Esters of 1,3,3-trimethyl-6-cis-piperidino-2-oxabicyclo[2.2.2]octan-5-cis-ol endowed with hypotensive activity.
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Acetylcholine↗
Biomedical subjects
P Schenone
Publications and source records attributed to P Schenone.
N-monosubstituted urethanes and esters of 6-cis-dimethylamino-1,3,3-trimethyl-2-oxabicyclo-[2.2.2]octan-5-trans-ol with hypotensive and other activities.
The synthesis of 6-cis-dimethylamino-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-5-trans-ol (III) starting from 1,3,3-trimethyl-6-nitrimino-2-oxabicyclo[2.2.2]octane is described. Starting from aminoalcohol (III), a series of N-substituted urethanes (IV) and esters (V), as well as the rigid analogue of acetylcholine (VII), were prepared. A number of compounds (V) and particularly (IV) showed remarkable hypotensive and bradycardic activities in rats, whereas the p-aminobenzoate (V h) showed infiltration anesthesia in mice comparable to that of lidocaine. Antiarrhythmic activity in mice and antiacetylcholine activity in vitro are also reported.
Acetylcholine↗
Derivatives of 4,5,6,7-tetrahydro-7,8,8-trimethyl-3-phenylamino-4,7-methano-2H-indazole with hypoglycemic and hypotensive activities.
By reaction of camphor enamine (I) with phenyl isothiocyanate, the N-phenyl thiocarboxamide (II) was obtained in excellent yield, and in turn gave 4,5,6,7-tetrahydro-7,8,8-trimethyl-3-phenylamino-4,7-methano-2H-indazole (III) in very good yield by reaction with hydrazine hydrate. A series of N-substituted ureas (IV) were synthesized in satisfactory yield by reaction of (III) with alkyl and aryl isocyanates. Ureas (IV) showed in general hypoglycemic and in some cases hypotensive activity in rats, whereas only hypotensive activity was present in the thiocarboxamide (II). Effects on heart rate, antiinflammatory and antipyretic activities in rats, infiltration anesthesia and antiarrhythmic activity in mice, as well as antiacetylcholine activity in vitro, are also reported.
Anesthesia, Intravenous↗
Derivatives of 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane with hypotensive activity. I.
The synthesis of three series of glycinamides (IV), amides (V) and diamines (VI) starting from 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane is described. Some of compounds (IV), (V) and (VI) showed a moderate hypotensive activity in rats. Effects on heart rate in rats, infiltration anesthesia and antiarrhythmic activity in mice, as well as antiacetylcholine activity in vitro, are also reported.
Acetylcholine↗
Derivatives of 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane with hypotensive activity. II.
The synthesis of a series of alkyl and aryl ureas (II) starting from 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane is described. Some of these compounds showed a moderate hypotensive activity in rats. Effects on heart rate in rats, infiltration anesthesia and antiarrhythmic activity in mice, as well as antiacetylcholine activity in vitro, are also reported.
Acetylcholine↗
Synthesis and pharmacological activity of derivatives of exo-trimethylenenorbornane, IV.
The syntheses of (+/-)-1-(exo-5,6-trimethylenenorbornan--2-yl)2-propanamine (IV) starting from (exo-5-trimethylenenobornan-2-yl)acetic acid (I) or (exo-5,6-trimethylenenorbornan-2-yl)acetonitrile (II), as well as a series of amides (V) described. None of compounds (IV) and (V) showed amphetamine-like activity in mice.
Amphetamine↗
N-Phenyl-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-cis-amine derivatives with hypotensive and other activities.
The synthesis of N-phenyl-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-cis-amine (III) starting from 6-nitrimino-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, as well as of a series of amides (IV) and ureas (VI) derived from (III), is described. A number of compounds (IV) showed strong hypotensive and bradycardic activity in rats, whereas the urea (IVb) showed infiltration anesthesia in mice similar to that of lidocaine. Antiarrhythmic activity in mice and antiacetylcholine activity in vitro are also reported.
Acetylcholine↗
N-Monosubstituted urethanes of 6-cis-dialkylamino-1,3,3-trimethyl-2-oxabicyclo [2.2.2] octan-5-trans-ols with hypotensive and other activities.
The synthesis of three series of N-monosubstituted urethanes of 6-cis-dialkylamino-1,3,3-trimethyl-2-oxabicyclo [2.2.2] octan-5-transols (IV), (V) and (VI) (dialkylamino = pyrrolidino, piperidino, morpholino) by reaction of the corresponding aminoalcohols with alkyl or aryl isocyanates, is described. A number of compounds (IV) and (V) showed remarkable hypotensive and bradycardic activity in rats, whereas (IV c) showed infiltration anesthesia and (IV n) antiarrhythmic activity in mice comparable to those of lidocaine. Antiacetylcholine activity in vitro is also reported.
Acetylcholine↗
Derivatives of 5,7,7-trimethyl-6-oxa-3-azabicyclo[3.2.2.] nonane with antiarrhythmic, local anesthetic and hypotensive activities. III.
The synthesis of alkyl and aryl ureas (II) derived from 5,7,7-trimethyl-6-oxa-3-azabicyclo[3.2.2.]nonane (I), as well as hydrazides (V), (VI) and (VII) derived from 5,7,7-trimethyl-6-oxa-3-azabicyclo[3.2.2]-nonan-3-amine (IV), is described. A number of theses compounds showed strong hypotensive and bradycardic activities in rats, as well as weak infiltration anesthesia and antiarrhythmic activity in mice. Antiacetylcholine activity in vitro is also reported.
