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Synthesis of 3,4-diaryl- and 4-acyl-3-arylpyrroles and study of their antimitotic activity

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Abstract

The Barton–Zard reaction of nitro substituted stilbenes and chalcones with ethyl isocyanoacetate afforded 3,4-diaryl- and 4-acyl-3-arylpyrroles, respectively. 3-Arylpyrrole-2,4- dicarboxylates and 4-arylisoxazoline N-oxides were side reaction products. Antimitotic activity of target 3,4-disubstituted pyrroles was studied on a sea urchin embryo model. Pyrroles unsubstituted at positions 2 and 5 were the most active. The activity increased with the number of methoxy groups in the Ar substituent.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. V. Samet, E. A. Sil’yanova, V. I. Ushkarov & V. V. Semenov

  2. D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125047, Moscow, Russian Federation

    E. A. Sil’yanova

  3. N. K. Kol’tsov Institute of Developmental Biology, Russian Academy of Sciences, 26 ul. Vavilova, 119334, Moscow, Russian Federation

    M. N. Semenova

Authors
  1. A. V. Samet
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  2. E. A. Sil’yanova
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  3. V. I. Ushkarov
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  4. M. N. Semenova
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  5. V. V. Semenov
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Correspondence to A. V. Samet.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 0858–0865, May, 2018.

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Samet, A.V., Sil’yanova, E.A., Ushkarov, V.I. et al. Synthesis of 3,4-diaryl- and 4-acyl-3-arylpyrroles and study of their antimitotic activity. Russ Chem Bull 67, 858–865 (2018). https://doi.org/10.1007/s11172-018-2150-3

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  • DOI: https://doi.org/10.1007/s11172-018-2150-3

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