One-Pot Synthesis, Pharmacological Evaluation, Docking Study, and DFT Calculations for Selected Imidazolidine-2,4-Diones

  • Zanko S. Jawhar Department of Clinical Biochemistry, College of Health Sciences, Hawler Medical University, Hawler, Kurdistan Region, Iraq.
  • Hiwa O. Ahmed Department of Pharmaceutical Chemistry, College of Pharmacy, Hawler Medical University, Hawler, Kurdistan Region, Iraq.
  • Asmaa A. Haydar Department of pharmacology, College of Pharmacy, Hawler Medical University, Hawler, Kurdistan Region, Iraq.
  • Halala A. Abdullah Department of chemistry, College of Science, Soran University, Kurdistan Region, Iraq.
  • Sawza A. Mahamad Department of chemistry, College of Science, Soran University, Kurdistan Region, Iraq.
Keywords: imidazolidine-2, 4-dione derivatives, Prostate cancer, computational study, Energy, biological activity

Abstract

The title compounds with different 5-substituted imidazolidine-2,4-dione were synthesized through a solvent-free reaction. Imidazolidine-2,4-dione derivatives are found to be an active pharmacophore for design and development of various bioactive lead compounds.  Positive values of energy obtained for compound 1and 3, while a negative value for compound 2 was calculated by DFT in Gaussian. keto-enol tautomerism was supported by energy values  and indicated the most stable tautomeric form. The biological evaluation has been supported by docking studies using molecular operating environment program to show binding with androgen receptor. 

Supplementary Materials: https://sjuoz.uoz.edu.krd/suppma

Author Biographies

Zanko S. Jawhar, Department of Clinical Biochemistry, College of Health Sciences, Hawler Medical University, Hawler, Kurdistan Region, Iraq.

Department of Clinical Biochemistry, College of Health Sciences, Hawler Medical University, Hawler, Kurdistan Region, Iraq.

Hiwa O. Ahmed, Department of Pharmaceutical Chemistry, College of Pharmacy, Hawler Medical University, Hawler, Kurdistan Region, Iraq.

Department of Pharmaceutical Chemistry, College of Pharmacy, Hawler Medical University, Hawler, Kurdistan Region, Iraq.

Asmaa A. Haydar, Department of pharmacology, College of Pharmacy, Hawler Medical University, Hawler, Kurdistan Region, Iraq.

Department of pharmacology, College of Pharmacy, Hawler Medical University, Hawler, Kurdistan Region, Iraq.

Halala A. Abdullah, Department of chemistry, College of Science, Soran University, Kurdistan Region, Iraq.

Department of chemistry, College of Science, Soran University, Kurdistan Region, Iraq.

Sawza A. Mahamad, Department of chemistry, College of Science, Soran University, Kurdistan Region, Iraq.

Department of chemistry, College of Science, Soran University, Kurdistan Region, Iraq.

