1-Hydroxy-3-(3-methylbut-2-enyloxy)anthracene-9,10-dione

Siti Nurbayti,Yana Syah,Didin Mujahidin

doi:10.3390/m888

Abstract

An anthraquinone derivative, 1-hydroxy-3-(3-methylbut-2-enyloxy)anthracene-9,10-dione (4), has been synthesized in two steps from benzoic acid, 3,5-dihydroxybenzoic acid, and prenylbromide.

Highlights

After being cooled to room temperature, water (10 mL) was added and the products were extracted with dichloromethane (3 ˆ 15 mL)
The residue was purified by centrifugal planar chromatography to give compound 4 (63 mg, 49%)
HRESIMS (Waters LCT Premier XE) m/z: found [M H] ́ 307.0977; calcd. [M H] ́ for C19H16O4 307.0970. These 1H- and 13C-NMR paramerers were assigned by the analysis of HSQC and HMBC spectra of 4, see Supplementary Materials

Summary

Introduction

91.,1I0n-tArondturcatqiouninones are a class of secondary metabolites that have been found in plants, bacteria, 9f,u10n-gAin, traanqduinloicnheesnasre[1a].claTssheosfeseccoomndpaoryunmdestaabroelitecshatrhaacttehraivzeedbebeny faoucnodreinstprluacnttus,re of anthrbaaccetenreia-9, ,1fu0n-dgii,onaendanlidchaenres d[1i]v.erTshiefiseedcfoumrpthoeurndbsy atrhee cphraersaectnecriezeodf obyxyagecnoarteedstrfuucntuctrieonoaf lities whichantdhirfafecernien-9,n10u-mdiobneer, atnydpeasr,e adnivderpsiofiseidtiofunr.theIrn baydtdhietiopnre,semncaenyof 9o,1xy0g-aennathterdaqfuuninctoionneasliatirees C-mewCth-hmyicleahttheyddliaf,ftCeerd-f,oinrmCn-yufolmarmtbeeydrl,,atateyndpd,esC,a-ncaadnrdboCpx-ocysailrtaibtooenxd.y.lIHanteoadwd. deivtHieoorn,w,9e,m1v0ea-rna, ynt99h,,1r10a0-q-aaunnittnhhroraanqqeuusiinnbooennaeersisngabrpeearraeilnnsygolated or geprraennyyllaatteeddoarrgeervaenryylatleimd iatreedv[e2ry]. limInitesdea[2rc].hInofsebaricohacotfivbeioaccotmivepocuomndpsoufnodrs afnortiabnattiebraitaelriaalgents we haagdenstys nwtheesihzaedd saynntuhemsibzeedr oaf 9n,u10m-baenrtraoqf u9in,1o0-naentdraeqruivinaotniveesd, eirnivcalutivdeisn,g inaclnuedwingO-aprneenwylated anthrOa-qpuriennoynlaete1d-hayndthroraxqyu-i3n-o(n3-em1e-hthyydlrbouxyt--23--(e3n-myleotxhyy)lbauntt-h2r-eancyelnoex-y9),a1n0t-hdriaocnenee(-49),1. 0T-dhiiosnceom(4)p.oTuhnisd was synthceosmizpeodunind twwaossstyenptsh,esstiazretdinign ftrwomo satecposn, dsteanrtsiantgiofnroomf baencoznodicenascaitdio(n1)oafnbden3z,5o-icdiahcyiddr(o1)xyabnednzoic acid 3(,25)-dtiohy1d,r3o-xdyihbeyndzrooicxyacaindt(h2r)atoce1n,3e--d9i,h1y0d-droixoynaent(h3r)a,ceanned-9,f1o0l-ldoiwoneed(3b),yanad rfeoallcotwioend boyf acroemacptionund 3 with opf rceonmyploburondm3idweithtoprgeinvyelbrcoommidpeotuongdive4co(Smcphoeumned 41()S. cheSmime i1l)a.rSimreialacrtiroenactoiofncoofmcopmopuonudnd33 with prenywlbitrhopmreidneylibnrotmheidperiensetnheceporefsseondceiuomf smodeituhmoxmideethwoxaisderewpoasrtreedpotortegdivteo agiCv-epareCn-yplraetnioynlatpiornoduct, 1,3-diphryodduroctx,y1-,34--d(miheytdhryolxbyu-4t--(2m-eenthyyl)lbauntt-h2r-eancyenl)aen-9th,1r0a-cdenioen-9e,1[03-,d4i]o.ne [3,4]. AbstAraccatd:eAmnic Eadnitthorr:aNqouribneortnHeadideerrivative, 1-hydroxy-3-(3-methylbut-2-enyloxy)anthracene-9,10-dione (4), Rheacesivebde: e3n1 Descyenmtbheer s2i0z1e5d; Acicneptetdw: 1o9 Fsetberupasry f2r0o16m; Publeisnhzeod:ic25 Faecbirdu,ary32,051-6dihydroxybenzoic acid, and prenylbromide. CheSmime i1l)a.rSimreialacrtiroenactoiofncoofmcopmopuonudnd33 with prenywlbitrhopmreidneylibnrotmheidperiensetnheceporefsseondceiuomf smodeituhmoxmideethwoxaisderewpoasrtreedpotortegdivteo agiCv-epareCn-yplraetnioynlatpiornoduct, 1,3-diphryodduroctx,y1-,34--d(miheytdhryolxbyu-4t--(2m-eenthyyl)lbauntt-h2r-eancyenl)aen-9th,1r0a-cdenioen-9e,1[03-,d4i]o.ne [3,4].

Results

Conclusion