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ß-Phenylethylamines and the isoquinoline alkaloids - Nat Prod Reports - 1989-01-01

ß-Phenylethylamines and the isoquinoline alkaloids - Nat Prod Reports - 1989-01-01

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Article Title: ß-Phenylethylamines and the isoquinoline alkaloids - Nat Prod Reports – Natural Product Reports – K.W. K. W. KW Bentley
Author: K.W. K. W. KW Bentley
http://pubs.rsc.org

structure-activity relationships, SARs, analgetics, acetylfentanyl, 3-methylfentanyl, 3MF, TMF, AMF, alphamethylfentanyl, Ohmefentanyl, beta-hydroxy, alpha-methyl, Mefentanyl, 4-methoxymethylcarbonyl, 4-methoxycarbonyl, 4-substituted piperidines, 4,4-disubstituted piperidines, 4-piperidines, 4-substituted, 4,4-disubstituted, fentanil, phentanyl, phentanil, N-phenylethyl-4-piperidones, piperid-4-ones, N-phenylethyl-4-piperidinones, piperidin-4-ones, NPP, ANPP, Sigfreid Sigfried fentanyl opioid opiate synthesis, mu u delta d Kappa K opioid receptor, opiate alkaloid, poppy alkaloids, subutex, suboxone, reducing agents, LiAlH4, lithium aluminum hydride, sodium borohydride, platinum oxide, catalytic hydrogenation, N-debenzylation, morphine-like, Paul A.J. PAJ Adrian Jan Janssen, Pharmaceuticals, pharma, Pharmacy, pharmacology, pharamcokinetics, P. Papaver somniferum, dipipanone, phenadoxone, 4-phenylpiperidines, organic synthesis, novel organic synthesis, 4-anilinopiperidine 4-propionanilinopiperidine 4-anilidopiperidine 4-propionanilidopiperidine chemistry, piperidine nitrogen chemistry, organic heterocyclic nitrogen compounds, opioid chemistry, opioid synthesis, chemical syntheses, pseudoephedrine, ephedra, phenylacetone, phenyl-2-propanone, P2P, methylamine, MDMA, MDA, methamphetamine amphetamine synthesis manufacture precursors, saffrole oil, methylenedioxymethamphetamne, ecstasy, x, XTC, ADAM, EVE, Alexander T. Shulgin, PiHKAL: A Chemical Love Story, TiHKAL, 2-CE, 2-CB, 2-CI, 2CE 2CI 2CB, PEA, phenylethylamines, psychoactive drugs, psychedelic, psychogenic, psychotropic, phenethylamines, Sympathomimetic amines, dopaminergic, serotonin, norepinephrine, noradrenaline, adrenaline, dopamine, catecholamines, central sympathetic parasympathetic nervous system, sympatholytics, parasympatholytics, anxiolytics, diuresis, diuretics, methyltestosterone, 5-alpha-reductase inhibitor, testosterone, dihydrotestosterone, PDE5, viagra, cialis, levitra, Sildenafil citrate, tadalafil, vardenafil, cGMP-specific phosphodiesterase type 5, BPH, benign prostate hyperplasia, avodart, Dutasteride CNS, SSRI, antidepressants, prozac, paxil, Zoloft, venlafaxine, fluoxetine, fluvoxamine, SNRI, Bupropion, Wellbutrin, Zyban, oxirane, MOR, DOR, KOR, naloxone, naltrexone, DXM, dextromethorphan, levorphanol, dextropropoxyphene, dextromoramide, phenacyl, arylmorphan, azabicyclo, azaprocin mixed partial agonist antagonist, binding affinity, EC50 ED50 IC50, concentration molarity osmolarity, molecules, molecular biology, biochemistry, drug substance abuse addiction potential dependency tolerance modulation, science, physics, levomethorphan, Alvimopan, Loperamide, Picenadol, oxycodone, oxycontin, hydromorphone, hydrocodone, darvocet, pethidine, meperidine, demerol, darvon, 6,7-benzomorphans, benzodiazepines, flunitrazepam, xanax, klonopin, clonazepam, alprazolam, diazepam, anticonvulsant, antidiuretic, diabetes, insulin, genetic engineering, formulations, tramadol, ultram, viminol, bromedol, Daniel Lednicer, Philip F. VonVoightlander, A.F. Casy, Parfitt, Opioid Analgesics: Chemistry and Receptors, narcotics, PCP, oxycodone, oxycontin, hydromorphone, hydrocodone, darvocet, pethidine, meperidine, demerol, darvon, Codeine-N-Oxide (Genocodeine) Dihydromorphine-6-glucuronide Hydromorphone-N-Oxide Heroin-7,8-Oxide Morphine-6-glucuronide, 6-Acetylmorphine Morphine-N-Oxide (Genomorphine) Naltrexol Norcodeine Normorphine, NSAIDs, tylenol, ibuprofen, controlled substance schedule I II III IV V 1 2 3 4 5, COX COX-2 COX-1 COX1 COX2 inhibitors, antipsychotic, DEA, DMT, DIPT, DBT, DET, harmine, dimethyltryptamine, DPT, LSD, Lysergic acid diethylamide, Albert Hofmann, UV-Vis, Raman IR infrared spectroscopy, organic microwave synthesis chemistry, empathogens, entactogens, chemical derivatives,
Article Title: ß-Phenylethylamines and the isoquinoline alkaloids - Nat Prod Reports – Natural Product Reports – K.W. K. W. KW Bentley
Author: K.W. K. W. KW Bentley
http://pubs.rsc.org

structure-activity relationships, SARs, analgetics, acetylfentanyl, 3-methylfentanyl, 3MF, TMF, AMF, alphamethylfentanyl, Ohmefentanyl, beta-hydroxy, alpha-methyl, Mefentanyl, 4-methoxymethylcarbonyl, 4-methoxycarbonyl, 4-substituted piperidines, 4,4-disubstituted piperidines, 4-piperidines, 4-substituted, 4,4-disubstituted, fentanil, phentanyl, phentanil, N-phenylethyl-4-piperidones, piperid-4-ones, N-phenylethyl-4-piperidinones, piperidin-4-ones, NPP, ANPP, Sigfreid Sigfried fentanyl opioid opiate synthesis, mu u delta d Kappa K opioid receptor, opiate alkaloid, poppy alkaloids, subutex, suboxone, reducing agents, LiAlH4, lithium aluminum hydride, sodium borohydride, platinum oxide, catalytic hydrogenation, N-debenzylation, morphine-like, Paul A.J. PAJ Adrian Jan Janssen, Pharmaceuticals, pharma, Pharmacy, pharmacology, pharamcokinetics, P. Papaver somniferum, dipipanone, phenadoxone, 4-phenylpiperidines, organic synthesis, novel organic synthesis, 4-anilinopiperidine 4-propionanilinopiperidine 4-anilidopiperidine 4-propionanilidopiperidine chemistry, piperidine nitrogen chemistry, organic heterocyclic nitrogen compounds, opioid chemistry, opioid synthesis, chemical syntheses, pseudoephedrine, ephedra, phenylacetone, phenyl-2-propanone, P2P, methylamine, MDMA, MDA, methamphetamine amphetamine synthesis manufacture precursors, saffrole oil, methylenedioxymethamphetamne, ecstasy, x, XTC, ADAM, EVE, Alexander T. Shulgin, PiHKAL: A Chemical Love Story, TiHKAL, 2-CE, 2-CB, 2-CI, 2CE 2CI 2CB, PEA, phenylethylamines, psychoactive drugs, psychedelic, psychogenic, psychotropic, phenethylamines, Sympathomimetic amines, dopaminergic, serotonin, norepinephrine, noradrenaline, adrenaline, dopamine, catecholamines, central sympathetic parasympathetic nervous system, sympatholytics, parasympatholytics, anxiolytics, diuresis, diuretics, methyltestosterone, 5-alpha-reductase inhibitor, testosterone, dihydrotestosterone, PDE5, viagra, cialis, levitra, Sildenafil citrate, tadalafil, vardenafil, cGMP-specific phosphodiesterase type 5, BPH, benign prostate hyperplasia, avodart, Dutasteride CNS, SSRI, antidepressants, prozac, paxil, Zoloft, venlafaxine, fluoxetine, fluvoxamine, SNRI, Bupropion, Wellbutrin, Zyban, oxirane, MOR, DOR, KOR, naloxone, naltrexone, DXM, dextromethorphan, levorphanol, dextropropoxyphene, dextromoramide, phenacyl, arylmorphan, azabicyclo, azaprocin mixed partial agonist antagonist, binding affinity, EC50 ED50 IC50, concentration molarity osmolarity, molecules, molecular biology, biochemistry, drug substance abuse addiction potential dependency tolerance modulation, science, physics, levomethorphan, Alvimopan, Loperamide, Picenadol, oxycodone, oxycontin, hydromorphone, hydrocodone, darvocet, pethidine, meperidine, demerol, darvon, 