Regioselectivity of the Diels-Alder reactions of 2,5,8(1H)-quinolinetriones

Synthesis of Casimiroin and Optimization of Its Quinone Reductase 2 and Aromatase Inhibitory Activities

“…This compound was prepared in 80% yield as a colorless solid by following Method B: mp 122–124 °C (lit20 mp 122–123 °C). IR (KBr) 1644, 1593, 1478, 1459, 1437, 1398, 1263 cm −1 ; 1 H NMR (CDCl 3 , 300 MHz) δ 6.98 (d, J = 8.7 Hz, 1 H), 6.58 (d, J = 8.7 Hz, 1 H), 6.41 (s, 1 H), 3.80 (s, 3 H), 3.79 (s, 3 H), 3.77 (s, 3 H), 2.55 (s, 3 H); 13 C NMR (CDCl 3 , 75 MHz) δ 163.8, 152.7, 147.4, 143.2, 133.9, 121.9, 115.4, 104.1, 57.8, 55.8, 36.0, 25.1; EIMS ( m/z , relative intensity) 233 (M + , 52), 218 (100), 203 (38), 190 (34), 175 (68), 147 (14), 132 (10), 118 (12), 91 (8), 77 (7); HRMS calcd for C 13 H 15 NO 3 233.1052, found 233.1056.…”

“…(lit20 99–100 °C). IR (KBr) 3360, 2936, 1617, 1499, 1469, 1227, 1124, 1079, 1044, 1007 cm −1 ; 1 H NMR (CDC1 3 , 300 MHz) δ 6.05 (s, 1 H), 3.90 (s, 3 H), 3.76 (s, 3 H), 3.75 (s, 3 H), 3.73 (s, 3 H); 13 C NMR (CDCl 3 , 75 MHz) δ 149.7, 147.3, 135.7, 134.6, 94.9, 61.3, 61.0, 60.4, 56.0; EIMS ( m/z , relative intensity) 213 (60), 198 (100), 183 (13), 168 (10), 155 (17), 140 (22), 112 (11), 84 (10), 68 (5), 53 (6); HRMS calcd for C 10 H 15 NO 4 213.1001, found 213.0994.…”

“…Yield 80%, colorless solid: mp 69–71 °C (lit20 mp 68.5–69 °C). IR (KBr) 1720, 1658, 1611, 1508, 1464, 1424, 1376, 1310, 1274, 1219, 1181, 1107, 1041, 728 cm −1 ; 1 H NMR (CDCl 3 , 300 MHz) δ 6.81 (m, 2 H), 6.67 (m, 1 H), 3.70 (s, 3 H), 3.69 (s, 3 H), 3.12 (m, 5 H), 2.08 (s, 3 H); 13 C NMR (CDCl 3 , 75 MHz) δ 202.3, 167.3, 153.6, 148.7, 132.0, 114.6, 114.2, 112.5, 55.6, 49.5, 35.9, 29.7; positive ion ESIMS ( m/z , relative intensity) 274 (MNa + , 100), HRMS calcd for C 13 H 17 NO 4 + Na + 274.1055, found 274.1056.…”

Total Syntheses of Cytotoxic, Naturally Occurring Kalasinamide, Geovanine, and Marcanine A

“…Perez et al reported its synthesis several years before the isolation. [5] Azaanthracenones show several biological activities. Soonthornchareonnon et al [4a] reported on the cytotoxicity of marcanine A and its derivitives, which displayed IC 50 values between 80 nm and 2.1 mm against several human tumor cell lines.…”

Totalsynthese der zytotoxischen Naturstoffe Kalasinamid, Geovanin und Marcanin A

“…[3] Marcanin A (2) wurde von Soonthornchareonnon et al [4] 1999 aus Goniothalamus marcani in Thailand isoliert, nachdem Perez et al die Synthese von Marcanin A bereits einige Jahr vor der Isolierung veröffent-licht hatten. [5] Die Azaanthracenone weisen verschiedene biologische Aktivitäten auf. Soonthornchareonnon et al [4a] berichteten über die Zytotoxizität von Marcanin A und seinen Derivaten, die IC 50 -Werte zwischen 80 nm und 2.1 mm gegen verschiedene Krebzelllinien zeigten.…”