Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The . gov means it’s official. Federal government websites often end in . gov or . mil. Before sharing sensitive information, make sure you’re on a federal government site VSports app下载. .

Https

The site is secure. The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely V体育官网. .

Review
. 2020 Jul 27;10(8):1111.
doi: 10.3390/biom10081111.

"VSports最新版本" More Than Resveratrol: New Insights into Stilbene-Based Compounds

Paulina Pecyna  1 , Joanna Wargula  2 , Marek Murias  3 , Malgorzata Kucinska  3
Affiliations
Review

More Than Resveratrol: New Insights into Stilbene-Based Compounds

V体育官网 - Paulina Pecyna et al. Biomolecules. .

Abstract

The concept of a scaffold concerns many aspects at different steps on the drug development path. In medicinal chemistry, the choice of relevant "drug-likeness" scaffold is a starting point for the design of the structure dedicated to specific molecular targets. For many years, the chemical uniqueness of the stilbene structure has inspired scientists from different fields such as chemistry, biology, pharmacy, and medicine. In this review, we present the outstanding potential of the stilbene-based derivatives. Naturally occurring stilbenes, together with powerful synthetic chemistry possibilities, may offer an excellent approach for discovering new structures and identifying their therapeutic targets. With the development of scientific tools, sophisticated equipment, and a better understanding of the disease pathogenesis at the molecular level, the stilbene scaffold has moved innovation in science. This paper mainly focuses on the stilbene-based compounds beyond resveratrol, which are particularly attractive due to their biological activity. Given the "fresh outlook" about different stilbene-based compounds starting from stilbenoids with particular regard to isorhapontigenin and methoxy- and hydroxyl- analogues, the update about the combretastatins, and the very often overlooked and underestimated benzanilide analogues, we present a new story about this remarkable structure VSports手机版. .

Keywords: DMU-212; benzanilide derivatives; combretastatin; isorhapontigenin; pinosylvin; stilbene analogues; thiobenzanilides. V体育安卓版.

PubMed Disclaimer

"VSports手机版" Conflict of interest statement

The authors declare no conflict of interest.

Figures (VSports注册入口)

