The preparation and properties of some derivatives of 1-phenylpyrazole

Finar, I. L.; Godfrey, K. E.

doi:10.1039/jr9540002293

Cited by 53 publications

(15 citation statements)

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“…As illustrated in Figure B, the synthetic route began with 1‐(4‐fluorophenyl)‐1 H ‐pyrazole ( 5 ) and proceeded through the classical method described by Finar and Godfrey . Chemoselective and regiospecific formylation of 1‐(4‐fluorophenyl)‐1 H ‐pyrazole ( 7 ) to 1‐(4‐fluorophenyl)‐1 H‐ pyrazole‐4‐carbaldehyde ( 8 ) was performed under Duff's conditions .…”

Section: Resultsmentioning

confidence: 99%

New pyrazole derivative 5‐[1‐(4‐fluorophenyl)‐1H‐pyrazol‐4‐yl]‐2H‐tetrazole: synthesis and assessment of some biological activities

et al. 2016

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The molecular modification and synthesis of compounds is vital to discovering drugs with desirable pharmacological and toxicity profiles. In response to pyrazole compounds' antipyretic, analgesic, and anti-inflammatory effects, this study sought to evaluate the analgesic, anti-inflammatory, and vasorelaxant effects, as well as the mechanisms of action, of a new pyrazole derivative, 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole. During the acetic acid-induced abdominal writhing test, treatments with 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole reduced abdominal writhing, while during the formalin test, 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole reduced licking times in response to both neurogenic pain and inflammatory pain, all without demonstrating any antinociceptive effects, as revealed during the tail flick test. 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole also reduced carrageenan-induced paw edema and cell migration during the carrageenan-induced pleurisy test. As demonstrated by the model of the isolated organ, 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole exhibits a vasorelaxant effect attenuated by Nω-nitro-l-arginine methyl ester, 1H-[1,2,4]oxadiazolo[4,3-alpha]quinoxalin-1-one, tetraethylammonium or glibenclamide. 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole also blocked CaCl -induced contraction in a dose-dependent manner. Suggesting a safe toxicity profile, 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole reduced the viability of 3T3 cells at higher concentrations and was orally tolerated, despite signs of toxicity in doses of 2000 mg/kg. Lastly, the compounds' analgesic activity might be attributed to the involvement of the NO/cGMP pathway and K channels observed in the vasorelaxant effect.

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Section: Resultsmentioning

confidence: 99%

New pyrazole derivative 5‐[1‐(4‐fluorophenyl)‐1H‐pyrazol‐4‐yl]‐2H‐tetrazole: synthesis and assessment of some biological activities

et al. 2016

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“…O n using dim ethylam ine in the M annich reaction w ith com pound 1, com pound 4 was isolated as a sole product instead of the expected M annich base 3. The form ation of 4, may be rationalized in term s of the form ation [11,12] T he involvem ent of both C-5 and am ino group in this reaction is in line with our w ork [13,14] and the w ork of R oth and H agen [15].…”

Section: Resultsmentioning

confidence: 63%

Enaminouraciles as Precursors for Synthesis of Pyrimido[4,5-a]pyrimidine- 2,4-diones

Hamama

2000

Zeitschrift Für Naturforschung B

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The reaction of 6-aminouracil 1 with formaldehyde and secondary amines in ethanol at room temperature gave the corresponding 5-alkylaminomethyl derivatives (2a-c) and bis(4- pyrimidyl) methane (4). Also, Mannich reaction with primary aliphatic and aromatic amines at room temperature afforded pyrimid[4,5-d]pyrimidine (5 and 6). Treatment of 1 with o-phenylenediamine through transamination gave com pound 7 which cyclized through intramolecular Mannich reaction with formalin to yield pyrimido[4,5-e]-[l,4]diazepine (8).

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“…1, the synthetic route began with 1-(3-fluorophenyl)-1H-pyrazole (3) and proceeded through the classical method described by Finar and Godfrey. 25) Chemoselective and regiospecific formylation of 1-(3-fluorophenyl)-1H-pyrazole (3) to 1-(3-fluorophenyl)-1H-pyrazole-4-carbaldehyde (4) was performed under Duff's conditions. 26,27) The synthesis of 1-(3-fluorophenyl)-1H-pyrazole-4-carbonitrile (5) was carried out through the formation of the oxime by reaction of 1-(3-fluorophenyl)-1H-pyrazole-4-carbaldehyde (4) with hydroxylamine.…”

Section: Experimental Synthesis Steps Synthesis Of 1-(3-fluorophenylmentioning

confidence: 99%

Synthesis, Docking Studies, Pharmacological Activity and Toxicity of a Novel Pyrazole Derivative (LQFM 021)—Possible Effects on Phosphodiesterase

Martins

Pazini

Alves

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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This study describes the synthetic route and molecular computational docking of LQFM 021, as well as examines its biological effects and toxicity. The docking studies revealed strong interaction of LQFM 021 to phosphodiesterase-3 (PDE-3). In isolated arteries, the presence of endothelium potentiates the relaxation for LQFM 021 and the inhibition cyclic nucleotides reduced the relaxation. Pre-contraction with KCl (45 mM), the treatment with tetraethylammonium (TEA) (5 mM) and inhibition of reticular Ca(2+)-ATPase showed an inhibitory effect on relaxation. Moreover, the compound reduced the contraction evoked by the Ca(2+) influx. Acute toxicity tests revealed that the compound was practically nontoxic. In conclusion, this study showed that a new synthetic derivative of pyrazole is a possible PDE-3 inhibitor and has vasorelaxant activity and low toxicity.

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The preparation and properties of some derivatives of 1-phenylpyrazole

Abstract: The preparation of 1 -phenylpyrazole from epichlorohydrin and phenylhydrazine has been improved, and the method has been extended to include the use of nitrophenylhydrazines. Some 4-substituted derivatives of 1-phenylpyrazole have been prepared, and their properties have been investigated.

Cited by 53 publications

References 0 publications

New pyrazole derivative 5‐[1‐(4‐fluorophenyl)‐1H‐pyrazol‐4‐yl]‐2H‐tetrazole: synthesis and assessment of some biological activities

New pyrazole derivative 5‐[1‐(4‐fluorophenyl)‐1H‐pyrazol‐4‐yl]‐2H‐tetrazole: synthesis and assessment of some biological activities

Enaminouraciles as Precursors for Synthesis of Pyrimido[4,5-a]pyrimidine- 2,4-diones

Synthesis, Docking Studies, Pharmacological Activity and Toxicity of a Novel Pyrazole Derivative (LQFM 021)—Possible Effects on Phosphodiesterase

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