Synthesis of Aminoalkylated Aziridines from (+)-3-Carene
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CURLAT, Serghei; BARBĂ, Alic; BOLDESCU, Veaceslav; PANEKOK, K.; MACAEV, Fliur. Synthesis of Aminoalkylated Aziridines from (+)-3-Carene. In: Chemistry of Natural Compounds. 2019, nr. 2(55), pp. 269-274. ISSN 0009-3130.
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Chemistry of Natural Compounds
Numărul 2(55) / 2019 / ISSN 0009-3130

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


DOI: 10.1007/s10600-019-02664-0
Pag. 269-274

Curlat Serghei1, Barbă Alic1, Boldescu Veaceslav1, Panekok K.2, Macaev Fliur1
 
1 Institute of Chemistry,
2 Rega Institute
 
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