6,7-benzomorphans, benzodiazepines, flunitrazepam, xanax, klonopin, clonazepam, alprazolam, diazepam, anticonvulsant, antidiuretic, diabetes, insulin, genetic engineering, formulations, tramadol, ultram, viminol, bromedol, Daniel Lednicer, Philip F. VonVoightlander, A.F. Casy, Parfitt, Opioid Analgesics: Chemistry and Receptors, narcotics, PCP, oxycodone, oxycontin, hydromorphone, hydrocodone, darvocet, pethidine, meperidine, demerol, darvon, Codeine-N-Oxide (Genocodeine) Dihydromorphine-6-glucuronide Hydromorphone-N-Oxide Heroin-7,8-Oxide Morphine-6-glucuronide, 6-Acetylmorphine Morphine-N-Oxide (Genomorphine) Naltrexol Norcodeine Normorphine, NSAIDs, tylenol, ibuprofen, controlled substance schedule I II III IV V 1 2 3 4 5, COX COX-2 COX-1 COX1 COX2 inhibitors, antipsychotic, DEA, DMT, DIPT, DBT, DET, harmine, dimethyltryptamine, DPT, LSD, Lysergic acid diethylamide, Albert Hofmann, UV-Vis, Raman IR infrared spectroscopy, organic microwave synthesis chemistry, empathogens, entactogens, chemical derivatives,

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/?-Phenylethylaminesand the lsoquinoline Alkaloids
K.
W.
Bentley
Department
of
Chemistry, Loughborough University
of
Technology, Loughborough, Leicestershire
L
El
l
3TU
Reviewing the literature published between July
1987
and June 1988(Continuing the coverage
of
literature in
Natural Product Reports,
1988,
Vol.
5,
p.
265)
1
23
4
5
6
7
8910
11
1213141516
17
1818.118.218.318.418.518.618.718.818.9192021222324/3-PhenylethylaminesIsoquinolinesBenzylisoquinolinesBisbenzylisoquinolinesCularinesPavines and IsopavinesBenzopyrrocolinesBerberines and TetrahydroberberinesAzaberberinesSecober beri nesProtopinesPhthalide-isoquinolines
Spirobenzylisoquinolines
Isoindolo benzazepinesRhoeadinesEmetine and Related CompoundsBenzophenanthridinesAporphinoid AlkaloidsProaporphinesAporphinesDimeric Aporphines
Benzylisoquinoline-Aporphine
DimersOxoaporphinesDioxoaporphinesPhenanthrenesAristolochic Acids and AristolactamsAzahomoaporphinesMorphine AlkaloidsPhenet hylisoquinolinesHomoaporphinoid AlkaloidsColchicineOther AlkaloidsReferencescyclized by treating it with a base to give an approximate 2:
1
excess of the base
(2)
over its enantiomer, and catalyticdesulphurization of
(2)
yielded
(
+
-(R)-carnegine. The
(2)-
isomer of
(1)
cyclized to a 1:5 mixture of (2) and itsenantiomer.I5.l6Reduction of the chiral iminium ions (3; R
=
Me) and (3; R
=
CH,Ar) with sodium borohydride yielded thebases
(4)
nd their C-1 epimers in the ratio
7.5:
1
for R
=
Meand 16:for R
=
CH,Ar. Catalytic removal of the N-benzylicgroup from (4; R
=
Me) afforded (-)-(S)-salsolidine.” Con-version of the dihydroisoquinoline
(5)
into the enamide (6),followed by oxidation with osmium tetroxide, yielded thehydroxy-ketone (7), which, on reductive removal
of
thebenzyloxycarbonyl group, suffered reductive cyclization to
(
+)-calycotomine (8).’* Condensation of the aldehyde
(9)
withethyl azidoacetate led to the diester
(lo),
which was reduced by
I
8-
P
hen
y
let h
y
I
a
m nes
Candicinerom
Denmoza
as
rhodacantha,2
een isolated romrom
puntialphonseaickenii,,clerocarpa,’
nd from
Trichocereus andagalensis,,
hordenine has been isolated from
Trichocereus andagalensis,2
and
trimethyl(p-phenylethy1)am-
monium hydroxide has been isolated from
Alphonsea sclero-
(5)
(6)
carpa.l
Absorption ~pectra,~olecular-orbital
calculation^,^
thermodynamic parameters,4 and methods of determination5.of ephedrine and pseudoephedrine have been studied andephedrineeterogeneoushat catalysts graftedor ontoichaelilicondditionas beeneactions.’sed ashe
““w$O2CH2Phe0
\
effects
of
ephedrine on muscle* and of mescaline
on
behaviourg
:Izq
C02CH2Ph
have been reported.
