[生物医药论文精品]海洋生物碱pityriacitrin及其衍生物的合成与生物活性研究

海洋生物碱PITYRIACITRIN及其衍生物的合成与生物活性研究A1A0A2A3A4A5A6A7A8A9A10A11A12A13A14A15A16A17A18A19A20PITYRIACITRINA14A21A22A23A24A25A26A12A27A28A29A30A31A32A33A34A35A36A37A18A19A14A22A23A38A39A40A41A42A43A44A45A46A45A46A47A48A49A50A51A52A53A54A55A56A57A14A49A50A51A245A56A57A58A59A60A61A62A63A64A65A35A66A67A68A30A14PICTETSPENGLERA69A70A22A23A32PITYRIACITRINA71A36A37A18A19A44A72A73A74A75A76A22A19A77A66A67A78A26A79A80A81A82A83A84A85A79A80A81A82A83A86A85A87A88A85A30A31A32A89A90A91A92A44A7A93A94A12A27MDA231A30A31A32A25A26A14A12A27A28A29A95A96A35A36A97A76A22A19A98A99A100A7MDA231A101A75A102A103A29IC50008UMA104A72A105A15A16A17A18A19A20PITYRIACITRINA39A106A107A89A90A108A109A14A101A75A110A93A94A103A29A14A111A112A76A22A19A35A74A47A48A14A21A22A23A14A69A70A113A114A61A115A116A117A118A19A14A22A23A119A120A32A121A122A14A123A124A44A125A126A127A2PITYRIACITRINA128A15A16A17A128A110A93A94A128A21A22A23A128A10A11A18A19A20A128PICTETSPENGLERA69A70SYNTHESISANDBIOACTIVITYOFTHEMARINEALKALOIDPITYRIACITRINANDITSDERIVATIVESABSTRACTA129OBJECTIVETOTALCHEMICALSYNTHESISANDINVITROCYTOTOXICEVALUATIONOFCARBOLINEALKALOIDPITYRIACITRIN,ORIGINALLYISOLATEDFROMAMARINEBACTERIUM,ANDITSDERIVATIVESISREPORTEDFORTHEFIRSTTIMEMETHODSUSINGTRYPTOPHANOR5HYDROXYLTRYPTOPHANAND5SUBSTITUTEDINDOLEASSTARTINGMATERIALS,VIATHEMODIFIEDPICTETSPENGLERREACTION,PITYRIACITRINANDITSDERIVATIVESWERESYNTHESIZEDRESULTSALLCOMPOUNDSHAVEBEENCHARACTERIZEDBYIR,NMRANDMASSSPECTROMETRYALLTHECOMPOUNDSWERETESTEDFORINVITROCYTOTOXICITYAGAINSTMDA231COMPOUND5EXHIBITEDHIGHCYTOTOXICITYIC50008UMAGAINSTMDA231CELLLINECONCLUSIONCARBOLINEALKALOIDPITYRIACITRINWASALEADCOMPOUNDOFANTITUMOR,THEROUTEOFSYNTHESISMAYBEASTHEREFERENCEFORTHESYNTHESISOFANOLOGUESKEYWORDSPITYRIACITRINCARBOLINEANTITUMORTOTALSYNTHESISMARINEALKALOIDPICTETSPENGLERREACTIONA130A131A132A133A134A135A136A137A138A139A140A141A142A143A144A145A133A146A147A148A136A149A150A151A152A153A148A136A154A155A156A157A158A159A160A161A162A161A163A143A164A165A166A130A131A132A137A144A167A168A169A170A171A172A173A174A175A143A146A147A176A177A178A133A134A135A136A150A168A169A130A131A132A174A175A143A179A180A148A136A149A181A182A183A184A143A169MANZAMINES,DIDEMNOLINES,EUDISTOMINS,FASCAPLYSINS,PLAKORTAMINESA185SHISHIJIMICINSA150A186A187A162A138A179A180A143A130A131A132A187A134A135A136A188A189A190A191A192A143A148A136A154A155A150A193A194A150A193A195A196A150A193A197A198A150A199A200A154A1551A166A201A202A137A203A204A205A206A207A208A162A143A191A192A143A193A195A196A154A155A150A209A153A210A211A212A204A143A213A214A166A151A152A130A131A134A135A136A205A168A169A143A215A201A143A216A155A170A171A217A218A219A173A220A221A174A175A150A222A153A223A224A225A226DNAA150A227A228A229A230A192A175A231A150CDKA232A233A234A235A236A237A238A239A231A240A185IBA239A231A241A242A195A196DNAA243A244A135A2452A150A176A246A247A248A176A249A250A251A210A243BZRA1855A252A253A254A210A243A169A255A192A143A0A185