Potential nootropic agents: Synthesis of some (2-oxo-1-pyrrolidinyl)acetamides and some related compounds

1990 ◽  
Vol 55 (11) ◽  
pp. 2756-2764 ◽  
Author(s):  
Vladimír Valenta ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Martin Valchář ◽  
Ivan Krejčí ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Survival Time ◽  
Acetyl Chloride ◽  
The Other ◽  
Anticonvulsant Effect ◽  
Mixed Anhydride ◽  
Ester Exchange ◽  
Nootropic Agents ◽  
The One ◽  
Related Compounds

Ethyl (2-oxo-1-pyrrolidinyl)acetate was transformed by ester exchange to the 2-dimethylaminoethyl ester VI which was converted to the choline iodide ester VII. The mixed anhydride of (2-oxo-1-pyrrolidinyl)acetic acid and monoethyl carbonate was reacted with ethyl aminoacetate to give the ester VIII which was transformed on the one hand to the amide IX, and to the 2-dimethylaminoethyl ester X on the other. Reaction of the latter with methyl iodide afforded a further choline iodide ester XI. Reactions of (2-oxo-1-pyrrolidinyl)acetyl chloride with 4-chloroaniline and 3-aminopyridine gave the amides XII and XIV. The anilide XIII was obtained from 2-(2-oxo-1-pyrrolidinyl)butyric acid and 4-chloroaniline by means of dicyclohexylcarbodiimide. The benzo analogue (XV) of piracetam (I) was synthesized from oxindole via the ester XVI. The anilide XII (V⁄FB-16 536) was found to potentiate significantly the anticonvulsant effect of diazepam in mice, to prolong the survival time of mice under conditions of nitrogen anoxia, and to prolong significantly the duration of the "gasping reflex" in mice.

Pyrimidine Derivatives and Related Compounds, V Synthesis of Some Isoxazolo [2,3-a] pyrimidines. A New Ring System

1977 ◽  
Vol 32 (3) ◽  
pp. 311-314 ◽  
Author(s):  
Mohamed Hilmy Elnagdi ◽  
Ezzat Mohamed Kandeel ◽  
Kamal Usef Sadek
Keyword(s):  
Acetic Acid ◽  
Hydrochloric Acid ◽  
Ethyl Acetoacetate ◽  
Pyrimidine Derivative ◽  
Ring System ◽  
The Other ◽  
Acid Mixture ◽  
Pyrimidine Derivatives ◽  
Benzoyl Isothiocyanates ◽  
Related Compounds

3-Amino-5-phenyl-4-phenylazoisoxazole (1) reacts with ethyl acetoacetate to yield the corresponding ethyl isoxazolylaminocrotonate derivative (2) which could be thermally cyclized into the isoxazolopyrimidine derivative (4). On the other hand, condensation of 1 with ethoxymethylenemalononitrile has resulted in the formation of the aminoethylene derivative (5).Compound 1 reacted with acrylonitrile to yield the isoxazolo[2,3-a]pyrimidine derivative (6). The latter was converted into the corresponding exo derivative (8) by the action of acetic acid-hydrochloric acid mixture.Compound 1 also reacted with methoxycarbonyl-, ethoxycarbomyl- and benzoyl isothiocyanates to yield the isoxazolylthioureas (10a, b) and (11), respectively. The reaction of 2 with acetic acid-hydrochloric acid and with phenylhydrazine is reported.

1-[2-(2-Hydroxymethylphenylthio)benzyl]-4-methylpiperzine and related compounds as potential antidepressants: Synthesis and pharmacological acreening

1984 ◽  
Vol 49 (4) ◽  
pp. 1009-1020 ◽  
Author(s):  
Irena Červená ◽  
Miroslav Protiva
Keyword(s):  
Potassium Carbonate ◽  
Secondary Alcohol ◽  
The Other ◽  
Lithium Aluminium Hydride ◽  
Keto Acid ◽  
Open Model ◽  
Lithium Aluminium ◽  
Neuroleptic Agent ◽  
The One ◽  
Related Compounds

