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Mar. Drugs 2018, 16(3), 97; https://doi.org/10.3390/md16030097

Function-Oriented Synthesis of Marine Phidianidine Derivatives as Potential PTP1B Inhibitors with Specific Selectivity

1,2
,
1
,
1
,
1,3
,
1,3
,
1,3
,
1,3,* and 1,3,*
1
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China
2
Nano Science and Technology Institute, University of Science and Technology of China, 166 Ren Ai Road, Suzhou 215123, China
3
Open Studio for Druggability Research of Marine Natural Products, Qingdao National Laboratory for Marine Science and Technology, 1 Wenhai Road, Aoshanwei, Jimo, Qingdao 266237, China
*
Authors to whom correspondence should be addressed.
Received: 25 January 2018 / Revised: 7 March 2018 / Accepted: 7 March 2018 / Published: 20 March 2018
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Abstract

Phidianidines A and B are two novel marine indole alkaloids bearing an uncommon 1,2,4-oxadiazole ring and exhibiting various biological activities. Our previous research showed that the synthesized phidianidine analogs had the potential to inhibit the activity of protein tyrosine phosphatase 1B (PTP1B), a validated target for Type II diabetes, which indicates that these analogs are worth further structural modification. Therefore, in this paper, a series of phidianidine derivatives were designed and rapidly synthesized with a function-oriented synthesis (FOS) strategy. Their inhibitory effects on PTP1B and T-cell protein tyrosine phosphatase (TCPTP) were evaluated, and several compounds displayed significant inhibitory potency and specific selectivity over PTP1B. The structure–activity relationship (SAR) and molecular docking analyses are also described. View Full-Text
Keywords: phidianidine; marine natural products; PTP1B inhibitor; specific selectivity; docking analysis; Function Oriented Synthesis; structure-activity relationship phidianidine; marine natural products; PTP1B inhibitor; specific selectivity; docking analysis; Function Oriented Synthesis; structure-activity relationship
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Liu, J.; Chen, Y.; Li, J.-Y.; Luo, C.; Li, J.; Chen, K.-X.; Li, X.-W.; Guo, Y.-W. Function-Oriented Synthesis of Marine Phidianidine Derivatives as Potential PTP1B Inhibitors with Specific Selectivity. Mar. Drugs 2018, 16, 97.

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