Synthesis of Benzophenonehydrazone Schiff Bases and their In Vitro Antiglycating Activities

Khalid      Mohammed Khan; Fazal      Rahim; Nida      Ambreen; Muhammad      Taha; Momin      Khan; Humaira      Jahan; Najeebullah; Azizuddin      Shaikh; Sarosh      Iqbal; Shahnaz      Perveen; Muhammad      Iqbal Choudhary

doi:10.2174/1573406411309040013

Abstract

Benzophenonehydrazone Schiff bases 1-25 were synthesized and their in vitro antiglycation potential has been studied. Out of twenty-five compounds, thirteen showed varying degrees of antiglycation activity with IC₅₀ values ranging between 25.7 - 305 μM, if compared with the standard rutin (IC₅₀ = 70.5 ± 0.50 μM). Compounds 21 (2,3- dihydroxybenzaldehyde N-(diphenylmethylene)hydrazine) IC₅₀ = 25.7 ± 0.003 μM, 14 (diphenylmethanone N-[1-(2,4- dihydroxy-5-nitrophenyl)ethylidene]hydrazine) IC₅₀ = 36.6 ± 0.004 μM, 6 (3,4-dihydroxybenzaldehyde N- (diphenylmethylene)hydrazine) IC₅₀ = 49.5 ± 0.001 μM, 13 (diphenylmethanone N-[1-(2,5-dihydroxyphenyl)ethylidene] hydrazine) IC₅₀ = 52.6 ± 0.023 μM, and 15 (diphenylmethanone N-[1-(3,4-dihydroxyphenyl)ethylidene]hydrazine) IC₅₀ = 57 ± 0.002 μM, showed showed much better antiglycation potential superior to the standard rutin. The compounds 7 (2,5- dihydroxybenzaldehyde N-(diphenylmethylene)hydrazine) IC₅₀ = 66 ± 0.002 μM, and 25 (diphenylmethanone N-[1-(2,5- dihydroxyphenyl)propylidene] hydrazine) IC₅₀ = 67.9 ± 0.001 μM showed compareably good antiglycation activity to standard rutin. All compounds were characterized by spectroscopic techniques and gave satisfactory elemental analysis.

Keywords: Benzophenonehydrazone, Schiff bases, antiglycation, AGEPs

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