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Title: Synthesis of 4-(benzamide)-and 4- (phthalimide)-substituted phenoxypropanolamines and their 1-, 2-adrenergic receptor binding studies
Authors: Jindal, Dharam Paul
Singh, Babita
Coumar, Mohane Selvaraj
Keywords: Phenoxypropanolamines;isoindoline;adrenergic receptor;4-benzamide;4-phthalimide
Issue Date: Jul-2005
Publisher: CSIR
IPC Code: Int.Cl.7 C 07 D
Abstract: N-[4-(2-Hydroxy-3-isopropylaminopropoxy)phenyl]-1-oxo-isoindoline 3 possess a cardioselective -adrenergic receptor binding affinity. Herein we attempted to synthesize the unreduced compound N-[4-(2-hydroxy-3-isopropyl­aminopropoxy)phenyl]phthalimide 4. But, reaction of N-[4-(2,3-epoxypropoxy)phenyl]phthalimide 10 with isopropyl­amine opened the phthalimide ring to give N-[4-(2-hydroxy-3-isopropylaminopropoxy)phenyl]-2-isopropylcarbamoylbenzamide 12 instead of 4 as expected. While treatment of 10 with tert-butylamine gives N-[4-(3-tert-butylamino-2-hydroxy­pro­poxy)phenyl]phthalimide 15. Further, reaction of 15 with isopropylamine opened the phthalimide ring to yield N-[4-(3-tert-butylamino-2-hydroxypropoxy)phenyl]-2-isopropylcarbamoylbenzamide 16. Also, reaction of N-[4-(2,3-epoxy­pro­poxy)­phenyl]-5,6-dimethoxyphthalimide 11 with isopropylamine affords the phthalimide ring opened analogue N-[4-(2-hydroxy-3-isopropylaminopropoxy)phenyl]-2-isopropylcarbamoyl-5,6-dimethoxybenzamide 13. Compounds 12, 13, 15 and 16 have been tested for their in vitro 1- and 2-adrenergic receptor binding affinity using turkey erythrocyte membrane (1) and lung homogenate of rats (2). The percentage inhibition of [3H]DHA binding to both 1- and 2-adrenergic receptors are compared with that of the standard non-selective -adrenergic blocking agent propranolol 1 and selective agent atenolol. All the tested compounds exhibit binding affinity to 1-adrenergic receptors at the tested concentration [10-5 M] and most of them (12, 15, 16) exhibit cardioselectivity (selectivity ratio > 1). The dimethoxy analogue 13 shows selectivity towards 2-adrenergic receptor (selectivity ratio < 1).
Page(s): 1441-1445
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.44B(07) [July 2005]

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