Research Journal of Pharmacy and Technology

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Prediction of Antitumor Activity of 3-substituted Quinazolinone Derivatives Synthesized in One-pot Method Catalyzed by Bi(Otf)3


Affiliations
1 Department of Medicinal Chemistry, National University of Pharmacy, Pushkinska 53, 61002, Kharkiv,, Ukraine
2 Department of Chemistry, Vikrama Simhapuri University, Nellore-524001, Andhra Pradesh,, India
     

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A series of 3-substituted guinazolinone derivatives have been synthesized in good to excellent yields and high selectivity by one-pot reaction using anthranilic acid, amine and orthoester in ethanol under mild conditions, respectively. The reaction was efficiently promoted by Bi(OTf)3 and the catalyst could be recovered easily after the reactions and reused without evident loss of reactivity. Docking studies have shown that the tested molecules have an affinity for anticancer targets. The data obtained can be used in planning experimental screening for antitumor activity.

Keywords

Synthesis, Bi(OTf)3, anthranilic acid, orthoester, one-pot union, аmine, quinazolinone derivatives, molecular docking, antitumor activity.
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  • Shaheda Sultana Sk, Parveen P, Usha P, Vasu Naik V, Rajesh Ak, Gayatri Ramya M. Pharmacological Evaluation of Synthesized Test Compounds of Quinazolinones and Pyrazolinones. Asian J Research Chem. 2014; 7(1): 33-40.

  • Niraimathi V, Vamsadhara C. Analgesic Activity of 2-Hetero Substituted -4-Quinazolinones. Research J Pharm and Tech. 2010; 3 (4): 1093-1095.

  • Girija K, Sathiyaraj S,. Rajendiran V, Hemalatha K. 2, 3-Disubstituted Quinazolinones: Study of its Anti-microbial Activity. Research J Pharm and Tech. 2017; 10(4): 1020-1024. doi: 10.5958/0974-360X.2017.00184.6.

  • Hemalatha K, Selvin J,. Girija K. Synthesis, In silico Molecular Docking Study and Anti-bacterial Evaluation of some Novel 4-Anilino Quinazolines. Asian J Pharm Res. 2018; 8(3): 125-132. doi: 10.5958/2231-5691.2018.00022.9.

  • Battin SN, Manikshete AH,. Sarasamkar SK, Asabe MR, Sathe DJ. Synthesis, Spectral, Antibacterial, Antifungal and Anticancer activity Studies of Schiff bases Derived from O-Vanillin and Aminoquinolines. Asian J Research Chem. 2017; 10(5): 660-668. doi: 10.5958/0974- 4150.2017.00112.2.

  • Rishipathak DD, Kokate AB, Madhawai KS. Activity of Quinazoline Derivatives: A Review. Asian J. Res. Pharm. Sci. 2017; 7(4):209-211. doi: 10.5958/2231-5659.2017.00032.7

  • Virupakshi Prabhakar, Venkateswarlu B, Punagani Bhargavi, Sura Jagadeesh. Design, Synthesis and Activity of Novel Quinazoline Derivatives Linked with various Sulphonamides. Asian J. Research Chem. 2016; 9(10):485-504. doi: 10.5958/0974-4150.2016.00073.0

  • Dinesh D Rishipathak, Trupti A Jadhav, Sonal P Tathe, Pavan B Udavant. Microwave Assisted Synthesis and Pharmacological Evaluation of Few 4-Quinazolinone Derivatives. Asian J. Pharm. Res. 2019; 9(3):147-154. doi: 10.5958/2231-5691.2019.00023.6

  • Dahikar G. D., Yeole P.G., Ganjiwale R.O., Rahangdale V.T.. The Preparation and Biological Evaluation of Some New 6-Iodo-2-Ethyl- 4(3H)-3 (5-Substituted Benzothiazole-2’-Yl) Quinazolinone Derivatives as an Anticonvulsant. Asian J. Research Chem. 3(3): July- Sept. 2010; Page 555-557.

