Synthesis and Acaricidal Activities of Scopoletin Phenolic Ether Derivatives: QSAR, Molecular Docking Study and in Silico ADME Predictions

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2018 Apr 27

PMID 29695088

Citations 10

Authors

Jinxiang Luo

Ting Lai

Tao Guo

Fei Chen

Linli Zhang

Wei Ding

Yongqiang Zhang

Affiliations

Soon will be listed here.

Abstract

Thirty phenolic ether derivatives of scopoletin modified at the 7-hydroxy position were synthesized, and their structures were confirmed by IR, ¹H-NMR, C-NMR, MS and elemental analysis. Preliminary acaricidal activities of these compounds against female adults of (Boisduval) were evaluated using the slide-dip method. The results indicated that some of these compounds exhibit more pronounced acaricidal activity than scopoletin, especially compounds , , , and which exhibited about 8.41-, 7.32-, 7.23-, 6.76-, and 6.65-fold higher acaricidal potency. Compound possessed the the most promising acaricidal activity and exhibited about 1.45-fold higher acaricidal potency against than propargite. Statistically significant 2D-QSAR model supports the observed acaricidal activities and reveals that polarizability (HATS5p) was the most important parameter controlling bioactivity. 3D-QSAR (CoMFA: q² = 0.802, r² = 0.993; CoMSIA: q² = 0.735, r² = 0.965) results show that bulky substituents at R₄, R₁, R₂ and R₅ (C₆, C₃, C₄, and C₇) positions, electron positive groups at R₅ (C₇) position, hydrophobic groups at R₁ (C₃) and R₂ (C₄), H-bond donors groups at R₁ (C₃) and R₄ (C₆) will increase their acaricidal activity, which provide a good insight into the molecular features relevant to the acaricidal activity for further designing novel acaricidal agents. Molecular docking demonstrates that these selected derivatives display different bide modes with from lead compound and they interact with more key amino acid residues than scopoletin. In silico ADME properties of scopoletin and its phenolic ether derivatives were also analyzed and showed potential to develop as good acaricidal candidates.

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References

Ojewole J, Adesina S . Cardiovascular and neuromuscular actions of scopoletin from fruit of Tetrapleura tetraptera. Planta Med. 1983; 49(2):99-102. DOI: 10.1055/s-2007-969824. View

Carpinella M, Ferrayoli C, Palacios S . Antifungal synergistic effect of scopoletin, a hydroxycoumarin isolated from Melia azedarach L. fruits. J Agric Food Chem. 2005; 53(8):2922-7. DOI: 10.1021/jf0482461. View

Kang S, Sung S, Park J, Kim Y . Hepatoprotective activity of scopoletin, a constituent of Solanum lyratum. Arch Pharm Res. 1998; 21(6):718-22. DOI: 10.1007/BF02976764. View

Zhao Y, Abraham M, Le J, Hersey A, Luscombe C, Beck G . Rate-limited steps of human oral absorption and QSAR studies. Pharm Res. 2002; 19(10):1446-57. DOI: 10.1023/a:1020444330011. View

Goodarzi M, Jensen R, Vander Heyden Y . QSRR modeling for diverse drugs using different feature selection methods coupled with linear and nonlinear regressions. J Chromatogr B Analyt Technol Biomed Life Sci. 2012; 910:84-94. DOI: 10.1016/j.jchromb.2012.01.012. View

Kwon Y, Choi W, Kim W, Kim W, Kim M, Kang W . Antimicrobial constituents of Foeniculum vulgare. Arch Pharm Res. 2002; 25(2):154-7. DOI: 10.1007/BF02976556. View

Sangshetti J, Kalam Khan F, Kulkarni A, Patil R, Pachpinde A, Lohar K . Antileishmanial activity of novel indolyl-coumarin hybrids: Design, synthesis, biological evaluation, molecular docking study and in silico ADME prediction. Bioorg Med Chem Lett. 2016; 26(3):829-835. DOI: 10.1016/j.bmcl.2015.12.085. View

Lipinski C, Lombardo F, Dominy B, Feeney P . Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev. 2001; 46(1-3):3-26. DOI: 10.1016/s0169-409x(00)00129-0. View

Sun C, Jin J, Zhu J, Wang H, Yang D, Xing J . Discovery of bis-aromatic ring neonicotinoid analogues fixed as cis-configuration: Synthesis, insecticidal activities, and molecular docking studies. Bioorg Med Chem Lett. 2010; 20(11):3301-5. DOI: 10.1016/j.bmcl.2010.04.050. View

10.

