= seven.3 Hz), 2.79 (4H, s), five.93 (2H, s), 9.84 (2H, brs), 10.12 (2H, brs) ppm; 13C
= seven.three Hz), 2.79 (4H, s), 5.93 (2H, s), 9.84 (2H, brs), ten.twelve (2H, brs) ppm; 13C NMR data in Table two; UV-Vis information in Table 4; CD information in Table 8.PDE11 drug NIH-PA Writer Manuscript NIH-PA Author Manuscript NIH-PA Writer ManuscriptMonatsh Chem. Author manuscript; obtainable 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 Author 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 thirty cm3 CH3OH in 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 extra. The resulting MGMT Gene ID mixture was stirred and heated at reflux for 20 h, throughout which a green strong created within the response mixture. The solid was isolated by filtration and characterized as the preferred item 2e. Yield: 250 mg (25 ); m.p.: 23940 ; 1H NMR: = 1.09 (6H, t, J = 7.0 Hz), 1.twenty (6H, s), 1.85 (4H, quint, J = 7.0 Hz), two.ten (6H, s), 2.32 (4H, q, J = 7.two Hz), 2.41 (4H, t, J = seven.2 Hz), two.52 (3H, t, J = 7.two Hz), three.twelve (4H, s), 3.70 (6H, s), five.86 (2H, s), ten.27 (2H, brs), 11.03 (2H, brs) ppm; 13C NMR information in Table one. (4Z,15Z)-2,two -(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 beneath an N2 ambiance. Then 14 mg DDQ (0.061 mmol) in 5 cm3 THF was extra, and the mixture was stirred for 60 min. The response 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 mixed CH2Cl2 extractions had been washed with saturated aq. NaHCO3, dried over sodium sulfate, and evaporated to offer crude 3e. The crude solution was purified using radial chromatography working with 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.five Hz), one.95 (6H, s), 2.05 (6H, s), 2.50 (4H, q, J = 7.two Hz), 2.50 (4H, t, J = seven.5 Hz), two.80 (4H, t, J = seven.5 Hz), 3.60 (6H, s), 5.90 (2H, s), six.90 (2H, s), ten.twenty (2H, brs), ten.thirty (2H, brs) ppm; 13C NMR information in Table 3; UV-Vis information in Table 5; FABHRMS: precise mass calculated for C36H44N4O6 628.3261, discovered 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) Within a 25 cm3 round bottom flask twenty mg 1 (0.033 mmol) was dissolved in ten cm3 distilled dimethyl sulfoxide. DDQ (17 mg, 0.083 mmol) in 2 cm3 dimethyl sulfoxide was extra at after, along with the solution was permitted to stir for thirty min (on addition from the DDQ the option straight away turned a blue colour). The answer was poured into 50 cm3 ice water containing one hundred mg ascorbic acid, along with 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 way of a column of silica employing CH2Cl2:CH3OH (93:seven by vol). A deep red compound was collected. The solvent was removed 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.