Journal of Kerman University of Medical Sciences

Synthesis and Biological Evaluation of 4-hydroxychromenyl arylmethyl-6-hydroxy pyrimidine-2, 4-dione Derivatives

Document Type : Original Article

Authors

Khalil Eskandari 1
Bahador Karami 2
Yaghoub Pourshojaei 1
Zahra Lori-Gooini 3
Elham Soltanipour-Joneghani 4
Mohammad-Taghi Moradi 3
Ali Asadipour 5

1 Assistant Professor, Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutics Research Center, Kerman University of Medical Sciences, Kerman, Iran

2 Professor, Department of Chemistry, Faculty of Basic Sciences, Yasouj University, Yasouj, Iran

3 Assistant Professor, Medical Plants Research Center, Basic Health Sciences Institute, Shahrekord University of Medical Sciences, Shahrekord, Iran

4 Student's research committee, Shahrekord University of Medical Sciences, Shahrekord, Iran

5 Professor, Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutics Research Center, Kerman University of Medical Sciences, Kerman, Iran

Abstract
Background: An efficient, promoted tri-component catalytic reaction between barbituric acid (or N,N-dimethyl barbituric acid), 4-hydroxy coumarin, and a wide range of aryl aldehydes using zinc oxide nanowires (ZnO NWs) to obtain some new 4-hydroxychromenylarylmethyl-6-hydroxypyrimidine-2,4-diones is described.
Method: The reactants were successfully condensed via three C-C bond formation by zinc oxide nanowires (ZnO NWs) as an efficient, environmentally safe and recyclable nano catalyst to produce target molecules. In addition, the biological effects of synthesized products by the use of DPPH and acyclovir as positive controls and also Hep-2, vero cell, HSV-1, and adenovirus as four applied cell lines have been evaluated.
Results: The results showed that synthesized products have anti-oxidant, cytotoxic and anti-viral activities and can offer promising prospect as biologically active agents.
Conclusion: This achievement in an efficient and eco-friendly synthesis of novel analogous of hybrid molecules in aqueous media with special biological properties may engross chemists and pharmacologists as well as pharmacists in future.

