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Synthesis of fluoromethyl-containing analogs of antitumor alkaloid luotonin A

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Abstract

A convenient method for the synthesis of hitherto unknown 3-bromomethyl-2-chloro-4-fluoromethylquinolines has been developed. Coupling of 3-bromomethyl-2-chloro-4-trifluo-romethylquinoline with 4(3H)-quinazolinone with subsequent intramolecular Heck cyclization leads to 7-trifluoromethylluotonin, an analog of the antitumor alkaloid luotonin A. 7-Trifluo-romethylluotonin retains the antitumor activity including apoptosis of cultured tumor cells and inhibiting DNA-topoisomerase I.

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Authors and Affiliations

  1. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    A. S. Golubev, V. O. Bogomolov, A. F. Shidlovskii, A. S. Peregudov & N. D. Chkanikov

  2. F. Gause Research Institute of New Antibiotics, Russian Academy of Medical Sciences, 11 ul. B. Pirogovskaya, 119021, Moscow, Russian Federation

    L. G. Dezhenkova

  3. N. Blokhin Russian Cancer Scientific Center, Russian Academy of Medical Sciences, 24 Kashirskoe shosse, 115478, Moscow, Russian Federation

    A. A. Shtil

Authors
  1. A. S. Golubev
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  2. V. O. Bogomolov
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  3. A. F. Shidlovskii
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  4. L. G. Dezhenkova
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  5. A. S. Peregudov
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  6. A. A. Shtil
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  7. N. D. Chkanikov
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Corresponding author

Correspondence to A. S. Golubev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 205–214, January, 2010.

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Golubev, A.S., Bogomolov, V.O., Shidlovskii, A.F. et al. Synthesis of fluoromethyl-containing analogs of antitumor alkaloid luotonin A. Russ Chem Bull 59, 209–218 (2010). https://doi.org/10.1007/s11172-010-0064-9

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  • DOI: https://doi.org/10.1007/s11172-010-0064-9

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