NMR ((CD3)2SO): = one.07 (6H, t, J = 7.three Hz), 1.77 (6H, s), two.04 (6H, s
NMR ((CD3)2SO): = one.07 (6H, t, J = seven.three Hz), 1.77 (6H, s), 2.04 (6H, s), two.33 (4H, t, J = seven.three Hz), 2.51 (4H, q, J = 7.three Hz), two.76 (3H, t, J = 7.three Hz), five.94 (2H, s), 6.88 (2H, s), ten.17 (2N-H, bs), 10.28 (2N-H, bs), 12.20 (2COOH, vbs) ppm; 13C NMR ((CD3)2SO): = 8.61, 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, 147.55, 172.56, 174.40 ppm; UV-Vis data in Table five.Monatsh Chem. Author manuscript; accessible in PMC 2015 June 01.Pfeiffer et al.Web page(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-butanoic acid] dimethyl ester (4eC38H48N4O6)NIH-PA Author Manuscript NIH-PA Writer Manuscript NIH-PA Author ManuscriptHomorubin dimethyl ester 2e (forty mg, 0.061 mmol) was taken care of as within the synthesis of 3e above to provide crude 4e. The crude item was purified utilizing radial ADAM17 Inhibitor Source chromatography employing CH2Cl2:CH3OH (99:one by vol). Yield: 28 mg (72 ); m.p.: 264 ; 1H NMR: = 1.10 (6H, t, J = 7.2 Hz), one.70 (4H, quint, J = seven.5 Hz), one.90 (6H, s), 2.05 (6H, s), two.30 (4H, t, J = 7.five Hz), 2.50 4H, q), 2.60 (4H, t, J = 7.five Hz), three.55 (6H, s), five.95 (2H, s), six.90 (2H, s), 10.twenty (2H, brs), 10.30 (2H, brs) ppm; 13C NMR in Table three; UV-Vis information in Table five; FAB-HRMS: calcd for C38H48N4O6 [M]+ 656.3574, found 656.3589. 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-butanoic acid] (4C36H46N4O6) To a resolution of 20 mg homorubin acid two (0.03 mmol) in ten cm3 dry CH3)2SO 17 mg DDQ (0.083 mmol) was added at as soon as, and the resolution was permitted to stir for 15 min. The response mixture was then poured into ice-water and stirred in an ice bath. The resulting strong 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 making use of CH2Cl2:CH3OH (50:50 by vol) as eluent. The pure fractions were evaporated in vacuo to get pure 4. Yield: ten mg (47 ); m.p.: 273 (dec); 1H NMR ((CD3)2SO): = one.ten (6H, t, J = seven.3 Hz), one.75 (4H, m), 1.80 (6H, s), two.07 (6H, s), two.36 (4H, t, J = seven.0 Hz), two.51 (4H, q, J = seven.three Hz), two.79 (4H, t, J = 7.0 Hz), five.96 (2H, s), six.90 (2H, s), 10.16 (2H, s), ten.29 (2H, s), 12.04 (2H, brs) ppm; UV-Vis data in Table five. (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 equipped having a magnetic stirrer was dissolved forty mg homorubin dimethyl ester 1e (0.063 mmol) in thirty cm3 THF. To this resolution was additional 32 mg DDQ (0.130 mmol). The mixture was stirred for twenty min, then quenched with 75 cm3 water containing one hundred mg ascorbic acid, and extracted with 50 cm3 CH2Cl2. The CH2Cl2 extract was washed with 20 cm3 aq. ten NaHCO3, water (3 20 cm3), and dried over TXA2/TP list anhydrous Na2SO4. The CH2Cl2 was removed (rotovap), as well as the remaining strong was purified utilizing radial chromatography (CH2Cl2:CH3OH, 97:3 by vol), resulting in 5e like a violet strong. 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.three Hz), 1.95 (6H, s), 2.ten (6H, s), two.53 (4H, q, J = 7.three Hz), 2.61 (4H, t, J = seven.two Hz), two.90 (4H, t, J = 7.two Hz), three.67 (6H, s), five.88 (2H, s), seven.75 (2H, s), 10.five (2N-H, bs) ppm; 13C NMR in Table 3; UV-Vis information in Table five; FAB-HRMS: exact mass calculated for C36H44N4O6 626.3104, located 626.3084. Within a separate experiment, 40 mg homorubin d.