Molecular Modellig Studies of an Epoxyisoindole Derivative Compound

Year 2018, , 189 - 199, 31.12.2018

Ersin Temel , Can Alaşalvar

https://doi.org/10.31466/kfbd.491184

Cited By: 1

Abstract

In this study, 2-methyl-3a, 4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3 (2H) -dione compound, which is an epoxyisoindole derivative, has been studied theoretically. In the literature, the endo and exo isomers of the compound are present. These isomers were taken as starting geometry to optimize the molecules. HOMO-LUMO orbitals and electrostatic potential surfaces (EPS) of molecules were drawn by using optimized structures. Additionally, Hirshfeld surfaces and fingerprint diagrams were drawn to understand the packaging behavior of the molecules. DFT B3LYP/ 6-311 base set was used in the calculations.

Keywords

Epoxyisoindole, Density Functional Theory, Hirshfeld Surface

Epoksiisoindol Türevi bir Bileşiğin Moleküler Modelleme Çalışmaları

Abstract

Bu çalışmada epoksiisoindol türevi olan 2-metil-3a,4,7,7a-tetrahidro-1H-4,7-epoksiisoindol-1,3(2H)-dion bileşiği kuramsal olarak incelenmiştir. Literatürde söz konusu bileşiğin endo ve ekso izomerleri mevcuttur. Bu izomerler başlangıç noktası alınarak moleküller optimize edildi. Optimize yapılar kullanılarak moleküllerin HOMO-LUMO orbitalleri ve elektrostatik potansiyel yüzeyleri (EPS) çizdirildi. İlave olarak moleküllerin paketlenme davranışlarını anlamak için Hirshfeld yüzeyleri ve parmak izi diyagramları çizdirildi. Hesaplamalarda DFT B3LYP/6-311 baz seti kullanıldı.

Keywords

Epoksiisoindol, Yoğunluk Fonksiyoneli Teorisi, Hirshfeld Yüzeyi

References

• Referans1 Becke, A. D. (1992) ‘Density-functional thermochemistry. II. The effect of the Perdew–Wang generalized-gradient correlation correction’, The Journal of Chemical Physics, 97(12), p. 9173. doi: 10.1063/1.463343.
• Referans2 Chen, Y. J., Chang, W. M., Liu, Y. W., Lee, C. Y., Jang, Y. H., Kuo, C. D. and Liao, H. F. (2009) ‘A small-molecule metastasis inhibitor, norcantharidin, downregulates matrix metalloproteinase-9 expression by inhibiting Sp1 transcriptional activity in colorectal cancer cells’, Chemico-Biological Interactions, 181(3), pp. 440–446. doi: 10.1016/j.cbi.2009.07.004.
• Referans3 Cheng, S. S., Shi, Y., Ma, X. N., Xing, D. X., Liu, L. D., Liu, Y., Zhao, Y. X., Sui, Q. C. and Tan, X. J. (2016) ‘Synthesis, crystal structure, spectroscopic properties and potential anti-cancerous activities of four unsaturated bis-norcantharimides’, Journal of Molecular Structure. Elsevier B.V, 1115, pp. 228–240. doi: 10.1016/j.molstruc.2016.02.093.
• Referans4 Dennington, R., Keith, T. and Milliam, J. (2009) ‘GaussView, Version 5’, Semichem Inc., Shawnee Mission, KS.
• Referans5 Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.;Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenber, D. J. (2009) ‘Gaussian 09’, Gaussian, Inc. Wallingford CT, pp. 2–3. doi: 111.
• Referans6 Gurven, M. and Hill, K. (2010) ‘Moving beyond Stereotypes of Men’s Foraging Goals’, Current Anthropology, 51(2), pp. 265–267. doi: 10.1016/j.ijpharm.2013.05.052.
• Referans7 Kadioglu, O., Kermani, N. S., Kelter, G., Schumacher, U., Fiebig, H. H., Greten, H. J. and Efferth, T. (2014) ‘Pharmacogenomics of cantharidin in tumor cells’, Biochemical Pharmacology. Elsevier Inc., 87(3), pp. 399–409. doi: 10.1016/j.bcp.2013.10.025.
• Referans8 Lee, C., Yang, W. and Parr, R. G. (1988) ‘Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density’, Physical Review B, 37(2), pp. 785–789. doi: 10.1103/PhysRevB.37.785.
• Referans9 Li, M., Xu, X., Lu, F. and Guo, S. (2014) ‘Primary in vitro and in vivo evaluation of norcantharidin-chitosan/poly (vinyl alcohol) for cancer treatment’, Drug Delivery, 21(4), pp. 293–301. doi: 10.3109/10717544.2013.840692.
• Referans10 Liu, X., Han, M., Xu, J., Geng, S., Zhang, Y., Ye, X., Gou, J., Yin, T., He, H. and Tang, X. (2017) ‘Asialoglycoprotein receptor-targeted liposomes loaded with a norcantharimide derivative for hepatocyte-selective targeting’, International Journal of Pharmaceutics. Elsevier B.V., 520(1–2), pp. 98–110. doi: 10.1016/j.ijpharm.2017.02.010.
• Referans11 Tarleton, M., Gilbert, J., Sakoff, J. A. and McCluskey, A. (2012) ‘Synthesis and anticancer activity of a series of norcantharidin analogues’, European Journal of Medicinal Chemistry. Elsevier Masson SAS, 54, pp. 573–581. doi: 10.1016/j.ejmech.2012.06.010.
• Referans12 Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J., Jayatilaka, D. and Spackman, M. A. (2012) ‘CrystalExplorer (Version 3.1)’. University of Western Australia.
• Referans13 Yang, P. Y., Chen, M. F., Kao, Y. H., Hu, D. N., Chang, F. R. and Wu, Y. C. (2011) ‘Norcantharidin induces apoptosis of breast cancer cells: Involvement of activities of mitogen activated protein kinases and signal transducers and activators of transcription’, Toxicology in Vitro. Elsevier Ltd, 25(3), pp. 699–707. doi: 10.1016/j.tiv.2011.01.011.
• Referans14 Yit, W. G., Pool, B. R. and White, J. M. (2008) ‘Structural studies on cycloadducts of furan, 2-methoxyfuran, and 5-trimethylsilylcyclopentadiene with maleic anhydride and N-methylmaleimide’, Journal of Organic Chemistry, 73(1), pp. 151–156. doi: 10.1021/jo7018575.
• Referans15 Zeng, Q. and Sun, M. (2009) ‘Poly(lactide-co-glycolide) nanoparticles as carriers for norcantharidin’, Materials Science and Engineering C. Elsevier B.V., 29(3), pp. 708–713. doi: 10.1016/j.msec.2009.01.004.
• Referans16 Zhao, J., Guan, X. W., Chen, S. W. and Hui, L. (2015) ‘Synthesis and biological evaluation of norcantharidin derivatives as protein phosphatase-1 inhibitors’, Bioorganic and Medicinal Chemistry Letters. Elsevier Ltd, 25(2), pp. 363–366. doi: 10.1016/j.bmcl.2014.11.032.