Synthesis And Physiological Activity Of Solanesyl Derivatives

Three kinds of solanesyl derivatives were designed and synthesized using solanesol, a kind of polyisoprenols extracted from tobacco waste, as the starting material. Forty-eight new compounds, including ten key intermediates and thirty-eight target compounds were prepared through different routes and their structures were confirmed by spectral analyses. Twenty-seven compounds of them were tested preliminarily in vitro for their anti-tumor activity on KB(human oral epitheliocellalar carcinoma), Bel-7402(human hepatocellalar carcinoma), HCT-8 (human colocellalar carcinoma) cells. The tested compounds showed only weak or moderate activities on the chosen biological models. 1 Solanesylamine Derivatives1.1 Synthesis of N,N—Di(acyloxyethyl)solanesylamineSolanesyl bromide, prepared by solanesol and PBr3, reacted with diethanolamine to give solanesyl diethanolamine which was then acylated with 3,4,5-trimethoxybenzoyl chloride, acetic anhydride, benzoyl chloride and cinnamyl chloride to give N,N-di[(3,4,5- tri- methoxybenzoyloxy)ethyl]solanesylamine,N,N-di[(acetyloxy)ethyl]solanesylamine, N,N-di[(benzoyloxy) ethyl]solanesylamine, N,N-di[(cinny loxy)ethyl]solanesylamine respectively.1.2 Synthesis of 3,4,5-trimethoxybenzoyloxysolanesylamide 3,4,5-Trimethoxybenzoyloxysolanesylamide was synthesized from solanesol through a four-step route. Thus,solanesyl bromide was prepared by the reaction of solanesol and PBr3.Then solanesyl bromide was reacted with potassium phthalimide to give N-solanesylphthalimide,which was refluxed with N2H4.H2O in 95% EtOH to give solanesylamine. At last,solanesylamine was reacted with 3,4,5-Trimethoxybenzoyloxyl chloride to give 3,4,5-Trimethoxybenzoyloxysolanesylamide.1.3 Synthesis of N-acylsolanesylpiperazinesFour N-acylsolanesylpiperazines were designed and synthesized .Thus, solanesyl bromide reacted with piperazine to get solanesoylpiperazine, which were then reacted with different anhydride or acid chloride to get N-acylsolanesylpiperazines.2 Diacid Solanesyl Glycosyl Esters2.1 Synthesis of Diacid Solanesyl Glucosyl DiestersSolanesol reacted with seven diprotic anhydrides to give seven compounds of diacid solanesyl esters(2). Then seven compounds of Diacid Solanesyl Glucosyl Diesters were synthesized by reaction of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide with compounds 2, using tetrabutyl ammonium bromide as the phase-transfer catalyst . 2.2 Synthesis of the Diacid Solanesyl Glycosyl EstersFourteen diacid solanesyl glycosyl esters were synthesized by the reaction of O-acetyllactopyranosyl bromide or O-acetylmaltopyranosyl bromide with diacid solanesyl monoesters, using tetrabutyl ammonium bromide as phase-transfer catalyst . 3 Solanesylamino Glycosyl Esters3.1 Synthesis of 4-N-Solanesylamino-benzoic Acid Glycosyl EstersFour glycosyl esters were synthesized by the reaction of 4-N-solanesylamino-benzoic acid with O-acetylglucopyranosyl bromide, O-acetylgalacopyranosyl bromide,O-acetyllactosyl bromide and O-acetyl- maltobiosyl bromide in the presence of Bu4NBr.3.2 Synthesis of 2-N-Solanesylamino-benzoic Acid Glycosyl EstersFour glycosyl esters were synthesized by the reaction of 2-N-solanesylamino-benzoic acid with O-acetylglucopyranosyl bromide, O-acetylgalacopyranosyl bromide,O-acetyllactosyl bromide and O-acetylmaltobiosyl bromide in the presence of Bu4NBr as the phase-transfer catalyst.