Tetracyclic benzodiazepines. 4. Synthesis of the novel benzo[c]pyrrolo[1,2,3‐ef][1,5]benzodiazepine ring system, and derivatives with potential antipsychotic activity

Abstract

The synthesis of the novel benzo[c]pyrrolo[1,2,3‐ef][1,5]benzodiazepine ring system is described. This was achieved by cyclization of an appropriately substituted (7‐aminoindolin‐1‐yl)benzamide or benzoic acid. The resulting tetracyclic lactams were reacted with N‐methylpiperazine in the presence of titanium tetrachloride to provide derivatives which were tested for potential antipsychotic activity.

Synthesis and in vitro anti-HIV evaluation of a new series of 6-arylmethyl-substituted S-DABOs as potential non-nucleoside HIV-1 reverse transcriptase inhibitors

“…Flash chromatography separations were obtained on silica gel (300-400 mesh). Compounds 6a-e and 6g were obtained commercially; 3,5-dimethylpheny acetic acid (6f) was synthesized according to the literature procedure [11,12]; and b-ketoesters 7o and p were prepared following the procedure described previously [9]. Ar To a well-stirred solution of substituted diethyl malonate (517 mmol) in anhydrous EtOH (345 mL) was added dropwise a solution of KOH (29 g, 517 mmol) in EtOH (345 mL) at room temperature over 4 h. Then the resulting mixture was allowed to stand at this temperature for 4-12 h until the pH of the final mixture had a value between 7 and 8.…”

Furan ring opening–pyrrole ring closure: a new synthetic route to aryl(heteroaryl)-annulated pyrrolo[1,2-a][1,4]diazepines

“…Chem., 2010, 8, 3316-3327 | 3323 iodide (3.26 g, 23 mmol); eluent: benzene-petroleum ether (1 : 1). Product was isolated as white solid by recrystallization from petroleum ether below 0 • C; 86% (2.72 g); mp 73-74 • C; d H (300 MHz, CDCl 3 ) (two rotamers) 2.24/2.29 (3H, s, Me), 2.77/3.11 (3H, s, NMe), 4.17/4.72 (2H, br s/s, CH 2 ), 5.86/5.94 (1H, d, 3 J = 3.0 Hz, H Fur ), 6.01/6.27 (1H, d, 3 J = 3.0 Hz, H Fur ), m,H Ar ),m,H Ar ),m,H Ar ),m,H Ar ); d C (75 MHz, CDCl 3 ) (two rotamers) 13.5/13.6, 32.3/35.6, 43.2/47.7, 106.2/106.4, 109.7/109.9, 124.6/124.7, 128.2/128.7, 129.7/129.8, 132.9/133, 134.3/134.5, 144.9/145.3, 147.0/147.9, 152.2/152.7, 167.7/167.7; n max (KBr)/cm -1 1648, 1564,1520,1488,1424,1400,1348,1284,1224,1028,800; m/z (EI) 274 (M + , 15%), 257 (22), 150 (10), 134 (15), 123 (82), 104 ( 14), 95 (100), 76 (26), 65 (13), 51 (39), 43 (46); Found: C, 61.68; H, 5.26; N, 10.26. Calc.…”

“…The formed precipitate was filtered off, air-dried and purified by flash chromatography on silica gel using the specified eluent and recrystallized from the specified solvents. 13.9, 34.6, 46.0, 105.1, 109.2, 124.2, 126.1, 129.3, 130.6, 130.8, 131.2, 135.1(2C), 167.7; n max (KBr)/cm -1 1628, 1520,1488,1456,1408,1392,1336,1232,1148,784,760,712; m/z (EI) 226 (M + , 96%), 211 (100), 197 (10), 184 (25), 168 (36), 154 (52), 99 (13)…”

“…Synthesized according to General procedure C from 27a (1 g, 3.79 mmol); 79% (0.7 g); colorless needles; mp 101-102 • C (aq. EtOH); d H (300 MHz, CDCl 3 ) 2.24 (3H, s, Me), 2.92 (2H, br s, NH 2 ), 4.12 (3H, s, Me), 4.49 (2H, d, 3 J = 5.7 Hz, CH 2 ), 5.88 (1H, d, 3 J = 3.0 Hz, H Fur ), 6.11 (1H, d, 3 J = 3.0 Hz, H Fur ), 7.17 (1H, s, H Het ), 8.55 (1H, br t, 3 J = 5.7 Hz, NH); d C (75 MHz, CDCl 3 ) 13.5, 35.8, 40.2, 106.2, 108.1, 127.0, 127.1, 133.1, 149.4, 151.9, 159.9; n max (KBr)/cm -1 3348, 3280,1652,1640,1616,1568,1548,1424,1356,1312,1292,1204,1024,980,912,812; m/z (EI) 234 (M + , 17%), 124 (11), 110 (52), 95 (100), 69 (10), 53 (11),42 (36);Found: C,56.43;H,6.16;N,24. Org. Biomol.…”

Σύνθεση Και Μελέτη Δομής Συμπυκνωμένων Βενζοδιαζεπινικών Παραγώγων Με Πιθανή Βιολογική Δράση

“…Στη βιβλιογραφία αναφέρονται πολλά παραδείγματα 1,5-βενζοδιαζεπινών με βιολογική δράση, οι οποίες έχουν έναν ή δύο ετεροκυκλικούς δακτυλίους σε διαφορετική θέση του επταμελούς δακτυλίου. Είναι γνωστά παραδείγματα αζιρινο-, [77][78][79] πυρρολο-, [80][81][82][83] φουρο-, [84][85][86] βενζοφουρο-, 87 θειενο-, [88][89] πυραζολο-, [90][91][92][93] ιμιδαζολο-, θειαζολο-, [94][95] ισοθειαζολο-, τριαζολο-, [96][97][98][99][100] οξαδιαζολο-, [101][102] πυριδο-, [103][104][105][106][107] κινο, 108 πυρανo-, βενζοπυρανο-, πυριμιδο-, [116][117][118] πυραζινο-, [119][120] κινοξαλινο- [112][113][114][115][116][117][118][119][120]…”