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Synthetic Approach for Novel Fluorine Substituted α-Aminophosphonic Acids Containing 1,2,4-Triazin-5-One Moiety as Antioxidant Agents

DOI: 10.4236/ijoc.2018.81001, PP. 1-15

Keywords: Synthetic, Fluorine α-Amino Acids, 1,2,4-Triazin-5-One Moiety, Antioxidants Activity

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Abstract:

Novel fluorine substituted α-amino phosphonic acids containing 1,2,4-triazin- 5-one (6a-f) have been obtained from fluoroacylation of 6-(2-amino-5-nitrophenyl)-3-thioxo-1,2,4-triazin-5(4H)-one (1) followed by ammonilysis to give the corresponding 3-amino-derivative 3. Condensation of compound 3 with nitro/halogenated aromatic aldehydes yielded the Schiff bases 4. The simple addition of diethyl phosphonate to compound 4 produced the α-amino phosphonates 5. Acidic hydrolysis of compound 5 produced the fluorine substituted α-amino acids derivatives 6. Structures of the new compounds have been established with the help of elemental analysis and spectral measurements. Also, the products evaluated as antioxidants, where the fluorinated α-amino phosphonic acids 6 are more active than the other synthesized systems.

References

[1]  Abdel-Rahman, R.M., Ali, T.E. and Abdel-Kariem, S.M. (2016) Methods for Synthesis of N-Hetrocyclyl/Hetroaryl-α-Aminophosphonates and α-(Azahetrocyclyl) Phosphonates. ARKIVOC, 1, 183-211.
[2]  Gholivand, K., Shariatinia, Z., Mahzouni, H.R. and Amiri, S. (2007) Phosphorus Heterocycles: Synthesis, Spectroscopic Study and X-Ray Crystallography of Some New Diazaphosphorinanes. Structural Chemistry, 18, 653-660.
https://doi.org/10.1007/s11224-007-9197-3
[3]  Abdel-Rahman, R.M. and Ali, T.E. (2013) Synthesis and Biological Evaluation of Some New Polyfluorinated 4-Thiazolidinone and α-Aminophosphonic Acid Derivatives. Monatsheftefür Chemie—Chemical Monthly, 144, 1243-1252.
https://doi.org/10.1007/s00706-013-0934-6
[4]  Peyman, A., Budt, K.H., Spanig, J., Stowasser, B. and Ruppert, D. (1992) C2-Symmetric Phosphinic Acid Inhibitors of HIV Protease. Tetrahedron Letters, 33, 4549-4552.
https://doi.org/10.1016/S0040-4039(00)61309-6
[5]  Markwell, R. (2000) Aminophosphonic and Aminophosphinic Acid Derivatives as Inhibitors of Human Collagenase. In: Kukhar, V.P. and Hudson, H.R., Eds., Amino-phosphonic and Aminophosphinic Acids: Chemistry and Biological Activity, Wiley, Chichester, 579-621.
[6]  Kenawy, E.-R.S., Azaam, M.M. and Saad-Allah, K.M. (2015) Synthesis and Antimicrobial Activity of α-Aminophosphonates Containing Chitosan Moiety. Arabian Journal of Chemistry, 8, 427-432.
https://doi.org/10.1016/j.arabjc.2013.12.029
[7]  Reddy, Y.H., Kumar, B.S., Reddy, G.C., Dadapeer, E. and Reddy, K.S. (2012) Synthesis and Bioassay of α-Aminophosphonates. Der Chemica Sinica, 3, 817-823.
[8]  Zhang, Y., Bai, S., Song, B., Bhadury, P.S., Hu, D., Yang, S., Zhang, X., Fan, H. and Lu, P. (2010) Enantioseparation and Plant Virucidal Bioactivity of New Quinazoline Derivatives with α-Aminophosphonate Moiety. Journal of Chromatography B, 878, 1285-1289.
https://doi.org/10.1016/j.jchromb.2009.11.024
[9]  Ali, T.E., Abdel-Aziz, S.A., Somaya, M., Mohamed, E.H.A. and Abdel-Kariem, S.M. (2013) Synthesis and Biological Evaluations of a Series of Novelazolyl, Azinyl and Azepinyl Phosphonates. Heterocycles, 87, 2513-2522.
https://doi.org/10.3987/COM-13-12836
[10]  Abdel-Rahman, R.M., Makki, M.S., Ali, T.E. and Ibrahim, M.A. (2015) 1,2,4-Triazine Chemistry Part IV: Synthesis and Chemical Behavior of 3-Functionalized 5,6-Diphenyl-1,2,4-Triazines towards Some Nucleophilic and Electrophilic Reagents. Journal of Heterocyclic Chemistry, 52, 1595-1607.
https://doi.org/10.1002/jhet.2014
[11]  Abdel-Rahman, R.M., Makki, M.S.T., Ali, T.E. and Ibrahim, M.A. (2013) 1,2, 4-Triazine Chemistry Part III: Synthetic Strategies to Functionalized Bridgehead Nitrogen Heteroannulated 1,2,4-Triazine Systems and Their Regiospecific and Pharmacological Properties. Current Organic Synthesis, 10, 136-160.
[12]  Abdel-Rahman, R.M. and Saad, H.A. (2016) Synthesis and Chemical Behavior of 1,2,4-Triazine Derivatives Bearing Phosphorus Amides as Donor-Acceptors: A Review. Current Organic Synthesis, 13, 408-425.
