Original article
Synthesis and evaluation of antitumor activities of novel chiral 1,2,4-triazole Schiff bases bearing γ-butenolide moiety
1 Key Laboratory of Energy Sources & Chemical Engineering, Development Center of Natural Products and Medication and School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan, 750021, China
2 Key Lab of Ministry of Education for Protection and Utilization of Special Biological Resources in Western China, School of Life Science, Ningxia University, Yinchuan, 750021, China
3 Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, Yunnan University, Kunming, 650091, China
Organic and Medicinal Chemistry Letters 2012, 2:26 doi:10.1186/2191-2858-2-26
Published: 3 July 2012Abstract
Background
1,2,4-Triazole derivatives have received much attention due to their versatile biological properties including antibacterial, antifungal, anticonvulsant, antiinflammatory, anticancer, and antiproliferative properties. 1,2,4-Triazole nucleus has been incorporated into a wide variety of therapeutically interesting molecules to transform them into better drugs. Schiff bases of 1,2,4-triazoles have also been found to possess extensive biological activities. On the other hand, γ-substituted butenolide moiety represents a biological important entity that is present in numerous biologically active natural products.
Results
We have described herein the synthesis of 12 hybrid 1,2,4-triazole Schiff bases bearing γ-substituted butenolide moiety. These compounds were synthesized by utilizing the tandem asymmetric Michael addition/elimination reaction as the key step. All the new compounds were evaluated for their in vitro anticancer activity.
Conclusions
Tandem asymmetric Michael addition/elimination approach has offered an easy access to new chiral 1,2,4-triazole compounds 7a-7l. All these chiral 1,2,4-triazole derivatives exhibited good anticancer activities towards Hela. Of all the tested compounds, the chiral compound 7l with an IC50 of 1.8 μM was found to be the most active.
