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Updated: May 22, 2026
Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Synthesis, structure analysis, and antitumor evaluation of 3,6-dimethyl-1,2,4,5-tetrazine-1,4-dicarboxamide
Guo-Wu Rao1, Yan-Mei Guo, Wei-Xiao Hu
1College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, PR China. rgw@zjut.edu.cn
Abstract:
3,6-Dimethyl-1,2,4,5-tetrazine-1,4-dicarboxamide derivatives were synthesized, and their structures were confirmed by single-crystal X-ray diffraction. This reaction yields the 1,4-dicarboxamide derivatives rather than the 1,2-dicarboxamide derivatives. Their in vitro antitumor activities were evaluated against SGC-7901, HO-8910, MCF-7, and A-549 cells. The results showed several compounds to be endowed with cytotoxicity in the low micromolar range. One compound (IC(50) =0.57 μM) was further evaluated in vivo against an A-549 xenograft in BALB/cA nude mice; it effected 76.4% inhibition of tumor weight through intraperitoneal (i.p.) administration of 40 mgkg(-1) body weight. Moreover, its acute toxicity was evaluated, and the i.p. LD(50) value was 325 mgkg(-1) in mice.
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Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...