Synthesis of Triterpene A-Condensed Azoles

• DOI: 10.1007/s10593-014-1449-8
• Publication Date: 2014-03-21T00:45:15Z
• Authors: N. V. Galaiko; A. V. Nazarov; I. A. Tolmacheva; P. A. Slepukhin; Yu. B. Vikharev; O. A. Maiorova; V. V. Grishko
• Keywords: 01 natural sciences; 0104 chemical sciences

Lupane and 18αH-oleanane α-hydroximino ketones were used to synthesize derivatives condensed at ring A with a substituted azole fragment, namely, C(2)–C(3)-fused oxazoles and 1,2,3-triazoles. Triterpene isoxazoles fused at the C(1)–C(2) bond are described for the first time. An optimized method was proposed for the synthesis of unsubstituted 1,2,3-triazoles, displaying cytotoxic activity (IC50 8.4-40.7 μM) relative to rhabdomyosarcoma, lung carcinoma, and MS melanoma cell lines.