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Three-component condensation of trifluoromethyl-substituted cyanovinylphosphonates, arylamines, and ketones and cytotoxic activity of products thus obtained

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Abstract

A three-component condensation of trifluoromethyl-substituted cyanovinylphosphonates, arylamines, and ketones (acetone, cyclopentanone, or cyclohexanone) has been studied. A possibility of using trifluoromethyl-substituted cyanovinylphosphonates as precursors of 1,4-dihydropyridines, 4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridines, 1,4,5,6,7,8-hexahydro-quinolines, and 1,4,4a,5,6,7-hexahydroquinolines, modified with both trifluoromethyl and di-ethoxyphosphoryl groups, has been demonstrated. Using X-ray diffraction analysis, it was found that in some cases of the three-component condensation under study a mixture of 1-aryl-2-amino- and 2-arylamino-substituted products was formed. Migration of the multiple bond onto the ring fused with the dihydropyridine ring has been inferred from the NMR spectra and X-ray diffraction data. Cytotoxic activity of some compounds synthesized has been studied in the US National Cancer Institute.

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Authors and Affiliations

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

    A. F. Shidlovskii, A. S. Peregudov, B. B. Averkiev, M. Yu. Antipin & N. D. Chkanikov

  2. Research Institute for Tumor Experimental Diagnostics and Therapy, N. N. Blokhin Russian Cancer Scientific Center, Russian Academy of Medical Sciences, 24 Kashirskoe shosse, 115478, Moscow, Russian Federation

    Yu. N. Bulychev

Authors
  1. A. F. Shidlovskii
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  2. A. S. Peregudov
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  3. B. B. Averkiev
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  4. Yu. N. Bulychev
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  5. M. Yu. Antipin
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  6. N. D. Chkanikov
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Corresponding author

Correspondence to A. F. Shidlovskii.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 143–159, January, 2010.

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Shidlovskii, A.F., Peregudov, A.S., Averkiev, B.B. et al. Three-component condensation of trifluoromethyl-substituted cyanovinylphosphonates, arylamines, and ketones and cytotoxic activity of products thus obtained. Russ Chem Bull 59, 144–161 (2010). https://doi.org/10.1007/s11172-010-0057-8

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  • DOI: https://doi.org/10.1007/s11172-010-0057-8

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