= seven.three Hz), 2.79 (4H, s), five.93 (2H, s), 9.84 (2H, brs), 10.12 (2H, brs) ppm; 13C
= seven.three Hz), two.79 (4H, s), 5.93 (2H, s), 9.84 (2H, brs), 10.12 (2H, brs) ppm; 13C NMR data in Table 2; UV-Vis information in Table four; CD information in Table 8.NIH-PA Writer Manuscript NIH-PA Writer Manuscript NIH-PA Author ManuscriptMonatsh Chem. Author manuscript; available in PMC 2015 June 01.Pfeiffer et al.Web page(4Z,15Z)-2,2 -(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 Author Manuscript NIH-PA Author Manuscript2,2-(one,2-Ethanediyl)bis[5-(ethoxycarbonyl)-4-methyl-1H-pyrrole-3-butanoic acid] (14686 mg, 1.53 mmol) was dissolved in 30 cm3 CH3OH in a 100 cm3 round bottom flask to which 662 mg 5-(bromomethylene)-3-pyrrolin-2-one (153.07 mmol) and 3 drops aq. HBr were added. The resulting mixture was stirred and heated at reflux for twenty h, for the duration of which a green solid created inside the reaction mixture. The strong was isolated by filtration and characterized as the preferred solution 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 = 7.0 Hz), two.10 (6H, s), two.32 (4H, q, J = seven.two Hz), two.41 (4H, t, J = seven.2 Hz), two.52 (3H, t, J = seven.two Hz), 3.twelve (4H, s), three.70 (6H, s), five.86 (2H, s), 10.27 (2H, brs), eleven.03 (2H, brs) ppm; 13C NMR information in Table one. (4Z,15Z)-2,two -(1,2-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 30 cm3 THF below an N2 environment. Then 14 mg DDQ (0.061 mmol) in 5 cm3 THF was added, and the mixture was stirred for 60 min. The response mixture was then poured into 100 cm3 ice-cold water 5-HT6 Receptor Modulator site 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 over sodium sulfate, and evaporated to offer crude 3e. The crude product was purified applying radial chromatography employing 99:1 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: = 1.ten (6H, t, J = 7.5 Hz), one.95 (6H, s), two.05 (6H, s), 2.50 (4H, q, J = 7.2 Hz), two.50 (4H, t, J = 7.five Hz), two.80 (4H, t, J = 7.5 Hz), 3.60 (6H, s), 5.90 (2H, s), 6.90 (2H, s), ten.20 (2H, brs), 10.30 (2H, brs) ppm; 13C NMR information in Table three; UV-Vis data in Table 5; FABHRMS: precise mass calculated for C36H44N4O6 628.3261, located 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 twenty mg one (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 as soon as, plus the option was allowed to stir for thirty min (on addition of the DDQ the option quickly ROCK1 Molecular Weight turned a blue colour). The resolution was poured into 50 cm3 ice water containing one hundred mg ascorbic acid, and also a precipitate formed. The precipitate was separated and washed by centrifugation and isolated by filtration. The solid was dried (high vacuum), dissolved in CH2Cl2:CH3OH (90:ten by vol), and eluted through a column of silica making use of 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.