Hou Q, Luo J, Zhang B, Jiang G, Ding W, Zhang Y . 3D-QSAR and Molecular Docking Studies on the TcPMCA1-Mediated Detoxification of Scopoletin and Coumarin Derivatives. Int J Mol Sci. 2017; 18(7). PMC: 5535873. DOI: 10.3390/ijms18071380. View

11.

Bi J, Niu Z, Yu L, Toscano N . Resistance status of the carmine spider mite, Tetranychus cinnabarinus and the twospotted spider mite, Tetranychus urticae to selected acaricides on strawberries. Insect Sci. 2014; 23(1):88-93. DOI: 10.1111/1744-7917.12190. View

12.

Cassady J, OJIMA N, Chang C, McLaughlin J . An investigation of the antitumor activity of Micromelum integerrimum (Rutaceae). J Nat Prod. 1979; 42(3):274-8. DOI: 10.1021/np50003a005. View

13.

Zhou A, Hu J, Wang L, Zhong G, Pan J, Wu Z . Combined 3D-QSAR, molecular docking, and molecular dynamics study of tacrine derivatives as potential acetylcholinesterase (AChE) inhibitors of Alzheimer's disease. J Mol Model. 2015; 21(10):277. DOI: 10.1007/s00894-015-2797-8. View

14.

Pingaew R, Prachayasittikul V, Worachartcheewan A, Nantasenamat C, Prachayasittikul S, Ruchirawat S . Novel 1,4-naphthoquinone-based sulfonamides: Synthesis, QSAR, anticancer and antimalarial studies. Eur J Med Chem. 2015; 103:446-59. DOI: 10.1016/j.ejmech.2015.09.001. View

15.

Yu H, Yue Y, Dong X, Li R, Li P . The Acaricidal Activity of Venom from the Jellyfish Nemopilema nomurai against the Carmine Spider Mite Tetranychus cinnabarinus. Toxins (Basel). 2016; 8(6). PMC: 4926145. DOI: 10.3390/toxins8060179. View

16.

Pan R, Gao X, Lu D, Xu X, Xia Y, Dai Y . Prevention of FGF-2-induced angiogenesis by scopoletin, a coumarin compound isolated from Erycibe obtusifolia Benth, and its mechanism of action. Int Immunopharmacol. 2011; 11(12):2007-16. DOI: 10.1016/j.intimp.2011.08.012. View

17.

Wang Y, Zhao S, Shi L, Xu Z, He L . Resistance selection and biochemical mechanism of resistance against cyflumetofen in Tetranychus cinnabarinus (Boisduval). Pestic Biochem Physiol. 2014; 111:24-30. DOI: 10.1016/j.pestbp.2014.04.004. View

18.

Pingaew R, Mandi P, Prachayasittikul V, Prachayasittikul S, Ruchirawat S, Prachayasittikul V . Synthesis, molecular docking, and QSAR study of sulfonamide-based indoles as aromatase inhibitors. Eur J Med Chem. 2017; 143:1604-1615. DOI: 10.1016/j.ejmech.2017.10.057. View

19.

Cui Y, Chen Q, Li Y, Tang L . A new model of flavonoids affinity towards P-glycoprotein: genetic algorithm-support vector machine with features selected by a modified particle swarm optimization algorithm. Arch Pharm Res. 2016; 40(2):214-230. DOI: 10.1007/s12272-016-0876-8. View

20.

Jalali-Heravi M, Asadollahi-Baboli M, Shahbazikhah P . QSAR study of heparanase inhibitors activity using artificial neural networks and Levenberg-Marquardt algorithm. Eur J Med Chem. 2007; 43(3):548-56. DOI: 10.1016/j.ejmech.2007.04.014. View