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PubMed1977

Pharmacological properties of the anti-inflammatory agent pyridyl-biphenylyl-acetamide (diphenpyramide).

Pyridyl-biphenylyl-acetamide (diphenpyramide, Z-876) is a new bisphenylalcanoic derivative with marked anti-inflammatory, analgesic, antipyretic and uricosuric properties. It is more active than phenylbutazone in the adjuvant polyarthritis in the rat when given prophylactically or therapeutically. It is thrice as active as phenylbutazone and ten times as active as acetylsalicylic acid (ASA) on the carrageenin-induced edema of the hind-paw. Diphenpyramide is characterized by low acute toxicity and by weak ulcerogenic activity. On the carrageenin-induced edema the therapeutic index of diphenpyramide is 30 times higher than that of indometacin and the ratio between the ED50 and the UD50 (ulcerogenic dose in 50% of the treated rats) is 39 times higher than that of ASA.

Acetamides↗
PubMed1987

Synthesis and biological activity of acetamides, arylureas and 2-alkoxyphenyl-6-phenyl-1,3,4-oxa(thia)diazole-[3,2-a]-S- triazin-5,7-diones derived from 2-amino-5-alkoxyphenyl-1,3,4-oxa(thia)diazole.

The syntheses of some acetamides (II) and phenylureas (III) derived from 2-amino-5-alkoxyphenyl-1,3,4-oxa(thia)diazoles (I) and some 2-alkoxyphenyl-6-phenyl-1,3,4-oxa(thia)diazole-[3,2-a]-s- triazin-5,7-diones (IV) are described. Pharmacological tests showed antiinflammatory and analgesic activities of bicyclic derivatives. A probable influence of alkoxyphenyl substituents, present in three kinds of structures, was observed.

Acetamides↗
PubMed1987

Muscarinic and antimuscarinic activity of acetamides related to oxotremorine in the guinea pig urinary bladder.

Eight acetamide analogs of oxotremorine, shown previously to be full or nearly full muscarinic agonists on the isolated guinea pig ileum, were investigated for muscarinic activity on muscle strips of guinea pig urinary bladder. Several compounds demonstrated pronounced organ selectivity when compared to carbachol by being partial agonists or antagonists on the bladder. For example, oxotremorine and BM 34, both potent, full agonists on the ileum, were partial agonists, the latter producing less than one-half the maximum response of carbachol. BM 5 elicited no significant response, but instead was a potent antagonist to carbachol. Schild analysis with BM 5 and BM 61 indicated no muscarinic receptor heterogeneity between the bladder and ileum. Also dissociation constants of agonists and partial agonists generally agreed with those determined previously on the ileum. Furthermore, the relative efficacy of each agonist appeared to be similar in the two tissues, confirming the homogeneity of muscarinic receptors in the bladder and ileum with respect to the compounds studied. Compounds having high affinity and low intrinsic efficacy, e.g., BM 5, thus may stimulate contractile responses on the ileum and block responses on the bladder and therefore display tissue selectivity without discriminating between tissue receptors. It is suggested that this selectivity is derived from a smaller effective receptor reserve for muscarinic agonists in the bladder.

Acetamides↗
PubMed1982

Influence of allyl isopropyl acetamide on d-aminolevulinic acid and aminoacetone synthesis during postnatal development in rats.

In contrast to other groups we found an allyl isopropyl acetamide (AIA)-mediated induction of aminoketones (AK) in newborn rats. To further clarify this phenomenon, the development of d-amino-levulinic acid synthesis (ALAS) and aminoacetone synthesis (AAS) and their inducibility by AIA were determined during the first days of life, daily until the 5th day of life, and then up to an age of 240 days. Both ALAS and AAS decrease during the first 24 h of life; the inducibility of both is detectable 6 h after birth, and develops during the first day of life to reach maximal inducibility. Minimum values are observed between day 30-45 of life; thereafter a tendency of increasing basic activity (AAS) and constant (ALAS) or decreasing (AAS) inducibility is detectable.

5-Aminolevulinate Synthetase↗
PubMedDate not supplied

Local anaesthetic activity of some sec-amino-N-(aryl-aralkyl)-ethyl acetamides.

