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IJC-B Vol.47B(06) [June 2008] >

Title: Synthesis, -adrenergic receptor binding and antihypertensive potential of vanillin-derived phenoxypropanolamines
Authors: Coumar, Mohane S
Jindal, Dharam P
Bruni, Giancarlo
Massarelli, Paola
Singh, Randhir
Sharma, Amit K
Nandakumar, K
Bodhankar, Subhash L
Keywords: β-Adrenergic blocking agents
β-adrenergic receptor binding
Issue Date: Jun-2008
Publisher: CSIR
Abstract: Synthesis of vanillin-derived phenoxypropanolamines is carried out by condensing 4-hydroxy-3-methoxybenzaldehyde (vanillin) 1 with epichlorohydrin, followed by treatment with iso-propylamine or tert-butylamine to open the epoxy ring. Percentage inhibition of [³H]dihydroalprenolol binding to both β₁⁻ and β₂⁻adrenergic receptors by the newly synthesized compounds is assessed in vitro using turkey erythrocyte membrane (β₁) and lung homogenate of rats (β₂). Formyl derivatives 8 and 9 showed maximum inhibitory effect in binding assay and are non-selective similar to propranolol. On the other-hand, aldoxime compounds 10 and 11 have preference for 1-adrenergic receptors similar to atenolol. Also four of the compounds 8-11 are evaluated for their anti-hypertensive potential, in left renal artery ligation and fructose induced hypertension models. 4-(3-tert-Butylamino-2-hydroxy-propoxy)-3-methoxy-benzaldehyde oxime 11 shows antihypertensive effect better than propranolol.
Page(s): 903-909
ISSN: 0376-4699
Source:IJC-B Vol.47B(06) [June 2008]

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