Mechanisms involved in the antinociceptive and anti-inflammatory effects of a new triazole derivative: 5-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1H-tetrazole (LQFM-096)

Cardoso, Carina Sofia; Silva, Daiany P.B.; Silva, Dayane M.; Florentino, Iziara Ferreira; Fajemiroye, James Oluwagbamigbe; Moreira, Lorrane Kelle da Silva; Vasconcelos, José P; Sanz, Germán; Vaz, Boniek G.; Lião, Luciano M.; Lima, Danilo da Silva; Santos, Fernanda C. A.; Menegatti, Ricardo; Costa, Élson Alves

doi:10.1007/s10787-020-00685-8

Cited by 22 publications

(10 citation statements)

References 64 publications

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“…[ 42,43 ] Furthermore, there have been new reports on the importance of lowering PGE 2 in anti‐inflammatory activities. [ 44 ] A study was performed to determine the ability of 7j , 7k , and 7l to inhibit PGE 2 in PGE 2 serum rat levels in blood samples obtained after 5 h of subcutaneous carrageenan injections. Table 5 shows the proportion of PGE 2 inhibition.…”

Section: Resultsmentioning

confidence: 99%

New pyrimidine/thiazole hybrids endowed with analgesic, anti‐inflammatory, and lower cardiotoxic activities: Design, synthesis, and COX‐2/sEH dual inhibition

Abdel‐Aziz

Taher

Lan

et al. 2022

Archiv der Pharmazie

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Some cyclooxygenase (COX)-2 selective medications were withdrawn from the market just a few years after their production due to cardiovascular side effects. In this study, a new series of pyrimidine/thiazole hybrids 7a-p was synthesized as selective COX-2/soluble epoxide hydrolase (sEH) inhibitors with analgesic and antiinflammatory effects, and lower cardiotoxicity effects. The target compounds were synthesized and in vitro tested against COX-1, COX-2, and sEH enzymes. Hybrids 7j, 7k, and 7i showed the greatest COX-2-inhibitory activity and were discovered to be the most potent dual COX-2/sEH inhibitors. In vivo tests revealed that these hybrids were the most active analgesic/anti-inflammatory agents, with improved ulcerogenic and cardioprotective properties. Finally, the most active dual inhibitors were docked into COX-2/sEH active regions to explain their binding mechanisms.

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Section: Resultsmentioning

confidence: 99%

New pyrimidine/thiazole hybrids endowed with analgesic, anti‐inflammatory, and lower cardiotoxic activities: Design, synthesis, and COX‐2/sEH dual inhibition

Abdel‐Aziz

Taher

Lan

et al. 2022

Archiv der Pharmazie

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“…Thin layer chromatographic (TLC) analyses were performed on 200 µm silica gel (Sorbent Technologies ® , Norcross GA, USA) and visualized using UV light (254 and 365 nm). NMR analyses and 2D experiments were run on Varian ® INOVA 500, operating at 500 MHz for 1 H and 125 MHz for 13 C (11.7 T), using TMS as an internal standard. Standards of the C-flavones apigenin-7-methoxy-6-C-β-d-glucopyranoside (4) and apigenin-6-C-β-d-glucopyranosyl-8-C-βd-xylopyranoside (5) were previously obtained from the leaves of M. hirtum [6].…”

Section: Extraction and Isolationmentioning

confidence: 99%

“…The model used was as described by Hunskaar and Hole (1987), with a few modifications [13,14]. Male Swiss mice (n = 6−10 per group) were treated by gavage with HEMh (32.25, 62.5, 125, or 250 mg/kg, oral) or vehicle (saline 10 mL/kg, oral), used as negative control.…”

Section: Formalin-induced Nociceptionmentioning

confidence: 99%

“…Phytochemical studies of the HEMh allowed the isolation of five compounds. Compounds 1 and 2 were identified as α-amyrin (1) and β-amyrin (2) based on their 13 C NMR spectra and comparison with the literature data [26]. The identification of allantoin (3) was permitted after the analysis of 13 C NMR and 1 H NMR spectral data [27].…”

