New substituted 2-(pyrazol-1-yl)-dialkylacetanilides with potential local anesthetic and antiarrhythmic action. Part II

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

doi:10.1016/s0014-827x(02)00014-9

Cited by 24 publications

(14 citation statements)

References 7 publications

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“…Therefore, the structures of the other reported compounds are based on the plausible reaction mechanism as described above, and the involved steric and electronic repelling effects have been strongly supported by similar earlier reports. [15][16][17][18] In addition to the synthesis of all the 5 under ultrasound irradiation at room temperature and 6 under ultrasound microwave irradiation, some randomly selected compounds, 5a and 5b, were also obtained by conventional reaction conditions (stirring at room temperature), and 6a and 6c by conventional refluxing in acetonitrile from 2 and corresponding 4 or under ultrasound irradiation at reflux temperature of acetonitrile. In the case of the synthesis of 5, as summarized in Table 2, utilizing ultrasound irradiation to replace the conventional stirring significantly enhanced the reaction rates and slightly improved the yields, while generating identical compounds correspondingly, which have been substantiated by m.p., mixed m.p., IR, and 1 H NMR.…”

Section: Resultsmentioning

confidence: 99%

An Unexpected and Green Synthetic Protocol for Ethyl 1-Aroyl/Aroylmethyl-5-methyl-3-methylthiopyrazole-4-carboxylates: High Regioselectivity in Alkylation and Acylation Reactions between N-1 and N-2 of a Pyrazole Ring

Wen

Wang

et al. 2005

Jnl Chinese Chemical Soc

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Two series, totaling twelve, of new compounds, ethyl 1-aroyl/(aroylmethyl)-5-methyl-3-methylthiopyrazole-4-carboxylates (5/6), have been synthesized via highly regioselectively acylation and alkylation reactions of ethyl 3-methyl-5-methylthio-1H-pyrazole-4-carboxylate (2a) with aroyl chloride (3) and eco-friendly reagents alpha-tosyloxysubstituted acetophenones (4), respectively, and a green protocol has been developed. The acylation reactions were carried out under ultrasound irradiation, and the alkylation reactions were under microwave irradiation and ultrasound irradiation, respectively. Conventional reaction conditions, as well as the use of alpha-bromosubstituted acetophenone (4¢) have also been applied in the synthesis of some randomly selected compounds in both series and have generated identical compounds correspondingly. Unexpected structures of compounds were unambiguously determined by X-ray crystallographic analysis.

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Section: Resultsmentioning

confidence: 99%

An Unexpected and Green Synthetic Protocol for Ethyl 1-Aroyl/Aroylmethyl-5-methyl-3-methylthiopyrazole-4-carboxylates: High Regioselectivity in Alkylation and Acylation Reactions between N-1 and N-2 of a Pyrazole Ring

Wen

Wang

et al. 2005

Jnl Chinese Chemical Soc

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“…Variable DRY-DRY 37 describes distance/energies product of the DRY probe interaction between the phenyl and the pyrazolyl ring substituted with À NO 2 group or À I, when both rings are in the favorable spatial arrangement (3,4,11,15,18,21,25 -all geometries were derived as explained in the computational methods). DRY nodes have IEs of À 2.1 and À 1.8 kcal/mol.…”

Section: Acute Toxicity Obtained By Oral Administrationmentioning

confidence: 99%

Acute Toxicity of Substituted 2‐(1H‐pyrazol‐1‐yl)acetanilides and Related Commercially Available Local Anesthetics Toward Mice. A GRIND/ALMOND‐Based 3‐D QSAR Study

