Supplementary Materialsmolecules-24-00766-s001. antiproliferative activity of the GA heterocyclic derivative 10. Attempts are currently underway to elucidate further its mechanism of action. 3. Materials and Methods 3.1. Chemistry Glycyrrhetinic acid and all reagents were purchased from Sigma-Aldrich Co (St. Louis, MO, USA). The solvents used in the reactions were from Merck Co (kenilworth, NJ, USA). and were purified and dried according to the literature methods. The solvents used in workups were purchased from VWR Portugal (Radnor, PA, USA). Thin-layer chromatography (TLC) analysis was performed in Kieselgel 60HF254/Kieselgel 60G. Purification of compounds by adobe flash column chromatography (FCC) was carried out using Kiesegel 60 (230C400 mesh, Merck) (kenilworth, NJ, USA). Melting points were determined using a BUCHI melting point B-540 apparatus and were uncorrected. IR spectra were obtained on a Fourier transform spectrometer. 1H and 13C NMR spectra (observe Supplementary Materials) were recorded on a Bruker Avance-400 Digital NMR spectrometer, in CDCl3,, with Me4Si as the internal standard. Chemical shifts ideals () are given SKQ1 Bromide (Visomitin) in parts per million (ppm) and coupling Mouse monoclonal to EphB6 constants ((2): Compound 2 was prepared according to the books [38], from 1 to provide a white solid (90%). m.p.: 315C317 C. (3): Substance 3 was ready based SKQ1 Bromide (Visomitin) on the books [39], from 1 to provide a colorless solid (90%). m.p.: 254C256 C (4): Substance 4 was ready from 2, using the same technique for the planning of 3, using the obtention of the white solid (88%). m.p.: 239C242 C. (5): Substance 5 was ready based on the books [40], from 3 to provide a white solid (94%). m.p.: 248C250 C. (6): Substance 6 was ready from 4, using the same technique for the planning of 5, using the obtention of the white solid. (92%). m.p.: 185C188 C (7): Substance 7 was ready based on the books [40], from 5 to provide a colorless solid (82%). m.p.: 231C234 C. (8): Substance 8 was ready from 6, using the same technique for the planning of 7, using the obtention of the white solid (80%). m.p.: 136C139 C. (9): To a remedy of substance 7 (300 mg, 0.59 mmol) in anhydrous THF (5 mL), CDI (191 mg, 1.18 mmol) was added. After 4 h under magnetic stirring at reflux heat range and N2 atmosphere, the response was completed. Drinking water (50 mL) and ethyl acetate (50 mL) had been put into the reaction mix. The aqueous stage was additional extracted with ethyl acetate (2 50 mL). The mixed organic remove was then cleaned with drinking water (2 50 mL) and brine (50 mL), dried out over Na2SO4, evaporated and filtered to dryness. The causing solid was put through FCC [petroleum ether/ ethyl acetate from (1:1) to (1:2)] to cover 9 being a white solid. (67%). m.p.: 249C251 C. IR potential/cm?1 (KBr): 3113, 2953, 1728, 1685, 1649, 1601, 1518, 1485, 1458, 1385, 1306, 1028. 1H NMR (400MHz, CDCl3): 7.76 (1H,s), 7.66 (1H, s), 7.33 (1H,s), 7.10 (1H, s), 5.75 (1H, s), 4.19 (1H, d, = 16.5), 3.67 (3H, s), 2.52 (1H, s), 1.39 (3H, s), 1.18 (3H, s), 1.16 (3H, s), 1.13 (6H, s), 1.12 (3H, s), 0.81 (3H, s). 13C NMR (100MHz, CDCl3): 206.2, 199.2, 176.8, 170.6, 139.1, 130.7, 130.3, 128.4, 122.1, 119.0, 59.2, 52.8, 51.7, 48.4, 45.3, 44.8, 44.0, 43.3, 43.2, 41.2, 37.6, 35.9, 31.8, 31.3, 31.0, 29.7, 28.5, 28.2, 26.5, 26.3, 23.1, 22.3, 19.5, 17.9, 15.5. ESI-MS (10): SKQ1 Bromide (Visomitin) The technique followed that defined for substance 9 but using substance 8 (300 mg, 0.60 mmol) and CDI (195 mg, 1.20 mmol) in anhydrous THF (5 mL) at reflux for 5 h. The causing solid was purified by FCC with petroleum ether/ethyl acetate (1:1) and afforded substance 10 being a white solid (60%). m.p.: 151C154 C. IR.