-
Molecules (Basel, Switzerland) Nov 2022Two unique structures were isolated from the phosphorylation reaction of 10-phenothiazine. The 5,5-dimethyl-2-(10-phenothiazin-10-yl)-1,3,2-dioxaphosphinane 2-oxide ()...
Two unique structures were isolated from the phosphorylation reaction of 10-phenothiazine. The 5,5-dimethyl-2-(10-phenothiazin-10-yl)-1,3,2-dioxaphosphinane 2-oxide () illustrates the product of -phosphorylation of phenothiazine. Moreover, a potential product of instability, a thiophosphoric acid , was successfully isolated and structurally characterized. Molecule , similarly to sulfoxide derivative , possesses interesting phosphorescence properties due to the presence of d-pπ bonds. The X-ray, NMR, and DFT computational studies indicate that compound exhibits an anomeric effect. Additionally, the syntheses of selected symmetrical and unsymmetrical pyridine-embedded phenazines were elaborated. To compare the influence of phosphorus and sulfur atoms on the structural characteristics of 10-phenothiazine derivatives, the high-quality crystals of (4a,12a-dihydro-12-benzo[5,6][1,4]thiazino[2,3-]quinoxalin-12-yl)(phenyl)methanone () and selected phenazines 5,12-diisopropyl-3,10-dimethyldipyrido[3,2-:3',2'-]phenazine () and 5-isopropyl-,3-trimethylpyrido[3,2-]phenazin-10-amine () were obtained. The structures of molecules , , 2-mercapto-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide (), 3,7-dinitro-10-phenothiazine 5-oxide (), and were determined by single-crystal X-ray diffraction measurements.
Topics: Density Functional Theory; Phenothiazines; Magnetic Resonance Spectroscopy; Phenazines; Oxides
PubMed: 36364378
DOI: 10.3390/molecules27217519 -
British Medical Journal Oct 1959
Topics: Antipsychotic Agents; Heterocyclic Compounds; Phenothiazines; Trifluoperazine
PubMed: 13856813
DOI: No ID Found -
Research Publications - Association For... 1962
Topics: Chlorpromazine; Manganese; Phenothiazines; Tranquilizing Agents; Trifluoperazine
PubMed: 14023385
DOI: No ID Found -
Psychosomatics 1964
Topics: Antipsychotic Agents; Anxiety; Chlorpromazine; Fluphenazine; Humans; Hypnotics and Sedatives; Mental Disorders; Perphenazine; Phenothiazines; Stress, Physiological; Thioridazine; Toxicology; Trifluoperazine; Triflupromazine
PubMed: 14149372
DOI: 10.1016/s0033-3182(64)72437-1 -
Xenobiotica; the Fate of Foreign... Dec 1978The previously reported N-oxidation products phenothiazine-N-OH, N-O. and -NOOH obtained upon chemical and metabolic oxidation of phenothiazine nuclei are now shown to...
The previously reported N-oxidation products phenothiazine-N-OH, N-O. and -NOOH obtained upon chemical and metabolic oxidation of phenothiazine nuclei are now shown to be the C-oxidation products, 7-hydroxyphenothiazines, phenothiazin-3-ones and phenothiazin-7-ones which have the para-hydroquinoneimino and para-quinoneimino type systems. 2. The metabolism of various 2-substituted phenothiazines in vitro gave mainly ring-hydroxylated metabolites and sulphoxides. The phenolic metabolites were further oxidized to phenothiazones either as metabolites or as 'metabonates'. 3. After metabolism of chlorpromazine, nor1-chlorpromazine and nor2-chlorpromazine in vitro, phenothiazones ('pink compounds') were obtained as N-dealkylated products of the phenolic derivatives 7- or 3-hydroxy compounds. 4. The synthesis and physicochemical characteristics including t.l.c., u.v., g.l.c. and mass spectra of the oxidized phenothiazine nuclei and of 8-(N-methyl-anilino)-2-chlorophenothiazin-7-one are reported.
Topics: Animals; Chemical Phenomena; Chemistry; Chromatography, Thin Layer; Guinea Pigs; Hydroxylation; In Vitro Techniques; Male; Microsomes, Liver; Oxidation-Reduction; Phenothiazines; Rabbits
PubMed: 726516
DOI: 10.3109/00498257809069585 -
The Medical Clinics of North America Mar 1964
Review
Topics: Chlorpromazine; Fluphenazine; Humans; Perphenazine; Pharmacology; Phenothiazines; Prochlorperazine; Promazine; Rauwolfia; Reserpine; Thioridazine; Toxicology; Tranquilizing Agents; Trifluoperazine; Triflupromazine
PubMed: 14149245
DOI: 10.1016/s0025-7125(16)33476-9 -
Journal of Applied Toxicology : JAT Apr 2023In this review, we summarized the current literature on the impact of phenothiazine derivatives on autophagy in vitro. Phenothiazines are antipsychotic drugs used in the... (Review)
Review
In this review, we summarized the current literature on the impact of phenothiazine derivatives on autophagy in vitro. Phenothiazines are antipsychotic drugs used in the treatment of schizophrenia, which is related to altered neurotransmission and dysregulation of neuronal autophagy. Thus, phenothiazine derivatives can impact autophagy. We identified 35 papers, where the use of the phenothiazines in the in vitro autophagy assays on normal and cancer cell lines, Caenorhabditis elegans, and zebrafish were discussed. Chlorpromazine, fluphenazine, mepazine, methotrimeprazine, perphenazine, prochlorperazine, promethazine, thioridazine, trifluoperazine, and novel derivatives can modulate autophagy. Stimulation of autophagy by phenothiazines may be either mammalian target of rapamycin (mTOR)-dependent or mTOR-independent. The final effect depends on the used concentration as well as the cell line. A further investigation of the mechanisms of autophagy regulation by phenothiazine derivatives is required to understand the biological actions and to increase the therapeutic potential of this class of drugs.
Topics: Animals; Antipsychotic Agents; Zebrafish; Promazine; Phenothiazines; Chlorpromazine; Mammals
PubMed: 36165981
DOI: 10.1002/jat.4397 -
Drug Discovery Today Feb 2011Rooted in the early days of organic dye chemistry, the phenothiazine structure and its derivatives have since held a prominent place in pharmacology and biomedicine.... (Review)
Review
Rooted in the early days of organic dye chemistry, the phenothiazine structure and its derivatives have since held a prominent place in pharmacology and biomedicine. Initially used for histochemical stains of plasmodia by Paul Ehrlich, anthelmintic and antibiotic properties of phenothiazines were globally exploited in the 1930s and 1940s. Clinical use of N-substituted phenothiazines as antihistaminics (1940s), sedatives and antipsychotics (1950s) followed and continues to this day. Recently, interest in these structures has re-emerged for a variety of fascinating features in relation to neurodegenerative disease, spearheaded by the unique redox chemistry of phenothiazine--arguably the most potent chain-breaking antioxidant ever identified.
Topics: Drug Discovery; Models, Molecular; Molecular Structure; Phenothiazines; Structure-Activity Relationship
PubMed: 21237283
DOI: 10.1016/j.drudis.2011.01.001 -
Journal of the American Medical... Mar 1958
Topics: Perphenazine; Phenothiazines
PubMed: 13513367
DOI: No ID Found -
Perceptual and Motor Skills Oct 1963
Topics: Antipsychotic Agents; Black People; Chlorpromazine; Fluphenazine; Humans; Phenothiazines; Placebos; Schizophrenic Psychology; Thinking; Thioridazine
PubMed: 14057269
DOI: 10.2466/pms.1963.17.2.511