.Cl.Cl.Cl.NCCCCNCCCCNCC1C2C(=CC=CC=2)C=CC=1.Cl.Cl.Cl.NCCCCNCCCCNCC1C2C3=C4C(=CC=2)C=CC=C4C=CC3=CC=1.Cl.Cl.Cl.C1C2C(=CC3C(C=2CNCCCCNC2CCC(N)CC2)=CC=CC=3)C=CC=1>>[ClH:1].[ClH:1].[CH:27]1[C:28]2[C:23](=[CH:22][C:21]3[C:16]([C:15]=2[CH2:14][NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:24]=[CH:25][CH:26]=1Participants
Procedure
As is apparent from the above Tables 1–3, a limited class of N-alkylarylpolyamine compounds (i.e. N-naphthylalkyl, N-anthracenylalkyl and N-pyrenylalkyl) have unique properties of surprising cytotoxicity, unexpected selectivity in killing cancer cells (especially cells with high polyamine transport activity), and/or facilitate the delivery of known toxic agents into cancer cells. As shown in Table 2, the N-(3-Amino-propyl)-N-anthracen-9-ylmethyl-butane-1,4-diamine, trihydrochloride (8d), N-(4-Amino-butyl)-N-anthracen-9-ylmethyl-butane-1,4-diamine, trihydrochloride (8e), N-(4-Amino-butyl)-N-anthracen-9-ylmethyl-pentane-1,5-diamine, trihydrochloride (8g), N-(4-Amino-butyl)-N′-naphthalen-1-ylmethyl-butane-1,4-diamine trihydrochloride (27b), N-(4-Amino-butyl)-N′-pyren-1-ylmethyl-butane-1,4-diamine trihydrochloride (27d), and N-{4-[(Anthracen-9-ylmethyl)-amino]-butyl}-cyclohexane-1,4-diamine trihydrochloride (31) have outstanding selectivity in targeting and killing cells with active polyamine transporters.
Sources & evidence
- ORD record
- ord-04e08b1c1c1a4b738fb20761890184da
- Source dataset
- uspto-grants-2006_02
- Patent number
- US07001925B1
Reaction notes
Loading…