Figure 1
Figure 1
Selected biological activities and specific targets of the stilbene-based compounds. Abbreviations: 5-LOX, lipooxygenase; Akt, protein kinase B; AMPK, AMP-activated protein kinase; CDKs, cyclin-dependent kinases; CEBP/α, CCAAT-enhancer binding protein alpha; COX-2, cyclooxygenase-2; IL, interleukins; iNOS, Inducible nitric oxide synthase; mTOR, mammalian target of rapamycin kinase; Nrf2, nuclear factor erythroid 2–related factor 2; PI3K, phosphoinositide 3-kinases; PPARγ, Peroxisome proliferator-activated receptor gamma; Ras/Camp, cAMP-dependent protein kinase; TNFα, tumor necrosis factor α; VEGF, vascular endothelial growth factor.
Figure 2
Figure 2
The chemical structures of resveratrol, pinosylvin, isorhapontigenin, pterostilbene, and DMU-212.
Figure 3
Figure 3
The structure of CA-4 with marked sides of the most useful structural modification (A). The anticancer activity of CA-4 associated with disruption of microtubule dynamic and vascular effects are presented in panels (B) and (C), respectively.
Figure 4
Figure 4
The scheme presented the structure of hybrid compounds, which possess both CA-4 moiety and the additional active moiety [115,116,119,120]. This graph presents the general overview about combretastatin A4-basedh and does not present the detailed synthesis.
Figure 5
Figure 5
The structure and activity of CA-4, cisplatin, and CA-4-cisplatin prodrug against HepG2 cell line in vitro and in vivo [134]. This graph presents the general overview about combretastatin A4-based hybrid and does not present the detailed synthesis.
Figure 6
Figure 6
The structure of selected CA-4 derivatives with the modified hydroxyl group [137,138,139].
Figure 7
Figure 7
The structure of selected CA-4 derivatives with the modified methylene bridge [150,151,152,153].
Figure 8
Figure 8
The structures of selected benzanilides with different biological activities. 1: N-(4-Fluorophenyl)-4-phenoxybenzamide [165]; 2: N-(3,4-Dimethoxyphenyl)-4-(4-(((2-oxo-2H-chromen-4-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)benzamide [166]; 3: N-(3-((2,5-dimethylbenzyl)oxy)-4-(N-methylmethylsulfonamido)phenyl)benzo[d][1,3]dioxole-5-carboxamide [167]; 4: Bis[2-(2-hydroxyphenylcarbamoyl)]phenyl diselenide [168]; 5: Bis[2-(3,4,5-trimethoxyphenylcarbamoyl)]phenyl diselenide [168]; 6: 4-Chloro-2- (3,4-dichlorophenylcarbamoyl)phenyl benzenesulfonate [169]; 7: N-(4-Methylthiophenyl)-3,5-difluorobenzamide [170]; 8: N-(2-hydroxy-5-chlorophenyl)-(2-methoxy-5-chloro)-benzamide [171]; 9: N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-3-bromo-4-ethoxybenzamide [172]; 10: 2-amino-N-(3-bromophenyl)-4,5-dimethoxybenzamide [173]; 11: 6-amino-N-(3-bromophenyl)-2,3,4-trimethoxybenzamide [173]. Abbreviations: ABCG2, ATP Binding Cassette Subfamily G Member 2; DDR1, Discoidin domain receptor 1; EMCV, Encephalomyocarditis virus; HBV, Hepatitis B Virus, HHV, human Herpesvirus 1; HPV, human Papillomaviruse; IRF-1, interferon regulatory factor-1; MMP, matrix metalloproteinase; TRPV1, transient receptor potential vanilloid subfamily member 1; v-Src, Proto-oncogene tyrosine-protein kinase; V1A, Vasopressin receptor 1A; V2, Vasopressin receptor 2.
Figure 9
Figure 9
The development of osalmid and its derivatives, as a potent structure in the treatment of certain medical conditions [178,191]. Abbreviations: cccDNA, covalently-closed-circular DNA; DCZ0358 (5-(benzo[d] [1,3]dioxol-5-yl)-3,9,10-trimethoxy-2,3-dihydrooxazolo [2,3-a]isoquinolin- 4-ium chloride); RR, human ribonucleotide reductase; YZ51, 4-cyclopropyl-2-fluoro-N-(4-hydroxyphenyl) benzamide.
Figure 10
Figure 10
The structures of the most interesting thiobenzanilides with anticancer activity. 11: N-(4-Trifluoromethyl-phenyl)-4-nitrothiobenzamide [175]; 12: N,N’-(1,2-phenylene)bis(3,4,5-trifluorobenzothioamide [171,176,177,198]: 13: N,N’-(1,3-phenylene)bis(4-fluorobenzothioamide) [171].
See this image and copyright information in PMC

References (V体育官网入口)

    1. Zdrazil B., Guha R. The Rise and Fall of a Scaffold: A Trend Analysis of Scaffolds in the Medicinal Chemistry Literature. J. Med. Chem. 2018;61:4688–4703. - PubMed
    1. Giacomini E., Rupiani S., Guidotti L., Recanatini M., Roberti M. The Use of Stilbene Scaffold in Medicinal Chemistry and Multi- Target Drug Design. Curr. Med. Chem. 2016;23:2439–2489. doi: 10.2174/0929867323666160517121629. - DOI - PubMed
    1. Gaspar A., Matos M.J., Garrido J., Uriarte E., Borges F. Chromone: A Valid Scaffold in Medicinal Chemistry. Chem. Rev. 2014;114:4960–4992. doi: 10.1021/cr400265z. - DOI - PubMed
    1. Singh M., Kaur M., Silakari O. Flavones: An important scaffold for medicinal chemistry. Eur. J. Med. Chem. 2014;84:206–239. doi: 10.1016/j.ejmech.2014.07.013. - DOI - PubMed
    1. Tsutsumi L.S., Gündisch D., Sun D. Carbazole Scaffold in Medicinal Chemistry and Natural Products: A Review from 2010–2015. Curr. Top. Med. Chem. 2016;16:1290–1313. doi: 10.2174/1568026615666150915112647. - DOI - PubMed

Publication types

VSports注册入口 - LinkOut - more resources