Synthesis and cytotoxic properties of tryptamine derivatives

Salikov, Rinat F.; Belyy, Aleksandr Yu.; Khusnutdinova, Nailya S.; Vakhitova, Yu. V.; Tomilov, Yury V.

doi:10.1016/j.bmcl.2015.06.070

Cited by 13 publications

(5 citation statements)

References 18 publications

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“…As shown in Scheme , ethyl-2-aminopyrimidine-5-carboxylate ( 21 ) on reaction with 17o in the presence of palladium(II) acetate gave intermediate 22 , which on hydrolysis afforded acid precursor 23 . Requisite amines 7a – e (Supporting Information (SI), Figure 1) were synthesized using the known methods, , and they were individually coupled with 23 in the presence of DMAP and EDCI·HCl at 50 °C to furnish the final products 24a – e (Scheme ). Similarly, compound 24f was synthesized using acid 23 and 2-trifluroindole-3-ethanolamine ( 7f ), which was in turn prepared form 2-vinyl-pyrrolidin-2-one (SI Figure 1).…”

Section: Results and Discussionmentioning

confidence: 99%

Potent, Selective, Water Soluble, Brain-Permeable EP2 Receptor Antagonist for Use in Central Nervous System Disease Models

et al. 2020

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Activation of prostanoid EP2 receptor exacerbates neuroinflammatory and neurodegenerative pathology in central nervous system diseases such as epilepsy, Alzheimer’s disease, and cerebral aneurysms. A selective and brain-permeable EP2 antagonist will be useful to attenuate the inflammatory consequences of EP2 activation and to reduce the severity of these chronic diseases. We recently developed a brain-permeable EP2 antagonist 1 (TG6-10-1), which displayed anti-inflammatory and neuroprotective actions in rodent models of status epilepticus. However, this compound exhibited moderate selectivity to EP2, a short plasma half-life in rodents (1.7 h) and low aqueous solubility (27 μM), limiting its use in animal models of chronic disease. With lead-optimization studies, we have developed several novel EP2 antagonists with improved water solubility, brain penetration, high EP2 potency, and selectivity. These novel inhibitors suppress inflammatory gene expression induced by EP2 receptor activation in a microglial cell line, reinforcing the use of EP2 antagonists as anti-inflammatory agents.

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Section: Results and Discussionmentioning

confidence: 99%

Potent, Selective, Water Soluble, Brain-Permeable EP2 Receptor Antagonist for Use in Central Nervous System Disease Models

et al. 2020

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“…Tryptamine (indole‐3‐ethylamine) and its derivatives have high pharmaceutical significance because of their naturally occurring as well as their utility in several drugs . Tryptamine derivatives are used in the treatment of migraine, obesity and behave as antitumor active analogs …”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, biological evaluations, molecular docking, and in vivo studies of novel phthalimide analogs

Zahran

El‐Aarag

Mehany

et al. 2018

Archiv der Pharmazie

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A series of novel phthalimide analogs containing an indole or brominated indole moiety were synthesized and their antimicrobial activity was evaluated. Compound 8 showed a broad spectrum activity, revealing 53-67% of erythromycin activity on the tested bacteria and 60-70% of miconazole activity on the tested fungi. Anticancer activity was evaluated on the cell lines HepG2, MCF-7, A549, H1299, and Caco2. The results revealed that the new phthalimide analog 8 has broad-spectrum anticancer activity toward all the tested cancer cell lines, followed by compound 11, which showed good activity toward all the tested cell lines except for MCF-7. The ability of the promising analogs 5, 8, and 11 to bind to topoisomerase II DNA gyrase was investigated. Caspase-3 activation and Bcl-2 assay of the best active derivatives 8, 11 in addition to compound 5 were evaluated. The antifibrotic activity was studied in an in vivo model and the histopathological studies revealed that treatment with the new compound 8 improved the fibrotic liver tissues to normality.

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“…Tryptamine derivatives possess high potential for the treatment of various diseases ranging from migraine and obesity to tumors. − Nevertheless, the application of many amines in pharmaceutics is limited to a large extent by their ready degradation in an organism by such enzymes as monoamine oxidase . The chain branching in amines is known to be one of the methods to reduce the rate of drug metabolism .…”

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confidence: 99%

“…In the previous studies, we have found that the rearrangement proceeds using cyclopropyl methyl ketone and either arylhydrazine hydrochloride or free arylhydrazine as starting material, the latter requiring addition of ammonium iodide, in either ethanol or acetonitrile. 5,20 The use of arylhydrazine and NH 4 I gave lower yield of desired tryptamines and increased the yield of undesired tetrahydropyridazines. Although the reaction is slower in acetonitrile due to both the poor solubility of starting hydrochloride and its aprotic properties, this protocol is appealing since in most cases the product is separated by filtration.…”

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confidence: 99%

Synthesis of Branched Tryptamines via the Domino Cloke–Stevens/Grandberg Rearrangement

et al. 2016

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The rearrangement of cyclopropylketone arylhydrazones generated in situ from arylhydrazine hydrochlorides and ketones leads to formation of tryptamine derivatives. The use of (2-arylcyclopropyl)ethanones in the reactions with model 4-bromophenylhydrazine hydrochloride gives branched tryptamines with aryl groups in the α-position to the amino group, while (2-methylcyclopropyl)ethanone gives a mixture of α- and β-substituted products in a ratio of 1:3. The method was found effective in the synthesis of enantiomerically pure tryptamine. Thus, (R,R)-(2-phenylcyclopropyl)ethanone gives the (S)-α-phenyltryptamine derivative with an enantiomeric excess over 99%.

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Synthesis and cytotoxic properties of tryptamine derivatives

Cited by 13 publications

References 18 publications

Potent, Selective, Water Soluble, Brain-Permeable EP2 Receptor Antagonist for Use in Central Nervous System Disease Models

Potent, Selective, Water Soluble, Brain-Permeable EP2 Receptor Antagonist for Use in Central Nervous System Disease Models

Design, synthesis, biological evaluations, molecular docking, and in vivo studies of novel phthalimide analogs

Synthesis of Branched Tryptamines via the Domino Cloke–Stevens/Grandberg Rearrangement

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