Synthesis, antimicrobial evaluation and docking studies of some novel quinazolinone Schiff base derivatives

Rezvan Rezaee Nasab, Mahboubeh Mansourian, Farshid Hassanzadeh

Abstract


The quinazolin-4(3H)-one structural motif possesses a wide spectrum of biological activities. DNA gyrase play an important role in induction of bacterial death. It has been shown that many quinazolin-4(3H)-one derivatives have antibacterial effects through inhibition of DNA gyrase. Based on this information we decided to synthesize novel quinazolinone Schiff base derivatives in order to evaluate their antibacterial effects. A series of novel quinazolinone Schiff base derivatives were designed and synthesized from benzoic acid. The potential DNA gyrase inhibitory activity of these compounds was investigated using in silico molecular docking simulation. All new synthesized derivatives were screened for their antimicrobial activities against three species of Gram-negative bacteria including Escherichia coli, Pseudomonas aeruginosa, Salmonella entritidis and three species of Gram-positive bacteria comprising of Staphylococcus aurous, Bacillus subtilis, Listeria monocitogenes as well as for antifungal activities against Candida albicans using the conventional micro dilution method. Most of the compounds have shown good antibacterial activities, especially against E. coli at 128 μg/mL concentration while no remarkable antifungal activities were observed for these compounds. All the synthesized compounds exhibit dock score values between -5.96 and -8.58 kcal/mol. The highest dock score among them was -8.58 kcal/mol for compound 4c.


Keywords


Schiff base; Synthesis; Quinazoline-4(3H)-ones; Antibacterial activity; Docking study

Full Text:

PDF

References


Asadi P, Khodarahmi GA, Jahanian-Najafabadi A, Saghaie L, Hassanzadeh F. Synthesis, characterization, molecular docking studies and biological evaluation of some novel hybrids based on quinazolinone, benzofuran and imidazolium moieties as potential cytotoxic and antimicrobial agents. Iran J Basic Med Sci. 2017;20(9):975-989.

Collin F, Karkare S, Maxwell A. Exploiting bacterial DNA gyrase as a drug target: current state and perspectives. Appl Microbiol Biotechnol. 2011;92(3):479-497.

Ostrov DA, Hernández Prada JA, Corsino PE, Finton KA, Le N, Rowe TC. Discovery of novel DNA gyrase inhibitors by high-throughput virtual screening. Antimicrob Agents Chemother. 2007;51(10):3688-3698.

Heddle J, Maxwell A. Quinolone-binding pocket of DNA gyrase: role of GyrB. Antimicrob Agents Chemother. 2002;46(6):1805-1815.

Kumar R, Madhumathi BS, Nagaraja V. Molecular basis for the differential quinolone susceptibility of mycobacterial DNA gyrase. Antimicrob Agents Chemother. 2014;58(4):2013-2020.

Rezaee Nasab R, Karami B, Khodabakhshi S. Selective solvent-free biginelli condensation using tungstate sulfuric acid as powerful and reusable catalyst. Bull Chem React EngCatalys. 2014;9(2):148-154.

Rakesh KP, Darshini N, Shubhavathi T, Mallesha N. Biological applications of quinazolinone analogues: A review. Org Med Chem. 2017;2(2):1-5.

Farag AA, Khalifa EM, Sadik NA, Abbas SY, Al-sehemi AG, Ammar YA. Synthesis, characterization, and evaluation of some novel 4(3H)-quinazolinone derivatives as anti-inflammatory and analgesic agents. Med Chem Res 2013;22(1):440-452.

Agbo EN, Makhafola TJ, Choong YS, Maphahlele MJ, Ramasami P. Synthesis, biological evaluation and molecular docking studies of 6-aryl-2-styrylquinazolin-4(3H)-ones. Molecules. 2016;21(1):E28.

Gilbert IH. Inhibitors of dihydrofolate reductase in leishmania and trypanosomes. Biochim Biophys Acta. 2002;1587(2-3):249-257.

Jackman AL, Taylor GA, Gibson W, Kimbell R, Brown M, Calvert AH, et al. ICI D1694, a quinazoline antifolate thymidylate synthase inhibitor that is a potent inhibitor of L1210 tumor cell growth in vitro and in vivo: a new agent for clinical study. Cancer Res. 1991;51(20):5579-5586.

Sequist LV, Lynch TJ. EGFR tyrosine kinase inhibitors in lung cancer: an evolving story. Annu Rev Med. 2008;59:429-442.

Thomsen R, Christensen MH. MolDock: a new technique for high-accuracy molecular docking. J Med Chem. 2006;49(11):3315-3321.

Nanda AK, Ganguli S, Chakraborty R. Antibacterial activity of some 3-(arylideneamino)-2-phenylquinazoline-4(3H)-ones: synthesis and preliminary QSAR studies. Molecules. 2007; 12(10):2413-2426.

Bansal S, Kumar S, Aggarwal V, Joseph A. Design, synthesis, docking study & antibacterial evaluation of 1, 3-diarylpyrazolyl substituted indolin-2-ones. Indo Glob J Pharm Sci. 2014;4(1):1-7.

