Chemical Communications

, volume 49 , issue 98 , pages 11482-11484

A bioinspired route to indanes and cyclopentannulated hetarenes via (3+2)-cyclodimerization of donor-acceptor cyclopropanes

Olga Ivanova ¹

Ekaterina M Budynina ^{1, 2}

Dmitry Skvortsov ¹

Michelle Limoge ³

ANDREI V. BAKIN ³

Alexey O Chagarovskiy ^{1, 2}

Igor V Trushkov ^{1, 2}

Mikhail Y. Melnikov ¹

Hide authors affiliations Show authors affiliations: 3 affiliations

M.V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, 119991 Moscow, Russia |

Federal Research Center of Pediatric Hematology, Oncology and Immunology, Laboratory of Chemical Synthesis, ul. Samory Mashela 1, Moscow 117997, Russia |

Department of Cancer Genetics, Roswell Park Cancer Institute, Elm and Carlton Sts., Buffalo, NY 14263, USA |

Publication type: Journal Article

Publication date: 2013-07-04

Royal Society of Chemistry (RSC)

Chemical Communications

scimago Q1

wos Q2

SJR: 1.037

CiteScore: 7.4

Impact factor: 4.2

ISSN: 13597345, 1364548X

DOI: 10.1039/c3cc44475a

Copy DOI

PubMed ID: 23900594

Materials Chemistry

Metals and Alloys

Surfaces, Coatings and Films

General Chemistry

Ceramics and Composites

Electronic, Optical and Magnetic Materials

Catalysis

Abstract

A novel Lewis acid-catalyzed domino (3+2)-cyclodimerization of 2-arylcyclopropane-1,1-diesters and related stepwise cross-reaction of two different cyclopropanes were developed. These processes provide efficient and highly stereoselective access to polyoxygenated indanes and cyclopentannulated heteroarene derivatives, which display significant cytotoxicity against several lines of cancer cells (IC50 of 10(-6)-10(-5) M) while being non-toxic for normal cells.

Found

3 citations

Skvortsov Dmitry

🥼

PhD in Chemistry

128 publications, 1 860 citations, 1 review

h-index: 26

Lomonosov Moscow State University

3 citations

Andreev Ivan

PhD in Chemistry

41 publications, 500 citations, 10 reviews

h-index: 12

Peoples' Friendship University of Russia

Dmitry Rogachev National Research Center of Pediatric Hematology, Oncology and Immunology

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

2 citations

Potapov Konstantin

🥼

21 publications, 147 citations

h-index: 7

Engelhardt Institute of Molecular Biology of the Russian Academy of Sciences

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

1 citation

Uchuskin Maxim

🥼 🤝

PhD in Chemistry

56 publications, 781 citations

h-index: 16

Perm State National Research University

Research interests

Heterocyclic compounds

Organic synthesis

Synthetic Organic Chemistry

1 citation

Panikorovskii Taras

🥼

PhD in Geological and Earth sciences, associate professor

93 publications, 980 citations

h-index: 17

Kola Science Center of the Russian Academy of Sciences

Research interests

Crystal Chemistry

1 citation

Antonova Yulia

🤝

8 publications, 49 citations

h-index: 3

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

1 citation

Chusov Denis

DSc in Chemistry, professor

99 publications, 2 395 citations, 35 reviews

h-index: 25

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

Research interests

Asymmetric metal complex catalysis

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GOST |

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GOST Copy

Ivanova O. et al. A bioinspired route to indanes and cyclopentannulated hetarenes via (3+2)-cyclodimerization of donor-acceptor cyclopropanes // Chemical Communications. 2013. Vol. 49. No. 98. pp. 11482-11484.

GOST all authors (up to 50) Copy

Ivanova O., Budynina E. M., Skvortsov D., Limoge M., BAKIN A. V., Chagarovskiy A. O., Trushkov I. V., Melnikov M. Y. A bioinspired route to indanes and cyclopentannulated hetarenes via (3+2)-cyclodimerization of donor-acceptor cyclopropanes // Chemical Communications. 2013. Vol. 49. No. 98. pp. 11482-11484.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1039/c3cc44475a

UR - https://doi.org/10.1039/c3cc44475a

TI - A bioinspired route to indanes and cyclopentannulated hetarenes via (3+2)-cyclodimerization of donor-acceptor cyclopropanes

T2 - Chemical Communications

AU - Ivanova, Olga

AU - Budynina, Ekaterina M

AU - Skvortsov, Dmitry

AU - Limoge, Michelle

AU - BAKIN, ANDREI V.

AU - Chagarovskiy, Alexey O

AU - Trushkov, Igor V

AU - Melnikov, Mikhail Y.

PY - 2013

DA - 2013/07/04

PB - Royal Society of Chemistry (RSC)

SP - 11482-11484

IS - 98

VL - 49

PMID - 23900594

SN - 1359-7345

SN - 1364-548X

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2013_Ivanova,

author = {Olga Ivanova and Ekaterina M Budynina and Dmitry Skvortsov and Michelle Limoge and ANDREI V. BAKIN and Alexey O Chagarovskiy and Igor V Trushkov and Mikhail Y. Melnikov},

title = {A bioinspired route to indanes and cyclopentannulated hetarenes via (3+2)-cyclodimerization of donor-acceptor cyclopropanes},

journal = {Chemical Communications},

year = {2013},

volume = {49},

publisher = {Royal Society of Chemistry (RSC)},

month = {jul},

url = {https://doi.org/10.1039/c3cc44475a},

number = {98},

pages = {11482--11484},

doi = {10.1039/c3cc44475a}

}

MLA

Cite this

MLA Copy

Ivanova, Olga, et al. “A bioinspired route to indanes and cyclopentannulated hetarenes via (3+2)-cyclodimerization of donor-acceptor cyclopropanes.” Chemical Communications, vol. 49, no. 98, Jul. 2013, pp. 11482-11484. https://doi.org/10.1039/c3cc44475a.

Publisher

Royal Society of Chemistry (RSC)

Journal

Chemical Communications

scimago Q1

wos Q2

SJR

1.037

CiteScore

7.4

Impact factor

4.2

ISSN

13597345 (Print)

1364548X (Electronic)

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