Study on Anti-Tumor Activity of Novel 3-Substituted 4 Anilino-Coumarin Derivatives Using Quantitative Structure-Activity Relationship (QSAR)

Abstract:

Study on anti breast cancer activity of 3-substituted 4-anilino coumarin derivatives by using quantitative structure-activity relationship (QSAR) has been performed. The structures and the activity data were literatured from Guoshun et al. experiment. The molecular and electronic molecule properties were obtained from DFT/BPV86 6-31G method calculation after was through methods validation. The QSAR analysis were shown by Multi Linear Regression method (MLR). The best model of obtained for 3-substituted 4-anilino coumarin derivatives is: Log IC50 = 5.905 + (0.936 x qC1) + (-8.225 x qC8) + (-0.582 x qC13) + (11.273 x qC15) + (0.869 x ∆E) ; n = 26; r² = 0.704; Fcal/Ftab = 2.462; SEE = 0.184.

• Periodical: Materials Science Forum (Volume 948)
• Pages: 101-108
• DOI: https://doi.org/10.4028/www.scientific.net/MSF.948.101
• Online since: March 2019
• Authors: Daratu E.K. Putri*, Harno Dwi Pranowo, Winarto Haryadi
• Keywords: Anti-Cancer, Coumarin, QSAR

References

[1] Linsey A, Torre., Freddie Bray., Rebecca L, Siegel., Jacques, Ferlay., Joannie, Lortet-Tieulent., Ahmedin, Jemal., Global Cancer Statistic, Ca J Clin, (2015) 65:87-108.

DOI: 10.3322/caac.21262

[2] Marc, Mareel., and Ancy, Leroy., Clinical, Cellular, and Molecular Aspects of Cancer Invasion, Phys rev, (2003) 83: 337-376.

DOI: 10.1152/physrev.00024.2002

[3] Grant SK., Cell Mol Life Sci, (2009) 66: 1163.

[4] Guoshun, Luo., Moses, Muyaba., Weiting, Lyu., Zhichao, Tang., Design, Synthesis and Biological evaluation of novel 3-substituted 4-anilino-coumarin derivatives as antitumor agents, Bio Med Chem, (2017) 867-874.

DOI: 10.1016/j.bmcl.2017.01.013

[5] Erick M. Pasciak, Jonathan T. Rittichier, Chun-Hsing Chen, Mohammad S. Mubarak, Michael S. VanNieuwenhze, and Dennis G. Peters, Electroreductive Dimerization of Coumarin and Coumarin Analoguesat Carbon Cathodes, (2015) 274-280.

DOI: 10.1021/jo502272g

[6] Robert A. O'reilly, Paul M. Aggeler, And Lois S. Leong., Studies On The Coumarin Anticoagulant Drugs: The Pharmacodynamics Of Warfarin In Man, J Clin Invest, (1963).

DOI: 10.1172/jci104839

[7] Juliana F, Vasconcelos., Mauro M, Teixeira., Jose M, Barbosa-Filho., Maria F. Agra., Xirley P. Nunes, Effects of umbelliferone in a murine model of allergic airway inflammation, (2009) 126-131.

DOI: 10.1016/j.ejphar.2009.03.027

[8] Koneni V, Sashidhara., Abdhesh Kumar., Manavi Chatterjee., K. Bhaskara Rao, Seema Singh, Anil Kumar Verma, Gautam Palit, Discovery and synthesis of novel 3-phenylcoumarin derivatives as antidepressant agents, (2011) 1937-1941.

DOI: 10.1016/j.bmcl.2011.02.040

[9] Xiao Y. Huang, Zhi J. Shan, Hong L. Zhai,Li Su and Xiao Y. Zhang, Study on the Anticancer Activity of Coumarin Derivatives by Molecular Modeling, (2011) 78: 651-658.

DOI: 10.1111/j.1747-0285.2011.01195.x

[10] K. N. Venugopala, V. Rashmi, and B. Odhav, Review on Natural Coumarin Lead Compounds for Their Pharmacological Activity, Review Article (2013).

