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Fbamanea.kau.edu.sa

Design and synthesis of aryloxyalkylamines as h5-HT1B agonists
with potential analgesic activity.
A. M.Ismaiel, L. M. Gad , Salah A. Ghareib, F. H. Bamanie & M. A.Moustafa
Pharmaceutical chemistry department, *Pharmacology &Toxicology
department, Faculty of Pharmacy.
King Abdulaziz University,Jeddah,KSA.
It has been proposed that h5-HT and
receptors agonists are targeted for the development of novel analgesic and antimigraine agents, because h5-HT1B receptors might be primarily involved in neurogenic inflammation due to their preponderance in neuronal tissues, whereas h5-HT1D receptors might be involved more in vasoconstriction that occurred during migraine attack. Most of h5-HT1B serotonin sub receptors agonists bind with high affinity but with low selectivity. Aryloxyalkylamines are curious exception. In the present investigation
new series of aryloxyalkylamines ( III : target compounds 4-7,10&11 ) were designed and
synthesized in which structure modifications of the well-known analgesic β-blockers;
propranolol (I) had been done aiming to obtain new agonist series of aryloxyalkylamine with
enhanced affinity for human h5-5HT1B serotonin receptors and possess analgesic with possible
The naphthyl moiety in propranolol (I) is replaced by substituted phenyl group, in addition
the alkyl side chain is ethyl or α-substituted ethyl thus keeping the distance between O and N
atoms not changed as the case in (II) . The structures of the new compounds were confirmed
by microanalyses and 1H-and 13C-NMR spectroscopy. Some of them were subjected to 3D
studies and were found to be superimposed on compound (II).The binding affinity, for most of
the new compounds, at 5-HT1B and 5-HT1D were determined and some were found to bind with
high affinity and selectivity compared to (I) and with comparable affinity and selectivity to
(II). The analgesic activity of selected compounds were performed on experimental animals
and proved to be in the range of 66-100% activity compared to aspirin.
R : H , CH3 , C6H5
Target Compounds
4(a-e) , 5 , 6( a, b) ,7 (a, b),10 (a-f) &11
Synthesis of Piperazino and Morpholino Derivatives of Aryloxypropane with
Potential Analgesic and Possible Antimigraine Activity.
A. M.Ismaiel, L. M. Gad , Salah A. Ghareib, F. H. Bamanie & M. A.Moustafa
Pharmaceutical chemistry department, *Pharmacology &Toxicology
department, Faculty of Pharmacy.
King Abdulaziz University,Jeddah,KSA.
Development of drugs acting on h5-HT serotonin subreceptors represents an exciting new
area of research as a result of the increasing attention of the involvement of these receptors in
psychiatric disorders. Modeling studies demonstrate that aryl piperazines (I),
Aryloxyalkylamines (II), phenylalkykamines (III) and indolylalkylamines (VI) might interact
at 5-HT receptors in a similar manner. Inspection of these structures (I-VI) reveals that all
possess an aromatic moiety and terminal amine binding sites. In the present investigation new
series of aryloxyalkylamines (V,VI) were designed and synthesized, in which the aromatic
moiety is phenyl group substituted at 2,3-, 2,4-, 2,5-, or 2,6- positions by halogens and the
terminal amine is N-methylpiperazine or morpholine . In addition the alkyl side chain is ethyl
or substituted ethyl at α- or β-carbon by methyl group .The length of the alkyl chain that
separate the terminal amine from the ether oxygen atom of the aryloxy group is of major
importance and two-carbon chain appears optimal. The structures of the new compounds were
assessed by microanalyses, IR and NMR .The binding affinity for some of the new compounds
at 5-HT1B and 5-HT1D were determined. The analgesic activity of selected compounds were
performed on experimental animals and proved to be in the range of 85-100% activity compared to aspirin.
X: O, N,CH3
X: O, N,CH3
Target compounds A
Target compounds B
(4 a-c), (5a-f)
(8a,b) and (9a-g)

Source: http://fbamanea.kau.edu.sa/Files/0000619/Files/8529_Abstracts.pdf

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