Section: Phytochemical Profile Of Hemhmentioning

confidence: 99%

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Machaerium hirtum (Vell.) Stellfeld Alleviates Acute Pain and Inflammation: Potential Mechanisms of Action

et al. 2020

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Machaerium hirtum (Vell.) Stellfeld (Fabaceae) known in Brazil as “jacaranda de espinho” or “espinheira santa nativa” is a medicinal plant commonly used in folk medicine to treat ulcers, cough and diarrhea. This study aimed to investigate the anti-inflammatory and antinociceptive effects of hydroalcoholic extracts from M. hirtum twig (HEMh) using in vivo experimental models of nociception through the involvement of transient receptor potential channels, acid-sensing ion channel (ASIC), nitrergic, opioidergic, glutamatergic, and supraspinal pathways. Our results revealed an antinociceptive effect of HEMh mediated by the opioidergic, l-arginine-nitric oxide and glutamate systems, as well as by interactions with TRPA1/ASIC channels. The anti-inflammatory effect of HEMh evaluated with a xylene-induced ear edema and by the involvement of arachidonic acid and prostaglandin E2 (PGE2) showed involvement of the COX pathway, based on observed decreases in PGE2 levels. A phytochemical investigation of the HEMh led to the isolation of α-amyrin, β-amyrin, allantoin, apigenin-7-methoxy-6-C-β-d-glucopyranoside, and apigenin-6-C-β-d-glucopyranosyl-8-C-β-d-xylopyranoside. In conclusion, the acute oral administration of HEMh inhibits the nociceptive behavioral response in animals through the nitrergic, opioid, glutamatergic pathways, and by inhibition of the TRPA1 and ASIC channels, without causing locomotor dysfunction. In addition, its anti-inflammatory effect is associated with the COX pathway and decreased PGE2 levels.

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“…Tetrazole is the lead motif in the field of medicinal chemistry. The uncommon, polynitrogen, electron-rich planer structure of the tetrazole ring is answerable to exhibit widespread applications for the treatment of various diseases especially antimicrobial [11][12], antifungal [13][14], antiviral [15][16], antitubercular [17][18], anticancer [19][20], antimalarial [21][22], antiangiogenic [23][24], anti-inflammatory [25][26], anti-HIV [27][28], analgesic [29][30], anti-Alzheimer [31][32], antinociceptive [33][34], and anticonvulsant [35][36]. Weak interactions like hydrogen bonding, van der wals force, or coordination bonding are responsible for binding the tetrazole ring easily with the various enzymes or receptors of microbes and are successfully applied as components for comprehensive pharmaceutical applications [37].…”

mentioning

confidence: 99%

Design and Synthesis of Some New Derivatives of Chlorobenzyl-Oxy-Phenyl-Ethyl-Thio-1H-Tetrazole and Study Their Antibacterial and Antifungal Activity

Ambhore¹

2021

Preprint

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In recent years tetrazole scaffolds have been attracted interest in the field of synthetic and medicinal chemistry research. The unique structure of the tetrazole derivatives exhibits widespread applications in biology and technology. The close structural resemblance with carboxylic acid acts as a booster of the latter. Due to this diversified potential utilization, several methods are reported for the synthesis of tetrazole scaffolds. Here in this chapter, we describe the synthesis of chlorobenzyl-oxy-phenyl-ethyl-thio-1H-tetrazole derivatives ( 6a-p ). The newly synthesized derivatives are characterized by spectral characterization and screened for their antifungal activity. Among these, some of the newly synthesized compounds show potent antifungal activity.

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Mechanisms involved in the antinociceptive and anti-inflammatory effects of a new triazole derivative: 5-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1H-tetrazole (LQFM-096)

Cited by 22 publications

References 64 publications

New pyrimidine/thiazole hybrids endowed with analgesic, anti‐inflammatory, and lower cardiotoxic activities: Design, synthesis, and COX‐2/sEH dual inhibition

New pyrimidine/thiazole hybrids endowed with analgesic, anti‐inflammatory, and lower cardiotoxic activities: Design, synthesis, and COX‐2/sEH dual inhibition

Machaerium hirtum (Vell.) Stellfeld Alleviates Acute Pain and Inflammation: Potential Mechanisms of Action

Design and Synthesis of Some New Derivatives of Chlorobenzyl-Oxy-Phenyl-Ethyl-Thio-1H-Tetrazole and Study Their Antibacterial and Antifungal Activity

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