  • Kavitha K, Nehla Yahoob, Vijayakumar B, Reshma Fathima K. Synthesis and Evaluation of Quinazolinone Derivatives. Asian J. Research Chem. 2017; 10(4):577-581. doi: 10.5958/0974-4150.2017.00096.7.

  • Waisser K, Gregor J, Dostal H, Kunes J, Kubicova L, Klimesova V. Influence of the replacement of the oxo function with the thioxo group on the antimycobacterial activity of 3-aryl-6,8-dichloro-2H-1,3-benzoxazine-2,4(3H)-diones and 3-arylquinazoline-2,4(1H,3H)-diones. J Farmaco. 2001; 566: 803-807. doi: 10.1016/s0014-827x(01)01134-x.

  • Kunesˇ J, Bazant J, Pour M, Waisser K, losarek S, Janota M., Quinazoline derivatives with antitubercular activity. J Farmaco. 2000; 55: 725-729. doi: 10.1016/s0014-827x(00)00100-2.

  • Refaie FM, Esmat AY, Abdel-Gawad SM, Ibrahim AM, Mohamed MA. The antihyperlipidemic activities of 4(3H) quinazolinone and two halogenated derivatives in rats. Lipids Health Dis. 2005; 4: 22. doi: 10.1186/1476-511X-4-22.

  • Ganesh Akula, Rangu Nirmala, Shanthipriya CH, Rohini Reddy S, Jaswanth A. Synthesis of novel 3-[(dialkyl/aryl amino) methyl]-2-substituted-4(3H)-Quinazolinones and evaluation of their Anti-inflammatory activity. Asian J Pharm Res. 2017; 7(2): 60-62. doi: 10.5958/2231-5691.2017.00010.7.

  • Vinod GU, Sudhir GW, Chandrabhan T. Chopde. Design, Development and Screening of Some Novel Quinazolinones for Anticonvulsant Activity. Asian J Research Chem. 2011; 4(11): 1717-1721.

  • Khan I, Ibrar A, Ahmed W, Saeed A, et al. Synthetic approaches, functionalization and therapeutic potential of quinazoline and quinazolinone skeletons: the advances continue. Eur J Med Chem. 2015; 90: 124-169.

  • Khan I, Ibrar A, Abbas N, Saeed A. Recent advances in the structural library of functionalized quinazoline and quinazolinone scaffolds: synthetic approaches and multifarious applications. Eur J Med Chem. 2014; 76: 193-244.

  • Hrast M, Rozman K, Jukic M, Patin D, Gobec S, Sova M. Synthesis and structure eactivity relationship study of novel quinazolinone based inhibitors of Mur A. Bioorg Med Chem Lett. 2017; 27: 3529-3533.

  • Ighachane H, Sedra MH, Lazrek H, Synthesis and evaluation of antifungal activities of (3H)-quinazolin-4-one derivatives against tree plant fungi. J Mater Environ Sci. 2017; 8: 134-143.

  • Alaa AM, Abou-Zeid LA, ElTahir KEH, Ayyad RR, Magda AA, El-Azab AS. Synthesis, anti-inflammatory, analgesic, COX-1/2 inhibitory activities and molecular docking studies of substituted 2-mercapto-4 (3H)-quinazolinones. Eur J Med Chem. 2016; 121: 410-421.

  • Santosh Mhaske B, Narshinha Argade P. Concise and Efficient Synthesis of Bioactive Natural Products Pegamine, Deoxyvasicinone, and (-)-Vasicinone. J Org Chem. 2001; 66: 9038-9040. DOI: 10.1021/jo010727l.

  • Venkataramireddy V, Tejeswararao A, Jayashree A, Ravi Varala. Synthesis and biological evaluation of functionalized quinoxaline derivatives. Der Pharma Chemica. 2014; 6(6): 73-78.