A1553,4A166A197A1A206A2A130A131A132A133A134A135A136A142C1A49A159A226A3A4A143A5A203A6A150A148A136A154A155A15A169A7A8A9A10A143A11A125A166A151A152A253A254A185A146A147A121A13A14A148A136A137A179A180A16A148A136A179A17A185A179A180A18A194A143A19A20A21A22A23A136A150C1A49A24A146A147A14A148A136A54A21A143A130A131A132A148A136A149A137A162A138A179A180A148A136A143A174A175A255A153A25A26A143A134A135A136A166A181A139A150A217A27A10A28A220A29A179A180A179A17HERECTUSA90A30A31A32A33A34HYRTIOSULAWESINE6A80A35A36A37A38A39A39A40LISSOCLINUMFRAGILEA90A30A31A32A33A34EUDISTOMINU7A41PITYRIACITRINA42A35PARACOCCUSF1547A228A39A43A44A458A47MALASSEZIAFURFURA229A469A90A30A31A155A48A34A50A51A52A53A55A56A57A34A58A59A60A61A62A63A64A65C1A66A67A68A69A70A71A72A73A74A75A234A41A76A779A78A79A81PITYRIACITRINA82A83A84A85A86A87A34UVA237A88A89A91MAX389,315,289,212NMA64A35A125A85A92A93A94A51A95A96A97A34UVA242A72A98A63A64A244A61A62A63A99A84A85A34A100A95UVA237A88A89A91A97A39A43A58A59A60A101A63A102A90A42A103A104A105A106A34A41A107A108A39A43A109A101A63A34A110A111A112A33A113A95A114A115A34A116A117A64A118A119A120A122A123A124A126A127A135A128A129A130A131A169A132A133A134A136A137A124A138A140A141A124A142A143A245A144A145A129A205A169A146A147A148A149A148A150A151A152A153A154A156A157A158A159A160A161A162A124A163A164A165A252A166A167A168A170A171A172A173A174A141A124A175A176A177A140A178A179A136A180A181A182A164A165A170A171A183A141A184A185A186A187A188A124A178A189A140A178A190A136A175A191A167A168A120A183A141A152A153A169A132A148A149A193A194A195A124A154A156A133A196A165结果与讨论A198A199A200A201A202A204A206A207A208A209A210A211A212A213A204A214A215A216A218A219A221PICTETSPENGLERA222BISCHLERNAPIERALSKIA223A206A224A225A226A227A230A231A204A232A240A216A218A233PICTETSPENGLERA235A236A238A239A241A243A246A247A248A249A250A251A253A254A255A32A61A0A1A1A34A19A2A3A12A13A4A5A6A35A11A7A68A36A11A30A8A9A23910A233A129A38A128A32A39A68A40A129A197A10A41A14A15PICTETSPENGLERA235A236A11A43A16A17A29A46A18A11A197A10A32PICTETSPENGLERA143A241A30A8A239A47A50A20A129A69A48A21A61A0A22A23A24A11A235A236A25A26A125A27A52A22A42A28A31A63A33A32A239A47A238A37A44A197A10A11A53A45A49A51A233A61A54A128A57A32A58A141A11PICTETSPENGLERA235A236A59A11A238A55A164A5A60A233A11A56A62A64A193A55A65A119A248A66A69A67A11A70A19A32A222A250A71A72A233A119A73A239A72A90A32A248A66A69A74A75A76A3A77A193A115A119A73A189A72A90A32A78A222A79A69A11A164A5A80A11A81A82A1A254A83A55A79A84A77A193A85A83A9A86A11A222A83A87A5A19A32A76A3A88A89A5A11A91A92A12A12A13A4A32A125A93A58A0A74A92A94A95A250A12A13A4A233A116A125A32A119A96A44A11A97A98A90A32LA246A247A248A119A248A84A25A26A67A55A99A1003A101A102A101A6516A103A104A105A136A106A107A108A109A110A180A111A112A113A114A114A117A118A105A120A121A122A234A123A124A126A113A127A130A114A117A118PITYRIACITRIN1A131A132A133A134A135A216A1373A138NHNNHOCOOHNHNNHOHOCOOHNHNNHOH3COCOOHA1391A140A142A1449,10A14511A146A147A148A149FIG1STRUCTUREOFCOMPOUNDS9,10AND11NHNHCLOOR1NHHOOR1R1AB