Synthese von Guanidinverbindungen des Diphenylathers. I.

Ito, Genzo

doi:10.1248/cpb1953.5.397

Cited by 4 publications

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“…Among the guanidine derivatives displayed in Table , compounds 4b , 5b , 10b , 25a, 11b , 14a , 14b , ,20a, 15b , 21b , 22b , 23b , 27b , 30d,30e, 28b , and 29b 30d,35a have been prepared before to treat different conditions or as synthetic intermediates to obtain more complex molecules. However, none of them has been tested as α 2 -AR ligands in the human brain to evaluate their potential as antidepressants.…”

Section: Resultsmentioning

confidence: 99%

Guanidine and 2-Aminoimidazoline Aromatic Derivatives as α₂-Adrenoceptor Antagonists, 1: Toward New Antidepressants with Heteroatomic Linkers

et al. 2007

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The efficient preparation and pharmacological characterization of different families of (bis)guanidine and (bis)2-aminoimidazoline derivatives (“twin” and “half” molecules) as potential α2-adrenoceptor antagonists for the treatment of depression is presented. The affinity toward the α2-adrenoceptor of all the compounds prepared was measured in vitro in human brain tissue. Additionally, the activity as agonist or antagonist of those compounds with a pK i larger than 7 was determined in functional [35S]GTPγS binding assays in human brain tissue. Finally, the activity of the most promising compounds was confirmed by means of in vivo microdialysis experiments in rats. Compounds 1, 2b, 3b, 12b, 13b, 17b, 18b, 22b, 25b, 26b, 28b, and 30 showed a good affinity toward the α2-ARs. In general, the 2-aminoimidazoline derivatives displayed higher affinities than their guanidine analogues. Finally and most importantly, compounds 18b and 26b showed antagonistic properties over α2-ARs not only in vitro [35S]GTPγS binding but also in vivo microdialysis experiments. Moreover, both compounds have shown to be able to cross the blood−brain barrier and, therefore, they can be considered as potential antidepressants.

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Section: Resultsmentioning

confidence: 99%

Guanidine and 2-Aminoimidazoline Aromatic Derivatives as α₂-Adrenoceptor Antagonists, 1: Toward New Antidepressants with Heteroatomic Linkers

et al. 2007

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Preparation and properties of aromatic polyamide‐esters from aminophenols and aromatic diacid chlorides

Imai¹,

Abe²,

Ueda³

1981

J. Polym. Sci. Polym. Chem. Ed.

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Aromatic polyamide‐esters of moderately high molecular weight were prepared from various combinations of three aminophenols (m‐ and p‐aminophenol, and 4‐(4′‐aminophenoxy) phenol) and two aromatic diacid chlorides (isophthaloyl and terephthaloyl) by interfacial polycondensation in a cyclohexanone/water system and two‐phase polycondensation in a dichloromethane/water system with phase‐transfer catalysts. The solution polycondensation in dichloromethane/N,N‐dimethylacetamide was also successful for the production of high‐molecular‐weight polymers. The solubility of the aromatic polyamide‐esters varied markedly with polymer structure. Except for two polyamide‐esters derived from terephthaloyl chloride, all the other polymers were almost amorphous. These polymers had glass transition temperatures at around 200°C and showed 10% weight losses at about 400°C in both air and nitrogen atmospheres.

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Poly(arylether amides) and poly(aryletherketone amides) via aromatic nucleophilic substitution reactions of self‐polymerizable AB and AB₂ monomers

Baek

Harris

2003

J. Polym. Sci. A Polym. Chem.

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Two new extended self-polymerizable AB monomers, N-(4-fluorobenzoyl)-4-amino-4Ј-hydroxydiphenylether and N-(4-fluorobenzoyl)-4-amino-4Ј-hydroxybiphenyl, were prepared. The monomers were homopolymerized and copolymerized to highmolecular-weight, linear poly(arylether amides) in N-methylpyrrolidone (NMP)/toluene in the presence of potassium carbonate at elevated temperature. The polymers retained NMP up to 200°C. Samples containing small amounts of the solvent (5-10 wt %) were soluble in polar aprotic solvents. However, after complete removal of the NMP, the polymers were only soluble in strong acids such as sulfuric acid and methanesulfonic acid (MSA). The polymers, which had intrinsic viscosities of 0.57-1.49 dL/g (30.1 Ϯ 0.1°C in MSA), were semicrystalline with melting temperatures above 400°C. Two new self-polymerizable AB 2 amide monomers, N,NЈ-bis(4-fluorobenzoyl)-3,4-diamino-4Ј-hydroxydiphenylether and N,NЈ-bis(4-fluorobenzoyl)-3,5-diamino-4Ј-hydroxybenzophenone, were also prepared and polymerized to give a hyperbranched poly(arylether amide) and a hyperbranched poly(aryletherketone) amide. The arylfluoride-terminated, amorphous polymers had intrinsic viscosities of 0.34 and 0.24 dL/g (30.0 Ϯ 0.1°C in m-cresol), glass-transition temperatures of 210 -269°C, and were soluble in a wide variety of organic solvents. Matrix-assisted laser desorption/ionization time-of-flight analysis indicated that the components of the low-molecular-weight fractions contained cyclic structures.

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Synthese von Guanidinverbindungen des Diphenylathers. I.

Cited by 4 publications

References 0 publications

Guanidine and 2-Aminoimidazoline Aromatic Derivatives as α₂-Adrenoceptor Antagonists, 1: Toward New Antidepressants with Heteroatomic Linkers

Guanidine and 2-Aminoimidazoline Aromatic Derivatives as α₂-Adrenoceptor Antagonists, 1: Toward New Antidepressants with Heteroatomic Linkers

Preparation and properties of aromatic polyamide‐esters from aminophenols and aromatic diacid chlorides

Poly(arylether amides) and poly(aryletherketone amides) via aromatic nucleophilic substitution reactions of self‐polymerizable AB and AB₂ monomers

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Synthese von Guanidinverbindungen des Diphenylathers. I.

Cited by 4 publications

References 0 publications

Guanidine and 2-Aminoimidazoline Aromatic Derivatives as α2-Adrenoceptor Antagonists, 1: Toward New Antidepressants with Heteroatomic Linkers

Guanidine and 2-Aminoimidazoline Aromatic Derivatives as α2-Adrenoceptor Antagonists, 1: Toward New Antidepressants with Heteroatomic Linkers

Preparation and properties of aromatic polyamide‐esters from aminophenols and aromatic diacid chlorides

Poly(arylether amides) and poly(aryletherketone amides) via aromatic nucleophilic substitution reactions of self‐polymerizable AB and AB2 monomers

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Product

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Guanidine and 2-Aminoimidazoline Aromatic Derivatives as α₂-Adrenoceptor Antagonists, 1: Toward New Antidepressants with Heteroatomic Linkers

Guanidine and 2-Aminoimidazoline Aromatic Derivatives as α₂-Adrenoceptor Antagonists, 1: Toward New Antidepressants with Heteroatomic Linkers

Poly(arylether amides) and poly(aryletherketone amides) via aromatic nucleophilic substitution reactions of self‐polymerizable AB and AB₂ monomers