Chloroalkyl piperazine and nitrogen mustard porphyrins: synthesis and anticancer activity.
Fifteen new chloroalkyl piperazine and nitrogen mustard porphyrins have been synthesized by the direct condensation of chloroalkyl piperazine, nitrogen mustard benzaldehyde, and pyrrole. Each porphyrin bears 1-4 chloroalkyl piperazine or nitrogen mustard moieties, which have been used as drugs. The Lindsey method was modified to synthesize chloroalkyl piperazine and nitrogen mustard porphyrins. To successfully synthesize chloroalkyl piperazine and nitrogen mustard porphyrins, catalyst acidity was proved to be the key factor, while the ratio of pyrrole to aldehyde had great influence on product yield. The synthetic chloroalkyl piperazine and nitrogen mustard porphyrins were characterized by elementary analysis, MS, (1)H NMR, IR, and UV-vis. Their anticancer activity to bel-7404 liver cancer cells was tested by the MTT assay. Most of the synthetic porphyrins had good anticancer activity toward bel-7404 liver cancer cells in the absence of light. These compounds might be potential anticancer medicines.
Guo
Can-Cheng
CC
College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China. ccguo@hnu.net.cn
Tong
Rong-Biao
RB
Li
Ke-Lai
KL
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D006801:Humans; D008466:Mechlorethamine / Q000737:chemistry*; D010879:Piperazines / Q000737:chemistry*; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013057:Spectrum Analysis
D000970:Antineoplastic Agents; D010879:Piperazines; D011166:Porphyrins; D008466:Mechlorethamine