Six basic amides were screened for local anaesthetic activity and compared with procaine and lignocaine. Amongst the basic amides screened, piperidino-N-(alpha-4-ethoxy phenyl- beta-phenyl) ethyl and Diethylamino-N (alpha-4-ethoxy- beta-phenyl) ethyl acetamide were found to be more effective as compared to lignocaine. They were found to be non-irritant, and non-toxic even in high doses.

Acetamides↗
PubMedDate not supplied

[Effect of solvent structure on amide reaction with native DNA molecules. II. Aqueous acetamide mixtures].

The influence of acetamide (AA) on the native DNA molecule conformation has been studied by methods of flow birefringence and viscometry. On one hand, it was shown that hydrodynamical and optical behaviour of the macromolecule at extremely low additions of AA is qualitatively the same as in the presence of nonelectrolytes which stabilize the water structure. On the other hand, the influence of intermediate and large AA concentrations on the native DNA molecule conformation is qualitatively the same as of corresponding urea concentrations, which is known to be a structure-breaker. The influence of AA on the thermostability of the native DNA molecule as well as on the stacking-association constant of adenosine has been studied by a spectrophotometric method. The obtained data confirm the hypothesis of the importance of ion-dipole interactions between nonelectrolytes and the phosphate groups of the DNA molecule.

Acetamides↗
PubMed1980

The influence of allyl isopropyl acetamide on d-aminolevulinic acid synthetase and cytochrome P-450.

Allyl isopropyl acetamide (AIA) is believed to destroy P-450 and to enhance the d-aminolevulinic acid synthetase (ALAS) activity by lowering the heme pool of the liver parenchymal cell, in this way weakening the negative feed back mechanism, which regulates ALAS synthesis at the translational level. Dose and time dependence of the AIA influence on cytochrome P-450 concentration and P-450 activity argues against this theory, supporting the hypothesis that AIA destroys P-450 only after administration of higher doses (> 300 mg/kg i. p.), but does not influence or even enhances P-450 concentration when given in lower doses which exert an increase in ALAS activity. 25--100 mg/kg AIA i. p. have no significant effect on ALAS activity, 200 mg/kg and higher doses up to 400 mg/kg cause dose-dependent increases in ALAS activity.

5-Aminolevulinate Synthetase↗
PubMed1995

Neuroprotective actions of 2-amino-N-(1,2-diphenylethyl)-acetamide hydrochloride (FPL 13950) in animal models of hypoxia and global ischemia.

2-Amino-N-(1,2-diphenylethyl)-acetamide hydrochloride (FPL 13950) has been demonstrated to have good anticonvulsant efficacy and a relative lack of acute side effects in rodents. Similar in structure to remacemide hydrochloride, it was also shown to possess weak potency as an uncompetitive antagonist of N-methyl-D-aspartic acid (NMDA) receptors. In our study FPL 13950 was profiled preclinically as a potential neuroprotective agent with respect to lengthening the survival time of rodents exposed to hypoxia, as well as for ability to protect the vulnerable CA1 pyramidal neurons of the rat and dog from the consequences of global ischemia. Under conditions of hypoxia, pretreatment of rodents with FPL 13950 resulted in an extension in the time to loss of the righting reflex (rats) and mortality (rats and mice). This occurred whether the rats were maintained at ambient body temperature or made hyperthermic. When administered after 30 min of four-vessel occlusion global ischemia for periods of either 7 (b.i.d.) or 14 days (s.i.d.), FPL 13950 exhibited protection of the vulnerable CA1 hippocampal neurons in rat. In the 14-day treatment study the CA3 neurons were evaluated and FPL 13950 was found to prevent the lesser degree of ischemic-induced damage to this hippocampal region. In ischemic rats treated with FPL 13950 for 7 days, electrophysiological responses of CA1 neurons (orthodromic and antidromic population spikes, in vitro) were also preserved after FPL 13950 treatment. FPL 13950 was administered i.v. at 30 min after 8 min of clamping the ascending aorta in dogs, followed by a b.i.d./s.i.d. dosing regimen for 1 wk. Neuronal damage to CA1 was considerable in the saline-treated ischemic animals but significantly protected in dogs receiving FPL 13950. FPL 13950 continues to serve as a potential backup candidate for remacemide HCl which is currently in clinical trials for patients with stroke and epilepsy.

