Syntheses of phenyl benzoate compounds and their bioactivity investigation

doi:10.5246/jcps.2021.11.075

Abstract

Abstract:

Eight phenyl benzoate compounds were synthesized in one step, and then their antioxidant, anti-tyrosinase, and anti-pancreatic lipase activities were evaluated in the present study. The total yields ranged from 31% to 85%. Compound 4c exhibited a stronger antioxidant activity compared with Trolox, with half maximal inhibitory concentrations (IC₅₀) of approximately 13.06 μM, and the antioxidant mechanism was further studied using computational chemistry. Compounds 1c–5c exhibited minimal anti-tyrosinase activity. Compounds 4c, 5d, 6c and 6d exhibited weak anti-pancreatic lipase activity, with an inhibition rate of 33.52%, 15.76%, 18.37% and 20.77%, respectively. These results demonstrated that all compounds had reference significance, especially compound 4c.

Key words: Phenyl benzoate, Synthesis, Antioxidant, Anti-tyrosinase, Anti-pancreatic lipase

Supporting:

Beidou Zhou, Jiali Li, Baocheng Huang, Zihan Yu, Zetong Ma, Zhipeng Ruan, Qihong Cai, Dongbao Hu. Syntheses of phenyl benzoate compounds and their bioactivity investigation[J]. Journal of Chinese Pharmaceutical Sciences, 2021, 30(11): 874-882.

Figures/Tables 8

Table 1. Screening result of DPPH radical scavenging activity of compound 4c.

Table 2. The antioxidant IC50 values of compound 4c.

Table 3. The bond dissociation enthalpies for compound 4c.

Table 4. Anti-tyrosinase activities of compounds 1c–6c and 5d, 6d.

Table 5. Anti-pancreatic lipase activities of compounds 1c–6c and 5d, 6d.

References 10

[1]	Jiao, J.J.; Ni, L.Z.; Chen, Q.; Gao, Z.H.; Ma, F.; Hou, Y.X. Benzoic acid (benzotriazolyl) phenyl ester compounds [P]. CN101434582. 2009-05-20.
[2]	Yu, X.P.; Han, S.Z.; Gao, Z.H.; Ni, L.Z.; Chen, Q.; Jiao, J.J. Synthesis and characterization of phenyl-4-(2H-benzotriazol-2-yl)-benzoate light stabilizers. J. Funct. Polym. 2010, 23, 98–102.
[3]	Yang, H.L.; Xi, G.G. Preparation and properties of negative liquid crystals (II)-p-alkyl (alkoxy)phenyl-4-[p-alkyl (alkoxy) benzoyloxy]-3-fluorobenzoate. J. Nanjing Univ. Sci. Technol. 1994, 73, 59–63.
[4]	Krátký, M.; Bősze, S.; Baranyai, Z.; Szabó, I.; Stolaříková, J.; Paraskevopoulos, G.; Vinšová, J. Synthesis and in vitro biological evaluation of 2-(phenylcarbamoyl)phenyl 4-substituted benzoates. Bioorg. Med. Chem. 2015, 23, 868–875.
[5]	Sherin, L.; Shujaat, S.; Sohail, A.; Arif, F. Synthesis and biological evaluation of novel Gallic acid analogues as potential antimicrobial and antioxidant agents. Croat. Chem. Acta. 2018, 91, 551–565.
[6]	Wang, Y.J.; Xiong, L.D.; Song, C.W.; Li, L.; Li, Y.; Dong, L.; Yin, S.F. Synthesis and biological evaluation of novel methyl 2-hydroxy-5-substituted benzoate derivatives as mushroom tyrosinase inhibitors. Chem. Nat. Compd. 2014, 50, 598–602.
[7]	Huang, L.; Xu, J.G.; Hu, J.Q.; Liu, Y.S. Research on synthesis of phenyl benzoate. Shandong Chem. Ind. 2011, 40, 16–17.
[8]	Zhou, B.D.; Zeng, L.L.; Tong, Y.G.; Fang, J.Y.; Ruan, Z.P.; Zeng, X.Y.; Fang, Y.Y.; Xu, G.F.; Hu, D.B. Synthesis and antitumor, antityrosinase, and antioxidant activities of xanthone. J. Asian Nat. Prod. Res. 2018, 20, 467–476.
[9]	Zhou, B.D.; Weng, Z.M.; Tong, Y.G.; Ma, Z.T.; Wei, R.R.; Li, J.L.; Yu, Z.H.; Xu, G.F.; Fang, Y.Y.; Ruan, Z.P. Syntheses of xanthone derivatives and their bioactivity investigation. J. Asian Nat. Prod. Res. 2021, 23, 271–283.
[10]	Zhou, B.D.; Yu, Z.H.; Tong, Y.G.; Li, J.L.; Huang, B.C.; Wei, R.R.; Weng, Z.M.; Wang, X.; Ruan, Z.P.; Lin, J.; Xu, C.H.; Liu J.B. Synthesis of prenylated and geranylated xanthones and their bioactivity investigation. J. Chin. Pharm. Sci. 2020, 29, 564–576.

