65 (ddd, 1H, J = 8.3, 1.6 and 0.7 Hz), C NMR (CDCl 3 ) ? 108.2 (CH) ,
58 (ddd, 1H, J = 8.3, 1.6 and 0.7 Hz), C NMR (CDCl 3 ) ? 108.6 (CH) ,
The general procedure using benzothiophene (1a, 0.12 mL, 1.0 mmol) and carbazole (0.17 g, 1.5 mmol, 1.5 equiv) gave 1e (eluent: heptane-AcOEt 70:30) in 32% yield as a pale yellow powder: mp 96 °C; IR (ATR): 717 cm yield as a beige powder: mp 74 °C; IR (ATR): 737, pp.3026-3143, 1017. ,
7 Hz); 13 C NMR (CDCl 3 ) ? 109, p.377 ,
8 (C). 4.2.17. 2-(1-Indazolyl)benzothiophene (1g) The general procedure using benzothiophene (1a, 0.12 mL, 1.0 mmol) and indazole (0.11 g, 1.5 mmol, 1.5 equiv) gave 1g (eluent: heptane) 1171, 1184, CH), pp.3051-3052, 1350. ,
), C NMR (CDCl 3 ) ? 114.5 (CH)CH), p.813, 1996. ,
), 7.3 Hz) 0.9 Hz) C NMR (CDCl 3 ) ? 110.5 (CH)CH)CH), pp.32-39 ,
67 (s, 1H), 8.2 Hz) C NMR (CDCl 3 ) ? 110.4 (CH)CH), pp.52-59 ,
98 (dd, 1H, J = 8.1 and 0.6 Hz), dt, 1H, J = 8.3 and 0.9 Hz), p.1259 ,
CDCl 3 ) ? 114.0 (CH), Hz, vol.133, issue.1257 ,
CDCl 3 ) ? 111.1 (CH), Hz, vol.13, issue.1207, pp.125-132 ,
The antiproliferative activity of the synthesized bis-heterocycles was studied in the A2058 (ATCC ® CRL-11147) cell line. A2058 are highly invasive human epithelial adherent melanoma cells, derived from lymph nodes metastatic cells obtained from a 43 years male patient. They are tumorigenic at 100% frequency in nude mice, and considered as very resistant to anticancer drugs. All cell culture experiments were performed at 37°C. Cells were grown to confluence in 75 cm² flasks in DMEM supplemented with 10% fetal calf serum (FCS) and 1% Penicillin-streptomycin, human melanoma cells ,
10 -5 M solutions. Confluent cells were trypsinized and centrifuged in FCS at 1500 g for 5 min. The supernatant containing trypsin was discarded and the cell pellet was suspended in cell culture medium to obtain a 4.10 4 cell.mL -1 suspension. At Supplementary data associated with this article can be found, in the online version References and notes 1. For reviews, see for example: (a) Schlosser, M. Organometallics in Synthesis For reviews, see: (a), ARKIVOC Organometallics Angew. Chem. Int. Ed. Acc. Chem. Res, vol.2007, issue.42, pp.152-231, 2002. ,
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