Bioorganic and Medicinal Chemistry Letters

, volume 24 , issue 14 , pages 3118-3120

Synthesis and antituberculosis activity of novel 5-styryl-4-(hetero)aryl-pyrimidines via combination of the Pd-catalyzed Suzuki cross-coupling and SNH reactions

Marionella A. Kravchenko ¹

Egor V. Verbitskiy ^{2, 3}

Igor D Medvinskiy ¹

Gennady L. Rusinov ^{2, 3}

Valery Charushin ^{2, 3}

Hide authors affiliations Show authors affiliations: 3 affiliations

Ural Research Institute for Phthisiopulmonology, 22 Parts'ezda, 50, Ekaterinburg 620039, Russia. |

I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg 620990, Russia |

Ural Federal University, Mira St. 19, Ekaterinburg 620002, Russia |

Publication type: Journal Article

Publication date: 2014-07-01

Elsevier

Bioorganic and Medicinal Chemistry Letters

scimago Q2

wos Q2

SJR: 0.472

CiteScore: 5.1

Impact factor: 2.2

ISSN: 0960894X, 14643405

DOI: 10.1016/j.bmcl.2014.05.006

Copy DOI

PubMed ID: 24856062

Organic Chemistry

Drug Discovery

Biochemistry

Molecular Biology

Pharmaceutical Science

Clinical Biochemistry

Molecular Medicine

Abstract

Combination of the Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen (SN(H)) reactions proved to be a convenient method for the synthesis of 5-styryl-4-(hetero)aryl substituted pyrimidines from commercially available 5-bromopyrimidine. All intermediate 5-bromo-4-(hetero)aryl substituted pyrimidines and also the targeted 5-styryl-4-(hetero)arylpyrimidines were found to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H37Rv, avium, terrae, and multi-drug-resistant strain isolated from tuberculosis patients in Ural region (Russia). It has been found that some of these compounds possess a low toxicity and have a bacteriostatic effect, comparable and even higher with that of first-line antituberculosis drugs.

Found

2 citations

Dinastiya Ekaterina

29 publications, 586 citations, 33 reviews

h-index: 15

Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Saint Petersburg State University

1 citation

Eremenko Igor

DSc in Chemistry, professor, full member of the Russian Academy of Sciences

675 publications, 7 817 citations, 29 reviews

h-index: 35

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

1 citation

Kiskin Mikhail

🥼 🤝

DSc in Chemistry, professor

408 publications, 5 130 citations

h-index: 31

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

Research interests

Magnets

Nanoparticles

1 citation

Makarov Vadim

🥼 🤝

DSc in Chemistry

177 publications, 4 647 citations, 7 reviews

h-index: 36

Federal Research Centre “Fundamentals of Biotechnology” of the Russian Academy of Sciences

Research interests

Early drug discovery

Medicinal Chemistry

1 citation

Varaksin Mikhail

DSc in Chemistry

79 publications, 829 citations, 12 reviews

h-index: 18

Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

Ural Federal University

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GOST |

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GOST Copy

Kravchenko M. A. et al. Synthesis and antituberculosis activity of novel 5-styryl-4-(hetero)aryl-pyrimidines via combination of the Pd-catalyzed Suzuki cross-coupling and SNH reactions // Bioorganic and Medicinal Chemistry Letters. 2014. Vol. 24. No. 14. pp. 3118-3120.

GOST all authors (up to 50) Copy

Kravchenko M. A., Verbitskiy E. V., Medvinskiy I. D., Rusinov G. L., Charushin V. Synthesis and antituberculosis activity of novel 5-styryl-4-(hetero)aryl-pyrimidines via combination of the Pd-catalyzed Suzuki cross-coupling and SNH reactions // Bioorganic and Medicinal Chemistry Letters. 2014. Vol. 24. No. 14. pp. 3118-3120.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1016/j.bmcl.2014.05.006

UR - https://doi.org/10.1016/j.bmcl.2014.05.006

TI - Synthesis and antituberculosis activity of novel 5-styryl-4-(hetero)aryl-pyrimidines via combination of the Pd-catalyzed Suzuki cross-coupling and SNH reactions

T2 - Bioorganic and Medicinal Chemistry Letters

AU - Kravchenko, Marionella A.

AU - Verbitskiy, Egor V.

AU - Medvinskiy, Igor D

AU - Rusinov, Gennady L.

AU - Charushin, Valery

PY - 2014

DA - 2014/07/01

PB - Elsevier

SP - 3118-3120

IS - 14

VL - 24

PMID - 24856062

SN - 0960-894X

SN - 1464-3405

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2014_Kravchenko,

author = {Marionella A. Kravchenko and Egor V. Verbitskiy and Igor D Medvinskiy and Gennady L. Rusinov and Valery Charushin},

title = {Synthesis and antituberculosis activity of novel 5-styryl-4-(hetero)aryl-pyrimidines via combination of the Pd-catalyzed Suzuki cross-coupling and SNH reactions},

journal = {Bioorganic and Medicinal Chemistry Letters},

year = {2014},

volume = {24},

publisher = {Elsevier},

month = {jul},

url = {https://doi.org/10.1016/j.bmcl.2014.05.006},

number = {14},

pages = {3118--3120},

doi = {10.1016/j.bmcl.2014.05.006}

}

MLA

Cite this

MLA Copy

Kravchenko, Marionella A., et al. “Synthesis and antituberculosis activity of novel 5-styryl-4-(hetero)aryl-pyrimidines via combination of the Pd-catalyzed Suzuki cross-coupling and SNH reactions.” Bioorganic and Medicinal Chemistry Letters, vol. 24, no. 14, Jul. 2014, pp. 3118-3120. https://doi.org/10.1016/j.bmcl.2014.05.006.

Publisher

Elsevier

Journal

Bioorganic and Medicinal Chemistry Letters

scimago Q2

wos Q2

SJR

0.472

CiteScore

5.1

Impact factor

2.2

ISSN

0960894X (Print)

14643405 (Electronic)