Acetamides↗
PubMed1995

Anticonvulsant efficacy/safety properties of 2-amino-N-(1,2-diphenylethyl)acetamide hydrochloride.

2-Amino-N-(1,2-diphenylethyl)-acetamide-hydrochloride (FPL 13950) was profiled preclinically in rodents for efficacy against convulsions, as well as for acute safety/behavioral observations. FPL 13950 exhibited good oral efficacy and duration of action with respect to prevention of seizures elicited by maximal electroshock-shock in both rats and mice. Tolerance to protection against maximal electroshock and hexobarbital-induced sleep-time was not evident after subchronic drug administration. FPL 13950 also prevented convulsions/mortality in mice after i.v. dosing with N-methyl-D, L-aspartate, however, it was ineffective against other types of chemically induced convulsions, as well as bicorneal kindling. High oral doses produced neural impairment in both mice and rats and hyperactivity in rats. Sequential administration of yet higher doses elicited tonic/clonic convulsions culminating in death. During i.v. infusion of metrazol in mice, high i.p. doses of FPL 13950 shortened the latency to first twitch and clonus. No increase in the startle response or phencyclidine-like behavior was evident after oral dosing in rats.

Acetamides↗
PubMed1994

Pharmacokinetics of the organic nitrates trans-N-(4-nitroxycyclohexyl)-urea in dogs and trans-N-(4-nitroxycyclohexyl)-acetamide in dogs and in man.

The pharmacokinetic behavior of the organic nitrates BM 12.1247 (trans-N-(4-nitroxycyclohexyl)-urea) and BM 12.1307 (trans-N-(4-nitroxycyclohexyl)-acetamide, CAS 137291-91-3) were examined in beagle dogs after oral and intravenous administration. To this end, a reliable and specific assay using capillary gaschromatography with electron capture detection (GC-ECD) was developed. BM 12.1247 showed its maximum plasma level after 2.2 h by oral application; the bioavailability was nearly 100%. The elimination half-life of 8.8 h p.o. Corresponded to the half-life after i.v. administration, concerning BM 12.1307, the elimination half-lives were still longer, they reached 11-13 h and bioavailability reached 68-70%; these results were confirmed by crossover tests. In a first application of healthy volunteers it was possible to show that the organic nitrate BM 12.1307 is eliminated much more slowly in man than in dog, the half-life of the compound in man being longer than the half-life in dog by a factor of 2.3.

Acetamides↗
PubMed1994

Synthesis of some N-arylazole acetamide derivatives and their anticonvulsant and antimicrobial activities.

Some new N-arylazole acetamide derivatives have been prepared by the reaction of alpha-bromo-N-arylacetamide with imidazole, pyrazole and 1,2,4-triazole. The structures of these compounds have been confirmed by UV, IR, 1H-NMR and elementary analysis. Their anticonvulsant activities were determined by maximal electroshock (MES) and subcutaneous metrazol (Scmet) tests. Most of the compounds showed anticonvulsant activity with significantly low neurotoxicity according to Phase I tests. Compound 6 carrying alpha-naphthyl and 1,2,4-triazole was found active in the MES test with ED50 = 64.9 mg/kg and TD50 = 221.0 mg/kg but it was not active in corneally stimulated rats. Antibacterial and antifungal activities of the compounds were determined against S. aureus, E. coli, P. aeruginosa, C. albicans, C. parapsilosis, C. pseudotropicalis and C. stellatoidea by using the microdilution broth method. Compounds 8 and 10 showed significant activity (MIC < 32 micrograms/ml) against various Candida species.

Acetamides↗
PubMed1995

(E)-(arylmethyleneaminoxy)acetamides as analogues of neuroleptic benzamides: synthesis and D2-dopaminergic binding affinity.

