Synthesis and biological evaluation of piperazine derivatives on dipeptidyl peptidase-4

doi:10.5246/jcps.2013.02.023

• Original articles • Previous Articles Next Articles

Synthesis and biological evaluation of piperazine derivatives on dipeptidyl peptidase-4

Xiangguo Meng, Zhengyan Cai, Wei Zhang, Weicheng Zhou*

State Key Laboratory of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, Shanghai Institute of Pharmaceutical Industry, State Institute of Pharmaceutical Industry, Shanghai 200437, China

Received:2012-08-03 Revised:2012-12-10 Online:2013-03-18 Published:2013-03-18
Contact: Weicheng Zhou*

Abstract

Abstract:

A series of (4-(2,4,5-trifluorophenyl)piperazin-1-yl) methanone derivatives 9a-k as potential dipeptidyl peptidase-4 (DPP-4) inhibitors were synthesized by microwave assisted nucleophilic substitution of 1,2,4,5-tetrafluorobenzene with piperazine, followed by carbamoylation and condensation. The inhibitory activities of these new compounds on DPP-4 were evaluated in vitro, and compounds 9d and 9g showed moderate inhibitory activities.

Key words: DPP-4, DPP-4 inhibitor, Derivative, Synthesize

CLC Number:

R916

Supporting:

Xiangguo Meng, Zhengyan Cai, Wei Zhang, Weicheng Zhou*. Synthesis and biological evaluation of piperazine derivatives on dipeptidyl peptidase-4[J]. , DOI: 10.5246/jcps.2013.02.023.

[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]	Bo Fan, Xiao Yang, Shuang Hu. Vortex-assisted switchable solvent liquid-phase microextraction for preconcentration of cinnamic acid derivatives in traditional Chinese medicine [J]. Journal of Chinese Pharmaceutical Sciences, 2023, 32(7): 551-559.
[3]	Suqian Cai, Kefeng Zhang, Xiaohua Cai. Bergenin: a versatile and readily available precursor for bioactive modifications [J]. Journal of Chinese Pharmaceutical Sciences, 2023, 32(5): 333-350.
[4]	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.
[5]	Xixi Li, Qian Liu, Tao Sheng, Junyi Liu, Xiaowei Wang. Pyridin-2(1H)-ones as HIV-1 NNRTIs: a combinatorial optimization strategy [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(2): 79-89.
[6]	Xintong Wang, Wenxing Zou, Haoran Xiao, Wenjun Xie, Xin Li, Xiling Bian, Qi Sun, Kewei Wang. Electrophysiological characterization of furo[3,2-b]pyridine derivatives as negative allosteric modulator of a7 nicotinic acetylcholine receptor [J]. Journal of Chinese Pharmaceutical Sciences, 2019, 28(3): 160-166.
[7]	Yunqi Liu, Xixi Li, Xiaodong Dou, Chao Tian, Zhili Zhang, Junyi Liu, Xiaowei Wang. Similar pyridinone compounds with different activities of anti-HIV-1 reverse transcriptase [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(7): 469-477.
[8]	Ye Yao, Xiangfei Jiu, Siyuan Wang, Wei Lu, Tianyan Zhou. Mechanism-based pharmacokinetic/pharmacodynamic modeling of the effects of sitagliptin on DPP-4 activity, insulin and glucose in diabetic rats [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(6): 371-382.
[9]	Dini Kesuma, Siswandono, Bambang Tri Purwanto, Marcellino Rudyanto. Synthesis of N-(phenylcarbamothioyl)-benzamide derivatives and their cytotoxic activity against MCF-7 cells [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(10): 696-702.
[10]	Wanli Shen, Fei Yu, Lu Xu, Cong Chen, Yini Cao, Shu Liu, Nanyin Han, Chao Wang, Rong Qi. Protective effects of tanshinone IIA derivative on myocardial ischemia/reperfusion injury in rats [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(1): 1-13.
[11]	Yajing Ma, Huan Liu, Shunan Tang, Siwang Yu, Mingying Shang, Shaoqing Cai. Synthesis and cytotoxicity of kaempferol derivatives [J]. Journal of Chinese Pharmaceutical Sciences, 2017, 26(9): 660-665.
[12]	Yadav Rakesh, Maan Monika, Yadav Divya. Synthesis and characterization of pyrimidines analogues as anti-Alzheimer’s agents [J]. Journal of Chinese Pharmaceutical Sciences, 2017, 26(11): 834-846.
[13]	Quanzhi Yang, Tao Sheng, Ningning Fan, Yameng Hao, Yuanyuan Cao, Ying Guo, Zhili Zhang, Chao Tian, Junyi Liu, Xiaowei Wang. Design, synthesis and activity evaluation of novel pyridinone derivatives as anti-HIV-1 dual (RT/IN) inhibitors [J]. Journal of Chinese Pharmaceutical Sciences, 2017, 26(1): 31-44.
[14]	Li Yao, Fangfang Fan, Lan Hu, Shengjun Zhao, Lili Zheng. Efficacy and safety of saxagliptin in patients with type 2 diabetes mellitus: a meta-analysis of randomized controlled trials [J]. Journal of Chinese Pharmaceutical Sciences, 2016, 25(2): 128-139.
[15]	Guanyu Yang, Qi Sun, Chao Wang, Lei Liang, Fengrong Xu, Yan Niu, Ping Xu. Design, synthesis and biological evaluation of sulfonamide flavone derivatives as potential 20S proteasome inhibitors [J]. Journal of Chinese Pharmaceutical Sciences, 2014, 23(9): 626-630.

Synthesis and biological evaluation of piperazine derivatives on dipeptidyl peptidase-4

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments