Heteroarylisopropylamines as MAO inhibitors

Vallejos, Gabriel; Fierro, Angélica; Rezende, Marcos Caroli; Sepúlveda-Boza, Silvia; Reyes‐Parada, Miguel

doi:10.1016/j.bmc.2005.04.045

Cited by 32 publications

(31 citation statements)

References 22 publications

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“…Triethylamine in anhydrous Et 2 O (0.4 mL) and ethyl chloroformate (0.14 mL) in anhydrous Et 2 O (1 mL) were added to a suspension of 1-(3,4-ethylenedioxyphenyl)-2-aminopropane hydrochloride [19] (0.35 g) in anhydrous Et 2 O (10 mL) and stirred at room temperature under an N 2 atmosphere for 1 h. Reaction mixture was filtered and solvent removed under reduced pressure to afford the corresponding carbamate as a yellow oil (0.3 g, 79%); IR (Diamond, cm −1 ) 3066 (NH), 1754 (N-CO-O-), 1577 (CH 2 CH 2 O). A solution of the above carbamate (0.30 g, 1.13 mmol) in anhydrous THF (12 mL) was added in a dropwise manner at 0 °C to a stirred suspension of LiAlH 4 (0.13 g, 3.40 mmol) in anhydrous THF (12 mL).…”

Section: Methodsmentioning

confidence: 99%

“…A solution of 5 [19] (1.40 g, 6.33 mmol) in glacial AcOH (18 mL) was added in a dropwise manner at room temperature to a stirred suspension of Fe powder (4.80 g, 86.40 mmol) in glacial AcOH (18 mL). The resulting mixture was heated at reflux for 3 h, and then cooled to room temperature.…”

Section: Methodsmentioning

confidence: 99%

“…Compound (±) 3 was synthesized from 1-(3,4-ethylenedioxyphenyl)-2-aminopropane hydrochloride [19], by converting it into its carbamate analog followed by reduction using LiAlH 4 . Compound (±) 4 was synthesized by a nucleophilic substitution reaction using 1-(3,4-ethylenedioxyphenyl)-2-bromo-1-propanone [20] and N -methylamine.…”

Section: Chemistrymentioning

confidence: 99%

“…Reduction of nitroalkene 5 [19] with iron powder followed by heating an aqueous mixture gave the intermediate ketone 6 . The crucial step for this synthesis was the reductive amination using either S (−)- or R (+)-α-methylbenzylamine and sodium triacetoxyborohydride; this reaction selectively afforded S,S (−) 7 and R,R (+) 7 , whose hydrogenation at 50 p.s.i.…”

Section: Chemistrymentioning

confidence: 99%

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Ethylenedioxy homologs of N -methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine

Bello

Sakloth

Partilla

et al. 2015

Bioorganic & Medicinal Chemistry

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N -Methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA; ‘Ecstasy’; 1) and its β-keto analog methylone (MDMC; 2) are popular drugs of abuse. Little is known about their ring-expanded ethylenedioxy homologs. Here, we prepared N-methyl-(3,4-ethylenedioxyphenyl)-2-aminopropane (EDMA; 3), both of its optical isomers, and β-keto EDMA (i.e., EDMC; 4) to examine their effects at transporters for serotonin (SERT), dopamine (DAT), and norepinephrine (NET). In general, ring-expansion of the methylenedioxy group led to a several-fold reduction in potency at all three transporters. With respect to EDMA (3), S(+)3 was 6-fold, 50-fold, and 8-fold more potent than its R(−) enantiomer at SERT, DAT, and NET, respectively. Overall, in the absence of a β-carbonyl group, the ethylenedioxy (i.e., 1,4-dioxane) substituent seems better accommodated at SERT than at DAT and NET.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

See 2 more Smart Citations

Ethylenedioxy homologs of N -methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine

Bello

Sakloth

Partilla

et al. 2015

Bioorganic & Medicinal Chemistry

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“…1) were assayed as possible agents against T. cruzi. We have previously reported the synthesis and NMR characterization of all of the nitropropenes used (Vallejos et al 2005).…”

Section: Methodsmentioning

confidence: 99%

In vitro activity of thienyl-2-nitropropene compounds against Trypanosoma cruzi

Herrera

Vallejos

Loaiza

et al. 2009

Mem. Inst. Oswaldo Cruz

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Identification of (2‐aminopropyl)benzofuran (APB) phenyl ring positional isomers in Internet purchased products

Stanczuk

Morris

Gardner

et al. 2013

Drug Testing and Analysis

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5-(2-Aminopropyl)benzofuran (5-APB), a 'research chemical' that was first reported by UK authorities to the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) in 2010, is anecdotally reported to produce a combination of stimulant and entactogenic effects. More recently, in 2011, 6-(2-aminopropyl)benzofuran (6-APB) was identified by Hungarian authorities. To confirm positional isomer identity in Internet purchased products, 4- 5- 6- and 7-APBs were synthesized and found to be separable by gas chromatography (as heptafluorobutyramide derivatives) and liquid chromatography. The analyses of products purchased from online vendors of 'research chemicals' identified the presence of 5- or 6-APBs. These findings were further confirmed by liquid chromatography-mass spectrometry and (1) H nuclear magnetic resonance spectroscopy. In products containing 6-APB, the 4- positional isomer was also identified and this may have arisen during the manufacturing process.

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Heteroarylisopropylamines as MAO inhibitors

Cited by 32 publications

References 22 publications

Ethylenedioxy homologs of N -methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine

Ethylenedioxy homologs of N -methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine

In vitro activity of thienyl-2-nitropropene compounds against Trypanosoma cruzi

Identification of (2‐aminopropyl)benzofuran (APB) phenyl ring positional isomers in Internet purchased products

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