Error message

  • Deprecated function: Unparenthesized `a ? b : c ? d : e` is deprecated. Use either `(a ? b : c) ? d : e` or `a ? b : (c ? d : e)` in include_once() (line 1439 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Array and string offset access syntax with curly braces is deprecated in include_once() (line 3557 of /home/science2016/public_html/includes/bootstrap.inc).

Synthesis, Characterization and Antimicrobial Activity of New Nucleoside Analogues from Benzotriazole

Thanaa Al-muamin, Naeemah Al-lami, Suroor Rahman and Rana Ali
Affiliation: 
University of Bagdad, 10071 Jadriyah, Baghdad, Iraq
DOI: 
https://doi.org/10.23939/chcht10.03.271
AttachmentSize
PDF icon full_text.pdf149.94 KB

Keywords:

Abstract: 
Novel derivatives of 1-(´1, ´3, ´4, ´6-tetra benzoyl-β-D-fructofuranosyl)-1H- benzotriazole and 1-(´1, ´3, ´4, ´6-tetra benzoyl-β-D-fructofuranosyl)-1H-benzotriazole carrying Schiff bases moiety were synthesised and fully characterised. The protection of D-fructose using benzoyl chloride was synthesized, followed by nucleophilic addition/elimination between benzotriazole and chloroacetyl chloride to give 1-(1- chloroacetyl)-1H-benzotriazole. The next step was condensation reaction of protected fructose and 1-(1-chloroacetyl)-1H-benzotriazole producing a new nucleoside analogue. The novel nucleoside analogues underwent a second condensation reaction with different aromatic and aliphatic amines to provide new Schiff bases. The prepared analogues were characterised by FT-IR, 1H NMR, 13C NMR, HRMS(EI+) spectra. These analogues were tested against different bacteria to evaluate them as antimicrobial agents.
References: 

[1] Kukhanova M.: Mol. Biol., 2012, 46, 768.
https://doi.org/10.1134/S002689331206012X

[2] Damaraju V., Damaraju S., Young J. et al.: Oncogene, 2003, 22, 7524.
https://doi.org/10.1038/sj.onc.1206952

[3] Balckburn G.: Nucleosides and Nucleotides [in:] Balckburn G., Gait M., Loakes D. and Williams D. (Eds.) Nucleic Acids in Chemistry and Biology, 3rd edn. Royal Society of Chemistry: Cambridge 2006, 125-136.

[4] Martin J. (Ed.): Nucleoside Analogues as Antiviral Agents. Amer. Chem. Soc. Washington 1983.

[5] Whitley R., Aford C., Hess F. and Bunchanan R.: Drugs, 1980, 20, 267.
https://doi.org/10.2165/00003495-198020040-00002

[6] Mhristophe L. and Gerald E.: Molecules, 2015, 20, 4967.
https://doi.org/10.3390/molecules20034967

[7] Medela K. and McGuigan C.: Fut. Med. Chem., 2012, 4, 625.
https://doi.org/10.4155/fmc.12.10

[8] Romeo G., Ciacchio U. and Corsaro A.: Chem. Rev., 2010, 110, 3337.
https://doi.org/10.1021/cr800464r

[9] Katritzky A.: Lecture Presented at Various Locations. Florida Centre for Heterocyclic Compounds, 2007, 30, 1.

[10] Kale R., Virendra P., Prabhu P. and Vinod K.: Monatsh Chemistry, 2010, 141, 1159.
https://doi.org/10.1007/s00706-010-0378-1

[11] IUPAC, Compendium of Chemical Terminology, 2nd edn. The Gold Book 1997. Online corrected version. Schiff base. 2006.

[12] Hernandez-Molina R. and Mederos A.: Acyclic and Macrocyclic Schiff Base Ligands [in:] McCleverty J. and Meyer T. (Eds.), Comprehensive Coordination Chemistry II. 2003, 411-446.
https://doi.org/10.1016/B0-08-043748-6/01070-7

[13] Whilster R. and Wolfrom M.: Methods in Carbohydrate Chemistry. Academic press, New York and London 1962.

[14] Ishwar B., Sunil K., Jainey P. and Shastry C.: J. Chem. Pharm. Res., 2011, 3, 114.

[15] Reynolds D. and Evans W.: J. Am. Chem. Soc., 1938, 60, 2559.
https://doi.org/10.1021/ja01277a080

[16] Cordes E. and Jenck W.: J. Am. Chem. Soc., 1962, 84, 832.
https://doi.org/10.1021/ja00864a031