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

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-disubstitut...

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Bibliographic Details
Published inRussian chemical bulletin Vol. 67; no. 5; pp. 858 - 865
Main Authors Samet, A. V., Sil’yanova, E. A., Ushkarov, V. I., Semenova, M. N., Semenov, V. V.
Format Journal Article
LanguageEnglish
Published New York Springer US 01.05.2018
Springer Nature B.V
Subjects
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
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Inorganic Chemistry
Organic Chemistry
Pyrroles
Reaction products
combretastatin
nitrostilbenes
nitrochalcones
Barton–Zard reaction
3,4-diarylpyrroles
sea urchin embryo
ethyl isocyanoacetate
antimitotic activity
4-acyl-3-arylpyrroles
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Summary: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.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-018-2150-3