Synthesis and evaluation of solanesol derivatives as novel potent synergistic agents.
Novel solanesylpiperazinotriamines as well as their N-aryl-substituted analogs were synthesized starting from solanesol through a multistep procedure. Their structures were confirmed by IR, (1)H NMR, MS, and elemental analysis. The preliminary results indicated that these novel derivatives were preferentially toxic against tumor cells, and at non-cytotoxic concentration, the synergistic effect of solanesyltriamines (3a and 3c) was even superior to that of N,N'-bis(3,4-dimethoxybenzyl)-N-solanesylethylenediamine. Interestingly, the cytotoxicity of solanesylpiperazinotriamine derivatives was markedly enhanced when conjugating with aryl pharmacophores (7-9).
Wang
Jian-Hong
JH
Key Laboratory of Natural Medicinal and Immunotechnology, Henan University, Kaifeng, China.
Gao
Rui-Hong
RH
Gan
Ying
Y
Xie
Song-Qiang
SQ
Wang
Chao-Jie
CJ
Zhao
Jin
J
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D014026:Nicotiana / Q000737:chemistry
D000972:Antineoplastic Agents, Phytogenic; D010879:Piperazines; D013729:Terpenes; C017719:solanesol