Heating of 1-(2-iodobenzoyl)-4-methylpiperazine (II) with thiophenol and its 2-methyl, 4-methyl, 4-chloro and 2-hydroxymethyl derivatives in dimethylformamide in the presence of potassium carbonate, copper and cuprous iodide gave the piperazides IV-VIII; compound VIII was transformed by reduction with lithium aluminium hydride to the title compound I. The acid IX, obtained by a reaction of 5-chloro-2-iodobenzoic acid with 2-methylthiophenol, was reduced to the alcohol X, which was transformed via the chloride XI to 1-[5-chloro-2-(2-methylphenylthio)-benzyl]-4-methylpiperazine (XII), an open model of the neuroleptic agent clorothepin. Heating of 2,5-dichloroacetophenone with thiosalicylic acid afforded the keto acid XIII whose reaction with 1-methylpiperazine was carried out with the help of N,N"-carbonyldiimidazole. The piperazide XIV obtained was reduced on the one hand with sodium borohydride to the secondary alcohol XV, and with lithium aluminium hydride to 1-(2-[4-chloro-2-(1-hydroxyethyl)phenylthio]benzyl)-4-methylpiperazine (XVI) on the other. None of the dibasic piperazines (I, XII, XVI) did show antireserpine activity. In the general screening, some of the piperazides displayed a mild hypotensive (II, VIII, XIV, XV), adrenolytic (VIII), mild stimulating and antitussic (V), and spasmolytic, antiinflammatory and negatively ino- and chronotropic (XIV) activities.

Pyrimidine Derivatives and Related Compounds, VII Synthesis of Some New Pyrazolo [1,5-a] -S-triazines, Pyrazolo [3,4-c] -as-triazines, Pyrazolo [1,5-a] pyrimidines and Pyrazolo [3,4-b] pyrones

1977 ◽  
Vol 32 (4) ◽  
pp. 430-433 ◽  
Author(s):  
Mohamed Hilmy Elnagdi ◽  
Ezzat Mohamed Zayed ◽  
Ezzat Mohamed Kandeel ◽  
Sherif Mahmoud Fahmy
Keyword(s):  
Acetic Acid ◽  
Hydrochloric Acid ◽  
Sulphuric Acid ◽  
Sodium Ethoxide ◽  
Ethyl Acrylate ◽  
The Other ◽  
Acid Mixture ◽  
Pyrimidine Derivatives ◽  
Triazine Derivative ◽  
Related Compounds

3-Amino-4-phenylhydrazono-2-pyrazolin-5-one (1) reacts with isothiocyanate to yield the corresponding pyrazolylthiourea derivatives (2 a-c). Whereas 2 a reacted with hydrazines to yield the pyrazolylamino-1,2,4-triazoles (3 a, b), it cyclised into the pyrazolo-[3,4-e]-as-triazine derivative (4) upon treatment with concentrated sulphuric acid. On the other hand, the pyrazolo[1,5-c]-S-triazine derivative (5) was formed from reaction of 2a with ethanolic sodium ethoxide.3-Amino-2-pyrazolin-5-one (8) reacted with ethyl acrylate to yield a mixture of the 4-dialkylated derivative (9) and the pyrazolo[3,4-b]pyrone (11). Compound 11 could be converted into the corresponding pyrazolo[3,4-b]pyrones (12) and (13) by the action of acetic acid hydrochloric acid mixture and of concentrated sulphuric acid, respectively.

scholarly journals An Unusual Course of a Nitro Sugar Acetylation: Formation of a Crystalline Nitronic Acid – Acetic Acid Mixed Anhydride

1971 ◽  
Vol 49 (19) ◽  
pp. 3236-3238 ◽  
Author(s):  
Werner Rank ◽  
Hans H. Baer
Keyword(s):  
Acetic Acid ◽  
Acetyl Chloride ◽  
Acetyl Derivative ◽  
Acid Anhydride ◽  
Mixed Anhydride ◽  
Nitronic Acid

Whereas acetylation of methyl 4,6-O-benzylidene-3-deoxy-3-nitro-β-D-mannopyranoside (1) and its β-D-galacto isomer 2 with acetyl chloride and triethylamine in ether furnished the expected 2-O-acetylated nitro glycosides, 1a and 2a, the same method applied to the α-D-talo isomer 3 gave the 2-O-acetyl derivative of the corresponding nitronic acid – acetic acid anhydride, 4.

Hot-Tube Reactions of Dehydroabietic Acid with Ketene-Producing Reagents. Pyrolysis of the Acid Chloride and Symmetrical and Mixed Anhydride Derivatives of Dehydroabietic Acid

1973 ◽  
Vol 51 (19) ◽  
pp. 3236-3241 ◽  
Author(s):  
Ray F. Severson ◽  
Walter H. Schuller
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Acid Chloride ◽  
Acetyl Chloride ◽  
Dehydroabietic Acid ◽  
Mixed Anhydride ◽  
Temperature Range ◽  
Acid Isomerization ◽  
Derivatives Of ◽  
Isopropenyl Acetate

Dehydroabietic acid (1a) was reacted with diketene, acetic acid, acetic anhydride, isopropenyl acetate, acetyl chloride, and acetone on Vycor rod at 450 °C in a hot tube. Dehydroabietic anhydride (1b) and acetyl dehydroabietate (1c) were pyrolyzed at 450 °C and dehydroabietyl chloride (1d) was pyrolyzed over a temperature range of 290–500 °C. The major olefin products resulting from decarboxylation of the various derivatives were 19-norabieta-4,8,11,13-tetraene (2), 19-norabieta-4(18),8,11,13-tetraene (3), 19-norabieta-3,8,11,13-tetraene (4), and cis-1,10a-dimethyl-7-isopropyl-1,2,3,9,10,10a-hexahydrophenanthrene (5). High conversions to these compounds were obtained. In the presence of the ketene-producing reagents the olefins were oxidized to yield substantial amounts of retene (6), compounds 2 and 5 being the most readily dehydrogenated. The acid isomerization of 2, 3, 4, and 5 was studied using p-toluenesulfonic acid in toluene at 110 °C.

