1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist

8/2/2019 1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist.

1/6


2/6

]crj|jkfk 3 ( N \ 2 { 4 2 mejkf}|]mnchc 4

Ojsrkdg ji Hclfmfkdg Mnchf}|rv' 466> i +2' dkl ijr >(JN(LPD\ ud} 2+3 i +2 kH+ Kj| lc|crhfkcl+

\dbgc =+ Lrse Lf}mrfhfkd|fjk Ld|dlrse lj}c @hjg*ae& K #L #]LG CL30 @hjg*ae&d rjdmc|V4 fk gju vfcgl}+

prj|cm|fjk uf|n dk dmc|vg erjsp fk pgdmc ji |nc |rfigsj(2 0+>04+24

4+94= 0+40+394+429(4+5+34< 4< =< 0+6545 4> =3 .0+90(4+50&4> 04> 0 92+3 K L.0+96(4+35&b40 30 >044 52 40040 244 => =5+3 9042 45 >09 49 400

9 49 20 .0+93(4+0heae1 4>= khjg*ae&irjh }dgfkc+Rc}sg|}

Rdlfjgfedkl bfklfke ld|d drc prc}ck|cl fk \dbgc 2+Bj|n 3 dkl 9 }njucl gju diifkf|v ijr |nc }f|c gdbcgcl bv|nc { ( N \ { Dejkf}| >(JN LPD\+ Ijr mjhpc|f|fjk d| |nc}f|c gdbcgcl bv |nc 3(N\z{zm k|dejkf}| ac|dk}crfk' 9ud} kj| }fekfifmdk|gv lfiicrck| irjh


3/6


4/6

]crj|jkfk 3 ( N \ 2 { 4 2 mejkf}|dg|crd|fjk ji |nc bd}fm rcmcp|jr diifkf|v prjifgc ijr |nf}mgd}} ji mjhpjskl}+ \nc 3(N\2 bfklfke }f|c} dppcdr |jbc |jgcrdk| ji |nc nfengv cgcm|rjkced|fycvc| nvlrjpnjbfm|rfigsjrjhc|nvg erjsp+ \nf} mndrdm|crf}|fm hdv }seec}||nd| |nc 2 .d}' 9' JM)&' 2+62 .ll' 4'DrMNz&' 2+>5 .ll' 4'DrMNz&'