DOI: 10.1155/2013/963248

[11] J. R. S. Hoult and Miguel Paya, Pharmacological and Biochemical Actions of Simple Coumarins: Natural Products with Therapeutic Potential, (1996) 713-722.

DOI: 10.1016/0306-3623(95)02112-4

[12] Dong Cao, Yibin Liu,Wei Yan, Chunyu Wang, Peng Bai, Taijin Wang, Minghai Tang, Xiaoyan Wang, Zhuang Yang, Buyun Ma, Liang Ma, Lei Lei, Fang Wang, Bixue Xu, Yuanyuan Zhou, Tao Yang, and Lijuan Chen, Design, Synthesis, and Evaluation of in Vitro and in Vivo Anticancer Activity of 4-Substituted Coumarins: A Novel Class of Potent TubulinPolymerization Inhibitors, Med Chem J, (2016) 59: 5721-5739.

DOI: 10.1021/acs.jmedchem.6b00158

[13] Francisco J. Martínez-Martínez, Rodrigo Said Razo-Hernández, Ana Lilia Peraza-Campos, Manuel Villanueva-García, Maria Teresa Sumaya-Martínez, Daniel Jaramillo Cano and Zeferino Gómez-Sandoval, Synthesis and in Vitro Antioxidant Activity Evaluation of 3-Carboxycoumarin Derivatives and QSAR Study of Their DPPH• Radical Scavenging Activity, J Mol, (2012) 14882-14898.

DOI: 10.3390/molecules171214882

[14] V.K. Srivastav 1, M. Tiwari, QSAR and docking studies of coumarin derivativesas potent HIV-1 integrase inhibitors, (2013) S1081-S1094.

DOI: 10.1016/j.arabjc.2013.01.015

[15] P. Erzincan, M.T. Saçan, B. Yüce-Dursun, Ö. Danış, S. Demir, S.S. Erdemand A. Ogan, QSAR models for antioxidant activity of new coumarin derivatives, (2015).

DOI: 10.1080/1062936x.2015.1088571

[16] Jain, S.V., Ghate, M., Bhadoriya, K.S., Bar, S.B., Chaudari, A., and Borse, J.S., Org Med Chem Lett, 2, 1, (2012) 22-34.

[17] Veerasamy, R., Chean, O.C., Subramaniam, D.K., Ying, N.M., Sivasdasan, S., Rajak, H., and Rasheed, A., Med Che, Res., 22, (2013) 35-44.

[18] Young, David., Computational Chemistry, John Wiley and Sons, (2001).

[19] Rachid Hmamouchi, Majdouline Larif, Samir Chtita, Azeddine Adad, Mohammed Bouachrine, Tahar Lakhlifi., Predictive modeling of the LD50 activities of coumarin derivatives using neural statistical approaches: Electronic descriptor-based DFT, (2015) 451-461.

DOI: 10.1016/j.jtusci.2015.06.013

[20] Y. Yamaguchi, S. S. Pandey,N. Fujikawa, Y. Ogomi, S. Hayase, A Combined Theoretical And Experimental Approaches Towards Designing Nir Dyes For Dye-Sensitised Solar Cells, J. Eng.Sci. Tech., (2014) 51-65.

[21] Ach, Kholis., Qsar Analysis For Designing Prostate, Pancreas, AndColon Anticancer Compounds From Monoketone CurcuminAnalogs, Universitas Gadjah Mada, (2016).

[22] Ihsanul, Arief., Ria Armunanto., and Bambang, Setiaji., Indo. J. Chem, 13 (2) (2013) 129-135.

[23] Jafar, La Kilo, Kajian Hubungan Kuantitatif Struktur-Aktivitas Antimalaria Turunan Quinolon-4(1H)-imine Menggunakan Deskriptor Hasil Perhitungan metode Ab Initio Hartree-Fock, Universitas Gadjah Mada, (2014).

DOI: 10.34312/jambchem.v1i1.2104

[24] Pramesti, Getut, Statistika Penelitian dengan SPSS 24, Elex Media Komputindo, (2017).