12R1H13R1OCH316R1H17R1OCH314R1BR15R1NO218R1BR19R1NO2AA150A151A152,A153A154,0A155,1H,8095BA156A157A202A158A159A160,A153A161A153A162,RT,2H,6570A1632A165A166A167A168A169A170A171A172FIG2ROUTEOFSYNTHESISOFTHEINTERMEDIUMNHCOOHH2NNHHOOCNHNNHOR2R1R2R11R1HR2H2R1OCH3R2H3R1BRR2H4R1NO2R2H5R1HR2OH6R1OCH3R2OH7R1BRR2OH8R1NO2R2OHCA173A174A188A175A176,A174A177,50A178,2H,2030A1793A181A182A183A184A185A186A184A187A190A191FIG3ROUTEOFSYNTHESISOFTHETARGETCOMPOUNDSA192A194A195A196A198A199A200A201A203A204A205A206A207A20805A209A186A210A211A212A213A214A215A2171HA207A192906A186A218A219A220A221A223A2243A225A226A227A22812A229A230A231A232A235A236A237A238A23912A240A241A242A24313,14A24415A245A246A247A248A249A250A251A252A253A254A255A105A99A174A0A41A24A1A2A119A98A3A4A46A4A88A90A5A63A80A7A80A812A21A9A91A202A10A11A92A122A12A13A14A64A152HA16A17A18A193A20A81A20A2216A32A238A23673A25A93A26A27A28A29A30A31A3316A33A34A35A3617,18A3719A42A38A72A39A60A206A40A43A44A45A47A215A48A49A50A51A52A53A54A55A56A842A57A58A59A106A61A62A63A51A101A65A663A67A68A67A69A225A70LA71A73A74A75A76A67A77A78A94A74A40A67A79A82A83A40A104A85A86A63A51A87A8950A95A96A97A100A51A52A532HA57A102A50A40A103A215A107A38A108A109A110A111A112A113A40A104A85A82A114A115A116A117A118A114A120A121A123A124A125A125A126A127A222A128A51A50A70PITYRIACITRIN1A129A130A131274A132PITYRIACITRIN1A133A134A135A136A137A138A139A140A141A142A133A143A144A1459A132A146A147A148A149A129A150A153A151A152A154A155A156A157A133A158A159A160A129A231A161A162A224A163A164A165A166A167A168A169A170A171A172PITYRIACITRINB9A178A1731A186A175A176A177A179225A180A181PITYRIACITRINBA182A183IRLINGERA184A185A1872005A188A217MALASSEZIAFURFURA229A18911A190A191A192A193A194A195A196A195A197A198A199A200A201A203A204A205A207A20328A208A209A210A211A212A213A214A216A218A219A220A221A2235A2262A213A227A228A230A232A233A234A235A236A237A239A240A241A220A242A243A244A245A246A247A240A232A23310A24811A2491A250A251A252A253A254A255PICTETSPENGLERA64A0A60A139A32A63A1A255A2A129A3A69A64A0A254A119A4A1261A51A5A6A12A13A7A8A9A10A11A128A14A205A58A62A15A16A9A17A18A14A217A19A20A21A35A22A9A10A11A6A10A23A26A225A24A36A25A27A41A134A43A28A29A6PICTETSPENGLERA30A31A14A79A153A23A33A10A23A34PITYRIACITRINA66A37A35A22A38A39A11A41A67A40A6A96A42A215A11A44A62A45A46A72A73A47A48A49A50A52A72A73A47A48A49A53A52A54A55A52A29A56A34A57A16A59A61A14A143A65A9A10A11A70A68A71A74A43A9A75A76A77A10A23A6A78A9A10A11A41REFERENCES1SUWIGARNPEDPRADAB,RUANGELIEEDRADA,RAINEREBEL,ETALNEWCARBOLINEALKALOIDSFROMTHEANDAMANSEASPONGEDRAGMACIDONSPJJNATPROD2004,6712211321162HUAJIGUAN,XIAODONGLIU,WENLIEPENG,ETALBCARBOLINEDERIVATIVESNOVELPHOTOSENSITIZERSTHATINTERCALATEINTODNATOCAUSEDIRECTDNADAMAGEINPHOTODYNAMICTHERAPYJBIOCHEMICALANDBIOPHYSICALRESEARCHCOMMUNICATIONS,2006,3428949013MCNULTYJ,STILLIWJSYNTHETICAPPROACHESTOTHEEUDISTOMINMARINEALKALOIDSJCURRENTORGANICCHEMISTRY,2000,421211384SONGYC,WANGJ,TENGSF,ETALCARBOLINESASSPECIFICINHIBITORSOFCYCLINDEPENDENTK