GUANIDINE: A SIMPLE MOLECULE WITH GREAT POTENTIAL: FROM CATALYSTS TO BIOCIDES AND MOLECULAR GLUES

INEOS OPEN ◽  
2021 ◽  
Author(s):  
F. V. Drozdov ◽  
◽  
V. M. Kotov ◽  
Keyword(s):  
Smart Materials ◽  
Crucial Role ◽  
Chemical Properties ◽  
Structural Features ◽  
The Other ◽  
Synthetic Drugs ◽  
Guanidine Derivatives ◽  
Living Organisms ◽  
The One ◽  
Related Compounds

This review is devoted to the general methods for obtaining guanidine derivatives and related compounds, their chemical properties, and structural features. On the one hand, guanidine and its derivatives play a crucial role in the metabolism of living organisms. On the other hand, owing to their unique properties and simple synthesis, the guanidine derivatives are used as synthetic drugs and biocidal agents, catalysts, ligands, and sweeteners. Furthermore, the guanidine derivatives serve as a basis for the creation of modern smart materials.

Pyrimidine Derivatives and Related Compounds, IX / Preparation of 5-Aminopyrazolo[1,5-a]pyrimidines and of Oxazino[4,5 : 5,6]pyrazolo[1,5-a]pyrimidines, a New Ring System

1977 ◽  
Vol 32 (12) ◽  
pp. 1478-1481 ◽  
Author(s):  
Mohamed Hilmy Elnagdi ◽  
Sherif Mahmoud Fahmy ◽  
Mohamed Riffaat Hamza Elmoghayar ◽  
Abdalla Mohamed Negm
Keyword(s):  
Acetic Acid ◽  
Pyrimidine Derivative ◽  
Ring System ◽  
The Other ◽  
Reaction Products ◽  
Pyrimidine Derivatives ◽  
Other Hand ◽  
Related Compounds

Whereas the 5-aminopyrazole derivatives (1 a, b) react with ethyl β-amino-β-trichloro-methylmethylenecyanoacetate (2) in basic media to yield the corresponding 5-aminopyrazolo[1,5-a]pyrimidine derivatives (3a, b), the reaction of la, b with 2 in refluxing acetic acid has afforded oxazino[4,5:5,6]pyrazolo[1,5-a]pyrimidine derivatives.5-Amino-3-phenyl-4-phenylazopyrazole (12) reacted with 2 in refluxing pyridine to yield the 5-amino-2-phenyl-3-phenylazopyrazolo[1,5-a]pyrimidine derivative (18). On the other hand, the reaction of 12 and 2 in refluxing acetic acid has afforded a mixture of the oxazino[4,5:5′,6′]pyrazolo[1,5-a]pyrimidine derivatives (14) and the pyrazolo[3,4-d]-astriazine derivatives (15). The mechanism of the formation of reaction products is discussed.

α-Benzyldopamine and some related compounds: Synthesis and pharmacological screening

1984 ◽  
Vol 49 (4) ◽  
pp. 1002-1008
Author(s):  
Vladimír Valenta ◽  
Antonín Dlabač ◽  
Martin Valchář ◽  
Miroslav Protiva
Keyword(s):  
Thionyl Chloride ◽  
Hydrobromic Acid ◽  
The Other ◽  
Methyl Derivative ◽  
Claisen Reaction ◽  
Pharmacological Screening ◽  
The One ◽  
Related Compounds ◽  
Ethyl Phenylacetate ◽  
Antiarrhythmic Effects

Claisen reaction of 3,4-dimethoxyphenylacetonitrile with ethyl phenylacetate, the following stepwise hydrolysis and decarboxylation afforded the amide V 1-(3,4-dimethoxyphenyl)-3-phenylpropan-2-one (VI). Leuckart reaction resulted in the crude formamide derivative IIIb which was subjected to alkaline hydrolysis to the primary amine Ib on the one hand, and to reduction to the secondary amine IIb on the other. Demethylation with hydrobromic acid gave hydrobromides of 1-(3,4-dihydroxyphenyl)-3-phenyl-2-propylamine (title compound Ia) and its N-methyl derivative IIa. The alcohol VII, obtained by reduction of the ketone VI, was transformed by treatment with thionyl chloride to the chloro compound VIII which afforded by substitution reaction with 1-methylpiperazine the piperazine derivative IX. While the methoxylated amines Ib and IIb have mild stimulating and some antiarrhythmic effects, N-methyl-α-benzyldopamine (IIa) displayed a clear dopaminomimetic character.

