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Synthesis And Preliminary Study On In Vitro Antitumour Activities Of (Z)-1-[2-(tribenzylstannyl) Vinyl]-1-carbocyclol And Derivates

Posted on:2004-05-25Degree:DoctorType:Dissertation
Country:ChinaCandidate:Y J RenFull Text:PDF
GTID:1101360095955246Subject:Applied Chemistry
Abstract/Summary:PDF Full Text Request
1-Ethynyl-1-carbocyclol react with tribenzylstannylhydride (C6H5CH2)3SnH and generate the corresponding [Z]-1-[2-('tribenzylstannyl)vinyl]-cyclopentanol (1). [Z]-1-[2-(tribenzylstannyl)vinyl]-cyclohextanol(2), [Z]-1-[2-(tribenzylstannyl)-vinyl] -cycloheptanol (3) and [Z]-1-[2-(tribenzyl-stannyl)vinyl]-cycloocttanol (4). The Xray diffraction analysis of the compounds (3) and (4) shows the presence of an intramolecular coordination of oxygen to the tin atom (O-Sn) giving rise to a five-membered ring in which the melal exhibits a distorted trigonal bipyramidal geometry.The compounds (1)-(4) obtained react with halogen (I2 Br2 or IC1) to form the associated organotin monohalide (5)-(13) or dihalide compounds (14)-(19). respectively. The organotin hydroxide (20) was prepared by the reaction of (Z)-1-[2-(dibenzylbromostannyl)vinyl]-1-cycloheptanol (11) with KOH. The complexes (21)-(33) formed by reactions of organotin dibromide or dichloride with ligands Bipy(2?2'-bipyridyl), Phen( 1,10-phenanthroline), Dmph(2,9-dimethyl-1,10-phenanthroline) and Oxin(8-hydroxyquinoline) are also included in this dissertation. We synthesize 33 organotin compounds that have not been seen in the literature. They are characterized by Elemental analysis, IR and 'H NMR.9 organotin compounds synthesized were tested against P388 lymphocyte leukemia in mice and BEL-7402 liver cancer in human tumor cell lines. Most of these compounds show high in vitro antitumour activities. The organotin compoundsof (Z)-1-[2-(benzyldibromostannyl)vinyl]-l-cycloheptanol and (Z)-1-[2-(dibenzylchlorostannyl)vinyl]-1-cyclooctanol might become useful antitumour drugs in the future. (Z)-1-[2-(dibenzylhalostannyl)vinyl]-1-carbocyclol or (Z)-1-[2-(benzyldihalostannyl)vinyl]-1-carbocyclol were found to be more active than (Z)-1-[2-(tribenzylstannyl)vinyl]-1-carbocyclol against P388 lymphocyte leukemia and BEL-7402 liver cancer.
Keywords/Search Tags:Organotin compound, Synthesis, Characterize, Crystal structure, Antitumour activities
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