= seven.3 Hz), 2.79 (4H, s), five.93 (2H, s), 9.84 (2H, brs), 10.12 (2H, brs) ppm; 13C
= 7.3 Hz), two.79 (4H, s), five.93 (2H, s), 9.84 (2H, brs), 10.twelve (2H, brs) ppm; 13C NMR PDE2 Formulation information in Table 2; UV-Vis information in Table 4; CD information in Table eight.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptMonatsh Chem. Writer manuscript; accessible in PMC 2015 June 01.Pfeiffer et al.Page(4Z,15Z)-2,two -(1,2-Ethanediyl)bis[5-[(3-ethyl-1,5-dihydro-4-methyl-5-oxo-2H-pyrrol-2ylidine)methyl]-4-methyl-1H-pyrrole-3-butanoic acid] dimethyl ester (2eC38H50N4O6)NIH-PA Writer Manuscript NIH-PA Writer Manuscript NIH-PA Writer Manuscript2,2-(one,2-Ethanediyl)bis[5-(ethoxycarbonyl)-4-methyl-1H-pyrrole-3-butanoic acid] (14686 mg, one.53 mmol) was dissolved in 30 cm3 CH3OH MMP-13 Source inside a one hundred cm3 round bottom flask to which 662 mg 5-(bromomethylene)-3-pyrrolin-2-one (153.07 mmol) and three drops aq. HBr were extra. The resulting mixture was stirred and heated at reflux for 20 h, for the duration of which a green solid created inside the response mixture. The strong was isolated by filtration and characterized as the desired item 2e. Yield: 250 mg (25 ); m.p.: 23940 ; 1H NMR: = 1.09 (6H, t, J = 7.0 Hz), 1.20 (6H, s), 1.85 (4H, quint, J = seven.0 Hz), two.ten (6H, s), 2.32 (4H, q, J = 7.2 Hz), 2.41 (4H, t, J = seven.2 Hz), two.52 (3H, t, J = seven.2 Hz), 3.twelve (4H, s), 3.70 (6H, s), 5.86 (2H, s), ten.27 (2H, brs), eleven.03 (2H, brs) ppm; 13C NMR data in Table 1. (4Z,15Z)-2,2 -(one,2-Ethenediyl)bis[5-[(3-ethyl-1,5-dihydro-4-methyl-5-oxo-2H-pyrrol-2ylidine)methyl]-4-methyl-1H-pyrrole-3-propanoic acid] dimethyl ester (3eC36H44N4O6) Homorubin dimethyl ester 1e (40 mg, 0.063 mmol) was dissolved in thirty cm3 THF beneath an N2 environment. Then 14 mg DDQ (0.061 mmol) in 5 cm3 THF was additional, and the mixture was stirred for 60 min. The reaction mixture was then poured into one hundred cm3 ice-cold water containing 100 mg ascorbic acid. The resulting mixture was extracted with CH2Cl2 (3 75 cm3). The combined CH2Cl2 extractions had been washed with saturated aq. NaHCO3, dried more than sodium sulfate, and evaporated to give crude 3e. The crude item was purified applying radial chromatography working with 99:one CH2Cl2:CH3OH (by vol). Yield: 33 mg (81 ); m.p.: 250 (dec); IR (KBr): V = 3424, 2942, 2355, 1734, 1654, 1625, 1460, 1260, 1160 cm-1; 1H NMR: = one.10 (6H, t, J = seven.five Hz), one.95 (6H, s), two.05 (6H, s), 2.50 (4H, q, J = 7.two Hz), two.50 (4H, t, J = 7.five Hz), two.80 (4H, t, J = 7.five Hz), three.60 (6H, s), five.90 (2H, s), six.90 (2H, s), ten.twenty (2H, brs), 10.30 (2H, brs) ppm; 13C NMR data in Table 3; UV-Vis data in Table 5; FABHRMS: precise mass calculated for C36H44N4O6 628.3261, identified 628.3254. (4Z,15Z)-2,two -(one,2-Ethenediyl)bis[5-[(3-ethyl-1,5-dihydro-4-methyl-5-oxo-2H-pyrrol-2ylidene)methyl]-4-methyl-1H-pyrrole-3-propionic acid] (3C34H40N4O6) In a 25 cm3 round bottom flask 20 mg 1 (0.033 mmol) was dissolved in ten cm3 distilled dimethyl sulfoxide. DDQ (17 mg, 0.083 mmol) in two cm3 dimethyl sulfoxide was additional at after, as well as the resolution was permitted to stir for thirty min (upon addition with the DDQ the answer instantly turned a blue colour). The option was poured into 50 cm3 ice water containing 100 mg ascorbic acid, and also a precipitate formed. The precipitate was separated and washed by centrifugation and isolated by filtration. The solid was dried (higher vacuum), dissolved in CH2Cl2:CH3OH (90:10 by vol), and eluted via a column of silica applying CH2Cl2:CH3OH (93:7 by vol). A deep red compound was collected. The solvent was eliminated providing pure three. Yield: ten mg (50 ); m.p.: 276 ; IR (KBr): V = 3444, 2970, 1669, 1636, 1386, 1265, 1168, 981, 758, 669 cm-1; 1H.
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