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Brs), 10.12 (2H, brs) ppm; 13C NMR information in Table two; UV-Vis information in Table four; CD information in Table eight.NIH-PA Author RGS19 Inhibitor MedChemExpress manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptMonatsh Chem. Author manuscript; readily 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 Author Manuscript NIH-PA Author Manuscript NIH-PA Author Manuscript2,2-(1,2-Ethanediyl)bis[5-(ethoxycarbonyl)-4-methyl-1H-pyrrole-3-butanoic acid] (14686 mg, 1.53 mmol) was dissolved in 30 cm3 CH3OH within 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 have been added. The resulting S1PR2 Antagonist Gene ID mixture was stirred and heated at reflux for 20 h, through which a green strong developed inside the reaction mixture. The solid was isolated by filtration and characterized as the preferred solution 2e. Yield: 250 mg (25 ); m.p.: 239?40 ; 1H NMR: = 1.09 (6H, t, J = 7.0 Hz), 1.20 (6H, s), 1.85 (4H, quint, J = 7.0 Hz), 2.ten (6H, s), two.32 (4H, q, J = 7.2 Hz), 2.41 (4H, t, J = 7.two Hz), two.52 (3H, t, J = 7.two Hz), three.12 (4H, s), 3.70 (6H, s), 5.86 (2H, s), ten.27 (2H, brs), 11.03 (2H, brs) ppm; 13C NMR data in Table 1. (4Z,15Z)-2,2 -(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 under an N2 atmosphere. Then 14 mg DDQ (0.061 mmol) in five cm3 THF was added, plus the mixture was stirred for 60 min. The reaction mixture was then poured into 100 cm3 ice-cold water containing one hundred mg ascorbic acid. The resulting mixture was extracted with CH2Cl2 (three ?75 cm3). The combined CH2Cl2 extractions have been washed with saturated aq. NaHCO3, dried over sodium sulfate, and evaporated to give crude 3e. The crude item was purified using radial chromatography making use of 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: = 1.10 (6H, t, J = 7.5 Hz), 1.95 (6H, s), two.05 (6H, s), two.50 (4H, q, J = 7.two Hz), 2.50 (4H, t, J = 7.5 Hz), two.80 (4H, t, J = 7.5 Hz), three.60 (6H, s), 5.90 (2H, s), six.90 (2H, s), 10.20 (2H, brs), 10.30 (2H, brs) ppm; 13C NMR information in Table three; UV-Vis information in Table 5; FABHRMS: exact mass calculated for C36H44N4O6 628.3261, found 628.3254. (4Z,15Z)-2,2 -(1,2-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 added at after, as well as the solution was permitted to stir for 30 min (upon addition of the DDQ the solution instantly turned a blue color). The remedy was poured into 50 cm3 ice water containing 100 mg ascorbic acid, plus 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 (90:10 by vol), and eluted via a column of silica utilizing CH2Cl2:CH3OH (93:7 by vol). A deep red compound was collected. The solvent was removed giving pure 3. Yield: ten mg (50 ); m.p.: 276 ; IR (KBr): V = 3444, 2970, 1669, 1636, 1386, 1265, 1168, 981, 758, 669 cm-1; 1H NMR ((CD3)2SO): = 1.07 (6H, t, J = 7.3 Hz), 1.