Pyrimidine Derivatives and Related Compounds, III / Synthesis of Some New Pyrazolo [1,5-a] pyrimidines and Pyrazolo [3,4-d] pyrimidine Derivatives

1976 ◽  
Vol 31 (6) ◽  
pp. 795-800 ◽  
Author(s):  
Mohamed Hilmy Elnagdi ◽  
Sherief Mahmoud Fahmy ◽  
Ezzat Mohamed Zayed ◽  
Mohamed Ajmal Mohamed Ilias
Keyword(s):  
Acetic Acid ◽  
Carbon Disulphide ◽  
Pyrimidine Derivative ◽  
The Other ◽  
Acid Mixture ◽  
Pyrimidine Derivatives ◽  
Other Hand ◽  
Naoh Solution ◽  
Related Compounds ◽  
Hydrazone Derivative

Whereas β-cyanoethylhydrazine (1) reacts with the β-ethoxy-α,β-unsaturated nitriles (2a—c) to yield the 5-amino-1-B-cyanoethylpyrazoles (8a—c), 1 reacts with anilinomethylenemalononitrile (2d) to yield 3-amino-1-B-cyanoethyl-4-cyanopyrazole (4; R=H; X=CN). 3a readily cyclised into the 5-amino-6,7-dihydropyrazolo[1,5-a]pyrimidine derivative (6) by the action of ethanolic guanidine. 6 was readily converted into the oxo derivative (7) by the action of acetic acid. 7 was also obtained by the action of 1% NaOH on 3a. On the other hand, 3b afforded a mixture of the pyrazolo[1,5-a]pyrimidine derivative (8) and the carboxylic acid (9) when treated with 1% NaOH solution.3-Aminocrotononitrile (2e) reacted with 1 to yield the hydrazone derivative (12). The latter derivative was converted into the pyrazolo[1,5-a]pyrimidine derivative (14) by the action of acetic acid. On the other hand, the hydrochloride (15) was formed on treatment of 12 with acetic acid hydrochloric acid mixture.Compounds 8 a, b reacted with carbon disulphide to yield the pyrazolo[3,4-d]-6 (7 H)-m- thiazinethione derivatives (16a,b). The latter were readily converted into the pyrazolo-[3,4-d]pyrimidine derivatives (17 a, b) by the action of aqueous NaOH solution.

Snapping Together: Condensation Polymerization

Reactions ◽  
2011 ◽  
Author(s):  
Peter Atkins
Keyword(s):  
Acetic Acid ◽  
Protein Molecule ◽  
Proton Donor ◽  
The Other ◽  
Structural Motif ◽  
Proton Acceptor ◽  
Close Relative ◽  
Condensation Polymerization ◽  
A Chain ◽  
The One

One of the most famous of all plastics is nylon. I shall use it to represent how the second type of polymers is made. There are many varieties of nylon, but it will be enough to consider just one exemplar, the one known as ‘nylon-66’. It is so called because the repeating motif is a chain of six carbon atoms, then a group of atoms that provide a link, and then another chain of six carbon atoms. The pattern C6-link-C6 is repeated indefinitely to give the ‘66’ polymer. As you will see in more detail in Reaction 27, nylon is a very primitive version of a protein-like molecule, the molecules that control all bodily process and also form claws, nails, and hair. A protein molecule has the same links but more varied combinations of carbon atoms. It is, however, an interesting point that we clad our exteriors in material that emulates our interiors. One of the molecules used to build the polymer is 1 (on the next page; note the six C atoms). As it happens, this molecule is a close relative, with four and five C atoms respectively instead of six, of the two compounds cadaverine and putrescine, with names indicate their origin and odour. Thus, not only does nylon emulate the living, but we clad ourselves in molecules akin to the odour of death. The other molecule we need is 2 (note the six C atoms again). The task of the nylon manufacturer is to link the –NH2 end of one molecule to the –COOH end of the other molecule, then doing it over and over again to grow long spindly polymer molecules. You know from Reaction 2 that NH3 is a base (a proton acceptor), so you should be able to accept that the –NH2 business end of molecule 1 is also a base. Similarly, you saw in the same discussion that –COOH is a structural motif of acetic acid, an acid (a proton donor), so you should be able to see that the business end of molecule 2 is an acid.

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