Acetylcholine↗
N-Substituted 1,7,7-trimethyl-2-piperidinobicyclo[2.2.1]hept-2-ene 5-carboxamides and 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 3-carboxamides with hypotensive and other activities.
The synthesis of N-substituted 1,7,7-trimethyl-2-piperidinobicyclo[2.2.1]hept-2-ene 3 carboxamides (II) by reaction of 1,7,7-trimethyl-2-piperidinobicyclo[2.2.1]hept-2-ene (I) with alkyl and aryl isocyanates, as well as the alkaline hydrolysis of (II) to N-substituted 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 3 carboxamides (III), are described. A number of compounds (II) and (III) showed strong hypotensive and bradycardiac activities in rats, as well as weak infiltration anesthesia and antiarrhythmic activity in mice. Antiacetylcholine activity in vitro is also reported.
Acetylcholine↗
Derivatives of 5,7,7-trimethyl-6-oxa-3-azatricyclo[3.2.2.0(2.4)]nonane with antiarrhythmic, local anesthetic and hypotensive activities.
The synthesis of ureas (IV) and amides (V) derived from the tricyclic terpenoid amine 5,7,7-trimethyl-6-oxa-3-azatricyclo[3.2.2.0(2.4)]nonane (III) is described. A number of these compounds showed hypotensive and bradycardic activity in rats, as well as infiltration anesthesia and antiarrhythmic activity in mice. In particular, the n-butylurea (IV b) was superior to lidocaine concerning the anesthetic effect, and the benzamide (V f) showed the same degree of local anesthetic and antiarrhythmic activity as lidocaine. Antiacetylcholine activity in vitro and antitumor activity against P388 lymphocytic leukemia in mice are also reported.
Acetylcholine↗
Synthesis and pharmacological activity of (bicyclo [2.2.1] hept-2-ylidene)acetic acid amides and 2-(bicyclo [2.2.1] hept-2-ylidene)ethanamines.
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Acetylcholine↗
Derivatives of 5,7,7-trimethyl-6-oxa-3-azabicyclo [3.2.2] nonane with antiarrhythmic, local anesthetic and hypotensive activities. II.
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Acetylcholine↗
Esters of 1,7,7-trimethyl-2-exo-piperidinobicyclo[2.2.1]heptan-3-endo-ol with antiarrhythmic, local anesthetic and other activities.
A series of aliphatic and aromatic esters of 1,7,7-trimethyl-2-exo-piperidinobicyclo[2.2.1]heptan-3-endo-ol is described. A number of these compounds showed antiarrhythmic activity in guinea pigs and mice, as well as surface anesthesia in rabbits and infiltration anesthesia in mice. Circulatory, cardiac and respiratory effects in dogs are also described.
Acetylcholine↗
Ester of 6-cis-dialkylamino-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-5-trans-ol with hypotensive and other activities.
Three series of esters of 6-cis-dialkylamino-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-5-trans-ol (dialkylamino = pyrrolidino, piperidino, morpholino) are described. A number of these compounds showed strong hypotensive activity in rats, as well as infiltration anesthesia and antiarrhythmic activity in mice. The lowering effects on heart rate in rats are also described.
Anesthetics, Local↗
Derivatives of 5,7,7-trimethyl-6-oxa-3-azabicyclo[3.2.2]nonane with antiarrhythmic, local anesthetic and hypotensive activities. I.
The synthesis of three series of 3-acyl-, 3-alkyl- and 3-dialkylaminoacetyl-5,7,7-trimethyl-6-oxa-3-azabicyclo[3.2.2]nonanes, (III), (IV) and (V), respectively, is described. A number of these compounds showed surface anesthesia in rabbits and infiltration anesthesia in mice, and antiarrhythmic activity in guinea pigs and mice, all effects being superior or similar to those of lidocaine. The circulatory, cardiac and respiratory effects in dogs and hens are also described.
Anesthetics, Local↗
(+/-)-1-(Adamantan-2-yl)-2-propanamine and other amines derived from 2-adamantanone.
The synthesis of (+/-)-1-(adamantan-2-yl)-2-propanamine (VI), its N,N-dimethyl derivative (VII) and other amines (VIII), (IX) and (X), starting from 2-adamantanone, is described. Some of these amines showed antiparkinson activity in mice.
Acetylcholine↗
Derivatives of 1,2,3,3-tetramethyl-2-azabicyclo[2,2,2]octan-5-trans-ol with antiarrhythmic and other activities. V.
A series of N,N-dialkyl 5-trans-carbamoyloxy-1,2,3,3-tetramethyl-2-azabicyclo [2,2,2]octanes was prepared by reaction of 1,2,3,3-tetramethyl-2-azabicyclo [2,2,2]octan-5-trans-ol with phosgene, followed by aminolysis of the resulting chlorocarbonate with aliphatic secondary amines. 5-Chloro-1,2,3,3-tetramethyl-2-azabicyclo [2,2,2] octane (cis/trans mixture) was isolated as by-product of the reaction. A number of urethanes showed antiarrhythmic activity in guinea pigs and mice, as well as surface anesthesia in rabbits and infiltration anesthesia in mice, superior or similar to lidocaine. The circulatory, cardiac and respiratory effects in dogs and hens are also described.
Anesthetics, Local↗