Synthesis of 3-(7-triphenylphosphonioheptyl)-2,6-dimethyl-1,4-benzoquinone) and The Activity Test Toward Glycogen Phosphorylase Enzyme: In silico Approach

9th Annual Basic Science International Conference 2019

自然科学（总论）

Furoida, Andriani^1 ; Ulfa, Siti Mariyah^1

Chemistry Department, Faculty of Science, Brawijaya University, 65145, Indonesia^1

关键词: anticancer;    bromoalkylation;    Glycogen phosphorylase;    Thymoquinone;    triphenylphosphonium moiety;   

Others  :  https://iopscience.iop.org/article/10.1088/1757-899X/546/6/062008/pdf
DOI  :  10.1088/1757-899X/546/6/062008

学科分类：自然科学（综合）

来源: IOP

【 摘 要 】

The synthesis of 3-(7-triphenylphosphonioheptyl)-2,6-dimethyl-1,4-benzoquinone) (TFH) is carried out by bromoalkylation and insertion of triphenylphosphonium moiety by refluxed of 2,3-dimethyl-1,4-benzoquinone using bromooctanoic acid triphenylphosphine. The alkylation gave 17.14% yield of 2-(7-bromoheptyl)-3,5-dimethyl-1,4-benzoquinone (C7) and 3-(7-triphenylphosphonioheptyl)-2,6-dimethyl-1,4-benzoquinone) (TFH) is obtained at 40.35% yield. Structure characterization of the synthesized product was performed mainly using UV-Vis, FT-IR, and 1H-NMR. UV-Vis characterization showed maximum wavelength of TFH at 198 nm, 226 nm, and 260 nm. FT-IR characterization showed sp3 character at 2930.43 cm-1 and the disappearance of C-Br peak at 687.37 cm-1, indicates the presence of long chain alkyl group and the replacement of Br with triphenylphosphonium. In silico investigation by using Glycogen Phosphorylase enzyme as molecular target estimated IC50 value of thymoquinone, C7, and TFH, that is, 16.14 ppm, 162.2 ppm, and 1.26 ppm, respectively. Thus, TFH has the smallest IC50 value suggested that most effective drug candidate compared with thymoquinone and C7.