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The synthesis of 9-hydroxy methyl analogue of Nos was carried out by Blanc reaction and 9-carbaldehyde oxime was engineered by oxime formation method and characterized using FT-IR, <jats:sup>1<\/jats:sup>H NMR, <jats:sup>13<\/jats:sup>C NMR, mass spectroscopy, and so on techniques. <jats:italic>In silico<\/jats:italic> docking techniques informed that 9-hydroxy methyl and 9-carbaldehyde oxime analogues of Nos had higher binding energy score as compared to Nos. The IC50 of Nos was estimated to be 46.8\u2009\u00b5M signficantly (P\u2009&lt;\u20090.05) higher than 8.2\u2009\u00b5M of 9-carbaldehyde oxime and 4.6\u2009\u00b5M of 9-hydroxy methyl analogue of Nos in U87, human glioblastoma cells. Moreover, there was significant (P\u2009&lt;\u20090.05) difference between the IC50 of 9-carbaldehyde oxime and 9-hydroxy methyl analogue of Nos. Consistent to <jats:italic>in vitro<\/jats:italic> cytotoxicity data, 9-hydroxy methyl analogue of Nos induced significantly (P\u2009&lt;\u20090.05) higher degree of apoptosis of 84.6% in U87 cells as compared to 78.5% and 64.3% demonstrated by 9-carbaldehyde oxime and Nos, respectively. 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