57359-33-8Relevant academic research and scientific papers
Heterocyclic and phenyl double-bond-locked combretastatin analogues possessing potent apoptosis-inducing activity in HL60 and in MDR cell lines
Simoni, Daniele,Grisolia, Giuseppina,Giannini, Giuseppe,Roberti, Marinella,Rondanin, Riccardo,Piccagli, Laura,Baruchello, Riccardo,Rossi, Marcello,Romagnoli, Romeo,Invidiata, Francesco Paolo,Grimaudo, Stefania,Jung, M. Katherine,Hamel, Ernest,Gebbia, Nicola,Crosta, Lucia,Abbadessa, Vincenzo,Di Cristina, Antonietta,Dusonchet, Luisa,Meli, Maria,Tolomeo, Manlio
, p. 723 - 736 (2007/10/03)
Two new series of combretastatin (CA-4) analogues have been prepared. The alkenyl motif of CA-4 was replaced either by a five-membered heterocyclic (isoxazoline or isoxazole) or by a six-membered ring (pyridine or benzene). The new compounds have been evaluated for their effects on tubulin assembly and for cytotoxic and apoptotic activities. Five compounds (18b, 20a, 21a, 34b, and 35b) demonstrated an attractive profile of cytotoxicity (IC50 1 μM) and apoptosis-inducing activity but poor antitubulin activity. The isoxazoline derivatives 18b, 20a, and 21a, demonstrated potent apoptotic activity different from that of natural CA-4. Their ability to block most cells in the G2 phase suggests that these compounds could act on targets different from the mitotic spindle. This would indicate activation of both the intrinsic and the extrinsic apoptotic pathways. The data suggest unambiguously that structural alteration of the stilbene motif of CA-4 can be extremely effective in producing potent apoptosis-inducing agents.
Synthesis and pharmacological evaluation of cis-2,3,3a,4,5,6,7,7a-octahydro-3-oxoisoxazolo[5,4-c]pyridine: A structural analogue of the GABA agonist THIP
Nordmann,Graff,Maurer,Gahwiler
, p. 1109 - 1111 (2007/10/02)
The pharmacological activities of the GABA agonist muscimol and its dihydro analogue have been shown to be almost identical. The closely related 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol (THIP) although biologically less active than muscimol, was selected for clinical trials. We report the synthesis of the so far elusive cis-2,3,3a,4,5,6,7,7a-octahydro-3-oxoisoxazolo[5,4-c]pyridine (cis-DH-THIP), which - surprisingly - is devoid of any GABAergic activity.
Acid-Catalyzed Nitronate Cycloaddition Reactions. Useful Syntheses and Simple Transformations of 3-Acyl- and 3-Alkenylisoxazolines
Wade, Peter A.,Amin, Nayan V.,Yen, Hwa-Kwo,Price, David T.,Huhn, George F.
, p. 4595 - 4601 (2007/10/02)
Nitronic esters derived from primary nitro ketones, ethyl nitroacetate, and (phenylsulfonyl)nitromethane react with dipolarophiles in the presence of nonaqueous protic and Lewis acids to give nitrile oxide cycloadducts. α-Nitro ketones, ethyl nitroacetate
