Novel allocolchicinoids with an eight membered B-ring

Insertion Reactions on Carbopalladated Benzyne: From Eight- to Nine- and Ten-Membered Palladacycles. Applications to the Synthesis of N-Heterocycles

“…A few examples of eight-membered lactams arising from alkene/CO or alkyne/CO sequential insertion reactions into the Pd–C bond have been reported. This method constitutes a new synthetic route to prepare biaryl lactams, which exhibit moderate albeit significant cytotoxicities and may serve as structural models for future medicinal chemistry developments. , Previous syntheses of similar dihydro-dibenzazocinones are carried out by cyclization of o -(2′-carboxylphenyl)­phenylalanine or by azidotrimethylsilane-mediated Schmidt rearrangements using oximes as starting materials …”

“…19,34 Previous syntheses of similar dihydro-dibenzazocinones are carried out by cyclization of o-(2′-carboxylphenyl)phenylalanine 35 or by azidotrimethylsilanemediated Schmidt rearrangements using oximes as starting materials. 36 The organic derivatives 5a and 5b have been characterized by IR and NMR spectroscopy and high-resolution mass spectrometry (HRESIMS). The NMR data support the structures of these compounds, shown in Scheme 5.…”

β-Phenylethylamines and the isoquinoline alkaloids (July 1999 to June 2000)

“…472 The allocolchinoid ketones 241a and 241b have been prepared from the corresponding amines; the former has been demethylated to all four O-demethyl compounds 473 and the oxime of the latter, on Beckmann rearrangement afforded the isomeric lactams 242 and 243. 474 ESR studies have detected a radical anion intermediate in the cathodic reduction of colchicine 475 and a correction has been made to the stereochemistry of the laevorotatory colchinoids and allocolchinoids. 476 The physiological effects of colchicine 477-485 and of thiocolchiside 486 have been studied.…”

Synthesis of indole-derived allocolchicine congeners exhibiting pronounced anti-proliferative and apoptosis-inducing properties

“…Along with several classes of structurally related compounds (e.g. combretastatins [14][15][16][17] and 4-arylcoumarins 18 ), allocolchicine (2) 19 and its analogues [9][10][11][20][21][22][23][24][25][26][27] were identified as promising candidates for further development. Recently, our group reported the synthesis and biological evaluation of a series of heterocyclic allocolchicine congeners (for instance 3 and 4, Fig.…”