Keywords

Synthesis
Ultrasound assisted
Bio-assay
Anti-oxidant
Cytotoxic
Anti-viral
Nano-catalyst
  1. Dong A, Sun Y, Lan S, Wang Q, Cai Q, Qi X, et al. Barbituric acid-based magnetic N-halamine nanoparticles as recyclable antibacterial agents. ACS Appl Mater Interfaces 2013; 5(16):8125-33.
  2. Mahmudov KT, Kopylovich MN, Maharramov AM, Kurbanov MM, Gurbanov AV, Pombeiro AJ. Barbituric acids as a useful tool for the construction of coordination and supramolecular compounds. Coord Chem Rev 2014; 265:1-37.
  3. Baruah B, Naidu PS, Borhan P, Bhuyan PJ. Synthesis of 5-alkylated barbituric acids and 3-alkylated indoles via microwave-assisted three-component reactions in solvent-free conditions using Hantzsch 1,4-dihydropyridines as reducing agents.Molecular Diversity 2012; 16(2):291-8.
  4. Ma L, Li S, Zheng H, Chen J, Lin L, Ye X, et al. Synthesis and biological activity of novel barbituric and thiobarbituric acid derivatives against non-alcoholic fatty liver disease. Eur J Med Chem 2011; 46(6):2003-10.
  5. Loscher W, Rogawski MA. How theories evolved concerning the mechanism of action of barbiturates. Epilepsia 2012; 53(Supple8):12-25.
  6. Dhorajiya BD, Dholakiya BZ, Mohareb RM. Hybrid probes of aromatic amine and barbituric acid: highly promising leads for anti-bacterial, anti-fungal and anti-cancer activities. Med Chem Res 2014; 23(9):3941-52.
  7. Singh P, Kaur J, Bhardwaj A. Synthesis of highly functionalized barbituric acids and study of their interactions with p-glycoprotein and Mg2+ Potential candidates for multi drug resistance modulation. Eur J Med Chem 2010; 45(3):1256-62.
  8. Irgashev RA, Kim GA, Rusinov GL, Charushin VN. 5-(Methylidene)barbituric acid as a new anchor unit for dye-sensitized solar cells (DSSC). Arkivoc 2014; 5:123-31.
  9. Ghosh PP, Das AR. Nano crystalline ZnO: a competent and reusable catalyst for one pot synthesis of novel benzylamino coumarin derivatives in aqueous media. Tetrahedron Lett 2012; 53(25):3140-43.
  10. Hesse S, Kirsch G. A rapid access to coumarin derivatives (using Vilsmeier–Haack and Suzuki cross-coupling reactions). Tetrahedron Lett 2002; 43(7):1213-15.
  11. Karami B, Eskandari K, Khodabakhshi S. An efficient synthesis of new khellactone-type compounds using potassium hydroxide as catalyst via one-pot, three-component reaction. J Iran Chem Soc 2014; 11(3):631-37.
  12. Karami B, Khodabakhshi S, Eskandari K. Alternative two-step route to khellactone analogues using silica tungstic acid and sodium hydrogen phosphate. Chem Pap 2013; 67(11):1474-78.
  13. Lee BH, Clothier MF, Dutton FE, Conder GA, Johnson SS. Anthelmintic β-hydroxyketoamides (BKAS). Bioorg Med Chem Lett 1998; 8(23):3317-20.
  14. Jung JC, Jung YJ, Park OS. A convenient one-pot synthesis of 4-hydroxycoumarin, 4-hydroxythio-coumarin, and 4-hydroxyquinolin-2(1h)-one. Synth Commun 2001; 31(8):1195-200.
  15. Melagraki G, Afantitis A, Igglessi-Markopoulou O, Detsi A, Koufaki M, Kontogiorgis C, et al. Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their alpha-lipoic acid adducts. Eur J Med Chem 2009; 44(7):3020-6.
  16. Karami B, Khodabakhshi S, Eskandari K. Regiospecific Synthesis of Novel Furo [4,5-c] coumarins in a One-Pot Reaction. Synlett 2012; 24(8):998-1000.
  17. Mohammadi-Khanaposhtani M, Safavi M, Sabourian R, Mahdavi M, Pordeli M, Saeedi M,·et al. Design, synthesis, in vitro cytotoxic activity evaluation, and apoptosis-induction study of new 9(10H)-acridinone-1,2,3-triazoles. Molecular Diversity 2015; 19(4):787-95.
  18. Arab S, Sadat-Ebrahimi SE, Mohammadi-Khanaposhtani M, Moradi A, Nadri H, Mahdavi M, et al. Synthesis and evaluation of chroman‐4‐one linked to N‐benzyl pyridinium derivatives as new acetylcholinesterase inhibitors. Arch Pharm (Weinheim) 2015; 348(9):643-9.
  19. Lanoot B, Vancanneyt M, Cleenwerck I, Wang L, Li W, Liu Z, et al. The search for synonyms among streptomycetes by using SDS-PAGE of whole-cell proteins. Emendation of the species Streptomyces aurantiacus, Streptomyces cacaoi subsp. cacaoi, Streptomyces caeruleus and Streptomyces violaceus. Int J Syst Evol Microbiol 2002; 52(Pt 3):823-9
  20. Jameel E, Umar T, Kumar J, Hoda N. Coumarin: a privileged scaffold for the design and development of antineurodegenerative agents. Chem Biol Drug Des 2016; 87(1):21-38.
  21. Dewick PM. Medicinal Natural Products: A Biosynthetic Approach. 3rd ed. UK: John Wiley & Sons; 2009.
  22. Bartnik M, Mazurek AK. Isolation of Methoxyfuranocoumarins from Ammi Majus by Centrifugal Partition Chromatography. J Chromatogr Sci 2016; 54(1):10-6.
