Search results for "Oxindole"
showing 10 items of 31 documents
Regio- and Stereoselective Synthesis of 3-Pyrazolylidene-2-oxindole Compounds by Nucleophilic Vinylic Substitution of (E)-3-(Nitromethylene)indolin-2…
2019
[EN] A highly regio- and stereoselective synthesis of 3-alkylidene-2-oxindoles has been described through a nucleophilic vinylic substitution (SNV) of (E)-3-(nitromethylene)indolin-2-one using pyrazol-3-ones as nucleophiles and Et3N as a base. The reaction affords selectively the Z-isomer when pyrazol-3-ones without substituents at the 4 position are used. While the reaction is E-selective with 4- substituted pyrazolones. The stereoselectivity (up to >20:1) and the yields (up to 98%) are very high under mild reaction conditions.
Asymmetric synthesis of 3,3′-pyrrolidinyl-dispirooxindoles via a one-pot organocatalytic Mannich/deprotection/aza-Michael sequence
2016
Chemical communications 52, 2249-2252 (2016). doi:10.1039/C5CC10057G
Roxindole, a dopamine autoreceptor agonist, in the treatment of major depression
1993
Roxindole is a potent autoreceptor-“selective” dopamine agonist originally developed for the treatment of schizophrenic syndromes. The drug also inhibits 5-HT uptake and has 5-HT1A agonistic actions. In this open clinical trial 12 in-patients suffering from a major depressive episode (DSM-III-R) were treated with roxindole for 28 days in a fixed dosage of 15 mg per day. A reduction of at least 50% in HAMD-17 total scores was observed in 8 out of 12 patients after 4 weeks (mean HAMD-17 reduction of 56% in all patients), while 4 patients did not respond to roxindole treatment. Half of the patients showed a complete psychopathological remission (HAMD-17 <8). Roxindole's onset of antidepressant…
The neuroendocrinological profile of roxindole, a dopamine autoreceptor agonist, in schizophrenic patients
1995
Roxindole is a potent autoreceptor-selective dopamine agonist with additional properties as a serotonin reuptake inhibitor and 5-HT1A agonist. In order to get more insight into its mode of action in various psychiatric populations, we evaluated the effects of subchronic roxindole treatment on pituitary and adrenal hormone secretion, i.e. release of prolactin, thyroid stimulating hormone (TSH), growth hormone (GH), luteinizing hormone (LH), and cortisol. Fifteen schizophrenic patients with positive and negative symptomatology, respectively, were treated with roxindole for 28 days. Both basal and thyrotropin releasing hormone (TRH) -induced prolactin secretion diminished significantly to 26.4…
Roxindole, a dopamine autoreceptor agonist, in the treatment of positive and negative schizophrenic symptoms
1994
Twenty schizophrenic inpatients with either predominantly positive or predominantly negative symptoms were treated with the dopamine autoreceptor agonist roxindole in prospective open clinical trials. There was no antipsychotic effect in the subgroup with positive symptoms, whereas the subgroup with negative symptoms, especially those with the residual type of schizophrenia, showed a moderate but significant 20% reduction in total scores on the Scale for the Assessment of Negative Symptoms.
Asymmetric Synthesis of Spiro-oxindole-ε-lactones through N-Heterocyclic Carbene Catalysis
2018
An unprecedented N-heterocyclic carbene-catalyzed annulation of isatin-derived enals and o-hydroxyphenyl-substituted p-quinone methides as bifunctional reagents has been discovered. The new protocol involves a 1,6-addition of the homoenolate equivalent intermediates to the hydroxy donor-1,6-Michael acceptors and leads to spirocyclic oxindole-ε-lactones in high yields and very good stereoselectivities.
Dopamine Autoreceptor Agonists in the Treatment of Schizophrenia and Major Depression*
1992
Dopamine autoreceptor agonists reduce the firing rate, synthesis, and release of dopamine in dopaminergic neurons by means of a negative feedback mechanism via stimulation of autoreceptors. Moreover, dopamine autoreceptor agonists are able to stimulate supersensitive but not normosensitive postsynaptic receptors. For dopamine autoreceptor agonists, therapeutic effects by readjustment of excessive or deficient dopaminergic function have been postulated for positive and negative schizophrenic symptomatology as well as for subtypes of depressive disorders. Investigations on the therapeutic effects of autoreceptor-nonselective dopamine agonists in schizophrenia or depression have yielded incons…
Direct synthesis of C3-mono-functionalized oxindoles from N-unprotected 2-oxindole and their antileishmanial activity.
2014
A novel approach for the synthesis of unprecedented C3-mono-functionalized indolin-2-ones is reported, starting from 2-oxindole and chalcones. The reactions proceed regioselectively under mild conditions, without di- and tri-alkylated side products. The new compounds have been evaluated in vitro for their antiproliferative effects against the protozoan Leishmania infantum. Interestingly, they appear able to kill L. infantum promastigotes and amastigotes, without significant cytotoxic effects.
Catalytic Enantioselective Addition of Me2Zn to Isatins
2017
Chiral α-hydroxyamide L5 derived from (S)-(+)-mandelic acid catalyzes the enantioselective addition of dimethylzinc to isatins affording the corresponding chiral 3-hydroxy-3-methyl-2-oxindoles with good yields and er up to 90:10. Furthermore, several chemical transformations were performed with the 3-hydroxy-2-oxindoles obtained.
5′-Benzylidene-1′′-methyl-4′′-phenyltrispiro[1,3-dioxolane-2,1′-cyclohexane-3′,3′′-pyrrolidine-2′′,3′′′-indole]-4′,2′′′-dione
2017
In the title compound, C32H30N2O4, two spiro links connect the methyl-substituted pyrrolidine ring to the oxindole and cyclohexanone rings. The cyclohexanone ring is further connected to the dioxalane ring by a third spiro junction. Both the pyrrolidine and dioxalane rings adopt a twist conformation. The indole ring is nearly planar, with a maximum deviation of 0.0296 (7) Å, and the cyclohexanone ring adopts a distorted boat conformation. In the crystal, C—H...O and N—H...N hydrogen-bonding interactions connect molecules into chains running parallel to thebaxis, which are further linked into layers parallel to theabplane by C—H...O hydrogen bonds.