[1]	Yuxia Zhu, Lingjian Zhang, Yiming Hu, Weihua Liu, Liping Guan, Lin Lin. Study on synthesis of naringenin derivatives and cholinesterase inhibitory activity in marine Chinese medicine [J]. Journal of Chinese Pharmaceutical Sciences, 2023, 32(8): 636-644.
[2]	Han Wang, Fanglong Li, Aga Er-bu, Xiaoxia Liang, Geng Sang, Car Rangnanjia. The in vitro antioxidant activities of the ethanol extract and its different polar fractions from Ephedra saxatilis Royle ex Florin in Tibet [J]. Journal of Chinese Pharmaceutical Sciences, 2023, 32(6): 478-486.
[3]	Ao Sun, Zipeng Li, Ting Liu, Xiangbao Meng, Shuchun Li, Zhongjun Li. Improvement of Kdo's efficient large-scale chemical synthesis method [J]. Journal of Chinese Pharmaceutical Sciences, 2022, 31(2): 97-107.
[4]	Huijie Lv, Tuo Xv, Jun Peng, Gang Luo, Jianqin He, Sisi Yang, Tiancheng Zhang, Shuidong Feng, Hongyan Ling. Dihydromyricetin improves liver fat deposition in high-fat diet-induced obese mice [J]. Journal of Chinese Pharmaceutical Sciences, 2022, 31(11): 824-839.
[5]	Yuehua Liu, Zhangqin Xue, Jianming Wei, Ruomeng Wei, Baodong Yin, Aiqin Liu. Study on drug synthesis and activity of sodium olpadronate [J]. Journal of Chinese Pharmaceutical Sciences, 2022, 31(11): 883-892.
[6]	Beidou Zhou, Chun Lei, Xuemei Liao, Hang Zhu, Zhipeng Ruan, Yuanyuan Fang, Guifen Xu, Yuli Chen. Biological investigation of phenyl benzoate, benzophenone, and xanthone compounds [J]. Journal of Chinese Pharmaceutical Sciences, 2022, 31(10): 738-745.
[7]	Lijuan Jiang, Tingting Cao, Ruoyi Yang, Ying Li, Lin Dong, Shufan Yin. Design, synthesis, and biological evaluation of a series of novel cordycepin derivatives [J]. Journal of Chinese Pharmaceutical Sciences, 2022, 31(1): 55-67.
[8]	Shiqi Xu, Liyan Zhu, Chao Hao, Wenqian Liu, Chenglong Chen, Yongyi Chen, Aiqin Liu. Synthesis of a novel series of amino acid prodrugs based on tegafur and evaluation of their antitumor activity [J]. Journal of Chinese Pharmaceutical Sciences, 2021, 30(9): 743-753.
[9]	State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center. Cyclic peptide molecular biosynthesis-the group of Professor Ming Ma discovered the first catalytic isomerization/cyclic bifunctional thioesterase and analyzed its crystal structure [J]. Journal of Chinese Pharmaceutical Sciences, 2021, 30(9): 778-779.
[10]	Zipeng Qiao, Qizhi Wang, Jianfu Liu, Mingyuan Wang. Antioxidant and antibacterial activities of the ethyl acetate extracts of endophytic fungi isolated from Ageratum conyzoides L. [J]. Journal of Chinese Pharmaceutical Sciences, 2021, 30(5): 421-433.
[11]	Xin Dong, Hong Wang, Feixiang Ma, Jianping Gao, Shizhong Chen, Peifeng Xue. A strategy for structure-activity relationship study on antioxidants in Echinops latifolius Tausch extracts by online HPLC-radical scavenging detection coupled with ESI-IT-TOF-MSn [J]. Journal of Chinese Pharmaceutical Sciences, 2021, 30(4): 267-279.
[12]	Yinyan Xu, Min Zhu, Kaiheng Zhou, Taotao Song, Lili Huang. 3,4-Dihydroxyacetophenone alleviates lipopolysaccharide-induced acute lung injury as a potential anti-inflammatory and anti-oxidative agent [J]. Journal of Chinese Pharmaceutical Sciences, 2021, 30(12): 956-968.
[13]	Xueni Cai, Ge Fu, Martin Lepšík, Emanuele Paci, Yuan Guo, Zhongjun Li, Qing Li. Synthesis of a series of novel homo- and hetero-glycoclusters and their binding activities to DC-SIGN [J]. Journal of Chinese Pharmaceutical Sciences, 2021, 30(11): 859-873.
[14]	Beidou Zhou, Zihan Yu, Yugui Tong, Jiali Li, Baocheng Huang, Rongrong Wei, Zhimin Weng, Xin Wang, Zhipeng Ruan, Jian Lin, Caihong Xu, Jianbo Liu. Synthesis of prenylated and geranylated xanthones and their bioactivities [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(8): 564-576.
[15]	Xiaoxia Liang, Cheng Xiong, Yingying Gao, Qiaojia Fan. Antioxidantive activities and gastrodin determination of extracts of endophytic fungi isolated from Gastrodia elata Bl. [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(3): 206-213.