Trifluoromethyl‐Containing Pyrazolinyl (p‐Tolyl) Sulfones: The Synthesis and Structure of Promising Antimicrobial Agents.

Bonacorso, Hélio G.; Wentz, Alexandre P.; Lourega, Rogério V.; Chechinel, Cleber A.; Moraes, Tatiana S.; Coelho, Helena S.; Zanatta, Nilo; Martins, Marcos A. P.; Hoeerner, Manfredo; Alves, Syndey H.

doi:10.1002/chin.200649122

Cited by 5 publications

(8 citation statements)

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“…1), named here compound A, was synthesized according to Bonacorso et al . [14]. Analyses of 1 H NMR and 13 C NMR spectra showed analytical and spectroscopic data in full agreement with the assigned structure.…”

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confidence: 55%

“…We have recently synthesized some trifluoromethyl‐containing pyrazolinyl sulfones with substitutions in 1,3 positions of the central pyrazole ring, using a regiospecific substitution method [14]. The aim of the present study was to investigate the antinociceptive effect of one of these compounds [3‐(4‐fluorophenyl)‐5‐trifluoromethyl‐1 H ‐1‐tosylpyrazole or compound A], in several models of pain in mice, and compare its effects with those produced by the trifluoromethyl‐containing pyrazole compound celecoxib.…”

mentioning

confidence: 99%

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Antinociceptive Effect of a Novel Tosylpyrazole Compound in Mice

Oliveira¹,

Gewehr²,

Dalmolin³

et al. 2009

Basic Clin Pharma Tox

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Pain is the most common complaint in the medical field and the identification of compounds that can effectively treat painful states without induction of side-effects remains a major challenge in biomedical research. The aim of the present study was to investigate the antinociceptive effect of a novel compound, 3-(4-fluorophenyl)-5-trifluoromethyl-1 H -1-tosylpyrazole (compound A) in several models of pain in mice and compare with those produced by the known trifluoromethyl-containing pyrazole compound celecoxib. Compound A or celecoxib were administrated by oral (78-780 μ mol/kg), intrathecal (9-22.5 nmol/site) or intracerebroventricular (9-22.5 nmol/site) routes. Oral administration of either compound A or celecoxib abolished the mechanical allodynia, but not the oedema caused by intraplantar injection of carrageenan. Similarly, compound A reduced the overt nociception, but not the oedema, produced by bradykinin or capsaicin. However, compound A (500 μ mol/kg, orally) did not alter nociception nor oedema caused by intraplantar injection of prostaglandin E 2 or glutamate, whereas celecoxib reduced only the nociception induced by the former. Moreover, oral and intrathecal administration of compound A or celecoxib also reduced the nociception induced by acetic acid. However, only celecoxib reduced the acetic acid-induced nociception when it was injected by the intracerebroventricular route. Finally, neither compound A nor celecoxib was able to produce antinociceptive effect in the tail-flick test or to alter the motor performance and the body temperature. Besides, compound A or celecoxib did not induce gastric lesion. Thus, compound A seems to be an interesting prototype for the development of novel analgesic drugs.

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supporting

confidence: 55%

mentioning

confidence: 99%

Antinociceptive Effect of a Novel Tosylpyrazole Compound in Mice

Oliveira¹,

Gewehr²,

Dalmolin³

et al. 2009

Basic Clin Pharma Tox

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“…[24]: 153e154 C); 1 H NMR (600 MHz, DMSO-d 6 ) d 7.88 (d,J ¼ 8.6,2H,Ar),7.55 (d,J ¼ 8.6,2H,Ar), 7.52 (s, 2H, NH 2 ), 7.25 (d,J ¼ 8.7,2H,Ar),7.16 (s,1H,6.98 (d,J ¼ 8.7,2H,Ar) 1614, 1596, 1499, 1453, 1336, 1234, 1157, 1124,1097, 1030MS-EI (m/z) ,3.55;N,10.57%. Found C,51.00;H,3.48;N,-3-(trifluoromethyl)-1H-pyrazol-1-yl) benzenesulfonamide (6e). White powder, 94% yield, m.p.…”

Section: General Procedures For the Synthesis Of 4-(5-aryl-3-(trifluormentioning

confidence: 99%

“…for C 17 H 14 F 3 N 3 O 2 S (381.08): C,53.54;H,3.70;N,11.02%. Found C,53.17;H,3.81;N,-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide (6d). Orange powder, 75% yield, m.p.…”

Section: General Procedures For the Synthesis Of 4-(5-aryl-3-(trifluormentioning

confidence: 99%

Regioselectively controlled synthesis of 3(5)-(trifluoromethyl)pyrazolylbenzenesulfonamides and their effects on a pathological pain model in mice

Lobo

Oliveira

Brusco

et al. 2015

European Journal of Medicinal Chemistry

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“…Fluorine is a well-known bioisostere in various organofluorine compounds as antimycobacterial agents [10]. The introduction of fluorine has already shown to modulate the stereoelectronic parameters of organic molecules [11,12]. Substitution of fluorine into a potential drug molecule not only alters the electronic environment, but also influences the p avalue of neighboring Bronsted acid/base centers, polarity, and the influence on lipophilicity as expressed by the distribution coefficient.…”

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confidence: 99%

Synthesis of New Fluorine Substituted Heterocyclic Nitrogen Systems Derived fromp-Aminosalicylic Acid as Antimycobacterial Agents

Makki

Abdel‐Rahman

Faidallah

et al. 2013

Journal of Chemistry

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Some new fluorine substituted heterocyclic nitrogen systems2–17have been synthesized from ring closure reactions of substitutedp-amino salicylic acids (PAS). The Schiffs base of PAS was cyclized with chloroacetyl chloride and mercaptoacetic acid to give azetidinone2, thiazolidinone3, and spiro-fluoroindolothiazoline-dione10. However, PAS when reacted directly with 4-fluorobenzoyl chloride and 5-oxazolinone yielded derivatives4,5, and7. Aminomethylation of PAS using formaldehyde and piperidine or piperazine formed N-alkyl and N,N′-dialkyl derivatives (11and12respectively) upon fluorinated benzoylation gave compounds13and14. Similarly, treatment of PAS with thiosemicarbazide15and subsequent cyclization with diethyl oxalate yielded the fluorinated heterocycle17. The structures of the fluorinated heterocyclic systems have been established on the basis of elemental analysis,1H NMR,13C NMR, and MS spectral data. Some of the targets exhibited a high inhibition towardsMycobacteriumstrain with favorable logPvalues.

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Trifluoromethyl‐Containing Pyrazolinyl (p‐Tolyl) Sulfones: The Synthesis and Structure of Promising Antimicrobial Agents.

Cited by 5 publications

References 1 publication

Antinociceptive Effect of a Novel Tosylpyrazole Compound in Mice

Antinociceptive Effect of a Novel Tosylpyrazole Compound in Mice

Regioselectively controlled synthesis of 3(5)-(trifluoromethyl)pyrazolylbenzenesulfonamides and their effects on a pathological pain model in mice

Synthesis of New Fluorine Substituted Heterocyclic Nitrogen Systems Derived fromp-Aminosalicylic Acid as Antimycobacterial Agents

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