Aminoalkylamides and Oxazolidinediones1

Shapiro, Seymour L.; Rose, Ira M.; Freedman, Louis

doi:10.1021/ja01521a043

Cited by 14 publications

(4 citation statements)

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“…3-[(1-Benzyl-1-methylamino)propylamine (12f). , N -(4-Bromopropyl)phthalimide (6 g, 22.4 mmol) in xylene (60 mL) was added dropwise to a warm (oil bath temperature ca. 70 °C) solution of N -benzyl- N -methylamine (6.2 mL, 48 mmol) in xylene (60 mL).…”

Section: Methodsmentioning

confidence: 99%

“…The filtrate was decanted and extracted with EtOAc. The organic layer was washed, dried over Na 2SO4, and evaporated under reduced pressure: yellow oil, yield 80%; 1 44,45 N-(4-Bromopropyl)phthalimide (6 g, 22.4 mmol) in xylene (60 mL) was added dropwise to a warm (oil bath temperature ca. 70 °C) solution of N-benzyl-N-methylamine (6.2 mL, 48 mmol) in xylene (60 mL).…”

Section: (B) 5-(1-benzyl-1-methylamino)pentylamine (12h)mentioning

confidence: 99%

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Aminopyridazines as Acetylcholinesterase Inhibitors

et al. 1999

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Following the discovery of the weak, competitive and reversible acetylcholinesterase (AChE)-inhibiting activity of minaprine (3c) (IC50 = 85 microM on homogenized rat striatum AChE), a series of 3-amino-6-phenylpyridazines was synthesized and tested for inhibition of AChE. A classical structure-activity relationship exploration suggested that, in comparison to minaprine, the critical elements for high AChE inhibition are as follows: (i) presence of a central pyridazine ring, (ii) necessity of a lipophilic cationic head, (iii) change from a 2- to a 4-5-carbon units distance between the pyridazine ring and the cationic head. Among all the derivatives investigated, 3-[2-(1-benzylpiperidin-4-yl)ethylamino]-6-phenylpyridazine (3y), which shows an IC50 of 0.12 microM on purified AChE (electric eel), was found to be one of the most potent anti-AChE inhibitors, representing a 5000-fold increase in potency compared to minaprine.1

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Section: Methodsmentioning

confidence: 99%

Section: (B) 5-(1-benzyl-1-methylamino)pentylamine (12h)mentioning

confidence: 99%

Aminopyridazines as Acetylcholinesterase Inhibitors

et al. 1999

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“…M.p. 48–50 °C; 1 H NMR (250 MHz , CDCl 3 ): δ =7.32–7.17 (m, 5 H), 7.11 (bs, 1 H), 4.44 (d, 3 J H,H =6.0 Hz, 2 H), 4.17 (q, 3 J H,H =6.8 Hz, 1 H), 1.45 ppm (d, 3 J H,H =6.8 Hz, 3 H); 13 C NMR (75.5 MHz , CDCl 3 ) δ =174.8 (C), 137.9 (C), 128.7 (CH), 128.6 (CH), 127.6 (CH), 68.4 (CH), 43.1 (CH 2 ), 21.2 ppm (CH 3 );24 ESI MS: m / z 180.1 [ M +1] + .…”

Section: Methodsmentioning

confidence: 99%

Solid‐state polymerization of poly(ethylene terephthalate). III. Thermal stabilities in terms of the vinyl ester end group and acetaldehyde

Kim

Jabarin

2003

J of Applied Polymer Sci

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Poly(ethylene terephthalate) (PET), precursors, and solid-stated samples were evaluated in terms of changing vinyl ester (VE) concentrations. The results obtained through the application of reaction kinetics gave VE contents ranging from 0.7 to 5.5 mmol/kg of PET. As the initial intrinsic viscosity (IV) of the precursor increased, the VE content also increased, representing the different thermal histories of the samples during melt-phase polymerization. The VE contents decreased as the solid-state polymerization (SSP) time increased from 0 to 12 h and as the temperature of SSP increased up to 220°C. A series of acetaldehyde (AA) generation experiments were conducted from 270 to 300°C with samples solid-stated from three precursors with different initial IVs. The rate of AA generation decreased as the final IV of the solid-stated PET increased, and this showed that the SSP process improved the thermal stability of PET. The AA generation rates of samples that had similar final IVs but were solid-stated from different IV precursors were also compared. When the heating temperature was low, the amount and rate of AA generation were higher for samples with higher initial precursor IVs. This tendency, however, became less clear as the generation temperatures increased, probably because interference from the dissociation reactions (occurring between the polymer chains to produce VE) increased with increasing temperature.

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“…In the second step, those intermediates were condensed with 5,5-diphenyl hydantoin and 5-phenyl oxazolidine-2,4-dione to furnish the title compounds 1-6, 7, 8 and 9-14, 15, 16, respectively. 5-Phenyl oxazolidine-2,4-dione and 5,5-diphenyl hydantoin were synthesized in the lab using reported procedures (31)(32)(33)(34). The title compounds were evaluated for anti-MES activity, neurotoxicity and in vivo receptor affinity for 5-HT 1A/2A .…”

Section: Chemistrymentioning

confidence: 99%

Design, synthesis, anticonvulsant screening and 5HT1A/2A receptor affinity of N(3)-substituted 2,4-imidazolidinediones and oxazolidinediones

Dhanawat

Das

Shrivastava

2011

DD&T

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In the present study, a series of N(3)-substituted 2,4-imidazolidinediones and oxazolidinediones derivatives (1-16) were synthesized and tested for anticonvulsant activity using the maximal electroshock seizure test. Affinity towards receptor (5-HT_1A/2A) was also studied. Their neurotoxicity was determined using the rotarod test. Structures of compounds were confirmed by spectroscopic methods. Compounds 1, 2, 5, 7, 9, and 10 exhibited significant anticonvulsant activity as compared to the standard drug phenytoin. Affinity toward receptor (5-HT_1A/2A) was studied in vivo for compounds 1, 2, 5, 7, 9, and 10. Rectal body temperature, lower lip retractions and head twitch responses in Wistar rats/albino mice were determined for this purpose. The tested compounds showed affinity for 5-HT_1A and 5-HT_2A receptors (agonists/antagonists and presynaptic/postsynaptic). Replacement of piperazine by aniline derivatives provides good outcomes in terms of affinity for 5-HT_1A/2A.

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Aminoalkylamides and Oxazolidinediones¹

Cited by 14 publications

References 0 publications

Aminopyridazines as Acetylcholinesterase Inhibitors

Aminopyridazines as Acetylcholinesterase Inhibitors

Solid‐state polymerization of poly(ethylene terephthalate). III. Thermal stabilities in terms of the vinyl ester end group and acetaldehyde

Design, synthesis, anticonvulsant screening and 5HT<sub>1A/2A </sub>receptor affinity of <i>N</i>(3)-substituted 2,4-imidazolidinediones and oxazolidinediones

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