  • Szczepankiewicz Suwinski W. One-pot synthesis of 3-(2-cyanophenyl)-quinazolin-4(3H)-one. J Chem Heterocycl Compd. 2000; 36: 809-10.

  • Das B. Banerjee. Silica-Supported Sodium Hydrogen Sulfate and Amberlyst-15: Two Efficient Heterogeneous Catalysts for Single-Step Synthesis of 4(3H)-Quinazolinones from Anthranilic Acid, Orthoesters, and Amines under Solvent-Free Conditions. J Chem Lett. 2004; 33: 960-61.

  • Jiang ZD, Chen RF. Synthesis of 3,4‐Dihydropyrimidine‐2(1H)‐thiones and Quinazolin‐4(3H)‐ones over Yb(III)‐Resin Catalyst Under Solvent‐free Conditions. Synth Commun. 2005; 35: 503-9. https://doi.org/10.1081/SCC-200049766.

  • Wang LM, Xia JJ, Qin F, Qian CT, Sun J. Yb(OTf)3-catalyzed one-pot synthesis of quinazolin-4(3H)-ones from anthranilic acid, amines, and ortho esters (or formic acid) in solvent-free conditions. Synthesis. 2003; 1241.

  • Khosropour AR, Mohammadpoor-Baltork I, Ghorbankhani H. Bi(TFA)3- [nbp]FeCl4: A new, efficient, and reusable promoter system for the synthesis of 4(3H)- quinazolinone derivatives. Tetrahedron Lett. 2006; 47: 3561.

  • Narasimhulu M, Mahesh KC, Reddy TS, Rajesh K, Venkateswarlu Y. Lanthanum(III) nitrate hexahydrate or p-toluenesulfonic acid–catalyzed one-pot synthesis of 4(3H)-quinazolinones under solvent-free conditions. Tetrahedron Lett. 2006; 47: 4381.

  • Ighilahriz K, Boutemeur B, Chami F, Rabia C, Hamdi M, Hamdi SM. A microwave-assisted and heteropolyacids-catalysed cyclocondensation reaction for the synthesis of 4(3H)-quinazolinones. Molecules. 2008; 13: 779.

  • Oskooie HA, Baghernezhad B, Heravi MM. SnCl4 4H2O as an efficient catalyst for the synthesis of 4(3H)-quinazolinone derivatives. Indian J Heterocycl Chem. 2007; 17: 95.

  • Chari MA, Mukkanti DSK. Silica gel=FeCl3: An efficient and recyclable heterogenous catalyst for one-step synthesis of 4(3H)-quinazolinones under solvent-free conditions. Catal Commun. 2006; 7: 787.

  • Drapak I, Suleiman M, Protopopov M, Yeromina H, Sych I, Ieromina Z, Sych I, Perekhoda L. The use of the docking studies with the purpose of searching potential antihypertensive drugs. Research Journal of Pharmacy and Technology. 2019; 12(10): 4889-4894. doi: 10.5958/0974-360X.2019.00846.1.

  • Hemalatha K, Girija K. Evaluation of Drug Candidature of some Benzimidazole Derivatives as Biotin Carboxylase Inhibitors: Molecular docking and Insilico studies. Asian J. Res. Pharm. Sci. 6(1): Jan.-Mar., 2016; Page 15-20. doi: 10.5958/2231-5659.2016.00002.3

  • Sindhu TJ, Arathi K N, Akhila Devi, Aswathi TA, Noushida M, Midhun M, Sajil Saju Kuttiyil. Synthesis, Molecular Docking and Antibacterial Studies of Novel Azole derivatives as Enoyl ACP Reductase Inhibitor in Escherichia coli. Asian J. Res. Pharm. Sci. 2019; 9(3): 174-180. doi: 10.5958/2231-5659.2019.00027.4

  • Radhika Chelamalla, Ajitha Makula. Molecular docking studies and ADMET Predictions of Pyrimidine Coumarin Scaffolds as Potential IDO Inhibitors. Asian J. Research Chem. 2017; 10(3):331-340. doi: 10.5958/0974-4150.2017.00056.6

