Synthesis of a new series of 4-aryl-1,4-dihydropyridines with calcium channel blocking and vasodilatory activity

P Jain, G Narang, D P Jindal, R Bansal, C Calle, R Carron, K Pemberton, A L Harvey

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Synthesis of a new series of 4-aryl-1,4-dihydropyridines possessing potential calcium channel blocking activity along with good vasodilatory profile is reported. The compounds were synthesized using modified Hantzsch condensation of various aldehydes with methyl 3-aminocrotonate in the presence of a catalytic amount of trifluoroacetic acid and subsequent alkylation with various hydrochlorides of dialkylaminoalkyl chlorides. In vitro calcium channel blocking activity has been evaluated in cultures of neonatal rat cortical neurons by measuring the inhibitory response at L-type calcium channels activated by veratridine. Many compounds exhibited moderate to significant calcium channel blockade around 1 microM. The vasodilatory activity was assessed on isolated rat thoracic aortic rings precontracted by phenylephrine/KCl (30 mM). Most of the compounds produced a concentration-dependent inhibition of the contractile response.
LanguageEnglish
Pages400-405
Number of pages6
JournalPharmazie
Volume61
Issue number5
Publication statusPublished - May 2006

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Calcium Channels
Veratridine
Trifluoroacetic Acid
L-Type Calcium Channels
Alkylation
Phenylephrine
Aldehydes
Chlorides
Thorax
Neurons
1,4-dihydropyridine

Keywords

  • animals
  • aorta
  • calcium channel blockers
  • calcium channels, L-type
  • cerebral cortex
  • dihydropyridines
  • female
  • indicators
  • magnetic resonance spectroscopy
  • male
  • neurons
  • phenylephrine
  • potassium chloride
  • rats
  • infrared spectrophotometry
  • ultraviolet spectrophotometry
  • vasoconstrictor agents
  • vasodilator agents
  • veratridine
  • thoracic
  • reagents
  • wistar

Cite this

Jain, P., Narang, G., Jindal, D. P., Bansal, R., Calle, C., Carron, R., ... Harvey, A. L. (2006). Synthesis of a new series of 4-aryl-1,4-dihydropyridines with calcium channel blocking and vasodilatory activity. Pharmazie, 61(5), 400-405.
Jain, P ; Narang, G ; Jindal, D P ; Bansal, R ; Calle, C ; Carron, R ; Pemberton, K ; Harvey, A L. / Synthesis of a new series of 4-aryl-1,4-dihydropyridines with calcium channel blocking and vasodilatory activity. In: Pharmazie. 2006 ; Vol. 61, No. 5. pp. 400-405.
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Jain, P, Narang, G, Jindal, DP, Bansal, R, Calle, C, Carron, R, Pemberton, K & Harvey, AL 2006, 'Synthesis of a new series of 4-aryl-1,4-dihydropyridines with calcium channel blocking and vasodilatory activity' Pharmazie, vol. 61, no. 5, pp. 400-405.

Synthesis of a new series of 4-aryl-1,4-dihydropyridines with calcium channel blocking and vasodilatory activity. / Jain, P; Narang, G; Jindal, D P; Bansal, R; Calle, C; Carron, R; Pemberton, K; Harvey, A L.

In: Pharmazie, Vol. 61, No. 5, 05.2006, p. 400-405.

Research output: Contribution to journalArticle

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T1 - Synthesis of a new series of 4-aryl-1,4-dihydropyridines with calcium channel blocking and vasodilatory activity

AU - Jain, P

AU - Narang, G

AU - Jindal, D P

AU - Bansal, R

AU - Calle, C

AU - Carron, R

AU - Pemberton, K

AU - Harvey, A L

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AB - Synthesis of a new series of 4-aryl-1,4-dihydropyridines possessing potential calcium channel blocking activity along with good vasodilatory profile is reported. The compounds were synthesized using modified Hantzsch condensation of various aldehydes with methyl 3-aminocrotonate in the presence of a catalytic amount of trifluoroacetic acid and subsequent alkylation with various hydrochlorides of dialkylaminoalkyl chlorides. In vitro calcium channel blocking activity has been evaluated in cultures of neonatal rat cortical neurons by measuring the inhibitory response at L-type calcium channels activated by veratridine. Many compounds exhibited moderate to significant calcium channel blockade around 1 microM. The vasodilatory activity was assessed on isolated rat thoracic aortic rings precontracted by phenylephrine/KCl (30 mM). Most of the compounds produced a concentration-dependent inhibition of the contractile response.

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Jain P, Narang G, Jindal DP, Bansal R, Calle C, Carron R et al. Synthesis of a new series of 4-aryl-1,4-dihydropyridines with calcium channel blocking and vasodilatory activity. Pharmazie. 2006 May;61(5):400-405.