Synthesis, characterization and biological activity of Schiff base analogues of indole-3-carboxaldehyde.

Eight novel heterocyclic Schiff bases derived from the condensation reactions of indole 3-carboxaldehyde with different l-amino acids (histidine, glutamic acid, aspartic acid, leucine, valine) as well as with some aminophenols, have been synthesized and characterized by various spectroscopic methods (IR, MS, (1)H NMR). Schiff base derivatives of indole 3-carboxaldehyde were labeled with (99m)Tc and radiochemical purity was above 97% which is ascertained by instant thin layer chromatography using different solvent conditions. Stability studies of all the derivatives of indole 3-carboxaldehyde was determined under physiological conditions and were stable for more than 24h. Blood clearance showed a quick wash out from the circulation and biological half life was found to be t((1/2))(F)=1h 15min; t((1/2))(S)=10h 05min. Excellent quality radioimages of tumor bearing mice were recorded showing rapid clearance of background activity, visualization of tumor at 3h and clearance from kidneys of histidine analogue which was further evidenced in biodistribution studies. Antimicrobial activity of these Schiff base compounds was evaluated against Bacillus subtilis, Pseudomonas fluorescence, Staphylococcus aureus, Aspergillus niger, Candida albicans and Trichophyton rubrum.
AuthorsDeepa Sinha, Anjani K Tiwari, Sweta Singh, Gauri Shukla, Pushpa Mishra, Harish Chandra, Anil K Mishra
JournalEuropean journal of medicinal chemistry (Eur J Med Chem) Vol. 43 Issue 1 Pg. 160-5 (Jan 2008) ISSN: 0223-5234 [Print] France
PMID17532543 (Publication Type: Journal Article)
Chemical References
  • Indoles
  • Schiff Bases
  • Glutamic Acid
  • Histidine
  • Technetium
  • indole-3-carbaldehyde
  • Animals
  • Bacteria (drug effects)
  • Fungi (drug effects)
  • Glutamic Acid (analogs & derivatives, pharmacokinetics)
  • Half-Life
  • Histidine (analogs & derivatives, pharmacokinetics)
  • Humans
  • Indoles (chemistry)
  • Mice
  • Neoplasms (metabolism)
  • Rabbits
  • Schiff Bases (chemical synthesis, chemistry, pharmacokinetics, pharmacology)
  • Technetium
  • Tissue Distribution

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