  • Sandip S Kshirsager, Dr. Siraj N Shaikh, Narendra B Patil, Ketan B Patil. Novel Molecule of Protein Tyrosine Kinase Enzyme Inhibitor in Treatment of Breast Cancer: Neratinib Maleate. Asian J. Res. Pharm. Sci. 2020; 10(2):100-102. doi: 10.5958/2231-5659.2020.00019.3

  • Sravani M, Duganath N, Deepak Reddy Gade, Sandeep Reddy CH. Insilico Analysis and Docking of Imatinib Derivatives Targeting BCR-ABL Oncoprotein for Chronic Myeloid Leukemia. Asian J. Research Chem. 5(1): January 2012; Page 153-158.

  • Park JH, Liu Y, Lemmon MA, Radhakrishnan R. Erlotinib binds both inactive and active conformations of the EGFR tyrosine kinase domain. Biochem J. 2012; 448: 417-423.

  • Stamos J, Sliwkowski MX, Eigenbrot C. Structure of the epidermal growth factor receptor kinase domain alone and in complex with a 4-anilinoquinazoline inhibitor. J Biol Chem. 2002; 277: 46265-46272.

  • Bart AG, Scott EE. Structures of human cytochrome P450 1A1 with bergamottin and erlotinib reveal active-site modifications for binding of diverse ligands. J Biol Chem. 2018; 293: 19201-192.


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  • Prediction of Antitumor Activity of 3-substituted Quinazolinone Derivatives Synthesized in One-pot Method Catalyzed by Bi(Otf)3

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Authors

L. Perekhoda
Department of Medicinal Chemistry, National University of Pharmacy, Pushkinska 53, 61002, Kharkiv,, Ukraine
M. Hari Krishna
Department of Chemistry, Vikrama Simhapuri University, Nellore-524001, Andhra Pradesh,, India
T . Sekhar
Department of Chemistry, Vikrama Simhapuri University, Nellore-524001, Andhra Pradesh,, India
A. Venkateswarlu
Department of Chemistry, Vikrama Simhapuri University, Nellore-524001, Andhra Pradesh,, India
P. Thriveni
Department of Chemistry, Vikrama Simhapuri University, Nellore-524001, Andhra Pradesh,, India
M. Suleiman
Department of Medicinal Chemistry, National University of Pharmacy, Pushkinska 53, 61002, Kharkiv,, Ukraine
A. Semenets
Department of Medicinal Chemistry, National University of Pharmacy, Pushkinska 53, 61002, Kharkiv,, Ukraine
A. Fedosov
Department of Medicinal Chemistry, National University of Pharmacy, Pushkinska 53, 61002, Kharkiv,, Ukraine
L. Grinevich
Department of Medicinal Chemistry, National University of Pharmacy, Pushkinska 53, 61002, Kharkiv,, Ukraine
N. Kobzar
Department of Medicinal Chemistry, National University of Pharmacy, Pushkinska 53, 61002, Kharkiv,, Ukraine
V. Yaremenko
Department of Medicinal Chemistry, National University of Pharmacy, Pushkinska 53, 61002, Kharkiv,, Ukraine

Abstract


A series of 3-substituted guinazolinone derivatives have been synthesized in good to excellent yields and high selectivity by one-pot reaction using anthranilic acid, amine and orthoester in ethanol under mild conditions, respectively. The reaction was efficiently promoted by Bi(OTf)3 and the catalyst could be recovered easily after the reactions and reused without evident loss of reactivity. Docking studies have shown that the tested molecules have an affinity for anticancer targets. The data obtained can be used in planning experimental screening for antitumor activity.

Keywords


Synthesis, Bi(OTf)3, anthranilic acid, orthoester, one-pot union, аmine, quinazolinone derivatives, molecular docking, antitumor activity.

References