Synthesis of 7-alkylidene-7,12-dihydroindolo[3,2-d]benzazepine-6-(5H)-ones (7-alkylidene-paullones) by N-cyclization–oxidative Heck cascade and characterization as sirtuin modulators

Abstract

An extension of our reported protocol to benzofused heterocyclic derivatives (benzofurans, indoles, isochromeneimines), involving a palladium-induced cascade of N-cyclization and oxidative Heck reactions of o-alkynylanilines, has allowed the preparation of indolobenzazepinones (paullones) with an alkylidene group at C7 in just 3-4 steps from ortho-iodoanilines. Some of these compounds behave as Sirt1 activators in biochemical assays.

Tumour cell population growth inhibition and cell death induction of functionalized 6‐aminoquinolone derivatives

“…Human breast cancer MCF‐7 cells (ATCC) were propagated in Dulbecco's modified Eagle's medium (DMEM) with 10% foetal bovine serum (FBS) (Sigma, St. Louis, MO, USA), 2 m m L‐glutamine (Euroclone, Pero MI, Italy) and antibiotics (100 U/ml penicillin, 100 μg/ml streptomycin) . Cells were stimulated with respective drugs for 24, 48 and 24 h + 24 h (drugs were added again post 24 h stimulation).…”

Nickel(II)- and Silver(I)-Catalyzed C–H Bond Halogenation of Anilides and Carbamates

“…6,135.1,134.2,131.3,122.7,116.4,114.1,40.2,27.5. MS (EI): m/z (%) = 337 (3), 335 (8), 333 (4) 316 (80), 256 (11), 254 (11), 191 (21), 147 (19), 97 (27), 83 (28), 71 (30), 57 (100).…”

5-Substituted 3-chlorokenpaullone derivatives are potent inhibitors of Trypanosoma brucei bloodstream forms

“…Although innovative new paullone syntheses catalyzed by transition metals have been reported lately, [36][37][38][39] we prepared 8 by a traditional acid-induced Fischer indolization procedure 40 for the sake of simplicity. 41 In brief, the synthesis of 8 started by the reaction of methyl 4-chloroanthranilate 4 with methyl succinylcloride.…”