2+3 n+ \GM dkdgv}f} }njucl |nd| |n c rcdm|fjk ndl ejkc | jmjhpgc|fjk+ Yjgd|fgc hd|crfdg} ucrc rchjycl bv rj|drv cydpj(rd|fjk ijggjucl bv lrvfke sklcr nfen ydmssh jycrkfen|+ \ncc}}ck|fdggv psrc igsiiv jii(unf|c mrv}|dg} ucfenfke 4+5 e ucrcrcmrv}|dggfzcl irjh 2(prjpdkjvc|nvg dmc|d|c | j vfcgl 4+9 e.62+4#&? hp 4=5 "M+ MFH] h g c 0 .} ' 4' DrN&' =+>6 .2}' 9'JMN=&' =+>< .h' 2' DrMNzMNz&' 2+64 .h' 2' DrMNz&+ Dkdg+4(.2'3(Lfhc|nj~v( 4(.2'3(lfhc|nj~v(= .2}' 9' JMNl' =+55 .h' 2'DrMNzMNz&' =+09 .h' 2' DrMNz&+ Dkdg+ .M4=N4=I9K0=& M' N'K+g(.2'3(Lfhc|nj~v( .4+0 e'2+6 hhjg& fk 53 hG ji 2(prjpdkjg ud} dllcl 3 hG ji 2 K AJN+\nc }jgs|fjk ud} }|frrcl d| rjjh |chpcrd|src ij r = n+ \nc}jgyck| ud} rchjycl bv rj|drv cydpjrd|fjk' dkl |nc rc}flscud} lf}}jgycl fk C|20 .53 hG&+ \nc }jgs|fjk ud} ud}ncl uf|nNzJ .23 hG&' ijggjucl bv c~|rdm|fjk uf|n = K NM4 .2 ~ 30hG&+ \nc pjjgcl dmflfm c~|rdm |} ucrc mjhbfkcl dkl hdlc}|rjkegv bd}fm uf|n |nc dllf|fjk ji 3 K KdJN+ \nc dtscjs}}jgs|fjk ud} c~|rdm|cl uf|n MNM4= .= ~ 30 hG&' |nc pjjgclc~|rdm |} ucrc lr fcl .He]03 .h' 2' DrMNl+ Dkdg+.MffNf3MgI=KJz& M' N' K+Pndrhdmjgjev c|njl}+ Lrse Lf}mrfhfkd|fjk+ \uck|vhdgc ]prdesc(Ldugcv rd| } .Ndrgdk Gdbjrd|jrfc}' Fklfdkdpj(gf}' FK& ucfenfke 200(220 e d| |nc bcefkkfke ji |nc lrself}mrfhfkd|fjk }|slv ucrc s}cl d} }sbocm|} |rdfkcl |j lf}(mrfhfkd|c G]L |dr |rd |c irjh }dgfkc+ Kjkc ji |nc rd| } ndlprcyfjs}gv rcmcfycl lrse} jr bcndyfjrdg |rdfkfke+ Ud|cr ud}irccgv dydfgdbgc fk |nc fklfyflsdg njhc mdec}' dkl d rd|fjkcldhjsk| ji }sppgchck|dg iccl .Psrfkd Gdb Bgj~& ud} hdlcdydfgdbgc di|cr c~pcrfhck|dg }c}}fjk} |j hdfk|dfk dpprj~f(hd|cgv >0#ji ircc(icclfke ucfen|+ Gfen|} ucrc jk irjh 0500|j 4600njsr}+ \nc gdbjrd|jrv dkl dkfhdg idmfgf|v |chpcrd|srcud} 22(2< "M' dkl |nc rcgd|fyc nshflf|v ud} =0 dkl 4500 njsr}cdmn ldv' Hjkldv(Irfldv+]f~ }|dkldrl jpcrdk| mndhbcr} .hjlcg C40(gJRI' Mjsg(bjsrk Fk}|rshck| }' Gcnfen Ydggcv' PD& mjk}f}|cl ji hjlsgdr|c}| mdec} ckmgj}cl uf|nfk }jskl(d||cksd|cl msbfmgc} uf|n idk}ij r yck|fgd|fjk dkl bdmaerjskl unf|c kjf}c+ D unf|c njs}cgfen| ud} mck|crcl kcdr |nc |jp ji |nc irjk| pdkcg ji |nc mdec'unfmn ud} dg}j ctsfppcl uf|n |uj rc}pjk}c gcycr}' }cpdrd|clbv d ijjl njppcr .mjhbfkd|fjk lfppcr pcggc| |rjsen' hjlcg C4


5/6

3#ud} kj| dmnfcycl jk |nc|uj |rdfkfke }c}}fjk} ijggjufke d |c}| }c}}fjk+ \c}| lrse} ucrcdlhfkf}|crcl fp =0 hfk prfjr | j |nc }c}}fjk}1 |c}| }c}}fjk} ucrcrsk sklcr mjklf|fjk} ji c~|fkm|fjk' uf|n rd |} rchjycl irjh |ncjpcrdk| mndhbcr unck 30 prc}}c} ucrc chf||cl jk jkc gcycr+Fi 30 prc}}c} jk jkc gcycr ucrc kj| mjhpgc|cl uf|nfk 3 hfk'|nc }c}}fjk ud} cklcl dkl }mjrcl d} d lf}rsp|fjk+ \rcd|hck|}ucrc rdkljhfzcl d| |nc bcefkkfke ji |nc }|slv+\nc |rd fkfke lrse ud} .!&(gv}crefm dmfl lfc|nvgdhflc |dr(|rd|c .G]L1 0+0> he*ae' 4>9 khjg*ae' KFLD&+ Dgg lrse} ucrclf}}jgycl fk 0+6# }dgfkc dkl ucrc fkocm|cl fk|rdpcrf|jkcdggvfk d yjgshc ji 4h s e ' =0 hfk bcijrc |nc }c}}fjk}+Ld|d irjh |nc lrse lf}mrfhfkd|fjk }|slv ucrc }mjrcl fk dtsdk |dg id}nfjk' uf|n |nc gcycr jk unfmn |nc r d| ifr}| chf||cl30 prc}}c} fk d |c}| }c}}fjk }mjrcl d} |nc }cgcm|clk cycr+ \ncpcrmck|dec ji rd |} }cgcm|fke |nc lrse gcycr .#]LG& ijr cdmnlj}c ji |c}| mjhpjskl ud} lc |crhfkcl+ \nc lcercc ji }sb(}|f|s|fjk ud} lc|crhfkcl bv |nc hd~fhsh #]LGij r dgg lj}c}ji |nc | c}| lrse+ Kj }sb}|f|s|fjk f} lcifkcl d} 36# ]LG jrgc}}' dkl pdr|fdg }sb}|f|s|fjk f} 90(56# ]LG+ Fi |nc lrseud} jkc unfmn mjhpgc|cgv }sb}|f|s|cl ijr |nc |rdfkfke lrse.d | gcd}| jkc lj}c rc}sg|cl fk d #]LG 8 >0# jr nfencr& |nchc|njl ji Gf|mnifcgl dkl Ufgmj~jk_5ud} s}cl |j lc|crhfkc|nc CL30 .gje(prjbf| dkdgv}f} d } |n c lj}c prjlsmfke 30#lrse(gcycr rc}pjklfke& dkl 63# mjkiflckmc fk|crydg .63# MF&+ \nf}hc|njl dg}j dggjucl ijr |c}|} ji pdrdggcgf}h bc|ucck lj}c(rc}pjk}c msryc} ji |nc lrse dkl |nc |r dfkfke lrse+ Fi 30#jrhjrc ji |nc dkfhdg} |c}|cl ucrc lf}rsp|cl d| d lj}c uncrc|nc kjklf}rsp|cl rd|} edyc >0#]LG' kj CL]Jud} mdgmsgd|cl+Rdlfjgfedkl Bfklfke D}}dv}+ Hdgc ]prdesc(Ldugcvrd| } .Ndrgdk Gdbjrd|jrfc}' Fklfdkdpjgf}' FK& ucfenfke 453(466 e ucrc s}cl+ \nc dkfhdg} ucrc acp| fk erjsp} ji ifyc rd|}pcr mdec' d| |nc }dhc mjklf|fjk} lc}mrfbcl dbjyc' bs| uf|n irccdmmc}} | j ijjl dkl ud|cr+Q42344(.)&(LJF'=NXac|dk}crfk' dkl Q=NX(>(JN(LPD\ ucrcpsrmnd}cl irjh Kcu Ckegdkl Ksmgcdr .Bj}|jk'HD& d| }pcmfifmdm|fyf|fc} ji 2200' 94' dkl 4=3+3(249 Mfghhjg' rc}pcm|fycgv+

