Studies on the studies of nitrophenothiazines by smiles rearrangement behaviour of halonitrobenzenes with -aminothiophenol

A forward chemical genetic approach was followed to discover new targets and lead compounds for Parkinson's disease (PD) treatment. By analysis of the cell protection produced by some small molecules, a diphenyl sulfide compound was revealed to be a new phosphodiesterase 7 (PDE7) inhibitor and identified as a new hit. This result allows us to confirm the utility of PDE7 inhibitors as a potential pharmacological treatment of PD. On the basis of these data, a diverse family of diphenyl sulfides has been developed and pharmacologically evaluated in the present work. Moreover, to gain insight into the safety of PDE7 inhibitors for human chronic treatment, we evaluated the new compounds in a surrogate emesis model, showing nonemetic effects.

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“…Purification: ethyl acetate:hexane (3:17). Yield: yellow solid (268.1 mg, 60%); mp 121–122 °C (lit . 122.0 °C).…”

Section: Methodsmentioning

confidence: 99%

Modulation of cAMP-Specific PDE without Emetogenic Activity: New Sulfide-Like PDE7 Inhibitors

et al. 2014

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Synthesis of 3‐substituted 7‐(3,3‐dimethyl‐1‐triazeno)‐10‐methylphenothiazines as potential antitumor agents

Lin¹,

KASINA

1981

Journal of Heterocyclic Chem

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A series of 3‐substituted (chloro, bromo, fluoro or methyl) 7‐(3,3‐dimethyl‐1‐triazeno)‐10‐methylphenothiazines were synthesized as potential antitumor agents. Treatment of p‐substituted anilines with ammonium thiocyanate in the presence of bromine gave 6‐substituted 2‐aminobenzthiazoles which, after methylation with methyl iodide were hydrolyzed in 50% potassium hydroxide to give 5‐substituted 2‐methylaminothiophenols in moderate yield. Condensation of methylaminothiophenols with 3,4‐dichloronitrobenzene in ethanol under an atomsphere of nitrogen gave adducts which were cyclized in dimethylformamide under the catalysis of copper and cuprous iodide to give 3‐substituted 7‐nitro‐10‐methylphenothiazines. The nitro group was reduced to the amino function with stannous chloride. Diazotization of the amines followed by coupling with dimethylamine gave the corresponding triazenes.

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Synthesis of heterocyclic systems on the basis of intramolecular nucleophilic substitution of a nitro group (review)

Migachev¹,

Danilenko²

1982

Chem Heterocycl Compd

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Studies on the studies of nitrophenothiazines by smiles rearrangement behaviour of halonitrobenzenes with -aminothiophenol

Cited by 7 publications

References 8 publications

Modulation of cAMP-Specific PDE without Emetogenic Activity: New Sulfide-Like PDE7 Inhibitors

Modulation of cAMP-Specific PDE without Emetogenic Activity: New Sulfide-Like PDE7 Inhibitors

Synthesis of 3‐substituted 7‐(3,3‐dimethyl‐1‐triazeno)‐10‐methylphenothiazines as potential antitumor agents

Synthesis of heterocyclic systems on the basis of intramolecular nucleophilic substitution of a nitro group (review)

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