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Table 1 Physicochemical properties and GK activity of the synthesized 3,5-disubstituted benzamide derivatives

From: Design, synthesis and evaluation of novel 3,5-disubstituted benzamide derivatives as allosteric glucokinase activators

Compound R Molecular Formula M. Pt. (°C) R f a % Yield GK activityb
5a –C6H5 C17H13N5O5S 140–142 0.62 56 1.43 ± 0.06
5b 2-ClC6H4 C17H12ClN5O5S 157–158 0.37 63 1.74 ± 0.08
5c 3-ClC6H4 C17H12ClN5O5S 161–162 0.53 62 1.34 ± 0.05
5d 4-ClC6H4 C17H12ClN5O5S 165–167 0.57 61 1.36 ± 0.03
5e 2-NO2C6H4 C17H12N6O7S 155–156 0.69 68 1.49 ± 0.07
5f 3-NO2C6H4 C17H12N6O7S 158–160 0.72 65 1.89 ± 0.06
5g 4-NO2C6H4 C17H12N6O7S 152–154 0.69 74 1.65 ± 0.04
5h –CH2C6H5 C18H15N5O5S 138–140 0.62 76 1.20 ± 0.06
5i –C2H5 C13H13N5O5S 147–148 0.56 69 1.68 ± 0.04
6a –C6H5 C16H12N4O5S2 154–160 0.75 76 1.65 ± 0.06
6b 2-ClC6H4 C16H11ClN4O5S2 181–182 0.56 66 1.59 ± 0.08
6c 3-ClC6H4 C16H11ClN4O5S2 189–191 0.64 59 2.11 ± 0.05
6d 4-ClC6H4 C16H11ClN4O5S2 185–186 0.62 77 1.55 ± 0.08
6e 2-NO2C6H4 C16H11N5O7S2 180–182 0.38 72 2.11 ± 0.09
6f 3-NO2C6H4 C16H11N5O7S2 176–177 0.48 68 1.37 ± 0.07
6g 4-NO2C6H4 C16H11N5O7S2 182–183 0.42 59 1.24 ± 0.08
6h –CH2C6H5 C17H14N4O5S2 164–166 0.55 53 1.99 ± 0.07
6i –C2H5 C12H12N4O5S2 162–163 0.58 48 1.08 ± 0.09
  1. aTLC mobile phase: Benzene: Ethyl acetate (7:3)
  2. bAll the values are mean of three measurements ± SD (as GK fold activation at 10 µM concentration compared to control i.e., DMSO only)