Kfmnjg} c| dg+.!&(G]L |d r|r d|c ud} jb|dfkcl irjh |nc Kd|fjkdg Fk}|f|s|c jkLrse Dbs}c+ Mfkdk}crfk ud} d efi | irjh |nc ]TSFBB Fk}|f|s|cijr Hclfmdg Rc}cdrmn dkl 3(N\ ud} psrmnd}cl irjh ]fehd.]| + Gjsf}' HJ&+\nc prjmclsrc ji Ojnk}jk c| dG< ud} chpgjvcl+ Brfcigv'|nc irjk|dg mjr|c~ jr nfppjmdhpdg brdfk rcefjk} irjh 20( i +09& uf|n B' ' ji 265+= )=6+9 ihjg*he prj|cfk dkl d A Lji 4+=5i 0+20 kH+ Q=Ng(>(JN(LPD\ bjskl |j d }fkegc }f|c .Nfgg mjciifmfck| 4+00i +04& uf|nd B' ' ji 446i ihjg*he prj|cfk dkl d A Lji 2+(40 mjkmck|rd|fjk} ji |c}| lrse |j mjhpc|c ijr0+53 kH Q=NXac|dk}crfk jr Q=NX(>(JN(LPD\ bfklfke ud}lc|crhfkcl fk lrse mjhpc|f|fjk }|slfc}+Pnj}pnjfkj}f|flc Nvlrjgv}f}+ ]|slfc} ucrc mjklsm|clfk D6 mcgg} c~prc}}fke |nc mgjkcl 3(N\zm rcmcp|jr dkl fk =\=mcgg} c~prc}}fke |nc mgjkcl { ( N \ { Dcmcp|jr dkl ndyc bccklc}mrfbcl fk lc|dfg cg {c un cr c+ {g ({ {jr cdmn c~pcrfhck| |ncmcgg} ucrc ndryc}|cl bv |rvp}fkfzd|fjk dkl }p gf| fk|j 2n uf|n fkj}f|jg(ircc LHCH mjk|dfkfke 4pMfghG Q=NXfkj}f|jgdkl 40# lfdgvzcl ic|dg mdgi }crsh+ Di|cr |nf}fkmsbd|fjk' |nc mcgg} ucrc rfk}cl |nrcc |fhc} uf|n d Arcb}bfmdrbjkd|c bsiicr mjhpj}cl ji .hH&? KdM4' 44>1AM4'


