Purines. LV. Syntheses and cytokinin activities of some adenine and adenosine derivatives related to 1'-methylzeatin

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Purines. LV. Syntheses and cytokinin

activities of some adenine and adenosine derivatives related to 1'‑methylzeatin

著者 Fujii Tozo, Ohba Masashi, Kawamura Hitoshi, Haneishi Tsuyoshi, Matsubara Satoshi

journal or

publication title

Chemical & pharmaceutical bulletin

volume 41

number 8

page range 1362‑1365

year 1993‑08‑15

URL http://hdl.handle.net/2297/7618

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Purines･ＬＶ.'）SJmtllesesandCytolKininActMtieｓｏｒＳｏｍｅＡｄｅｎｉｎｅｍ(I AdenosineDerivativesRelatedto’'一Metllylzeatill TozoFuJII,*，aMasashiOHBA,qHitoshiKAwAMuRA,aTsuyoshiHANEIsHI,aand

SatoshiMATsuBARAb

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（1'８)-1'一Methyl-伽-zeatin[(1'S)-2]anditsM-D-ribofhlranoside[(1''８)-4]weresynthesizedfromL-alaninethrough ^L1j^蚤］

[SL(2)]-4-amino-2-methyl-2-penten-1-olethanedioate[(S)-3]､Condensationsof2-hy伽oxy-6-methylthiopurine(16)with thelwz"s-isomericaminesalt[(S)-15],itsenantiomer[(R)-15],andtheracemicmo伽cation[(±)-15]fiurniShed(1'８)－，

繩鶴ｌｉｉ１ｌ;ＥＩｖｌｌｌ;::１１;;llilM1illllj辮霧iiiHIiHNliiii蝋flf鐺１１睾麗''''1;i:!';:脇珊鯛蹴

yielded2-hydroxy-Ⅳ6-methyMeme(7).T11eseadeninederivativesweretestedfDrcytokininactivityinthetobacco ^l

callusbioassay,andtheorderoftheiractivitywas(1'R)-6＞(±)-6＞(1'８)-2＞7;ontheotherhand,(1''８)-4and(1'８)－６ werecompletelyinactiveat0.1-100〃Ｍａｎｄ０．０１－１０/HMconcentrations,respectively・Asaresultoftheabovesyntheses ^iミナ of(1'R)-6,(1'S)-6,（±)-6,ａｎｄ７，thegrossstructuresofamarinegreenalgacytokininandofabluecoralcytokinin

wereestabUshedtobe6amd7,respectively．

鰹繍鳳}謡１９W撫繍｣塑hyl螺atmJibQ此;2-hyd川…th山catMml

worth-Emmonsreaction;diisobutylaluminumhydridereduction;cytokininactivity synthesis；Horner-Wads‐

ｍｏＭｍ･noMWLmhyMa…`mMD-oh……byｍ｢Ⅳ｡……．．…｡f;JJj ri…nosid.[(I"Ｗ)mll85伽i叩glyconM…hedaUylalc．h・IicC`川with…y…icCCn幟ｊ

(I川methyM…師m[(nＭ洲nM6from伽｡diacenMoqWWmThi`川u…Ｍｕ，:■

.､川1Ｍ゜･川…nmnmMhym…．mM…靴……圏……tM…i･Muip圏ilJ bacteriumhe"血molzqsMI"ｇａｅｐｖｓａｖａｓ/α"ojandthevanousanalogues,suchasthe(1'８)-enantiomer[(1'８)-11剣／

establishmentoftheirstructuresｂｙｍｅａｎｓｏｆｃｈｅｍｉｃａｌａｎｄｉｔｓ９－β-D-riboside［(1''８)-句4);ｔｈｅ４'-0-acetyl,４"-０６．

synthesis4)exemplifytherecentadditionsofnewmembersacetyl,anddihydroderivatives6)of(1'R)-1and(1"R)-5;thei

tMM川…kmmgroup動Th…wm……1．…glycono[(±)､]Ｍ…｡…[(r…i■■Ｉ

鶚し蹴重鶚

refIux,a5h ≦Ｉ

refIux,ａ５ｈＨＯ

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(１，s)-2:Ｒ'＝Ｈ,Ｒ２＝Ｍｅ (S)-3:Ｒ'＝Ｈ,Ｒ２＝Ｍｅ

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(1s)-6:Ｒ'＝Ｈ,Ｒ２＝Ｍｅ

Chartl

o1993PharmaceuticalSocietyofJapan 霞

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1111肌馴'''３ ¹³⁶³

TABLELCytokininActivityofl'一MethylzeatinAnaloguesTestedbytheTobaccoCallusBioassay

AveragefiBeshweightoftobaccocallus(Ing）

Compound Concentrationoftestcompound仏M）

００００１０．０１０．０４0.10.4１４１０４０１００４００１０００

(1'R)-1｡）

(l'S)-1α）

(1'R)-2b）

(1'S)－２ (1"R)-4b）

(l''S)－４ (rR)－６ (1'S)－６ (±)-６

７

７３６４８６１５９８１２１２２２３２２１

1２０ 1065 ６２１９

1490 ４３０２６

０２２２９００２４４２３２２３８２６１９ＺｌＣ

622 1025 １５３２１３７２３１１１８２８４７６

７２５３４７８０２３５１３２８２５３３２５５８４４１１Ｉ

1006 1869 ９４１８６２１９４８３２１５２９５５

1252 ８７５２１９１６５６９２５１０１３７５

567 1438 ６５７１８

１６１１０６７ 5２１７

２７３１

４７０８２４

189５３９２２２１０６ α)TakenBomref46．ｂ)TakenfiPomref86．

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