Synthesis and in vitro investigation of potential antiproliferative monosaccharide–d-secoestrone bioconjugates

Synthesis of Novel C-2- or C-15-Labeled BODIPY—Estrone Conjugates

“…Concerning the mode of conjugation, clicking via CuAAC reaction is one of the most feasible and effective strategies [ 15 , 16 , 23 ]. On the basis of our longstanding experience [ 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 ] in developing steroidal azides and alkynes suitable for the formation of biologically active triazolyl conjugates, here, we chose the CuAAC reaction for attaching the dye to the steroid. An added advantage of the presence of this heterocycle on a steroid core is due to its behavior being similar to that of a peptide bond [ 32 ].…”

Synthesis of Lapachol-Based Glycosides and Glycosyl Triazoles with Antiproliferative Activity Against Several Cancer Cell Lines

“…The combined organic layers were washed with water (3x 25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude classical lapachol glycosides obtained from D-glucose (5), D-galactose (14), D-Nacetylglucosamine ( 15) and L-fucose (16) were purified by recrystallization from methanol. UPLC purity = 98%, tR = 6.95 min; HRMS (ESI + ) m/z calcd for C29H33O12 573.20, found 573.25 (M+H + ).…”

“…4. Besides classical glycosides, obtained by direct glycosylation, one strategy widely used to link a carbohydrate moiety to a natural or synthetic compound is the Cu(I)-catalyzed cycloaddition reaction between an alkyne derivative of the compound with a glycosyl azide, to get glycosyl triazoles [16]. Based on this, several glycosyl triazoles derived from naphthoquinones with antitumor activity are described in the literature (Fig.…”

“…The combined organic layers were washed with water (3x 25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude classical lapachol glycosides obtained from D-glucose (5), D-galactose(14), D-Nacetylglucosamine(15) and L-fucose(16) were purified by recrystallization from methanol.4.2.1.1 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-(3-methyl-2-butenyl)-1,4-naphthoquinone (5). Yield: 60%; mp 60.2 -66.9 ºC (Lit: 62-65 °C) [13]; [α]D 20 -114.3 (c 0.42; CHCl3); IR max 2939, 1748, 1667, 1592, 1573, 1213, 1035 cm -1 ; 1 H NMR (CDCl3, 400 MHz) δ 1.66 (3H, s, CH3, H-15'), 1.79 (3H, s, CH3, H-14'), 1.98−2.12 (12H, s, CH3, CH3CO), 3.29 (1H, dd, J = 7.0, 13.1 Hz, H-11'a), 3.37 (1H, dd, J = 7.7, 13.1 Hz, H-11'b), 3.76 (1H, ddd, J = 2.4, 4.6, 10.0 Hz, H-5), 4.06 (1H, dd, J = 2.2, 12.4 Hz, H-6a), 4.21 (1H, dd, J = 4.7, 12.4 Hz, H-6b), 5.10 (1H, t, J = 7.2 Hz, H-12'), 5.15 (1H, d, J = 9.6 Hz, H-4), 5.26 (1H, dd, J = 7.8 Hz, 9.4 Hz, H-2), 5.33 (1H, t, J =9.3 Hz, H-3), 5.82 (1H, d, J = 7.7 Hz, H-1), 7.68-7.73 (2H, m, H-6'and H-7'), 8.03-8.08 (2H, m, H-5'and H-8'); 13 C NMR (CDCl3, 100 MHz) δ 18.0 (CH3, C-14'), 20.6-20.7 (CH3, CH3CO), 23.4 (CH2, C-11'), 25.8 (CH3, C-15'), 61.6 (CH2, C-6), 68.3 (CH, C-4), 71.7 (CH, C-2), 72.2 (CH, C-5), 72.7 (CH, C-3), 99.1 (CH, C-1), 119.3 (CH, C-12'), 126.1 (CH, C-5'), 126.5 (CH, C-8'), 131.3 (C, C-10'), 132.0 (C, C-9'), 133.5 (CH, C-6'), 134.0 (CH, C-7'), 134.2 (C, C-13'), 137.7 (C, C-3'),152.5 (C, C-2'), 169.4-170.5 (C, COCH3),181.0 (CO, C-4'), 184.9 (CO, C-1'); UPLC purity = 98%, tR = 7.00 min; HRMS (ESI + ) m/z calcd for C29H33O12 573.20, found 573.25 (M+H + ).…”

Steroid Conjugates as Potential Anti-Cancer Agents

“…В исследовании B. Bodnár и соавт. синтезировали 14 конъюгатов D-секоэстрона (содержащего 13-гидроксиметильную или 13-оксиминометильную группу) с О-ацильными производными α-и β-глюкопиранозидов, α-и β-маннопираноз, α-и β-галактопиранозидов и α-и β-рибопираноз [94].…”