None), four.1 (t, J = 7.six Hz, 2H, OCH2), 3.8 (s, 3H, OCH3), 1.5 (m, 2H

None), four.1 (t, J = 7.6 Hz, 2H, OCH2), three.eight (s, 3H, OCH3), 1.five (m, 2H, CH2), 1.3 (m, 2H, CH2), 0.8 (t, J = 7.six Hz, 3H, CH3); MS, m/z: 396, 281, 265, 253, 167, 149, 131, 115, 107, 81, 57, 41. Anal. Calcd for C23H24O6: C, 69.68; H, six.ten. Located: C, 69.80; H, 6.37.Synthesis of (E)-methyl 2-(2-((7-methoxy-4-oxo-2H-chromen3(4H)-ylidene)methyl)phenoxy)acetate (5j)A solution of 7-methoxychroman-4-one (4, 100 mg, 0.56 mmol), methyl 2-(3-formylphenoxy)acetate (11b, 109 mg, 0.56 mmol) in anhydrous MeOH (two ml) was stirred at space temperature for 30 min, whilst a stream of HCl gas was introduced. Just after 24 h at room temperature, the precipitation was filtrated, crystallized from methanol to provide compound five k as a pink strong in 79 yield. m.p. 11114 ; IR (KBr, cm-1): 1758 (C = O), 1670 (C = O); 1H NMR (DMSO-d6, 400 MHz) : 7.eight (d, J = eight.eight Hz, 1H, H5-chromanone), 7.7 (s, 1H, CH-vinylic), 7.four (t, J = six.8 Hz, 1H, H6-phenyl), 7.0 (m, 3H, H2 and H4- and H5-phenyl), 6.7 (dd, J = six.8 and 2.0 Hz, 1H, H6chromanone), six.five (d, J = two.0 Hz, 1H, H8-chromanone), five.four (s, 2H, OCH2CO), 4.9 (s, 2H, H2-chromanone), 3.8 (s, 3H, OCH3), three.7 (s, 3H, OCH3); MS, m/z: 354, 281, 178, 167, 150, 122, 107, 79, 69, 57, 43. Anal. Calcd for C20H18O6: C, 67.79; H, 5.12. Identified: C, 67.65; H, 5.33.Cytotoxicity assayThe in-vitro cytotoxic activity of every synthesized compounds 5a-k was assessed working with MTT colorimetric assay according to the literature system [22]. Every set of experiments was independently performed 3 instances. For every compound, the concentration causing 50 cell growth inhibition (IC50) compared together with the manage was calculated from concentration-response curves by regression analysis.Benefits and discussionChemistryA answer of 7-methoxychroman-4-one (4, 100 mg, 0.56 mmol), methyl 2-(2-formylphenoxy)acetate (11a, 109 mg, 0.56 mmol) in anhydrous MeOH (two ml) was stirred at room temperature for 35 min, while a stream of HCl gas was introduced. Following 24 h at room temperature, the precipitation was filtrated, crystallized from methanol to give compound 5j as yellow viscous oil in 32 yield. IR (KBr, cm-1): 1755 (C = O), 1664 (C = O); 1H NMR (CDCl3, 400 MHz) : 7.98 (br s, 1H, H5chromanone), 7.96 (s, 1H, CH-vinylic), 7.35 (d, J = 7.6 Hz, 1H, H3-phenyl), 7.07 (m, 2H, H4- and H5phenyl), 6.Dapansutrile 81 (d, J = eight Hz, 1H, H6-phenyl), 6.Mirvetuximab 62 (d, J = 7.PMID:34235739 six Hz, 1H, H6-chromanone), 6.4 (s, 1H, H8chromanone), five.22 (s, 2H, OCH2CO), 4.7 (s, 2H, H2chromanone), three.8 (s, 3H, OCH3), 3.79 (s, 3H, OCH3); MS, m/z: 354, 295, 281, 265, 151, 131, 77, 67, 57, 43.Reaction sequence employed for the synthesis of (E)-3benzylidene-7-methoxychroman-4-one derivatives 5a-k is shown in Scheme 1. The reaction of resorcinol 1 with 3-chloropropionic acid within the presence of trifluoromethane sulfonic acid furnished 2,4-dihydroxy3-chloropropiophenone (two) which was cyclized applying two M NaOH to offer 7-hydroxy-4-chromanone (three). Compound four was obtained by reacting intermediate three with iodomethane within the presence of potassium carbonate in DMF. Condensation of 7-methoxychroman-4-one (four) with suitable aldehydes 7 and 11 in acceptable alcohol within the presence of gaseous HCl gave the target compounds 5a-k. The corresponding aldehydes 7 and 11 have been prepared as shown in Scheme 2. Chlorination of 3-alkoxy4-hydroxybenzaldehyde 6a,b applying acetic acid as a solvent gave 3-chloro-4-hydroxy-5-alkoxybenzaldehyde 7a,b which was reacted with appropriate alkyl bromoacetate, inside the presence of potassium carbonate to give compoundsNoushini et al. DARU Journal of Ph.