2009

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Alignment-free three-dimensional quantitative structure -toxicity relationship models, developed on the basis of GRid INdependent Descriptors (GRIND), on acute toxicity data obtained by (i) oral administration of 25 pyrazolylacetanilides, and (ii) intravenous administration of 15 commercially available Local Anesthetics (LAs) to mice was reported. The most favorable interaction regions extracted from molecular interaction fields obtained with HBA, HBD, hydrophobic, and shape probes were correlated with toxicity data expressed as log[1/(LD 50 )] by partial Least Square Analysis (PLS). Variable selection was done by fractional factorial design. The best PLS models for set (i) comprises 3LV with r 2 ¼ 0.95 and q 2 ¼ 0.72; for set (ii) comprises 2LV with r 2 ¼ 0.95 and q 2 ¼ 0.58. Internal cross-validation was done by using three random groups of compounds for each set. External predictivity of the second model was checked by a test set consists of eight structurally diverse compounds. The PLS model related to orally administrated set of compounds was compared with the corresponding one related to intravenously administrate drugs. Variables having high impact on each model, positively or negatively correlated with toxicities, were discussed and an attempt was made to link those variables with calculated ADME related properties of compounds, as well as with literature data that describes probable interaction of LA drugs with the homology modeled voltage-gated sodium channels. According to the best of our knowledge this is first reported study that use GRIND methodology in structure -toxicity relationships on whole animals.

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“…[56789101112] On the other hand, pharmacologically, pyrazole and its derivatives represent one of the most important classes of organic heterocyclic compounds possessing antibacterial, antifungal, herbicidal and antiviral activities. [13141516] Some of its derivatives have been reported to exhibit significant anti-arrhythmic, sedative, hypoglycemic and anti-inflammatory activities. [17181920]…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and antimicrobial activity of some novel benzimidazole derivatives

Krishnanjaneyulu¹,

Govindaraj²,

Vamsi³

et al. 2014

J Adv Pharm Technol Res

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A series of novel N-((1H-benzoimidazol-1-yl) methyl)-4-(1-phenyl-5-substituted-4, 5-dihydro-1-benzoimidazol-1-yl) methyl)-4-(1-phenyl-5-substituted-4, 5-dihydro-1H-pyrazol-3-yl) benzenamine were synthesized by treating various 1-(4-((1H-benzoimidazol-1-yl) methylamino) phenyl)-3-substitutedprop-2-en-1-one with phenyl hydrazine in the presence of sodium acetate through a simple ring closure reaction. The starting material, 1-(4-((1H-benzoimidazol-1-yl) methylamino) phenyl)-3-substitutedprop-2-en-1-one,-benzoimidazol-1-yl) methylamino) phenyl)-3-substitutedprop-2-en-1-one, was synthesized from o-phenylenediamine by a multistep synthesis. All the synthesized compounds were characterized by spectroscopic means and elemental analyses. The title compounds were investigated for in vitro antibacterial and antifungal properties against some human pathogenic microorganisms by employing the agar streak dilution method using Ciprofloxacin and Ketoconazole as standard drugs. All title compounds showed activity against the entire strains of microorganism. Structural activity relationship studies reveal that compounds possessing an electron-withdrawing group display better activity than the compounds containing electron-donating groups, whereas the unsubstituted derivatives display moderate activity. Based on the results obtained, N-((1H-benzoimidazol-1-yl) methyl)-4-(1-phenyl-5-(4-(trifluoromethyl) phenyl)-4,5-dihydro-1H-pyrazol-3-yl) benzenamine 5i was found to be very active compared with the rest of the compounds and standard drugs that were subjected to antimicrobial assay.

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New substituted 2-(pyrazol-1-yl)-dialkylacetanilides with potential local anesthetic and antiarrhythmic action. Part II

Cited by 24 publications

References 7 publications

An Unexpected and Green Synthetic Protocol for Ethyl 1-Aroyl/Aroylmethyl-5-methyl-3-methylthiopyrazole-4-carboxylates: High Regioselectivity in Alkylation and Acylation Reactions between N-1 and N-2 of a Pyrazole Ring

An Unexpected and Green Synthetic Protocol for Ethyl 1-Aroyl/Aroylmethyl-5-methyl-3-methylthiopyrazole-4-carboxylates: High Regioselectivity in Alkylation and Acylation Reactions between N-1 and N-2 of a Pyrazole Ring

Acute Toxicity of Substituted 2‐(1H‐pyrazol‐1‐yl)acetanilides and Related Commercially Available Local Anesthetics Toward Mice. A GRIND/ALMOND‐Based 3‐D QSAR Study

Synthesis, characterization and antimicrobial activity of some novel benzimidazole derivatives

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