Jayashree BS, Thomas S, Nayak Y. Design and synthesis of 2-quinolones as antioxidants and antimicrobials: a rational approach. Med Chem Res. 2010;19(2):193-209.

Lafitte D, Lamour V, Tsvetkov PO, Makarov AA, Klich M, Deprez P, et al. DNA gyrase interaction with coumarin-based inhibitors: the role of the hydroxybenzoate isopentenyl moiety and the 5'-methyl group of the noviose. Biochemistry. 2002;41(23):7217-7223.

Rezaee Nasab R, Hassanzadeh F, Khodarahmi GA, Rostami M, Mirzaei M, Jahanian-Najafabadi A, et al. Docking study, synthesis and antimicrobial evaluation of some novel 4-anilinoquinazoline derivatives. Res Pharm Sci. 2017;12(5):425-433.

Mansourian M, Mahnam K, Madadkar-Sobhani A, Fassihi A, Saghaie L. Insights into the human A1 adenosine receptor from molecular dynamics simulation: Structural study in the presence of lipid membrane. Med Chem Res. 2015;24:3645-3659.

Mansourian M, Madadkar-Sobhani A, Mahnam K, Fassihi A, Lotfollah Saghaie L. Characterization of adenosine receptor in its native environment: insights from molecular dynamics simulations of palmitoylated/glycosylated, membrane-integrated human A2B adenosine receptor. J Mol Model. 2012;18:4309-4324.

Rezaee Nasab R, Hassanzadeh F, Khodarahmi GA, Mirzaei M, Rostami M, Jahanian-Najafabadi A. Synthesis, characterization, cytotoxic screeninig, and density functional theory studies of new derivatives of quinazolin-4(3H)-one Schiff bases. Res Pharm Sci. 2017;12(6):444-455.

Jayalakshmi B, Raveesha KA, Amruthesh KN. Evaluation of antibacterial and antioxidant potential of Euphorbia cotinifolia linn. leaf extracts. Chem Ind Chem Eng Q. 2014;20(1):19-28.

Wiegand I, Hilpert K, Hancock RE. Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances. Nat Protoc. 2008;3(2):163-175.

Baker CN, Banerjee SN, Tenover FC. Evaluation of Alamar colorimetric MIC method for antimicrobial susceptibility testing of gram-negative bacteria. J Clin Microbiol. 1994;32(5):1261-1267.

Khodarahmi GA, Jafari E, Hakimelahi Gh, Abedi D, Rahmani Khajouei M, Hassanzadeh F. Synthesis of some new quinazolinone derivatives and evaluation of their antimicrobial activities. Iran J Pharm Res. 2012;11(3):789-797.

Lipinski CA. Lead- and drug-like compounds: the rule-of-five revolution. Drug Discov Today Technol. 2004;1(4):337-341.

Kampranis SC, Gormley NA, Tranter R, Orphanides G, Maxwell A. Probing the binding of coumarins and cyclothialidines to DNA gyrase. Biochemistry 1999;38(7):1967-1976.

Lewis RJ, Singh OM, Smith CV, Skarzynski T, Maxwell A, Wonacott AJ, et al. The nature of inhibition of DNA gyrase by the coumarins and the cyclothialidines revealed by X-ray crystallography. EMBO J. 1996;15(6):1412-1420.

Blance SJ, Williams NL, Preston ZA, Bishara J, Smyth MS, Maxwell A. Temperature-sensitive suppressor mutations of the Escherichia coli DNA gyrase B protein. Protein Sci. 2000;9(5):1035-1037.

Boyapati S, Kulandaivelu U, Sangu S, Vanga MR. Synthesis, antimicrobial evaluation, and docking studies of novel 4‐substituted quinazoline derivatives as DNA‐gyrase inhibitors. Arch Pharm (Weinheim). 2010;343(10):570-576.

Mladenović M, Vuković N, Sukdolak S, Solujić S. Design of novel 4-hydroxy-chromene-2-one derivatives as antimicrobial agents. Molecules. 2010;15(6):4294-4308.

Rahimi H, Najafi A, Eslami H, Negahdari B, Moosazadeh Moghaddam M. Identification of novel bacterial DNA gyrase inhibitors: An in silico study. Res Pharm Sci. 2016; 11(3):250-258.

Patil RB, Sawant SD. Synthesis, characterization, molecular docking and evaluation of antimicrobial activity of some 3-heteroaryl substituted chromen-2-one derivatives. Der Pharma Chemica. 2015;7(3):26-37.

Patel NB, Patel JC. Synthesis and antimicrobial activity of Schiff bases and 2-azetidinones derived from quinazolin-4(3H)-one. Arab J Chem. 2011;4(4):403-411.

Wang X, Yin J, Shi L, Zhang G, Song B. Design, synthesis, and antibacterial activity of novel Schiff base derivatives of quinazolin-4(3H)-one. Eur J Med Chem. 2014;77:65-74.


Refbacks

  • There are currently no refbacks.


Creative Commons LicenseThis work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License which allows users to read, copy, distribute and make derivative works for non-commercial purposes from the material, as long as the author of the original work is cited properly.