References

Baeyer, Adolph. (1861). Vorläufige Notiz über das Hydantoïn. Justus Liebigs Annalen der Chemie, 117(2), 178-180.
Becke, Axel D. (1993). Density‐functional thermochemistry. III. The role of exact exchange. The Journal of chemical physics, 98(7), 5648-5652.
Bisello, Annalisa, Cardena, Roberta, Rossi, Serena, Crisma, Marco, Formaggio, Fernando, & Santi, Saverio. (2017). Hydrogen-Bond-Assisted, Concentration-Dependent Molecular Dimerization of Ferrocenyl Hydantoins. Organometallics, 36(11), 2190-2197.
Cheng, Cheng-Kuo, Wu, Jender, Liu, Yuan, Lee, Tong-Sheng, Kang, Shuo-Jhen, Sheu, Ming-Thau, & Lee, Wen-Sen. (2008). Structure and anti-proliferation function of 5, 5-diphenyl-2-thiohydantoin (DPTH) derivatives in vascular endothelial cells. Vascular pharmacology, 48(2-3), 138-142.
Colacino, Evelina, Lamaty, Frédéric, Martinez, Jean, & Parrot, Isabelle. (2007). Microwave-assisted solid-phase synthesis of hydantoin derivatives. Tetrahedron letters, 48(30), 5317-5320.
Dewar, Michael JS, Zoebisch, Eve G, Healy, Eamonn F, & Stewart, James JP. (1985). Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model. Journal of the American Chemical Society, 107(13), 3902-3909.
Etter, Margaret C. (1990). Encoding and decoding hydrogen-bond patterns of organic compounds. Accounts of Chemical Research, 23(4), 120-126.
Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., . . . Fox, D. J. (2016). Gaussian 16 Rev. B.01. Wallingford, CT.
Gao, Wenqing, Bohl, Casey E, & Dalton, James T. (2005). Chemistry and structural biology of androgen receptor. Chemical reviews, 105(9), 3352-3370.
Ghanbari, Mohammad M, Roohi, Zahra, & Safari, Javad. (2014). One-pot synthesis of imidazolidine-2-thiones, hydantoins and thiohydantoins under solvent-free and grinding conditions. Open Access Library Journal, 1(07), 1.
Heras-Vazquez, Francisco JL, Clemente-Jimenez, Josefa M, Martinez-Rodriguez, Sergio, & Rodriguez-Vico, Felipe. (2008). Optically pure α-amino acids production by the “Hydantoinase Process”. Recent patents on biotechnology, 2(1), 35-46.
Katritzky, Alan R, Strah, Sonja, & Belyakov, Sergei A. (1998). The preparation of functionalized amines and amides using benzotriazole derivatives and organozinc reagents. Tetrahedron, 54(25), 7167-7178.
Law, Vivian, Knox, Craig, Djoumbou, Yannick, Jewison, Tim, Guo, An Chi, Liu, Yifeng, . . . Neveu, Vanessa. (2013). DrugBank 4.0: shedding new light on drug metabolism. Nucleic acids research, 42(D1), D1091-D1097.
Li, Jie Jack. (2010). Name reactions: a collection of detailed mechanisms and synthetic applications: Springer Science & Business Media.
Nefzi, Adel, Giulianotti, Marc A, & Houghten, Richard A. (2000). Solid-phase synthesis of branched thiohydantoin benzimidazolinethiones and branched thiohydantoin tetrahydroquinoxalinediones. Tetrahedron Letters, 41(14), 2283-2287.
Nique, François, Hebbe, Séverine, Peixoto, Christophe, Annoot, Denis, Lefrançois, Jean-Michel, Duval, Eric, . . . Mollat, Patrick. (2012). Discovery of diarylhydantoins as new selective androgen receptor modulators. Journal of medicinal chemistry, 55(19), 8225-8235.
Pereira de Jesus-Tran, K., Cote, P. L., Cantin, L., Blanchet, J., Labrie, F., & Breton, R. (2006). Comparison of crystal structures of human androgen receptor ligand-binding domain complexed with various agonists reveals molecular determinants responsible for binding affinity. Protein Sci, 15(5), 987-999. doi: 10.1110/ps.051905906
Safari, J, Naeimi, H, Ghanbari, MM, & Fini, O Sabzi. (2009). Preparation of phenytoin derivatives under solvent-free conditions using microwave irradiation. Russian journal of organic chemistry, 45(3), 477-479.
Safari, Javad, Moshtael Arani, Naimeh, & Ramezan Isfahani, Anousheh. (2010). Ultrasound‐enhanced Green Synthesis of 5, 5‐Diphenylhydantoin Derivatives Using Symmetrical or Unsymmetrical Benzils. Chinese Journal of Chemistry, 28(2), 255-258.
Safi, Zaki S, Al Hasanat, Subhia J, & Wazzan, Nuha A. (2018). DFT investigation of the amino/imino proton transfer process of 2-amino-2-oxazolin-4-one in gas phase and solution. Journal of Theoretical and Computational Chemistry, 17(01), 1850004.
Safi, Zaki Sulieman. (2012). Theoretical density functional study of gas-phase tautomerization and acidity of 5-methylhydantoin and its thio derivatives. European Journal of Chemistry, 3(3), 348-355.
Tikhonov, Denis B, & Zhorov, Boris S. (2017). Mechanism of sodium channel block by local anesthetics, antiarrhythmics, and anticonvulsants. The Journal of general physiology, 149(4), 465-481.
Ware, Elinor. (1950). The chemistry of the hydantoins. Chemical Reviews, 46(3), 403-470.
Zhang, Mao, Liang, Yu-Ru, Li, Huan, Liu, Ming-Ming, & Wang, Yang. (2017). Design, synthesis, and biological evaluation of hydantoin bridged analogues of combretastatin A-4 as potential anticancer agents. Bioorganic & medicinal chemistry, 25(24), 6623-6634.
Zhang, Xuqing, Allan, George F, Sbriscia, Tifanie, Linton, Olivia, Lundeen, Scott G, & Sui, Zhihua. (2006). Synthesis and SAR of novel hydantoin derivatives as selective androgen receptor modulators. Bioorganic & medicinal chemistry letters, 16(22), 5763-5766.
Zuo, Minzan, Xu, Xi, Xie, Zhouling, Ge, Raoling, Zhang, Ziyu, Li, Zhiyu, & Bian, Jinlei. (2017). Design and synthesis of indoline thiohydantoin derivatives based on enzalutamide as antiproliferative agents against prostate cancer. European journal of medicinal chemistry, 125, 1002-1022.
Published
2018-12-30
How to Cite
Jawhar, Z., Ahmed, H., Haydar, A., Abdullah, H., & Mahamad, S. (2018). One-Pot Synthesis, Pharmacological Evaluation, Docking Study, and DFT Calculations for Selected Imidazolidine-2,4-Diones. Science Journal of University of Zakho, 6(4), 150-154. https://doi.org/10.25271/sjuoz.2018.6.4.541
Section
Science Journal of University of Zakho