Synthesis of 7-bromo, 7-phenylethynyl, 7-azido, and 7-nitro derivatives of N-acetyl-1,3a,4,8b-tetrahydrocyclopenta[b]indole

Synthesis of (1′S*,2R*,3R*)‐ and (1′S*,2R*,3S*)‐N‐arylsulfonyl‐2‐(1′‐halogenethyl)‐3‐methylindolines and their selective toxicity against SH‐SY5Y cell line

“…After appropriate treatment of the reaction mixture, 1.2 g of a crude residue was obtained, from which the compound trans-4a was isolated by chromatography on a silica gel column ( sulfonyl]indoline (cis-4d) was obtained according to the previously described procedure. [19] Colorless needles were crystallized from EtOH, m. p. (20). 1 H NMR spectral data corresponded to those described in the work.…”

“…Yield 11 g (78%). MS, (20 Tosylchloride (0.57 g, 3 mmol) was added to a solution of compound 1a [18] (0.65 g, 2.7 mmol) in dry pyridine (2 ml). The reaction mixture was kept for 24 hours at 20 C. Water (30 ml) was added and mixed for 30 minutes.…”

“…[19] At the same time, the contribution of substituents with other electronic effects at the aromatic ring on the ratio of isomers remains poorly studied. [20] Second, it is curious and informative to compare the biological activity of 2-(1-haloethyl)indoline derivatives differing only in configuration at the C-3 atom. Since the antiproliferative activity in products of the halogencyclization of tosylsubstituted ortho-alkenylanilines was found for the first time, their biological effectiveness is practically unexplored.…”