= seven.3 Hz), two.79 (4H, s), 5.93 (2H, s), 9.84 (2H, brs), ten.twelve (2H, brs) ppm; 13C
= 7.3 Hz), 2.79 (4H, s), five.93 (2H, s), 9.84 (2H, brs), ten.twelve (2H, brs) ppm; 13C NMR information in Table two; UV-Vis data in Table 4; CD data in Table 8.NIH-PA Writer Manuscript NIH-PA Author Manuscript NIH-PA Writer ManuscriptMonatsh Chem. Writer manuscript; readily available in PMC 2015 June 01.Pfeiffer et al.Web page(4Z,15Z)-2,2 -(one,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 Writer Manuscript NIH-PA Writer Manuscript2,2-(one,2-Ethanediyl)bis[5-(ethoxycarbonyl)-4-methyl-1H-pyrrole-3-butanoic acid] (14686 mg, 1.53 mmol) was dissolved in thirty cm3 CH3OH inside a one hundred cm3 round Nav1.8 manufacturer bottom flask to which 662 mg 5-(bromomethylene)-3-pyrrolin-2-one (153.07 mmol) and 3 drops aq. HBr have been extra. The resulting mixture was stirred and heated at reflux for twenty h, throughout which a green strong developed within the response mixture. The solid was isolated by filtration and characterized because the desired item 2e. Yield: 250 mg (25 ); m.p.: 23940 ; 1H NMR: = 1.09 (6H, t, J = seven.0 Hz), one.twenty (6H, s), one.85 (4H, quint, J = seven.0 Hz), 2.ten (6H, s), 2.32 (4H, q, J = 7.2 Hz), two.41 (4H, t, J = seven.two Hz), 2.52 (3H, t, J = 7.2 Hz), three.twelve (4H, s), 3.70 (6H, s), 5.86 (2H, s), ten.27 (2H, brs), 11.03 (2H, brs) ppm; 13C NMR information 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 30 cm3 THF under an N2 atmosphere. Then 14 mg DDQ (0.061 mmol) in five cm3 THF was extra, plus the mixture was stirred for 60 min. The reaction mixture was then poured into one hundred cm3 ice-cold water containing one hundred mg ascorbic acid. The resulting mixture was extracted with PPAR MedChemExpress CH2Cl2 (three 75 cm3). The combined CH2Cl2 extractions were washed with saturated aq. NaHCO3, dried more than sodium sulfate, and evaporated to provide crude 3e. The crude solution was purified employing radial chromatography utilizing 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), 1.95 (6H, s), 2.05 (6H, s), two.50 (4H, q, J = 7.two Hz), two.50 (4H, t, J = 7.five Hz), two.80 (4H, t, J = 7.five Hz), 3.60 (6H, s), five.90 (2H, s), six.90 (2H, s), 10.twenty (2H, brs), 10.thirty (2H, brs) ppm; 13C NMR data in Table 3; UV-Vis information in Table 5; FABHRMS: precise mass calculated for C36H44N4O6 628.3261, discovered 628.3254. (4Z,15Z)-2,2 -(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) Within a 25 cm3 round bottom flask 20 mg one (0.033 mmol) was dissolved in 10 cm3 distilled dimethyl sulfoxide. DDQ (17 mg, 0.083 mmol) in two cm3 dimethyl sulfoxide was extra at after, as well as the remedy was allowed to stir for 30 min (on addition with the DDQ the remedy immediately turned a blue color). The answer was poured into 50 cm3 ice water containing 100 mg ascorbic acid, as well as a precipitate formed. The precipitate was separated and washed by centrifugation and isolated by filtration. The strong was dried (higher vacuum), dissolved in CH2Cl2:CH3OH (90:10 by vol), and eluted by means of a column of silica applying CH2Cl2:CH3OH (93:seven by vol). A deep red compound was collected. The solvent was removed giving pure 3. Yield: 10 mg (50 ); m.p.: 276 ; IR (KBr): V = 3444, 2970, 1669, 1636, 1386, 1265, 1168, 981, 758, 669 cm-1; 1H.