CH2OH CH20H
(7)
(8)
2lsoquinolines
Thalifoline has been isolated from
Abuta pahni.
lo
Patents havebeen published covering the preparation1’.
l2
and p~rification’~of cotarnine. The crystal structures of salsoline and salsolidine-Asymmetric syntheses of some alkaloids of this group have
C02Et
phc
 
C02Et
hydrochlorides have been determined.
l4
phcH20a
hCH20
C02Et
PhCH20
been accomplished. The (E)-vinyl sulphoxide (1) has been
(9)
(10)
15
405
NPR
6
   D  o  w  n   l  o  a   d  e   d   b  y   U  n   i  v  e  r  s   i   t  y  o   f   M   i  s  s  o  u  r   i  -   C  o   l  u  m   b   i  a  o  n   1   7   S  e  p   t  e  m   b  e  r   2   0   1   0   P  u   b   l   i  s   h  e   d  o  n   0   1   J  a  n  u  a  r  y   1   9   8   9  o  n   h   t   t  p  :   /   /  p  u   b  s .  r  s  c .  o  r  g   |   d  o   i  :   1   0 .   1   0   3   9   /   N   P   9   8   9   0   6   0   0   4   0   5
View Online
 
406
NATURAL PRODUCT REPORTS,
1989
C02Et
phcH20Q7
hCH20
OEt
(1
1)
(13)
triethyl phosphite to the ester
(1
1). Conversion of the C0,Etgroup of this (through CH,OH and CH,Cl) into CH,, followedby treatment with boron tribromide, afforded siamine
(12).19
The anti-tumour effects
of
quinocarmycin have been stud-ied.zO
A
review of the chemistry of the naphthylisoquinolinealkaloids has been published.,l
3
Benzyl
isoquinoli
nes
Benzylisoquinoline alkaloids have been isolated from thefollowing plant species, that marked with an asterisk beingnew
:
Abuta pahni'OcoclaurineAlphonsea sclerocarpa'petaline methineCocculus laurifolius22coclaurine, N-methylcoclaurine, and reticulineCorydalis bungeanaz3juziphine and norjuziphineDuguetia ~pixiana~~~~~codamine cis-N-oxide
(1
3)*
Manglie
ia
duclouxiizmagnocurarineOxandra majorz7reticulineStephania gracilenta2gpapaverineStephania venosa2'reticulineThe isolation of papaverine from Stephania gracilenta is thefirst reported finding of this alkaloid outside the Papaveraceae.The conformation of the alkaloid in solution has been studiedby n.m.r. and the spectral characteristics ofseveral alkaloids
of
this group have been re~iewed.~' heoxidation of papaverine and other alkaloids of the group to N-oxides with m-chloroperoxybenzoic acid has been6'-Nitropapaverine, on oxidation with iodine, yields the meso-ionic azaberberine
(14)
and the zwitterionic compound (1
5)
;
f
heated with methanolic potassium hydroxide, it affords theisoxazole (1 6), which on thermolysis or photolysis gives acompound that was first assigned the structure
(17)33
ut whichhas been shown by X-ray studies to have the constitution
(18).34
The use of Reissert compounds in the synthesis of benzyl-isoquinoline alkaloids has been reviewed.35 The Reissertcompound (19) has been converted into
(20),
which, ontreatment with sodium hydroxide and then being debenzylated,yielded cristadine
(2
).36
The preparation
of
roemecarine andisoroemecarine from 1,4-trans- and 1,4-cis-4-acetoxy- -benzyl-
"'"qN
e0
\
R
R'
Me0@NMe
\
*.H
'0:
SbMe
Li+
(24)
OMePhCH2O TNC
0
P
h
CN
(19)
Me
OOH
   D  o  w  n   l  o  a   d  e   d   b  y   U  n   i  v  e  r  s   i   t  y  o   f   M   i  s  s  o  u  r   i  -   C  o   l  u  m   b   i  a  o  n   1   7   S  e  p   t  e  m   b  e  r   2   0   1   0   P  u   b   l   i  s   h  e   d  o  n   0   1   J  a  n  u  a  r  y   1   9   8   9  o  n   h   t   t  p  :   /   /  p  u   b  s .  r  s  c .  o  r  g   |   d  o   i  :   1   0 .   1   0   3   9   /   N   P   9   8   9   0   6   0   0   4   0   5
View Online
 
NATURAL PRODUCT REPORTS,
1989-K.
