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em s ry anthe Nervous
System
Dima Berbasov
May, 15, 2009
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• Medicinal chemistry
• Biochemistry
•
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• Nervous system
– Classification – Neurons
–
• Neurotransmitters – Acetylcholin and related chemicals
– Monoamines and related chemicals
– Aminoacids and related chemicals
• Conclusion
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http://en.wikipedia.org/wiki/Neuron
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Some facts
10
11‐
neurons
1015‐synapses
synaptic gap 2x10‐5
mm
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O
O
N
Acetylcholine
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• First isolated in 1914 by Henry Dale, Otto Loewi. Both received 1936
Nobel prize in Medicine• In the PNS, acetylcholine activates muscles, and is a major
neurotransmitter in the autonomic nervous system.
• In the CNS, acetylcholine and the associated neurons form a
neurotransmitter system, the cho inergic system, which tends to causeexcitatory actions.
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•
– a, su un ts aroun centra pore.
Similarities with GABA, glycine, 5HT receptors
– Nicotine, choline, epibatidine affinity
• Muscarinic acet lcholine rece tors mAChR
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E.J. Corey Synthesis of Epibatidine
Corey, E. J.; Loh, T. P.; Achyutha, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993 , 58, 5600
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Synthesis of Tebanicline
Sorbera, L.A., Revel, L., Leeson, P., Castaner, J. Drugs of the Future 2001, 26(10): 92
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Tetrodotoxin and Batrachotoxin
block Na channels in neuronsInhibitor of nAChr
O
OH
OHO
HO
HN NHOH
HN
HO
OH
• Y. Kishi 1972 racemic
• J. Am. Chem. Soc 94 (26): 9217
• Isobe J. Am. Chem. Soc 125 (29):
8798
• Du Bois 2003 asymetric
• J. Am. Chem. Soc 125 (38): 11510
Kurosu, M.;
Marcin,
L.R.;
Grinsteiner,
T.
J.;
Kishi,
Y.
J. Am. Chem. Soc. 1998, 120, 6627.
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Synthesis of (+)-Tetradotoxin
O
OH
O
HN N OHHN
HO
OH
, . , . . . . ,
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Synthesis of (+)-Tetradotoxine
Hinman, A.; Du Bois, J. 2003 J. Am. Chem. Soc 125, 11510
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Synthesis of (±)-Batrachotoxine
Kurosu, M.;
Marcin,
L.R.;
Grinsteiner,
T.
J.;
Kishi,
Y.
J. Am. Chem. Soc. 1998, 120, 6627.
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Diels-Alder Cyclization
OS
OH
HY
R
X
Kurosu, M.;
Marcin,
L.R.;
Grinsteiner,
T.
J.;
Kishi,
Y.
J. Am. Chem. Soc. 1998, 120, 6627.
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Completion
Kurosu, M.;
Marcin,
L.R.;
Grinsteiner,
T.
J.;
Kishi,
Y.
J. Am. Chem. Soc. 1998, 120, 6627.
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•
• Inhibited by
atropine
• Meta otropic in action
• Located in
CNS,
heart,
lungs,
sweat
glands
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• Acetylcholine esterase inhibitor
’
• Introduction 1996 (Eisai)
• Main treatment of Alzheimer’s desease
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HO
NH2
OH
HO
NH2
OHNorepinephrine Dopamine
NH2HO NH
O
O
N
NH
2
histamine
NH
Serotonin
NH
Melatonin
Monoamines
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-
2
2
• Discovered 1960’s
• Introduction in 1970 (Roche) racemic
• Cross blood-brain barrier while dopamine not
• - am . now es got o e pr ze n em stry w t . oyor , . arp ess or t e
development of asymetric hydrogenation
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Monsanto Process of Levodopa
OCH3
PCH3
William S. Knowles
CyCAMP
o e ecture o
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1958 discovered by Arvind Calrsson
2000
Nobel
prize
in
Medicine rs syn es s
Functions – Behavior and conditions
– Motor activity
– Motivation and reward
– Mood, learning, attention
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Dopamine Receptors
• Excitory
– D1 most abundant,
• Inhibitory
– D2 renal system,
neuronal growth,
D2-mediator.
antipsychotic drugs target
Antagonist:HO
r sper one, a oper o
–
N
HOOH
H
NH
HOCl
HO
– D5- limbic region of brain
(responsible for emotions)
,
– D , si nals cardial out ut
Dihydrexidine Fenoldopam
1 Antagonist without changing heartrate, ADHD
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An aiah S. Chandrasekhar S. Gree R. Adv. S nth. Catal. 2004 346 132
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+
• Bindes to dopamine transporter
• Initiate Parkinson desease in monkeys and rats
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Narcotic drugs among Dopamine and
Opioid receptors
N
O
O
HO
NO
AcO
NO
O
OCocaine
HO
MorphinFirst isolated
in 1803
AcOHeroin
sold as coughsuppresant
by Bayer till 1910
in USA till 1924
CH3O
OH
H
H
NN
O
Et
CH3
MDMA (ecstasy)
O
Tetrahydrocannabinolcannabinoid receptor
Fentanyl
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The last synthesis of Cocaine
Mans, D. M.; Pearson, W. H. Org. Lett. 2004, 6 , 3305
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Salvinorin A
-o ioid rece tor a onistO
O
OOO
BOMOMe
bis-Michael
OO
OAcO
H H
OHMe
(OMe)2HCMeMeO2C
Me
O
O
O
Me O
BOMO
(OMe)2HC
Scheerer, J.
R.;
Lawrence,
J.
F.;
Evans,
D.
A.
J. Am. Chem. Soc. 2007,
129,
8968
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Bis-Michael Addition Cascade
entry R yield(%) dr
:
2 CH(OMe)2 95 >95:5
Scheerer, J.R.;
Lawrence,
J.F.;
Evans,
D.A.
J. Am. Chem. Soc. 2007,
129,
8968
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‐Opioud receptor agonist
Analgesic
Derivatives used in heart surgery,
Sedation of bi animals
• Gupta, P.K.; Ganesan, K.; Pande, A.; Malhorta, R. J. Chem. Res. 2005, 452
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•
(historically first)
antidepressants)
• Se ective Serotonin Reupta e In i itors SSRIs
• Serotonin‐Norepinephrine Reuptake Inhibitors
(SNRIs)
C A i
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Common Antidepressants
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http://wpcontent.answers.com/wikipedia/en/1/1c/Dopamineseratonin.gif
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Serotonin or 5-hydroxytryptamine, 5-HT
Modulate Release
–
– Body temperature
– Mood Receptors
– Sleep – Apetite
– Metabolism
7 receptors
Only one 5‐HT is ionotropic
– Vomiting Others metabotropic
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Lysergic acid diethylamide (LSD)
• 5‐HT2A serotonin
receptor
• first synthesized in November 16, 1938 by Dr. Albert ,
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• Most abundant neurotransmitter (90%)
•
• Responsible for
synaptic
plasticity
• Learning and memory
•
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• Second most abundant neurotransmitter (9%)
•
• Chief inhibitory
neurotransmitter
• GABA A‐Chlorine transmiters
• GABAB‐ metabotropic receptor
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•
• Barbiturates
• Benzo iazepine
• Valleriana• Theanine (grean tea)
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• Correlation between neurotransmitters and dru
candidates (Epibatidine and Tebanicline)
• Recognizable part of certain types of specifically
acting drugs (benzodiazepines, barbiturates etc)
• 11 Industrial and total synthesis of drugs
discussed
• Important neurotransmitters were covered