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Synthesis, Beta-Adrenergic Blocking Activity and Beta-Receptor Binding Affinities of 1-substituted-3-(2-isopropyl-5-methyl-phenoxy)-propan-2-ol Oxalates

Synthesis, Beta-Adrenergic Blocking Activity and Beta-Receptor Binding Affinities of 1-substituted-3-(2-isopropyl-5-methyl-phenoxy)-propan-2-ol Oxalates

Dharam Paul Jindal, Mohane S Coumar, K Nandakumar, Subhash Laxmanrao Bodhankar, Prasad Gopal Purohit, Kakasaheb Ramoo Mahadik, Giancarlo Bruni, Elga Collavoli, Paola Massarelli

Farmaco. 2003 Aug;58(8):557-62.

PMID: 12875885

Abstract:

The compounds 1-isopropylamino-3-(2-isopropyl-5-methyl-phenoxy)-propan-2-ol oxalate (5) and 1-tert-butylamino-3-(2-isopropyl-5-methyl-phenoxy)-propan-2-ol oxalate (6) were synthesized from thymol (1), a naturally occurring agent in Thymus vulgaris L. Pharmacological evaluation of 5 and 6 were carried out using mouse ECG and isolated rat uterus models. Pretreatment of 5 (100 microg/kg, i.v.) and 6 (50 microg/kg, i.v.) antagonized isoprenaline (2 microg/kg, i.v.) induced tachycardia, similar to that of atenolol (CAS 29122-68-7, 20 microg/kg, i.v.) pretreatment in mouse ECG experiments as measured by R-R interval. Pretreatment of 5 and 6 blocked isoprenaline and adrenaline induced relaxation of isolated rat uterus (unprimed). Also the compounds 5 and 6 were subjected to in vitro beta1- and beta2-adrenergic receptor binding assay using turkey erythrocyte membrane (beta1) and lung homogenate of rats (beta2). Both 5 and 6 showed beta-adrenergic receptor affinity comparable with that of propranolol (propranolol hydrochloride, CAS 318-98-9) with out selectivity to any one beta-adrenergic receptor. These results suggest that both the compounds possess non-selective beta-adrenergic blocking activity, with the tert-butyl derivative 6 being more active than the isopropyl derivative 5.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP3506090	(±)-Propranolol, Hydrochloride - CAS 3506-09-0		3506-09-0	Price

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