Synthesis of 4-methoxyphenoxyacetic and 3,4,5-trimethoxyphenoxyacetic acid amides and hydrazides as potential neurotropic and cardiovascular agents

1987 ◽  
Vol 52 (12) ◽  
pp. 3013-3023 ◽  
Author(s):  
Vladimír Valenta ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Miroslav Protiva
Keyword(s):  
Methyl Ester ◽  
Antiarrhythmic Activity ◽  
Cardiovascular Agents ◽  
Quaternary Salts ◽  
Anorectic Effect ◽  
Pharmacological Screening

4-Methoxyphenoxyacetyl chloride, 3,4,5-trimethoxyphenoxyacetic acid and its methyl ester were reacted with 2-phenylethylamine, 1-benzylpiperazine, 1-(2-phenylethyl)piperazine, 1-(1-phenyl-2-propyl)piperazine, isopropylhydrazine, 1-aminopiperidine, and 4-aminomorpholine and afforded the amides and hydrazides Iab-IVab and Vb-VIIIb. 1-Amino-4-methylpiperazine and 1-amino-4-phenylpiperazine were transformed to the hydrazones XV and XVI, and to the quaternary salts XVII and XVIII. Pharmacological screening showed indications of thymoleptic activity with compounds Ia-IIIa, anorectic effect with IIa and IIIb, antiarrhythmic activity with IIIa, XVII, and XVIII, and myorelaxant effect with XVII and XVIII. Antimicrobial and anthelmintic effects were also noted.

Synthesis and antiarrhythmic activity of (1,3-dimethyl-5-nitro-5-hexahydropyrimidinyl)-propionic acid methyl ester

2006 ◽  
Vol 40 (1) ◽  
pp. 29-31 ◽  
Author(s):  
R. R. Shakirov ◽  
N. N. Yarmukhamedov ◽  
L. I. Vlasova ◽  
N. Z. Baibulatova ◽  
R. Yu. Khisamutdinova ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Propionic Acid ◽  
Acid Methyl Ester ◽  
Antiarrhythmic Activity ◽  
Acid Methyl

4-(Aminoacylamido)-s-hydrindacenes and related compounds: Synthesis and pharmacological screening

1982 ◽  
Vol 47 (12) ◽  
pp. 3297-3305 ◽  
Author(s):  
Zdeněk Vejdělek ◽  
Jiří Holubek ◽  
Marie Bartošová ◽  
Miroslav Protiva
Keyword(s):  
Methyl Iodide ◽  
Alkaline Hydrolysis ◽  
Local Anaesthetic ◽  
Antiarrhythmic Activity ◽  
Chloroacetyl Chloride ◽  
Benzoyl Isothiocyanate ◽  
Pharmacological Screening ◽  
High Degree ◽  
Related Compounds ◽  
Imidazoline Derivative

Chloracylamido derivatives IIIa-Va were obtained by acylation of 4-amino-s-hydrindacene with chloroacetyl chloride, 2-chloropropionyl chloride and 3-chloropropionyl chloride; their reactions with excessive diethylamine, pyrrolidine, piperidine and morpholine afforded the title compounds IIIbcde-Vbcde. A reaction of 4-amino-s-hydrindacene with benzoyl isothiocyanate gave 1-benzoyl-3-(s-hydrindacen-4-yl)thiourea (VI) whose mild alkaline hydrolysis resulted in N-(s-hydrindacen-4-yl)thiourea (VII). The following treatment with methyl iodide and then with ethylenediamine afforded the imidazoline derivative VIII in a low yield. N-(s-Hydrindacen-4-yl)-2-piperidinoacetamide (IIId) in the form of the hydrochloride revealed a high degree of local anaesthetic and antiarrhythmic activity.

ChemInform Abstract: Synthesis of Rigid Analogues of (D,L)-Arginine Methyl Ester with Antiarrhythmic Activity.

ChemInform ◽  
1990 ◽  
Vol 21 (11) ◽  
Author(s):  
A. BANFI ◽  
F. BENEDINI ◽  
G. CASANOVA ◽  
R. PEREGO ◽  
L. TOMA
Keyword(s):  
Methyl Ester ◽  
Antiarrhythmic Activity

2-Diethylaminoethyl esters of 1,3-disubstituted propane-2-carboxylic acids

1987 ◽  
Vol 52 (10) ◽  
pp. 2534-2544 ◽  
Author(s):  
Vladimír Valenta ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Vladimír Miller ◽  
Marie Vlková ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Methyl Ester ◽  
Potassium Carbonate ◽  
Sodium Salt ◽  
Dimethyl Sulfate ◽  
Crystal Form ◽  
Ester Exchange ◽  
Melting Crystal ◽  
Pharmacological Screening ◽  
Hydrolysis Of

Alkaline hydrolysis of diethyl 1-(tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylate (IV) gave the crude acid V which was purified via the dipotassium salt and was obtained as the homogeneous higher melting crystal form. Its thermic decarboxylation yielded the acid II as a mixture of two racemates (38 : 62); crystallization led to the almost homogeneous racemate B (10 : 90). Reaction of the sodium salt of II with dimethyl sulfate in methanol gave the methyl ester III which afforded by ester exchange with 2-diethylaminoethanol the ester I (mixture of two racemates 34 : 66). 2-Diethylaminoethyl 1,3-bis(1-naphthyl)propane-2-carboxylate (VII) was synthesized in three steps from diethyl (1-naphthylmethyl)malonate. Ester X was obtained from 1,3-bis(tetrahydro-2-furyl)propane-2-carboxylic acid by treatment with 2-diethylaminoethyl chloride in boiling 2-propanol in the presence of potassium carbonate. The acid V gave similarly the diester VI. 2-Diethylaminoethyl esters I, VI, VII, and X were transformed to the hydrogen oxalates. Pharmacological screening showed for the diester VI hypotensive, spasmolytic, antiarrhythmic, and antitussic activity.

