Abstract
A series of new chiral benzisoselenazol-3(2H)-ones and their corresponding diselenides bearing an o-amido function substituted on the nitrogen atom with various aliphatic and aromatic moieties were synthesized. All derivatives representing pairs of enantiomers or diastereoisomers were obtained to thoroughly evaluate the three-dimensional structure–activity correlation. First, bensisoselenazol-3(2H)-ones were synthesized by reacting 2-(chloroseleno)benzoyl chloride with an appropriate enantiomerically pure amine. Then, the Se–N bond was cleaved by a reduction–oxidation procedure using sodium borohydride and then air oxidation to obtain the corresponding diselenides. All derivatives were tested as antioxidants and anticancer agents. In general, the diselenides were more reactive peroxide scavengers, with the highest activity observed for 2,2′-diselenobis[N-(1S,2S)-(-)-trans-2-hydroksy-1-indanylbezamide]. The most cytotoxic derivative towards human promyelocytic leukemia HL-60 and breast cancer MCF-7 cell lines was N-[(1S,2R)-(-)-cis-2-hydroksy-1-indanyl]-1,2-benzizoselenazol-3(2H)-one. The structure–activity relationship of the obtained organoselenium derivatives was discussed.
Highlights
IntroductionAs the human body is a combination of permanent changes in concentration, tension and movement, the overall biochemical processes that occur are far from maintaining equilibrium
Potential drugs generally possess fixed stereocenters to efficiently interact with specific receptors that have a characteristic spatial structure at their binding side [4–6]
The primary biochemical role of selenium is associated with its activity as the chiral amino acid L-selenocysteine that forms the active center of the antioxidant enzyme glutathione peroxidase
Summary
As the human body is a combination of permanent changes in concentration, tension and movement, the overall biochemical processes that occur are far from maintaining equilibrium. 2,2 -diselenobis[N-(S)-(−)-1-(1-napthyl)ethylbezamide] 26b Yield: 70%; mp 262–64 ◦C; [∝]2D0 = −96 (c = 0.35, CHCl3); 1H NMR (700 MHz, DMSO) δ = 1.66 (d, J = 7.7 Hz, 3H), 5.95–6.01 (m, 1H), 7.31–7.36 (m, 2Har), 7.49–7.56 (m, 2Har), 7.58–7.62 (m, 1Har), 7.65–7.69 (m, 2Har), 7.86 (d, J = 8.4 Hz, 1Har), 7.90–7.94 (m, 1Har), 7.95–7.99 (m, 1Har), 8.26 (d, J = 8.4 Hz, 1Har), 9.26 (d, J = 7.7 Hz, 1H) 13C NMR (700 MHz, DMSO) δ = 21.87 (CH3), 45.64 (CH), 123.11 (CHar), 123.63 (CHar), 125.95 (CHar), 126.09 (CHar), 126.60 (CHar), 126.73 (CHar), 127.85 (CHar), 128.67 (CHar), 129.17 (CHar), 130.40 (CHar), 130.90 (CHar), 132.03 (Car), 132.45 (Car), 133.76 (Car), 133.90 (Car), 140.44 (Car), 167.10 (C=O) 77Se NMR (700 MHz, DMSO) δ = 442.72 ppm; IR: 3290, 2922, 1625, 1583, 1530, 1452, 1429, 1338, 1308, 1284, 1258, 1180, 1132, 1025, 871, 792, 773, 735, 693, 641, 448 cm−1.Elemental Anal. Calcd for C32H28N2O4Se2 (664.04): C, 58.01; H, 4.26; N, 4.23; Found C, 57.92; H, 4.27; N, 4.18
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