6/6

]crj|jkfk 3 ( N \ { { g z mejkf}| Ojsrkdg ji Hclfmfkdg Mnchf}|rv' 466 .ijrhd|c ijrh& rc}fk pdmacl fk dlf}pj}dbgc mjgshk+ \nc Q=NXfkj}f|jg hjkjpnj}pnd|c ud}cgs|cl d} lc}mrfbcl cg}cuncrc+=6 irjh |nc Kd|fjkdg Fk}|f|s|c jkLrse Dbs}c+

Rcicrckmc}.4& Egckk jk' R+ D'1 Vjske' R+1 Odmv kj' O+ H+ Bfklfke ji Pnckvg(dgavgdhfkc Lcrfyd|fyc} d| 3(N\4M dkl 3(N\2 ]crj|jkfkRcmcp|jr}? Cyflckmc ijr d Gdma ji ]cgcm|fyf|v+ O + Hcl+ Mnch+4662 =3' 5=='40'402'394>(3929+ (.44&Nd k}n ' M+1 Gcj' D+1 Skecr' ]+N+1 Afh' A N+1 Kfadf|dkf' L(f1 Gfck'L+ O+ Drjhd|fm ]sb}|f|sck| Mjk}|dk|} ijr ]|rsm|src(Dm|fyf|vMjrrcgd|fjk}+ O + Hcl+ Mnch+ 465='49' 205(4249+.42&Hdkk' O+ Hjlcrk Hc|njl} ijr |nc Fk |rjlsm|fjk ji Igsjrfkc Fk|jJredkfm Hjgcmsgc}? Dk Dpprjdmn |j Mjh pjskl} Uf|n Dg|crclMnchfmdg dkl Bfjgjefmdg Dm|fyf|fc}+ Mnch+ ]JM+ cy + 46>5' 9'.4=&Ucgmn' O+ \+ Dlydkmc} fk |nc Prc pdr d|fj k ji Bfjgjefmdggv Dm|fycJredkjigsjrfkc Mjhpjskl}+ \c|rdnclrjk 46>5'2+.43&]s'L+ B+1 Lsdk' O+ ^+1 Mnck' T+V+ Hc|nvg Mngjrjlfigsjrjdm(c|d|c? D Mjkyckfck| \rfigsjrjhc|nvgd|fke Deck|+ \c|rdnclrjkGc||+ 4664'=2' 9>6(5960+.49&HdmKcfg' O+ E+1 Bsr|jk' L+ O+ Eckcrd|fjk ji \rfigsjrjhc|nvgmjp(pcr Irjh Mngjrjlfigsjrjdmc|d|c+ O + Igsjrfkc Mnch+ 4664+ 3'

=>4(='=2' 295(425=+\rdk}ijrh Prc}}? Bcracgcv' MD' 4664+.22&Lf||rfmn ' D+ Dg|crd |fjk ji Bcnd yfjsrd g Mndk ec} Fklsmcl bv =''63'54(59+.29&Jbcr gcklc r' R+1 Kfmnjg}' L+ C+ .!&(K(Hc|nvg(g(.g'=(Bckzjlfj~jg(3(vg&(2(Bs|dkdhfkc d } d Lf}mrfhfkd|fyc ]|fh sgs} fk ]|slfc} ji='(4409+.25&Gf|mnifcgl' O+ \+1 Ufgmj~jk' I+D ]fhpgfifcl Hc|njl ji Cydgsd |fkeLj}c(Ciicm| C~pcrfhck |}+ O + Pndrhdmjg+ C~p+ \ncr+ 46& Ndh jk' H+1 H dggd|' H+1 Hc}|faduv' ]+ C+1 Pd}tsfcr' D+ Md2!(Esdkfkc Ksmgcj|flc Fk|crdm|fjk} fk Brdfk Hchbrdkc}+ 44+Mndrdm|crf}|fm} ji Q=Ng(Esdkj}fkc\rfpnj}pnd|c dkl PN(Bc|d'Edhh d(Fhfljesdkj}fkc 3(\rfpnj}pnd|c Bfklfke dkl Md |dbj(gf}h fk |n c Rd| Nfppjmdhps} dkl ] |rfd|sh +O + Kcsrjmnch+ 46>2'

.26&HmPncr}jk' E+ D+ D Prdm|fmdg Mjh ps|cr(Bd}cl Dpprjdmn |j | ncDkdgv}f} ji Rdlfjgfedkl Bfklfke C~pcrfhck|}+ Mjhps|+ Prje+Bfjhcl+ 46>='45'405(44' >0(3+

=>' 492(452+

Documents

1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist