NMR ((CD3)2SO): = 1.07 (6H, t, J = seven.3 Hz), one.77 (6H, s), 2.04 (6H, s
NMR ((CD3)2SO): = one.07 (6H, t, J = 7.3 Hz), 1.77 (6H, s), two.04 (6H, s), 2.33 (4H, t, J = seven.3 Hz), two.51 (4H, q, J = seven.three Hz), 2.76 (3H, t, J = 7.3 Hz), five.94 (2H, s), six.88 (2H, s), 10.17 (2N-H, bs), 10.28 (2N-H, bs), 12.twenty (2COOH, vbs) ppm; 13C NMR ((CD3)2SO): = eight.61, 9.68, 15.33, 17.63, 20.00, 35.63, 97.23, 113.41, 123.57, 124.04, 124.17, 125.79, 129.86, 132.54, 147.fifty five, 172.56, 174.40 ppm; UV-Vis information in Table five.Monatsh Chem. αvβ6 manufacturer Author manuscript; offered in PMC 2015 June 01.Pfeiffer et al.Web page(4Z,15Z)-2,two -(one,2-Ethenediyl)bis[5-[(3-ethyl-1,5-dihydro-4-methyl-5-oxo-2H-pyrrol-2ylidine)methyl]-RORα medchemexpress 4-methyl-1H-pyrrole-3-butanoic acid] dimethyl ester (4eC38H48N4O6)NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptHomorubin dimethyl ester 2e (forty mg, 0.061 mmol) was treated as in the synthesis of 3e above to provide crude 4e. The crude item was purified making use of radial chromatography applying CH2Cl2:CH3OH (99:1 by vol). Yield: 28 mg (72 ); m.p.: 264 ; 1H NMR: = 1.ten (6H, t, J = 7.2 Hz), one.70 (4H, quint, J = 7.five Hz), one.90 (6H, s), two.05 (6H, s), 2.thirty (4H, t, J = 7.5 Hz), two.50 4H, q), 2.60 (4H, t, J = 7.five Hz), 3.fifty five (6H, s), 5.95 (2H, s), 6.90 (2H, s), ten.20 (2H, brs), ten.30 (2H, brs) ppm; 13C NMR in Table three; UV-Vis information in Table 5; FAB-HRMS: calcd for C38H48N4O6 [M]+ 656.3574, identified 656.3589. 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-butanoic acid] (4C36H46N4O6) To a option of 20 mg homorubin acid 2 (0.03 mmol) in ten cm3 dry CH3)2SO 17 mg DDQ (0.083 mmol) was added at after, and the remedy was allowed to stir for 15 min. The response mixture was then poured into ice-water and stirred in an ice bath. The resulting solid was then eliminated by suction filtration, dissolved in 10 cm3 CH2Cl2:CH3OH (60:40 by vol), and purified by flash column chromatography on silica gel utilizing CH2Cl2:CH3OH (50:50 by vol) as eluent. The pure fractions were evaporated in vacuo to get pure four. Yield: ten mg (47 ); m.p.: 273 (dec); 1H NMR ((CD3)2SO): = one.ten (6H, t, J = 7.three Hz), one.75 (4H, m), 1.80 (6H, s), two.07 (6H, s), 2.36 (4H, t, J = seven.0 Hz), two.51 (4H, q, J = seven.three Hz), 2.79 (4H, t, J = seven.0 Hz), 5.96 (2H, s), 6.90 (2H, s), ten.sixteen (2H, s), 10.29 (2H, s), twelve.04 (2H, brs) ppm; UV-Vis information in Table 5. (4Z,15Z)-9,9 -(1,2-Ethanediylidene)bis[3-ethyl-1,9-dihydro-2,7-dimethyl-1-oxodipyrrin-8propionic acid methyl ester] (5eC36H42N4O6) Within a 50 cm3 round-bottom flask outfitted having a magnetic stirrer was dissolved 40 mg homorubin dimethyl ester 1e (0.063 mmol) in thirty cm3 THF. To this solution was additional 32 mg DDQ (0.130 mmol). The mixture was stirred for twenty min, then quenched with 75 cm3 water containing 100 mg ascorbic acid, and extracted with 50 cm3 CH2Cl2. The CH2Cl2 extract was washed with twenty cm3 aq. 10 NaHCO3, water (three 20 cm3), and dried more than anhydrous Na2SO4. The CH2Cl2 was eliminated (rotovap), along with the remaining solid was purified working with radial chromatography (CH2Cl2:CH3OH, 97:3 by vol), leading to 5e as a violet solid. Yield: 30 mg (76 ); m.p.: 260 (dec); IR (KBr): V = 3436, 2954, 2919, 2355, 1701, 1648, 1625, 1601 cm-1; 1H NMR: = 1.twenty (6H, t, J = 7.3 Hz), 1.95 (6H, s), 2.ten (6H, s), two.53 (4H, q, J = 7.3 Hz), two.61 (4H, t, J = 7.2 Hz), two.90 (4H, t, J = 7.2 Hz), three.67 (6H, s), five.88 (2H, s), seven.75 (2H, s), 10.five (2N-H, bs) ppm; 13C NMR in Table three; UV-Vis information in Table 5; FAB-HRMS: precise mass calculated for C36H44N4O6 626.3104, located 626.3084. In a separate experiment, forty mg homorubin d.