Synthesis of Aminoalkylated Aziridines from (+)-3-Carene

Curlat Serghei; Barba Alic; Boldescu Veaceslav; Pannecouque C.; Makaev Fliur

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968

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CURLAT, Serghei, BARBA, Alic, BOLDESCU, Veaceslav, PANNECOUQUE, C., MAKAEV, Fliur. Synthesis of Aminoalkylated Aziridines from (+)-3-Carene. In: Chemistry of Natural Compounds, 2019, nr. 2(55), pp. 269-274. ISSN 0009-3130. DOI: https://doi.org/10.1007/s10600-019-02664-0

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Chemistry of Natural Compounds

Numărul 2(55) / 2019 / ISSN 0009-3130

Synthesis of Aminoalkylated Aziridines from (+)-3-Carene

DOI:https://doi.org/10.1007/s10600-019-02664-0

Pag. 269-274

Curlat Serghei¹, Barba Alic¹, Boldescu Veaceslav¹, Pannecouque C.², Makaev Fliur¹

¹ Institute of Chemistry,
² Rega Institute for Medical Research

Disponibil în IBN: 6 iunie 2019

Rezumat

Aminoalkylated carane-type aziridines were synthesized via epoxidation of (+)-3-carene by H ₂ O ₂ solution (7%) in EtOAc catalyzed by α-Al ₂ O ₃ nanoparticles, opening of the epoxide by NaN ₃ , and cyclization of the azidoalcohol by Ph ₃ P followed by condensation of the resulting aziridines with formalin and secondary amines. The cytotoxicity of the aminoalkylated aziridines with heteroorganic substituents increased on going from a five-membered pyrrolidine ring substituent to a six-membered piperidine ring and decreased sharply upon replacing a piperidine by a morpholine ring or increased on going to a piperazine ring. The structures of products were established using IR and NMR spectroscopy and an X-ray crystal structure analysis. .

Cuvinte-cheie
( )-3-carene, aminoalkylation, aziridines, cytotoxicity

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<title xml:lang='en'>Synthesis of Aminoalkylated Aziridines from (+)-3-Carene</title>
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<subject>( )-3-carene</subject>
<subject>aminoalkylation</subject>
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<subject>cytotoxicity</subject>
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<description xml:lang='en' descriptionType='Abstract'><p>Aminoalkylated carane-type aziridines were synthesized via epoxidation of (+)-3-carene by H <sub>2</sub> O <sub>2</sub> solution (7%) in EtOAc catalyzed by &alpha;-Al <sub>2</sub> O <sub>3</sub> nanoparticles, opening of the epoxide by NaN <sub>3</sub> , and cyclization of the azidoalcohol by Ph <sub>3</sub> P followed by condensation of the resulting aziridines with formalin and secondary amines. The cytotoxicity of the aminoalkylated aziridines with heteroorganic substituents increased on going from a five-membered pyrrolidine ring substituent to a six-membered piperidine ring and decreased sharply upon replacing a piperidine by a morpholine ring or increased on going to a piperazine ring. The structures of products were established using IR and NMR spectroscopy and an X-ray crystal structure analysis. .</p></description>
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