131012-60-7Relevant academic research and scientific papers
New 1,2,4-oxadiazole nortopsentin derivatives with cytotoxic activity
Cascioferro, Stella,Attanzio, Alessandro,Di Sarno, Veronica,Musella, Simona,Tesoriere, Luisa,Cirrincione, Girolamo,Diana, Patrizia,Parrino, Barbara
, (2019)
New analogs of nortopsentin, a natural 2,4-bis(30-indolyl)imidazole alkaloid, in which the central imidazole ring of the natural lead was replaced by a 1,2,4-oxadiazole moiety, and in which a 7-azaindole portion substituted the original indole moiety, were efficiently synthesized. Among all derivatives, prescreened against the HCT-116 colon rectal carcinoma cell line, the two most active compounds were selected and further investigated in different human tumor cells showing IC50 values in the micromolar and submicromolar range. Flow cytometric analysis of propidium iodide-stained MCF-7 cells demonstrated that both the active derivatives caused cell cycle arrest in the G0-G1 phase. The cell death mechanism induced by the compounds was considered to be apoptotic by measuring the exposure of phosphatidylserine to the outer membrane and observed morphological evaluation using acridine orange/ethidium bromide double staining. Moreover, further tested on intestinal normal-like differentiated Caco-2 cell line, they exhibited preferential toxicity towards cancer cells.
Iminoxyl radicals and stable products from the one-electron oxidation of 1-methylindole-3-carbaldehyde oximes
Everett, Steven A.,Naylor, Matthew A.,Stratford, Michael R.L.,Patel, Kantilal B.,Ford, Eleonora,Mortensen, Alan,Ferguson, Amanda C.,Vojnovic, Borivoj,Wardman, Peter
, p. 1989 - 1997 (2007/10/03)
The radical intermediates and the stable products formed on one-electron oxidation of 1-methylindole-3-carbaldehyde oxime 2a were compared with those of 1-methylindole-3-carboxamidine oxime 4a in aqueous solution. The dibromide radical anion generated radiolytically by pulse radiolysis reacted with both 2a and 4a >C=NOH to yield the radical cations [>C=NOH]·+, which exist in prototropic equilibria with the neutral iminoxyl radicals [>C=NO]· (pKa = 3.53 ? 0.03 and 5.01 ± 0.01 at ionic strength 0.05 M, respectively). This was confirmed by the observed primary salt-effect which accelerated the decay of the radical cations but not the iminoxyl radicals. Methylation of the N-hydroxyimino function in both 2a and 4a precluded deprotonation of the corresponding radical cations [>C=NOCH3]·+. At low concentrations of 2a and high dose rates the 2a radicals [>C=NO]· decayed bimolecularly via unstable dimers to the aldehyde >C=O, with higher concentrations and lower dose rates favouring the chain-catalysed isomerisation of the N-hydroxyimino moiety. Radicals from 4a decay bimolecularly to form unstable dimers which degrade to produce an amide, nitrile and carboxylic acid. The observed differences in the oxidation chemistry of 2a and 4a probably reflect the enhanced stabilisation of iminoxyl radicals through α-amino substitution.
SYNTHESIS OF FUNCTIONAL DERIVATIVES OF INDOLE-3-CARBOXYLIC ACIDS
Kelarev, V. I.,Gasanov, S. Sh.,Karakhanov, R. A.,Polivin, Yu. N.,Kuatbekova, K. P.,Panina, M. E.
, p. 2069 - 2074 (2007/10/02)
Methods are described for the synthesis of the esters, hydrazides, amidines, N-phenylamidines, N1-phenylamidrazones, N1-acylamidrazones, and amide oximes of indole-3-carboxylic and 1-methylindole-3-carboxylic acids.
Novel 5-HT3 antagonists. Indole oxadiazoles.
Swain,Baker,Kneen,Moseley,Saunders,Seward,Stevenson,Beer,Stanton,Watling
, p. 140 - 151 (2007/10/02)
The synthesis and biochemical evaluation of a series of indole oxadiazole 5-HT3 antagonists are described. The key pharmacophoric elements have been defined as a basic nitrogen, a linking group capable of H-bonding interactions, and an aromatic moiety. Th
