苯甲酸苯酯类化合物的合成与生物活性调查

doi:10.5246/jcps.2021.11.075

中国药学(英文版) ›› 2021, Vol. 30 ›› Issue (11): 874-882.DOI: 10.5246/jcps.2021.11.075

苯甲酸苯酯类化合物的合成与生物活性调查

周北斗¹, 李佳莉¹, 黄堡城¹, 俞紫涵¹, 马泽通¹, 阮志鹏¹, 蔡其洪¹, 胡栋宝²^,^*()

1. 莆田学院药学与医学技术学院, 药物分析与检验医学福建省高校重点实验室; 医学微生态学福建省高校重点实验室, 福建莆田 351100
2. 玉溪师范学院化学生物与环境学院, 云南玉溪 653100

收稿日期:2021-05-23 修回日期:2021-07-15 接受日期:2021-08-19 出版日期:2021-11-28 发布日期:2021-11-28
通讯作者: 胡栋宝
作者简介:
+ Tel.: +86-18869712768, E-mail: hudongbao@126.com
基金资助:
Scientific Research Fund of the School of Pharmacy and Medical Technology of Putian University (Grant No. Z202102).

Syntheses of phenyl benzoate compounds and their bioactivity investigation

Beidou Zhou¹, Jiali Li¹, Baocheng Huang¹, Zihan Yu¹, Zetong Ma¹, Zhipeng Ruan¹, Qihong Cai¹, Dongbao Hu²^,^*()

1 School of Pharmacy and Medical Technology, Putian University; Key Laboratory of Pharmaceutical Analysis and Laboratory Medicine (Putian University), Fujian Province University; Key Laboratory of Medical Microecology (Putian University), Fujian Province University, Putian University, Putian 351100, China
2 School of Chemical Biology and Environment, Yuxi Normal University, Yuxi 653100, China

Received:2021-05-23 Revised:2021-07-15 Accepted:2021-08-19 Online:2021-11-28 Published:2021-11-28
Contact: Dongbao Hu

摘要/Abstract

摘要：

本研究采用一步法合成8个苯甲酸苯酯类化合物, 总产率在31%和85%之间, 并对其抗氧化、抗酪氨酸酶和抗胰脂肪酶活性进行了评估。化合物4c显示出比水溶性维生素E更强的抗氧化活性, 其半数抑制浓度(IC₅₀)约为13.06 μM, 通过计算化学对其抗氧化机制进行进一步研究。化合物1c–5c显示出低的抗酪氨酸酶活性。化合物4c、5d、6c和6d显示出弱的抗胰脂肪酶活性, 抑制率分别为33.52%、15.76%、18.37%和20.77%。研究显示所有的化合物都具有参考意义, 特别是化合物4c。

关键词: 苯甲酸苯酯, 合成, 抗氧化, 抗酪氨酸酶, 抗胰脂肪酶

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:

周北斗, 李佳莉, 黄堡城, 俞紫涵, 马泽通, 阮志鹏, 蔡其洪, 胡栋宝. 苯甲酸苯酯类化合物的合成与生物活性调查[J]. 中国药学(英文版), 2021, 30(11): 874-882.

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.

图/表 8

Scheme 1. Synthetic route of compounds 1c–4c.

Scheme 2. Synthetic routes of compounds 5c, 5d, 6c and 6d.

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

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

Scheme 3. Optimized four stable radicals 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.

参考文献 10

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苯甲酸苯酯类化合物的合成与生物活性调查

Syntheses of phenyl benzoate compounds and their bioactivity investigation

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