Some type B (E)-(arylmethyleneaminoxy)acetamides were synthesised as analogues of type A neuroleptic and antipsychotic benzamides, in which the aromatic group is substituted by a (methyleneaminoxy)methyl moiety (C = NOCH2, MAOMM). Theoretical studies were performed in order to verify whether conformational analogies could exist between type A and type B compounds. Type B compounds were tested for their D2-dopaminergic binding affinity which represents a valid indication of their potential neuroleptic and antipsychotic properties. Biological results indicate that the MAOMM is not able to substitute the aromatic group effectively in the field of neuroleptic benzamides. The results are discussed in the light of the structural analogies and the differences between the MAOMM and the aryl.

Acetamides↗
PubMed1996

(E)-(methyloxyimino)acetamides as analogues of neuroleptic benzamides: synthesis and D2-dopaminergic binding affinity.

Some type C (E)-(methyloxyimino)acetamides were synthesised as analogues of type A neuroleptic and antipsychotic benzamides, in which the aromatic group is substituted by a methyloxyiminomethyl moiety with the E configuration (CH2ON = CH, E-MOIMM). Type C compounds were tested for their D2-dopaminergic binding affinity in order to obtain an indication of their potential neuroleptic and antipsychotic properties. Biological results showed that only a few aryl-substituted E-MOIM derivatives possess a certain affinity for the D2-dopaminergic receptor, at least one order of magnitude lower than that of metoclopramide and sulpiride.

Acetamides↗
PubMed1997

N-(2-pyridinyl)-2-[2(3H)-benzazolone-3-yl]acetamides: synthesis, antinociceptive and anti-inflammatory activity.

Eighteen N-(2-Pyridyl)-2-[2(3H)-benzazolone-3-yl]acetamide derivatives have been synthesized. The chemical structure of the compounds have been elucidated by elemental analysis, IR and 1H NMR spectral data and their antinociceptive and anti-inflammatory activities were tested in mice. Compound VII o has shown the highest antinociceptive activity, and VII g, j, k, r exhibited relatively high antinociceptive activity. In addition, compounds VII d, f, j, p showed statistically significant anti-inflammatory activity.

Acetamides↗
PubMed1999

Enantioselective synthesis and teratogenicity of propylisopropyl acetamide, a CNS-active chiral amide analogue of valproic acid.

Propylisopropyl acetamide (PID), an amide analogue of the major antiepileptic drug valproic acid (VPA), possesses favorable anticonvulsant and CNS properties. PID contains one chiral carbon atom and therefore exists in two enantiomeric forms. The purpose of this work was to synthesize the two PID enantiomers and evaluate their enantiospecific teratogenicity. Enantioselective synthesis of PID enantiomers was achieved by coupling valeroyl chloride with optically pure (4S)- and (4R)-benzyl-2-oxazolidinone chiral auxiliaries. The two oxazolidinone enolates were alkylated with isopropyl triflate, hydrolyzed, and amidated to yield (2R)- and (2S)-PID. These two PID enantiomers were obtained with excellent enantiomeric purity, exceeding 99.4%. Unlike VPA, both (2R)- and (2S)-PID failed to exert teratogenic effects in NMRI mice following a single 3 mmol/kg subcutaneous injection. From this study we can conclude that individual PID enantiomers do not demonstrate stereoselective teratogenicity in NMRI mice. Due to its better anticonvulsant activity than VPA and lack of teratogenicity, PID (in a stereospecific or racemic form) has the potential to become a new antiepileptic and CNS drug.

Abnormalities, Drug-Induced↗
PubMed2001

Synthesis and antimicrobial activities of 5-fluoro-1,2,6-trisubstituted benzimidazole carboxamide and acetamide derivatives.

Some 5-fluoro-6-substitute-1 H-benzimidazole-2-carbamates (12a-e), 5-fluoro-6-substituted 1H-benzimidazole-2-acetate (13a-e) and 2-acetamide (14a-f) derivatives, 2-acetamido-5-fluoro-6-(morpholin-4-yl)-1-propyl-1H-benzimidazole (15), and 1-cyclopropyl-2-ethyl-5-fluoro-6-(4-methylpiperazin-1-yl)- 1H-benzimidazole (16) were synthesized, and their antimicrobial and antifungal activities evaluated. Compound 12c exhibited the best activity against Candida albicans.

Amides↗