New substituted 2-(pyrazol-1-yl) o-, m-, p-methylacetanilides with potential local anaesthetic and antiarrhythmic action. Part I

Iovu, M.; Zălaru, Christina; Dumitraşcu, Florea; Drăghici, Constantin; Cristea, E

doi:10.1016/s0014-827x(00)00052-5

Cited by 26 publications

(13 citation statements)

References 7 publications

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“…The aim of the present study was to confirm the earlier structural assignments based on spectroscopic data; to provide accurate structural parameters for future modelling studies; and to examine the effects of the structural variations in 1-4 on their molecular conformations, hydrogen bonding, crystal packing arrangements, and pharmacological properties. While data on the syntheses, spectroscopic characterization and pharmacological activities were reported earlier [2], the X-ray structural data reported here are new.…”

Section: Introductionmentioning

confidence: 58%

“…One variation in the design of potentially active analogs of lidocaine is the replacement of the amino-group by the less basic pyrazole moiety and its derivatives. Compounds based on this strategy have likewise been shown to display local anesthetic and antiarrhythmic properties [2,3].…”

Section: Introductionmentioning

confidence: 99%

“…1). Details of the syntheses of compounds 1-4 (by N-alkylation of pyrazole and its derivative with several 2-iodo-acetanilides), their spectroscopic characterization by UV-Vis, IR, 1 H-NMR, 13 C-NMR, and MS, and the methodology for assessing their pharmacological activities were reported earlier [2]. The aim of the present study was to confirm the earlier structural assignments based on spectroscopic data; to provide accurate structural parameters for future modelling studies; and to examine the effects of the structural variations in 1-4 on their molecular conformations, hydrogen bonding, crystal packing arrangements, and pharmacological properties.…”

Section: Introductionmentioning

confidence: 99%

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X-ray structures and pharmacological activities of lidocaine derivatives

et al. 2008

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The molecular and crystal structures of the lidocaine analogs 2-(pyrazol-1-yl)-2 0 -methylacetanilide (1), 2-(3,5-dimethyl-4-iodo-pyrazol-1-yl)-2 0 -methylacetanilide (2), 2-(3,5-dimethyl-4-iodo-pyrazol-1-yl)-3 0 -methylacetanilide (3), and 2-(pyrazol-1-yl)-4 0 -methylacetanilide (4), are reported, with a summary of their pharmacological activities. In this series, the moiety comprising the heterocyclic ring and the amide alkyl linker displays a common conformation. Molecules of 1-4 form identical hydrogen bonded motifs in their crystals, namely linear chains via intermolecular N-HÁÁÁO=C hydrogen bonding. Moderate anesthetic and anti-arrhythmic potencies recorded for 1-4 relative to lidocaine are countered by their significantly lower toxicities.

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Section: Introductionmentioning

confidence: 58%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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X-ray structures and pharmacological activities of lidocaine derivatives

et al. 2008

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“…1 In previous papers we reported the synthesis, characterization and pharmacological tests of some N-substituted 2-(1H-pyrazol-1-yl)acetamides. [4][5][6] The present paper reports on the synthesis and characterization of N-(chlorophenyl)-substituted 2-(1H-pyrazol-1-yl)acetamides. This research was devised to investigate the influence of the N-(chlorophenyl) substituents on the pharmacological activity of the new compounds was put in evidence.…”

Section: Introductionmentioning

confidence: 99%

New N-substituted 2-(1H-pyrazol-1-yl)acetamides with pharmacological activity

Zălaru¹,

Dumitraşcu²,

Drăghici³

et al. 2009

Arkivoc

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“…Some members of this class of compounds have also been investigated for their local anaesthesic and antiarrhythmic [28], herbicidal [29], and molluscicidal [30] properties. Despite the existing interest in this class of compounds, virtually nothing is known about the activities of its various members on Leishmania species.…”

Section: Introductionmentioning

confidence: 99%

Antileishmanial and Antibacterial Activity of a New Pyrazole Derivative Designated 4‐[2‐(1‐(Ethylamino)‐2‐methyl‐ propyl)phenyl]‐3‐(4‐methyphenyl)‐1‐phenylpyrazole

Dardari

Lemrani

Sebban

et al. 2006

Archiv der Pharmazie

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Here, we report for the first time the synthesis and the antileishmanial activity of a new pyrazole derivative, namely 4-[2-(1-(ethylamino)-2-methylpropyl)phenyl]-3-(4-methyphenyl)-1-phenylpyrazole). Micromolar concentrations of this compound were found to inhibit the in vitro multiplication of Leishmania tropica, Leishmania major, and Leishmania infantum, three species causing different forms of leishmaniasis. Furthermore, the 50% inhibitory concentration (IC50) values for the compound are only slightly higher than those of amphotericin B, one of the most active antileishmanial agents used as a satisfactory substitute in cases not responding to pentostam. The IC50 values after 48 h for L. tropica, L. major, and L. infantum promastigote growth were 0.48 microg/mL, 0.63 microg/mL and 0.40 microg/mL, respectively for the compound, while they were 0.23 microg/mL, 0.29 microg/mL and 0.24 microg/mL, respectively for amphotericin B. We also tested this compound for its antibacterial activity against several bacteria. The strongest antibacterial activity was observed against Entrococcus feacalis and Staphylococcus aureus with a minimal inhibitory concentration (MIC) of 60 microg/mL.

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New substituted 2-(pyrazol-1-yl) o-, m-, p-methylacetanilides with potential local anaesthetic and antiarrhythmic action. Part I

Cited by 26 publications

References 7 publications

X-ray structures and pharmacological activities of lidocaine derivatives

X-ray structures and pharmacological activities of lidocaine derivatives

New N-substituted 2-(1H-pyrazol-1-yl)acetamides with pharmacological activity

Antileishmanial and Antibacterial Activity of a New Pyrazole Derivative Designated 4‐[2‐(1‐(Ethylamino)‐2‐methyl‐ propyl)phenyl]‐3‐(4‐methyphenyl)‐1‐phenylpyrazole

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