Synthesis of Rigid Analogues of (D,L)-Arginine Methyl Ester with Antiarrhythmic Activity

1989 ◽  
Vol 19 (9-10) ◽  
pp. 1787-1799 ◽  
Author(s):  
A. Banfi ◽  
F. Benedini ◽  
G. Casanova ◽  
R. Perego ◽  
L. Toma
Keyword(s):  
Methyl Ester ◽  
Antiarrhythmic Activity

N-(Aminoacyl) and N-(aminoalkyl) derivatives of 4-cyclopentylaniline and N-ethyl-4-cyclopentylaniline; Synthesis and pharmacological screening

1983 ◽  
Vol 48 (1) ◽  
pp. 156-162 ◽  
Author(s):  
Zdeněk Vejdělek ◽  
Marie Bartošová ◽  
Miroslav Protiva
Keyword(s):  
Lithium Aluminium Hydride ◽  
Substitution Reactions ◽  
Rotarod Test ◽  
Lithium Aluminium ◽  
Local Anaesthetic Effect ◽  
Anorectic Effect ◽  
Pharmacological Screening ◽  
Derivatives Of ◽  
Higher Doses ◽  
Anaesthetic Effect

Acylation of 4-cyclopentylaniline (I) with chloracetyl chloride, 3-chloropropionyl chloride, 4-chlorobutyryl chloride and 2-bromo-4-methylvaleryl bromide gave the halogenoacyl derivatives IV - VII out of which the first two were subjected to substitution reactions with diethylamine and piperidine. The N-(aminoacyl) derivatives VIII - XI obtained were reduced with lithium aluminium hydride to the N-(aminoalkyl) derivatives XII and XV. N-Ethyl-4-cyclopentylaniline (XVI), prepared by reduction of N-(4-cyclopentylphenyl)acetamide (II), was similarly transformed via the chloroacetyl derivative XVII to the amide XVIII and the diamine XIX. Salts of the compounds prepared (amino amides and diamines) bring about in higher doses central excitation which is apparently in close connection with the found discoordinating effect of a part of products (VIII - XI, XIII) in the rotarod test, further with the antireserpine effects in the tests of antagonization of reserpine ptosis and hypothermia (VIII, X, XII, XIII) and finally with the anorectic effect of compound X. All substances showed a mild spasmolytic effect of the anticholinergic type. On the other hand, the expected local anaesthetic effect was found only with compounds VIII, XVIII, XIX.

Synthetic Communication: Synthesis of Optically Pure Analogues of D-Arginine Methyl Ester with Antiarrhythmic Activity

1990 ◽  
Vol 20 (10) ◽  
pp. 1531-1542 ◽  
Author(s):  
Aldo Banfi ◽  
Francesca Benedini ◽  
Alberto Sala ◽  
Giovanni Russo
Keyword(s):  
Methyl Ester ◽  
Antiarrhythmic Activity ◽  
Communication Synthesis ◽  
Optically Pure

N-substituted derivatives of 6,11-dihydrodibenzo[b,e]thiepin-11-amine and related compounds; Synthesis and pharmacological screening

1988 ◽  
Vol 53 (4) ◽  
pp. 860-869 ◽  
Author(s):  
Vladimír Valenta ◽  
Hana Hulinská ◽  
Jiří Holubek ◽  
Antonín Dlabač ◽  
Jan Metyš ◽  
...  
Keyword(s):  
Local Anaesthetic ◽  
Antiarrhythmic Activity ◽  
The Other ◽  
Gastric Ulcers ◽  
Substitution Reactions ◽  
Amino Esters ◽  
Pharmacological Screening ◽  
The One ◽  
Derivatives Of ◽  
Related Compounds

Reactions of N-(6,11-dihydrodibenzo[b,e]thiepin-11-yl)chloroacetamide (II) with dimethylamine, morpholine, and 2-(1-piperazinyl)ethanol afforded the amino amides III-V. Substitution reactions of 11-chloro-6,11-dihydrodibenzo[b,e]thiepin with ethylenediamine and N,N-dimethylethylenediamine gave the diamines VI and VII. 6,11-Dihydrodibenzo[b,e]thiepin-11-amine (I) was treated with ethyl chloroacetate and ethyl 2-bromopropionate to give the amino esters X and XI which were transformed on the one hand to the acids VIII and IX, and to the amides XII and XIII on the other. (6,11-Dihydrodibenzo[b,e]thiepin -11-yl)methylamine (XVIa) and (10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-yl)methylamine (XVIb) were transformed via the chloroacetamides XVIIa and XVIIb to the (4-methyl-1-piperazinyl)acetamides XVa and XVb. Compound V showed local anaesthetic and antiarrhythmic activity, the diamine VII had antihistamine and antireserpine effects, the amide XII was found to be an anticonvulsant, and the piperazines XVa and XVb inhibited effectively the formation of the indomethacin-induced gastric ulcers in rats.

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