Antinociceptive properties of chalcones. Structure-activity relationships

Corrêa, Rogério; Pereira, Márcia A. S.; Buffon, Daniela; Santos, Lorena dos; Filho, Valdir Cechinel; Santos, Adair Roberto Soares; Nunes, Ricardo José

doi:10.1002/1521-4184(200110)334:10<332::aid-ardp332>3.3.co;2-f

Cited by 8 publications

(6 citation statements)

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“…Synthesis of chalcones 1-12 by Claisen-Schmidt condensation. equimolar amounts of a substituted acetophenone with a substituted benzaldehyde in the presence of aqueous/ alcoholic alkaline hydroxide (Scheme 1) [25]. The synthetic reaction gave good yields (58 to 81%) for all the chalcones 1-12 reported here.…”

Section: Chemistrymentioning

confidence: 79%

Synthesis and inhibitory potential towards acetylcholinesterase, butyrylcholinesterase and lipoxygenase of some variably substituted chalcones

Arslanoğlu

Khan

Sher

et al. 2005

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of variably substituted chalcones were synthesized by condensation of substituted acetophenones with mono-, di- or trisubstituded benzaldehydes. It was observed that some of these compounds have the potential to inhibit acetylcholinesterase, whereas others show activity against butyrylcholinesterase, depending on the substitution pattern at the two aromatic rings of these chalcones. Similarly, lipoxygenase was inhibited by two of these compounds. It has been observed that inhibition of the three enzymes was concentration dependent with the IC50 values ranging from 28.2-134.5 microM against acetylcholinesterase, 16.0-23.1 microM against butyrylcholinesterase and 57.6-71.7 microM against lipoxygenase, respectively.

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Section: Chemistrymentioning

confidence: 79%

Synthesis and inhibitory potential towards acetylcholinesterase, butyrylcholinesterase and lipoxygenase of some variably substituted chalcones

Arslanoğlu

Khan

Sher

et al. 2005

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Despite their structural simplicity, these compounds exhibit diverse important pharmacological effects on biological systems including anti-inflammatory (Correa et al, 2001), anti-mycobacterial (Rojas et al, 2002), antimalarial (Chen et al, 1994), anti-fungal (Boeck et al, 2006;Lopez et al, 2001), anti-viral (Phrutivorapongkul et al, 2003), and anti-nociceptive (Correa et al, 2001). Previous studies have shown that chalcones bearing phenyl group with chloro and hydroxyl substituents inhibit nitric oxide (NO) synthesis as well as inducible nitric oxide synthase (iNOS) protein expression in RAW 264.7 cells (Ko et al, 2003;Won et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent

et al. 2011

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In this study, thirty-eight chalcone analogs were synthesized and evaluated for nitric oxide (NO) inhibition activity on RAW 264.7 cells. Among these compounds, chalcones bearing furanyl group showed remarkable anti-inflammatory activity. Both compounds 2d and 2j were identified as the most potent NO inhibitor on IFN-c/LPS-activated RAW 264.7 cells. In order to examine the structure-activity relationship, a 3D QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method on the selected chalcones. Partial least square analysis produced a statistically coherent model with good predictive value, r 2 = 0.989 and a good cross validated value, q 2 = 0.583.

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“…Chalcones or 1,3‐diaryl‐2‐propen‐1‐ones are a well‐known class of flavonoids that have been reported to possess both in vitro and in vivo biological activities including antimicrobial, anticancer, antiprotozoal, antiplatelet, antinociceptive and anti‐inflammatory [1–6]. It has been reported elsewhere that chalcones and their derivatives inhibited the synthesis of nitric oxide (NO), lipoxygenase as well as cyclo‐oxygenase activities which constitute the major pro‐inflammatory pathways and remain most targeted for anti‐inflammatory and antinociceptive drug development [7–10].…”

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confidence: 99%

Possible Participation of Nitric Oxide/Cyclic Guanosine Monophosphate/Protein Kinase C/ATP-Sensitive K+ Channels Pathway in the Systemic Antinociception of Flavokawin B

Mohamad

Akhtar

Khalivulla

et al. 2011

Basic &Amp; Clinical Pharmacology &Amp; Toxicology

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The possible mechanisms of action in the antinociceptive activity induced by systemic administration (intraperitoneal, i.p.) of flavokawin B (FKB) were analysed using chemical models of nociception in mice. It was demonstrated that i.p. administration of FKB to the mice at 0.3, 1.0, 3.0 and 10 mg ⁄ kg produced significant dose-related reduction in the number of abdominal constrictions. The antinociception induced by FKB in the acetic acid test was significantly attenuated by i.p. pretreatment of mice with L-arginine, the substrate for nitric oxide synthase or glibenclamide, the ATP-sensitive K + channel inhibitor, but was enhanced by methylene blue, the non-specific guanylyl cyclase inhibitor. FKB also produced dose-dependent inhibition of licking response caused by intraplantar injection of phorbol 12-myristate 13-acetate, a protein kinase C activator (PKC). Together, these data indicate that the NO ⁄ cyclic guanosine monophosphate ⁄ PKC ⁄ ATP-sensitive K + channel pathway possibly participated in the antinociceptive action induced by FKB.Chalcones or 1,3-diaryl-2-propen-1-ones are a well-known class of flavonoids that have been reported to possess both in vitro and in vivo biological activities including antimicrobial, anticancer, antiprotozoal, antiplatelet, antinociceptive and anti-inflammatory [1][2][3][4][5][6]. It has been reported elsewhere that chalcones and their derivatives inhibited the synthesis of nitric oxide (NO), lipoxygenase as well as cyclo-oxygenase activities which constitute the major pro-inflammatory pathways and remain most targeted for anti-inflammatory and antinociceptive drug development [7][8][9][10].In attempts to obtain active derivatives from chalcone that possesses anti-inflammatory and antinociceptive activities, our group previously isolated 6¢-hydroxy-2¢,4¢-dimethoxychalcone or flavokawin B (FKB) from Alpinia nutans Rosc. along with other chalcones such as cardamonin (6), 5,6-dehydrokawain, (-)-pinocembrin, (-)-pinostrobin and 2¢,3¢,4¢,6¢-tetrahydroxychalcone [11]. Recently, we chemically synthesized FKB and demonstrated that systemic administration of FKB exerted potent dose-dependent antinociceptive activity when assessed in the chemical and thermal models of nociception in mice, indicating involvement of the peripheral and central antinociceptive activities [12]. Moreover, in the same study, we demonstrated that the central antinociceptive activity of FKB was not mediated by the activation of opioid receptors. Besides, we also demonstrated that FKB produced marked inhibition of the nociceptive response caused by intraplantar injection of glutamate into mouse hind paw in the glutamate-induced nociception test and perhaps the inhibition of peripheral N-Methyl-D-aspartic acid (NMDA) receptors contributes to the antinociceptive effect of FKB [12]. As activation of the NO cascade is known to take place secondary to NMDA receptor activation and a great deal of evidence has demonstrated the role of NO in various models of nociception [13][14][15][16], this has led to the ...

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Antinociceptive properties of chalcones. Structure-activity relationships

Cited by 8 publications

References 0 publications

Synthesis and inhibitory potential towards acetylcholinesterase, butyrylcholinesterase and lipoxygenase of some variably substituted chalcones

Synthesis and inhibitory potential towards acetylcholinesterase, butyrylcholinesterase and lipoxygenase of some variably substituted chalcones

Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent

Possible Participation of Nitric Oxide/Cyclic Guanosine Monophosphate/Protein Kinase C/ATP-Sensitive K+ Channels Pathway in the Systemic Antinociception of Flavokawin B

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