Synthesis, β-adrenergic receptor binding and antihypertensive potential of vanillin-derived phenoxypropanolamines

Mohane S. Coumar, Dharam P. Jindal, Giancarlo Bruni, Paola Massarelli, Randhir Singh, Amit K. Sharma, K. Nandakumar, Subhash L. Bodhankar

Research output: Contribution to journalArticle

2 Citations (Scopus)

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 β1adrenergic 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.

Original languageEnglish
Pages (from-to)903-909
Number of pages7
JournalIndian Journal of Chemistry - Section B Organic and Medicinal Chemistry
Volume47
Issue number6
Publication statusPublished - 01-06-2008

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Phenoxypropanolamines
Adrenergic Receptors
Antihypertensive Agents
Propranolol
Propylamines
Epichlorohydrin
Dihydroalprenolol
Atenolol
Oximes
Erythrocyte Membrane
Renal Artery
Fructose
Ligation
Rats
Assays
Hypertension
Derivatives
Membranes
Lung
vanillin

All Science Journal Classification (ASJC) codes

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

Cite this

Coumar, M. S., Jindal, D. P., Bruni, G., Massarelli, P., Singh, R., Sharma, A. K., ... Bodhankar, S. L. (2008). Synthesis, β-adrenergic receptor binding and antihypertensive potential of vanillin-derived phenoxypropanolamines. Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 47(6), 903-909.
Coumar, Mohane S. ; Jindal, Dharam P. ; Bruni, Giancarlo ; Massarelli, Paola ; Singh, Randhir ; Sharma, Amit K. ; Nandakumar, K. ; Bodhankar, Subhash L. / Synthesis, β-adrenergic receptor binding and antihypertensive potential of vanillin-derived phenoxypropanolamines. In: Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry. 2008 ; Vol. 47, No. 6. pp. 903-909.
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Synthesis, β-adrenergic receptor binding and antihypertensive potential of vanillin-derived phenoxypropanolamines. / Coumar, Mohane S.; Jindal, Dharam P.; Bruni, Giancarlo; Massarelli, Paola; Singh, Randhir; Sharma, Amit K.; Nandakumar, K.; Bodhankar, Subhash L.

In: Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, Vol. 47, No. 6, 01.06.2008, p. 903-909.

Research output: Contribution to journalArticle

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AU - Coumar, Mohane S.

AU - Jindal, Dharam P.

AU - Bruni, Giancarlo

AU - Massarelli, Paola

AU - Singh, Randhir

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AU - Nandakumar, K.

AU - Bodhankar, Subhash L.

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