  23. Feng J, Wang Y, Yi X, Yang W, He X. Phenolics from durian exert pronounced no inhibitory and antioxidant activities. J Agric Food Chem 2016; 64(21):4273-9.
  24. Harinantenaina L, Brodie PJ, Slebodnick Carla, Callmander MW, Rakotobe E, Randrianasolo S, et al. Antiproliferative compounds from pongamiopsis pervilleana from the madagascar dry forest. J Nat Prod 2010; 73(9):1559-62.
  25. Hosseini-Sarvari M. Greener Solvent-Free Reactions on ZnO. InTech; 2012. P.103-20.
  26. Isley NA, Dobarco S, Lipshutz BH. Installation of protected ammonia equivalents onto aromatic & heteroaromatic rings in water enabled by micellar catalysis. Green Chem 2014; 16(3):1480-8.
  27. Klumphu P, Lipshutz BH. “Nok”: a phytosterol-based amphiphile enabling transition-metal-catalyzed couplings in water at room temperature. J Org Chem 2014; 79(3):888-900.
  28. Clark JH. Chemistry goes green. Nature Chem 2009; 1(1):12-3.
  29. Wagner P, Bollenbach M, Doebelin C, Bihel F, Bourguignon JJ, Salome C, et al. t-BuXPhos: a highly efficient ligand for Buchwald–Hartwig coupling in water. Green Chem 2014; 16(9):4170-8.
  30. Eskandari K, Karami B, Pourshojaei Y, Asadipour A. An eco-compatible, three-component synthesis of acyl-substituted bis(pyrazolyl)methanes by employing recyclable silica sodium carbonate as an efficient and environmentally benign catalyst in aqueous medium. Monatsh Chem 2018; 149(6):1075-81.
  31. Poorali L, Karami B, Eskandari K. New and rapid access to synthesis of novel polysubstituted imidazoles using antimony trichloride and stannous chloride dihydrate as effective and reusable catalysts. Journal of Chemical Sciences 2013; 125(3):591-9.
  32. Asadipour A, Pourshojaei Y, Eskandari K, Foroumadi A. A short synthesis of 7-amino alkoxy homoisoflavonoides. RSC Adv 2017; 7:44680-7.
  33. Karami B, Eskandari K, Azizi M. Tungstate sulfuric acid (TSA): a green and highly efficient catalyst for novel and known polysubstituted imidazoles synthesis. Lett Org Chem 2013; 10(10):722-32.
  34. Eskandari K, Karami B, Khodabakhshi S, Farahi M. A rapid tandem knoevenagel/michael reaction using mohr’s salt as a highly efficient catalyst: green synthesis of bis (pyrazolyl) methanes. Lett Org Chem 2015; 12(1):38-43.
  35. Mehrabi F, Pourshojaei Y, Moradi A, Sharifzadeh M, Khosravani L, Sabourian R, et al. Design, synthesis, molecular modeling and anticholinesterase activity of benzylidene-benzofuran-3-ones containing cyclic amine side chain. Future Med Chem 2017; 9(7):659-71.
  36. Asadipour A, Shams Z, Eskandari K, Moshafi MH, Faghih-Mirzaei E, Pourshojaei Y. Efficient, straightforward, catalyst-free synthesis of medicinally important S-alkyl/benzyl dithiocarbamates under green conditions.Research on Chemical Intermediates2018; 44(2):1295-304.
  37. Rahmani-Nezhad S, Safavi M, Pordeli M, Ardestani SK, Khosravani L, Pourshojaei Y, et al. Synthesis, in vitro cytotoxicity and apoptosis inducing study of 2-aryl-3-nitro-2H-chromene derivatives as potent anti-breast cancer agents. Eur J Med Chem 2014; 86:562-9.
  38. Eskandari K, Karami B. A green one-pot synthesis of 4-hydroxychromenylarylmethyl-6-hydroxypyrimidine-2, 4-diones using titanium dioxide nanowires as an effective and recyclable catalyst. Comb Chem High Throughput Screen 2016; 19(9):728-34.
  39. Eskandari K, Karami B, Farahi M, Mouzari V. Silica sodium carbonate catalyzed in water synthesis of novel benzylbarbituro-coumarin derivatives. Tetrahedron Lett 2016; 57(4):487-91.
  40. Gomathi A, Hoseini SJ, Rao CN. Functionalization and solubilization of inorganic nanostructures and carbon nanotubes by employing organosilicon and organotin reagents. J Mater Chem 2009; 19(7):988-95.
  41. Zervos M, Karipi C, Othonos A. The nitridation of ZnO nanowires. Nanoscale Res Lett 2012; 7:175
  42. Refouvelet B, Guyon C, Jacquot Y, Girard C, Fein H, Bevalot F, et al. Synthesis of 4-hydroxycoumarin and 2, 4-quinolinediol derivatives and evaluation of their effects on the viability of HepG2 cells and human hepatocytes culture. Eur J Med Chem 2004; 39(11):931-7.
  43. Moien S, Farzami B, Khaghani S, Moein MR, Larijani BA. Antioxidant properties and protective effect on cell cytotoxicity of salvia mirzayani. Pharm Biology 2007; 45(6):485-63.
  44. Mosmann T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65(1-2):55-63.
  45. Jadhav P, Kapoor N, Thomas B, Lal H, Kshirsagar N. Antiviral potential of selected Indian medicinal (ayurvedic) plants against herpes simplex virus 1 and 2. N Am J Med Sci 2012; 4(12):641-47
Journal of Kerman University of Medical Sciences
Volume 25, Issue 3
May and June 2018
Pages 213-227

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