Synthesis and Evaluation of Reducing Capacity and Calcium Channel Blocking Activity of Novel 3,5-Dipropargylcarbonyl-Substituted 1,4-Dihydropyridines

M. Rucins; M. Gosteva; I. Domracheva; I. Kanepe-Lapsa; S. Belyakov; M. Plotniece; K. Pajuste; B. Cekavicus; M. Jekabsone; A. Sobolev; I. Shestakova; A. Plotniece

doi:10.1007/s10593-014-1607-z

Synthesis and Evaluation of Reducing Capacity and Calcium Channel Blocking Activity of Novel 3,5-Dipropargylcarbonyl-Substituted 1,4-Dihydropyridines

M. Rucins, M. Gosteva, I. Domracheva, I. Kanepe-Lapsa, S. Belyakov, M. Plotniece, K. Pajuste, B. Cekavicus, M. Jekabsone, A. Sobolev, I. Shestakova, A. Plotniece

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

Novel pyridinium salts based on 4-(3-pyridyl)-3,5-dipropargylcarbonyl-1,4-dihydropyridine were obtained by quaternization of pyridine moiety with different alkyl halides. The reducing capacity of the synthesized compounds was evaluated using the phosphomolybdenum complex method. The obtained results confirmed that all tested compounds possessed reducing capacity. Ca²⁺ channel antagonist and agonist activities of the compounds were additionaly assayed by changes in intracellular Ca²⁺ ion concentration in H9C2 and A7R5 cell lines. The obtained data confirmed that all synthesized 1,4-dihydropyridine derivatives have smooth muscle selective antagonist activities, and in the case of 4-phenyl derivative the activity was 4.7 times higher than that of amlodipine.

Original language	English
Pages (from-to)	1431-1442
Number of pages	12
Journal	Chemistry of Heterocyclic Compounds
Volume	50
Issue number	10
DOIs	https://doi.org/10.1007/s10593-014-1607-z
Publication status	Published - 1 Jan 2015
Externally published	Yes

Keywords*

1,4-dihydropyridines
calcium antagonists
Hantzsch synthesis
N-alkyl pyridinium
quaternization
reducing capacity

Field of Science*

1.4 Chemical sciences

Publication Type*

1.1. Scientific article indexed in Web of Science and/or Scopus database

Access to Document

10.1007/s10593-014-1607-z

Cite this

Rucins, M., Gosteva, M., Domracheva, I., Kanepe-Lapsa, I., Belyakov, S., Plotniece, M., Pajuste, K., Cekavicus, B., Jekabsone, M., Sobolev, A., Shestakova, I., & Plotniece, A. (2015). Synthesis and Evaluation of Reducing Capacity and Calcium Channel Blocking Activity of Novel 3,5-Dipropargylcarbonyl-Substituted 1,4-Dihydropyridines. Chemistry of Heterocyclic Compounds, 50(10), 1431-1442. https://doi.org/10.1007/s10593-014-1607-z

@article{f44d87c3ea66427aa087d194f10c917c,

title = "Synthesis and Evaluation of Reducing Capacity and Calcium Channel Blocking Activity of Novel 3,5-Dipropargylcarbonyl-Substituted 1,4-Dihydropyridines",

abstract = "Novel pyridinium salts based on 4-(3-pyridyl)-3,5-dipropargylcarbonyl-1,4-dihydropyridine were obtained by quaternization of pyridine moiety with different alkyl halides. The reducing capacity of the synthesized compounds was evaluated using the phosphomolybdenum complex method. The obtained results confirmed that all tested compounds possessed reducing capacity. Ca2+ channel antagonist and agonist activities of the compounds were additionaly assayed by changes in intracellular Ca2+ ion concentration in H9C2 and A7R5 cell lines. The obtained data confirmed that all synthesized 1,4-dihydropyridine derivatives have smooth muscle selective antagonist activities, and in the case of 4-phenyl derivative the activity was 4.7 times higher than that of amlodipine.",

keywords = "1,4-dihydropyridines, calcium antagonists, Hantzsch synthesis, N-alkyl pyridinium, quaternization, reducing capacity",

author = "M. Rucins and M. Gosteva and I. Domracheva and I. Kanepe-Lapsa and S. Belyakov and M. Plotniece and K. Pajuste and B. Cekavicus and M. Jekabsone and A. Sobolev and I. Shestakova and A. Plotniece",

note = "Funding Information: This research work was supported by the European Social Fund Project No. ESF 2013/0002/1DP/1.1.1.2.0/13/APIA/VIAA/005 and the European Social Fund within the project “Support for Doctoral Studies at University of Latvia” (for Martins Rucins). Publisher Copyright: {\textcopyright} 2014 Springer Science+Business Media.",

year = "2015",

month = jan,

day = "1",

doi = "10.1007/s10593-014-1607-z",

language = "English",

volume = "50",

pages = "1431--1442",

journal = "Chemistry of Heterocyclic Compounds",

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Rucins, M, Gosteva, M, Domracheva, I, Kanepe-Lapsa, I, Belyakov, S, Plotniece, M, Pajuste, K, Cekavicus, B, Jekabsone, M, Sobolev, A, Shestakova, I & Plotniece, A 2015, 'Synthesis and Evaluation of Reducing Capacity and Calcium Channel Blocking Activity of Novel 3,5-Dipropargylcarbonyl-Substituted 1,4-Dihydropyridines', Chemistry of Heterocyclic Compounds, vol. 50, no. 10, pp. 1431-1442. https://doi.org/10.1007/s10593-014-1607-z

TY - JOUR

T1 - Synthesis and Evaluation of Reducing Capacity and Calcium Channel Blocking Activity of Novel 3,5-Dipropargylcarbonyl-Substituted 1,4-Dihydropyridines

AU - Rucins, M.

AU - Gosteva, M.

AU - Domracheva, I.

AU - Kanepe-Lapsa, I.

AU - Belyakov, S.

AU - Plotniece, M.

AU - Pajuste, K.

AU - Cekavicus, B.

AU - Jekabsone, M.

AU - Sobolev, A.

AU - Shestakova, I.

AU - Plotniece, A.

N1 - Funding Information: This research work was supported by the European Social Fund Project No. ESF 2013/0002/1DP/1.1.1.2.0/13/APIA/VIAA/005 and the European Social Fund within the project “Support for Doctoral Studies at University of Latvia” (for Martins Rucins). Publisher Copyright: © 2014 Springer Science+Business Media.

PY - 2015/1/1

Y1 - 2015/1/1

N2 - Novel pyridinium salts based on 4-(3-pyridyl)-3,5-dipropargylcarbonyl-1,4-dihydropyridine were obtained by quaternization of pyridine moiety with different alkyl halides. The reducing capacity of the synthesized compounds was evaluated using the phosphomolybdenum complex method. The obtained results confirmed that all tested compounds possessed reducing capacity. Ca2+ channel antagonist and agonist activities of the compounds were additionaly assayed by changes in intracellular Ca2+ ion concentration in H9C2 and A7R5 cell lines. The obtained data confirmed that all synthesized 1,4-dihydropyridine derivatives have smooth muscle selective antagonist activities, and in the case of 4-phenyl derivative the activity was 4.7 times higher than that of amlodipine.

AB - Novel pyridinium salts based on 4-(3-pyridyl)-3,5-dipropargylcarbonyl-1,4-dihydropyridine were obtained by quaternization of pyridine moiety with different alkyl halides. The reducing capacity of the synthesized compounds was evaluated using the phosphomolybdenum complex method. The obtained results confirmed that all tested compounds possessed reducing capacity. Ca2+ channel antagonist and agonist activities of the compounds were additionaly assayed by changes in intracellular Ca2+ ion concentration in H9C2 and A7R5 cell lines. The obtained data confirmed that all synthesized 1,4-dihydropyridine derivatives have smooth muscle selective antagonist activities, and in the case of 4-phenyl derivative the activity was 4.7 times higher than that of amlodipine.

KW - 1,4-dihydropyridines

KW - calcium antagonists

KW - Hantzsch synthesis

KW - N-alkyl pyridinium

KW - quaternization

KW - reducing capacity

UR - http://www.scopus.com/inward/record.url?scp=84940364839&partnerID=8YFLogxK

U2 - 10.1007/s10593-014-1607-z

DO - 10.1007/s10593-014-1607-z

M3 - Article

AN - SCOPUS:84940364839

SN - 0009-3122

VL - 50

SP - 1431

EP - 1442

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

IS - 10

ER -

Synthesis and Evaluation of Reducing Capacity and Calcium Channel Blocking Activity of Novel 3,5-Dipropargylcarbonyl-Substituted 1,4-Dihydropyridines

Abstract

Keywords*

Field of Science*

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