ChemInform Abstract: SYNTH. UND UNTERSUCHUNG VON 2‐(ALKOXYPHENYLMERCAPTO)‐AETHANTHIOLEN

Kuliev, A. M.; Gyul'akhmedov, L. M.; Kuliev, A. B.; Zeinalova, G. A.

doi:10.1002/chin.197116294

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“…The compound was purified by bulb-to-bulb distillation (105-110 °C/0.1 Torr) (lit. 33 bp 130-132 °C/0.4 mm) and had mp 36-37 °C. 1 H NMR (500 MHz, CDCl3): δ 6.83 (d, 1H, J ) 3.0 Hz, ArH), 6.77 (d, 1H, J ) 9.0 Hz, ArH), 6.67 (dd, 1H, J ) 6.0 Hz, J′ ) 3.0 Hz, ArH), 3.84 (s, 3H, OCH3), 3.78 (s, 3H, OCH3), 2.89 (t, 2H, J ) 7.0 Hz, CH3(CH2)2CH2S), 1.67 (quintuplet, 2H, J ) 7.0 Hz, CH3-CH2CH2CH2S), 1.48 (sextuplet, 2H, J ) 7.0 Hz, CH3CH2-(CH2)2S), 0.93 (t, 3H, J ) 7.0 Hz, CH3(CH2)3S).…”

Section: Methodsmentioning

confidence: 99%

Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors: Biological Activities, CoMFA Analysis, and Active Site Modeling

et al. 2005

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A series of phenethylamine derivatives with various ring substituents and with or without N-methyl and/or C-alpha methyl or ethyl groups was synthesized and assayed for their ability reversibly to inhibit monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). Several compounds showed potent and selective MAO-A inhibitory activity (IC(50) in the submicromolar range) but none showed appreciable activity toward MAO-B. A three-dimensional quantitative structure-activity relationship study for MAO-A inhibition was performed on the series using comparative molecular field analysis (CoMFA). The resulting model gave a cross-validated q(2) of 0.72 and showed that in this series of compounds steric properties of the substituents were more important than electrostatic effects. Molecular modeling based on the recently published crystal structure of inhibitor-bound MAO-A provided detailed evidence for specific interactions of the ligands with the enzyme, supported by previous references and consistent with results from the CoMFA. On the basis of these results, structural determinants for selectivity of substituted amphetamines for MAO-A are discussed.

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Section: Methodsmentioning

confidence: 99%

Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors: Biological Activities, CoMFA Analysis, and Active Site Modeling

et al. 2005

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ChemInform Abstract: SYNTH. UND UNTERSUCHUNG VON 2‐(ALKOXYPHENYLMERCAPTO)‐AETHANTHIOLEN

Abstract: Durch Reaktion mit Na‐thiosulfat in siedendem Äthanol‐Wasser erhält man aus den Arylmercapto‐chloräthanen (I) Gemische der Mercaptane (II) (Ausbeute 51‐56%) mit den Disulfiden (III) (39‐42%).

Cited by 1 publication

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Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors: Biological Activities, CoMFA Analysis, and Active Site Modeling

Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors: Biological Activities, CoMFA Analysis, and Active Site Modeling

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