https://doi.org/10.2174/1570179412666150905001956
[13]  Al-Romaizan, A.N., Makki, M.S.T. and Abdel-Rahman, R.M. (2014) Synthesis of New Fluorine/Phosphorus Substituted 6-(2'-Amino Phenyl)-3-Thioxo-1,2,4-Triazin-5(2H, 4H)One and Their Related Alkylated Systems as Molluscicidal Agent as against the Snails Responsible for Bilharziasis Diseases. International Journal of Organic Chemistry, 4, 154-168.
[14]  Ali, T.E., Abdel-Rahman, R.M., Hanafy, F.I. and El-Edfawy, S.M. (2008) Synthesis and Molluscicidal Activity of Phosphorus-Containing Heterocyclic Compounds Derived from 5,6-Bis (4-Bromophenyl)-3-Hydrazino-1,2,4-Triazine. Phosphorus, Sulfur, and Silicon and the Related Elements, 183, 2565-2577.
https://doi.org/10.1080/10426500801967864
[15]  Abdel-Rahman, R.M., Ibrahim, M.A. and Ali, T.E. (2010) 1,2,4-Triazine Chemistry Part II: Synthetic Approaches for Phosphorus Containing 1,2,4-Triazine Derivatives. European Journal of Chemistry, 1, 388-396.
https://doi.org/10.5155/eurjchem.1.4.388-396.154
[16]  Ali, T.E. (2009) Synthesis and Antibacterial Activity of Some New Thiadiaza/Triazaphospholes, Thiadiaza/Triaza/Tetrazaphosphinines and Thiadiaza/Tetrazaphosphepines Containing 1,2,4-Triazinone Moiety. European Journal of Medicinal Chemistry, 44, 4539-4546.
https://doi.org/10.1016/j.ejmech.2009.06.022
[17]  Abdel-Rahman, R.M. (2002) Chemoselectiveheterocyclization of Pharmacological Activities of New Heterocycles—A Review: Synthesis of New Phosphaheterobicyclic Systems Containing 1,2,4-triazine Moiety Part IX: Straightforward Synthesis of New Fluorine Bearing 5-Phospha-1,2,4-triazin/1,2,4-triazepine-3 thiones. Trends in Heterocyclic Chemistry, 8, 187-195.
[18]  Makki, M.S.T., Abdel-Rahman, R.M. and AbuAli, O.A. (2015) Synthesis of New Fluorinated 1,2,4-Triazino [3,4-b] [1,3,4]thiadiazolones as Antiviral Probes-Part II-Reactivities of Fluorinated 3-Aminophenyl-1,2,4-triazinothiadiazolon. International Journal of Organic Chemistry, 5, 153-165.
https://doi.org/10.4236/ijoc.2015.53017
[19]  Makki, M.S.T., Abdel-Rahman, R.M. and Khan, K.A. (2014) Fluorine Substituted 1,2,4-triazinones as Potential anti-HIV-1 and CDK2 Inhibitors. Journal of Chemistry, 2014, Article ID: 430573.
[20]  Abdel-Rahman, R.M., Makki, M.S.T. and Al-Romaizan, A.N. (2014) Synthesis of Novel Fluorine Substituted Isolated and Fused Heterobicyclic Nitrogen Systems Bearing 6-(2’-Phosphorylanilido)-1,2,4-Triazin-5-One Moiety as Potential Inhibitor towards HIV-1 Activity. International Journal of Organic Chemistry, 4, 247-268.
https://doi.org/10.4236/ijoc.2014.44028
[21]  Abdel-Rahman, R.M., Makki, M.S.T. and Bawazir, W.A. (2011) Synthesis of Some More Fluorine Heterocyclic Nitrogen Systems Derived From Sulfa Drugs as Photochemical Probe Agents for Inhibition of Vitiligo Disease—Part I. E-Journal of Chemistry, 8, 405-414.
https://doi.org/10.1155/2011/586063
[22]  Abdel-Rahman, R.M. (1991) Synthesis and Anti-Human Immune Virus Some New Fluorine-Containing Substituted-3-Thioxo-1,2,4-Triazin-5-Ones. IL Farmaco, 42, 379-389.
[23]  Abdel-Rahman, R.M. (2001) Chemistry of Uncondensed 1,2,4-Triazines, Part IV. Synthesis and Chemistry of Bioactive 3-Amino-1,2,4-Triazines and Related Com-pounds—An Overview. Pharmazie, 56, 275-286.
[24]  Ali, T.E. (2009) Synthesis of Some New 1,3,2-Oxazaphosphinine, 1,3,2-Diazaphos-phinine, Acyclic, and/or Cyclic α-Aminophosphonate Derivatives Containing the Chromone Moiety. Phosphorus, Sulfur, and Silicon and the Related Elements, 185, 88-96.
https://doi.org/10.1080/10426500802713309
[25]  Ali, T.E. and Halacheva, S.S. (2009) Synthetic Approach for Novel Bis(α-aminophos-phornic Acid) Derivatives of Chromone Containing 1,2,4,3-Triazaphosphole Moieties. Heteroatom Chemistry, 20, 117-122.
https://doi.org/10.1002/hc.20520
[26]  Pandeya, S.N., Kumar, R., Pathak, A.K. and Nath, G. (2010) Synthesis and Biological Evaluation of Triazine Derivatives. Der Pharma Chemica, 2, 257-266.
[27]  Siddhuraju, P. and Becker, K. (2007) The Antioxidant and Free Radical Scavenging Activities of Processed Cowpea (Vignaunguiculata (L.) Walp.) Seed Extracts. Food Chemistry, 101, 10-19.
https://doi.org/10.1016/j.foodchem.2006.01.004

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