W.
BENTLEY
407
OH
(26)
(28)
(30)
tetrahydroisoquinolines indicates that the former alkaloid hasthe structure (22;
R1
=
H,
R2
OH),
epimeric with thatoriginally assigned,
i.e.
(22;
R1
OH,
R2
=
H),
which repre-sents isoroemecarine.
37
(
-
-(S)-Norlaudanosine has beenprepared by catalytic reduction
of
(4;
R
=
3, 4-dimethoxy-benzyl).17 The seco-alkaloid cryptopleurospermine (26) hasbeen synthesized from the aldehyde (23) and the dilithio-salt(24), which gave (25;
R
=
C0,Et); this was reduced to (25;R
=
Me), which was hydrolysed and then oxidized with tri-fluoroacetic acid and sodium nitrite.3sThe biological effects of papa~erine,~~-~'f 4-[4-(2-methoxy-pheny1)piperazin-
1
-ylmethyl papaverine,
2,
43
of higena-mine,44-46 nd of atracuri~m~'-~~ave been studied and amethod of estimating higenamine in blood53has been described.
(29)
A
patent covering the manufacture of atracurium has beenpublished.54
4 Bisbenzyl soqui
no1
ines
Bisbenzylisoquinoline alkaloids have been isolated from thefollowing species, the twenty nine marked by an asterisk beingnew alkaloids.
Abuta pahni'"
daurisoline, 2'-nordaurisoline* (27;
R'
=
R3
Me,
R2
H),
lindholdamine, (27;
R'
=
R2
=
R3
=
H),
2-N-methyl-lindholdamine* (27;
R'
=
Me,
R2
=
R3
=
H),
2'-N-methyl-lindholdamine*
27;
R'
=
R3
=
H,
R2
=
Me), and
N,N-dimethyl-lindholdamine
27
;
R'
=
R2
=
Me,
R3
=
H)
apateline, 2,2'-noraromoline, coscoline, 0-methylcoscoline,cosculine, 2'-norcosculine* (28), daphnandrine, daphno-line, lindholdamine, pangkoramine*
(29),
pangkorimine*(30), and 2,2'-norphaeanthine*
(3
1)
geraldoamine* (32), pampulhamine [2'-nordaurisoline]
(27;
R'
=
R3
=
Me,
R2
=
H),
and pedroamine [2-N-methyl-lindholdamine] (27;
R1
=
Me,
R2
=
R3
=
H)
aromoline, berbamine, obamegine, and oxyacanthineoxyacanthine and 0-methyloxyacanthine
Albertisia pap~ana~~Aristolochia gigantea56Berberis k~reana~~Berberis pse~dambalata~~
15-2
   D  o  w  n   l  o  a   d  e   d   b  y   U  n   i  v  e  r  s   i   t  y  o   f   M   i  s  s  o  u  r   i  -   C  o   l  u  m   b   i  a  o  n   1   7   S  e  p   t  e  m   b  e  r   2   0   1   0   P  u   b   l   i  s   h  e   d  o  n   0   1   J  a  n  u  a  r  y   1   9   8   9  o  n   h   t   t  p  :   /   /  p  u   b  s .  r  s  c .  o  r  g   |   d  o   i  :   1   0 .   1   0   3   9   /   N   P   9   8   9   0   6   0   0   4   0   5
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