522-24-7

Usage

InChI:InChI=1/C16H18N2S/c1-17(2)11-12-18-13-7-3-5-9-15(13)19-16-10-6-4-8-14(16)18/h3-10H,11-12H2,1-2H3

Upstream product

• 92-84-2 10H-phenothiazine 
• 4584-46-7 (2-chloroethyl)dimethylamine hydrochloride 
• 50-00-0 formaldehyd 
• 50971-79-4 2-(10H-phenothiazin-10-yl)ethan-1-amine 
• 18956-87-1 10H-phenothiazine-10-carbonyl chloride 
• 31066-28-1 phenothiazine-10-carboxylic acid-(2-dimethylamino-ethyl ester) 
• 107-99-3 2-(dimethylamino)ethyl chloride 

Downstream Products

• 104295-13-8 2-(3,4-dimethoxyphenyl)-N-methyl-N-(2-phenothiazin-10-ylethyl)ethanamine 
• 311332-89-5 2-(4-methoxyphenyl)-N-methyl-N-(2-phenothiazin-10-ylethyl)ethanamine 

Relevant academic research and scientific papers

Phenothiazine compound as well as preparation method and application thereof

The invention discloses a phenothiazine compound which has the advantages of novel structural general formula and framework, high efficiency, low toxicity and better inhibitory activity on LSD1. The invention also discloses a preparation method of the compound. The preparation method has the characteristics of mild reaction conditions, simplicity in operation and high reaction yield. According to the invention, phenothiazine is taken as a raw material, active groups are respectively introduced to a parent of phenothiazine, and new phenothiazine pharmacophores are synthesized; and phenothiazine compounds are designed and synthesized by modification with piperazine, morpholine, piperidine and other groups. The compound retains the activity of phenothiazine and also has the characteristics of modification groups, so that the biological activity of original molecules is improved, and the anti-tumor activity of target molecules is improved. The invention also discloses an application of the compound in preparation of LSD1-targeted antitumor drugs, and the compound shows good inhibitory activity on LSD1 and shows good development potential.

A Focused Library of Psychotropic Analogues with Neuroprotective and Neuroregenerative Potential

Overcoming the lack of effective treatments and the continuous clinical trial failures in neurodegenerative drug discovery might require a shift from the prevailing paradigm targeting pathogenesis to the one targeting simultaneously neuroprotection and neuroregeneration. In the studies reported herein, we sought to identify small molecules that might exert neuroprotective and neuroregenerative potential as tools against neurodegenerative diseases. In doing so, we started from the reported neuroprotective/neuroregenerative mechanisms of psychotropic drugs featuring a tricyclic alkylamine scaffold. Thus, we designed a focused-chemical library of 36 entries aimed at exploring the structural requirements for efficient neuroprotective/neuroregenerative cellular activity, without the manifestation of toxicity. To this aim, we developed a synthetic protocol, which overcame the limited applicability of previously reported procedures. Next, we evaluated the synthesized compounds through a phenotypic screening pipeline, based on primary neuronal systems. Phenothiazine 2Bc showed improved neuroregenerative and neuroprotective properties with respect to reference drug desipramine (2Aa). Importantly, we have also shown that 2Bc outperformed currently available drugs in cell models of Alzheimer's and Parkinson's diseases and attenuates microglial activation by reducing iNOS expression.

NB 06: From a simple lysosomotropic aSMase inhibitor to tools for elucidating the role of lysosomes in signaling apoptosis and LPS-induced inflammation

Ceramide generation is involved in signal transduction of cellular stress response, in particular during stress-induced apoptosis in response to stimuli such as minimally modified Low-density lipoproteins, TNFalpha and exogenous C6-ceramide. In this paper we describe 48 diverse synthetic products and evaluate their lysosomotropic and acid sphingomyelinase inhibiting activities in macrophages. A stimuli-induced increase of C16-ceramide in macrophages can be almost completely suppressed by representative compound NB 06 providing an effective protection of macrophages against apoptosis. Compounds like NB 06 thus offer highly interesting fields of application besides prevention of apoptosis of macrophages in atherosclerotic plaques in vessel walls. Most importantly, they can be used for blocking pH-dependent lysosomal processes and enzymes in general as well as for analyzing lysosomal dependent cellular signaling. Modulation of gene expression of several prominent inflammatory messengers IL1B, IL6, IL23A, CCL4 and CCL20 further indicate potentially beneficial effects in the field of (systemic) infections involving bacterial endotoxins like LPS or infections with influenza A virus.

Cation Radicals of Phenothiazines. Part 4. Electron Transfer Between Aquamanganase(III) and N-Alkylphenothiazines

The kinetics of electron transfer between aquamanganase(III) and N-alkylphenothiazines, giving rise to the corresponding cation radicals, has been investigated in the range 0.20-1.50 mol dm-3 HClO4 at different temperatures.The main reaction path has been assigned to the unhydrolysed species Mn(3+)(aq), and there is a dependence of the rate constants on the corresponding reduction potentials.