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Synthesis, Antimicrobial Study, and Molecular Docking Simulation of 3,4-Dimethoxy-β-Nitrostyrene Derivatives as Candidate PTP1B Inhibitor

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Department of Chemistry, Faculty of Science and Technology, Universitas Airlangga, Kampus C-UNAIR, Mulyorejo, Surabaya 60115, Indonesia
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Department of Chemistry, Faculty of Science and Data Analytics, Institut Teknologi Sepuluh Nopember, Kampus ITS, Sukolilo, Surabaya 60111, Indonesia
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Proteomic laboratory, Research Center for Bio-Molecule Engineering, Universitas Airlangga, Kampus C-UNAIR, Mulyorejo, Surabaya 60115, Indonesia
*
Author to whom correspondence should be addressed.
Sci. Pharm. 2020, 88(3), 37; https://doi.org/10.3390/scipharm88030037
Received: 19 July 2020 / Revised: 29 August 2020 / Accepted: 3 September 2020 / Published: 7 September 2020
A derivative series of 3,4-dimethoxy-β-nitrostyrene was synthesized through nitroaldol reaction, including a new compound of 3,4-ethylenedioxy-β-bromo-β-nitrostyrene. The antimicrobial activity effect of 3,4-alkyloxy modification of β-nitrostyrene was investigated. A molecular docking study was also performed to obtain information about their interactions with protein tyrosine phosphatase 1B (PTP1B). The active residues of cysteine-215 and arginine-221 of PTP1B play a key role in signaling pathways that regulate various microorganism cell functions. It also acts as a negative regulator in signaling pathways of insulin that are involved in type 2 diabetes and other metabolic diseases. These derivatives exhibited potential antifungal activity. The studied compounds were also had potential as fragments to be PTP1B inhibitors by interacting with serine-216 and arginine-221 residues, according to their molecular docking. 3,4-Ethylenedioxy-β-methyl-β-nitrostyrene was the most successful potential candidate as a PTP1B inhibitor. However, further research is needed to investigate their potential for medicinal use. View Full-Text
Keywords: 3,4-dimethoxy-β-nitrostyrene derivatives; antimicrobial agent; PTP1B; molecular docking 3,4-dimethoxy-β-nitrostyrene derivatives; antimicrobial agent; PTP1B; molecular docking
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Alfarisi, S.; Santoso, M.; Kristanti, A.N.; Siswanto, I.; Puspaningsih, N.N.T. Synthesis, Antimicrobial Study, and Molecular Docking Simulation of 3,4-Dimethoxy-β-Nitrostyrene Derivatives as Candidate PTP1B Inhibitor. Sci. Pharm. 2020, 88, 37.

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