Oxidation of cationic 1,4-dihydropyridine derivatives as model compounds for putative gene delivery agents

Aiva Plotniece; Karlis Pajuste; Dainis Kaldre; Brigita Cekavicus; Brigita Vigante; Baiba Turovska; Sergey Belyakov; Arkadij Sobolev; Gunars Duburs

doi:10.1016/j.tet.2009.08.012

Oxidation of cationic 1,4-dihydropyridine derivatives as model compounds for putative gene delivery agents

Aiva Plotniece, Karlis Pajuste, Dainis Kaldre, Brigita Cekavicus, Brigita Vigante, Baiba Turovska, Sergey Belyakov, Arkadij Sobolev, Gunars Duburs

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

17 Citations (Scopus)

Abstract

A new synthetic approach to cationic pyridine derivatives is described here. Two different strategies for the synthesis of 1,1′-{[3,5-bis(ethoxycarbonyl)-4-phenylpyridine-2,6-diyl]dimethylene}bispyridinium salts have been developed. The key step of the first strategy relies on electrochemical and chemical oxidation of cationic 1,4-dihydropyridines; the second one involves nucleophilic substitution of pyridine dibromo derivatives.

Original language	English
Pages (from-to)	8344-8349
Number of pages	6
Journal	Tetrahedron
Volume	65
Issue number	40
DOIs	https://doi.org/10.1016/j.tet.2009.08.012
Publication status	Published - 3 Oct 2009
Externally published	Yes

Keywords*

Cationic 1,4-dihydropyridines and pyridines
Gene delivery
Oxidation

Field of Science*

1.4 Chemical sciences
3.1 Basic medicine

Publication Type*

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

Access to Document

10.1016/j.tet.2009.08.012

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@article{a9c865d847844b1e8ed39fb36cbececf,

title = "Oxidation of cationic 1,4-dihydropyridine derivatives as model compounds for putative gene delivery agents",

abstract = "A new synthetic approach to cationic pyridine derivatives is described here. Two different strategies for the synthesis of 1,1′-{[3,5-bis(ethoxycarbonyl)-4-phenylpyridine-2,6-diyl]dimethylene}bispyridinium salts have been developed. The key step of the first strategy relies on electrochemical and chemical oxidation of cationic 1,4-dihydropyridines; the second one involves nucleophilic substitution of pyridine dibromo derivatives.",

keywords = "Cationic 1,4-dihydropyridines and pyridines, Gene delivery, Oxidation",

author = "Aiva Plotniece and Karlis Pajuste and Dainis Kaldre and Brigita Cekavicus and Brigita Vigante and Baiba Turovska and Sergey Belyakov and Arkadij Sobolev and Gunars Duburs",

note = "Funding Information: This research work was supported by VP-05–08 and ES 05–27 from Latvian Ministry of Education and Science, fellowship “For Women in Science” from L'Oreal Latvia, Latvian National Commission for UNESCO and Latvian Academy of Sciences (for Aiva Plotniece) and European Social Foundation (for Karlis Pajuste). We are indebted to Dr. S. Grinberga for the mass spectral analyses, to Mrs. E. Sarule for the elemental analyses and Dr. A. Mishnev for powder X-ray diffraction analyses. ",

year = "2009",

month = oct,

day = "3",

doi = "10.1016/j.tet.2009.08.012",

language = "English",

volume = "65",

pages = "8344--8349",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "40",

}

TY - JOUR

T1 - Oxidation of cationic 1,4-dihydropyridine derivatives as model compounds for putative gene delivery agents

AU - Plotniece, Aiva

AU - Pajuste, Karlis

AU - Kaldre, Dainis

AU - Cekavicus, Brigita

AU - Vigante, Brigita

AU - Turovska, Baiba

AU - Belyakov, Sergey

AU - Sobolev, Arkadij

AU - Duburs, Gunars

N1 - Funding Information: This research work was supported by VP-05–08 and ES 05–27 from Latvian Ministry of Education and Science, fellowship “For Women in Science” from L'Oreal Latvia, Latvian National Commission for UNESCO and Latvian Academy of Sciences (for Aiva Plotniece) and European Social Foundation (for Karlis Pajuste). We are indebted to Dr. S. Grinberga for the mass spectral analyses, to Mrs. E. Sarule for the elemental analyses and Dr. A. Mishnev for powder X-ray diffraction analyses.

PY - 2009/10/3

Y1 - 2009/10/3

N2 - A new synthetic approach to cationic pyridine derivatives is described here. Two different strategies for the synthesis of 1,1′-{[3,5-bis(ethoxycarbonyl)-4-phenylpyridine-2,6-diyl]dimethylene}bispyridinium salts have been developed. The key step of the first strategy relies on electrochemical and chemical oxidation of cationic 1,4-dihydropyridines; the second one involves nucleophilic substitution of pyridine dibromo derivatives.

AB - A new synthetic approach to cationic pyridine derivatives is described here. Two different strategies for the synthesis of 1,1′-{[3,5-bis(ethoxycarbonyl)-4-phenylpyridine-2,6-diyl]dimethylene}bispyridinium salts have been developed. The key step of the first strategy relies on electrochemical and chemical oxidation of cationic 1,4-dihydropyridines; the second one involves nucleophilic substitution of pyridine dibromo derivatives.

KW - Cationic 1,4-dihydropyridines and pyridines

KW - Gene delivery

KW - Oxidation

UR - http://www.scopus.com/inward/record.url?scp=69249175300&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2009.08.012

DO - 10.1016/j.tet.2009.08.012

M3 - Article

AN - SCOPUS:69249175300

SN - 0040-4020

VL - 65

SP - 8344

EP - 8349

JO - Tetrahedron

JF - Tetrahedron

IS - 40

ER -

Oxidation of cationic 1,4-dihydropyridine derivatives as model compounds for putative gene delivery agents

Abstract

Keywords*

Field of Science*

Publication Type*

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