Synthesis, Analgesic, and Anti-Inflammatory Activities of [6-(3,5-Dimethyl-4-Chloropyrazole-1-yl)-3(2H)-Pyridazinon-2-yl]Acetamides

Şüküroğlu, Murat; Ergün, Burcu Çaliskan; Ünlü, Serdar; Şahi̇n, Mustafa; Küpeli, Esra; Yeşilada, Erdem; Banoğlu, Erden

doi:10.1007/bf02977751

Cited by 53 publications

(31 citation statements)

References 20 publications

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“…The structures of compounds 14 and 15 were elucidated on the basis of the elemental analyses and spectral data. 3 protons and also the absence of the CH 2 CN protons supported the proposed structures of compounds 14 and 15. The 13 C-NMR spectra were also in accordance with the proposed structures as they showed the presence of two CH 3 and twelve aromatic carbons.…”

Section: Chemistrysupporting

confidence: 64%

“…The IR spectrum of compound 6 showed bands for NH and C=O groups at 3195, 1675, 1661 and 1642 cm´1, respectively. Further evidence for the structure of compound 6 was gained from its 1 3 , respectively. However, the appearance of two exchangeable broad singlet signals, one in the upfield region and the second in the downfield region in the ratio of 35:65 suggests the existence of compound 7 as an equilibrium mixture of 7a and 7b (Scheme 2).…”

Section: Chemistrymentioning

confidence: 99%

“…Pyridazinone derivatives, a class of compounds containing the N-N bond, exhibit a wide range of pharmacological activity [1], including analgesic, antidepressant, anti-inflammatory [2][3][4][5][6], antimicrobial [7,8] as well as herbicidal activities [9]. There are numerous reports available in the literature, which indicate the potential anticancer effects of pyridazinones.…”

Section: Introductionmentioning

confidence: 99%

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Utilization of Cyanoacetohydrazide and Oxadiazolyl Acetonitrile in the Synthesis of Some New Cytotoxic Heterocyclic Compounds

Shaker

Marzouk

2016

Molecules

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A (pyridazinyl)acetate derivative was reacted with thiosemicarbazide and hydrazine hydrate to yield spiropyridazinone and acetohydrazide derivatives, respectively. The acetohydrazide derivative was used as a starting material for synthesizing some new heterocyclic compounds such as oxoindolinylidene, dimethylpyrazolyl, methylpyrazolyl, oxopyrazolyl, cyanoacetylacetohydrazide and oxadiazolylacetonitrile derivatives. The behavior of the cyanoacetylacetohydrazide and oxadiazolylacetonitrile derivatives towards nitrogen and carbon nucleophiles was investigated. The assigned structures of the prepared compounds were elucidated by spectral methods (IR, 1 H-NMR 13 C-NMR and mass spectroscopy). Some of the newly prepared compounds were tested in vitro against a panel of four human tumor cell lines, namely hepatocellular carcinoma (liver) HePG-2, colon cancer HCT-116, human prostate cancer PC3, and mammary gland breast MCF-7. Also they were tested as antioxidants. Almost all of the tested compounds showed satisfactory activity.

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Section: Chemistrysupporting

confidence: 64%

Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Utilization of Cyanoacetohydrazide and Oxadiazolyl Acetonitrile in the Synthesis of Some New Cytotoxic Heterocyclic Compounds

Shaker

Marzouk

2016

Molecules

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“…Also deracoxib (Deramaxxe) is already used for the treatment of pain and inflammation in dogs [2,3]. Furthermore, there are various reports which have demonstrated the analgesic-antiinflammatory effects of pyrazole derivatives [4][5][6][7][8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antinociceptive-antimicrobial activities of some new amide derivatives of 3,5-di/-and 1,3,5-trimethylpyrazoles

Koçyığıt‐Kaymakcioğlu

Toklu

İkiz

et al. 2008

Journal of Enzyme Inhibition and Medicinal Chemistry

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Some N-(3,5-di-/1,3,5-trimethylpyrazole-4-yl)-4-substitutedbenzamide derivatives were prepared as possible antiociceptiveantimicrobial agents. New amide derivatives (3-12) were synthesized by reacting 4-amino-3,5-di and 1,3,5-trimethylpyrazoles with 4-substitutedbenzoyl chlorides. Hotplate and tail-immersion tests were used for the determination of the antinociceptive activity. Morphine, was used as a standard test drug. All compounds were administered at a dose of 100 mg/kg ip and some of them had significant antinociceptive activity in both tests. Compound 10 (N-(1,3,5-trimethylpyrazole-4-yl)-4-bromobenzamide), was the most active one in both tests among the compounds. The antinociceptive activity of the compounds 10, 11 (N-(1,3,5-trimethylpyrazole-4-yl)-4-chlorobenzamide), and 12 (N-(1,3,5-trimethylpyrazole-4-yl)-4-fluorobenzamide), started at 30 minutes and continued up to 150 minutes in the hotplate test. Also compounds were tested for their in vitro antimicrobial activity, but exhibited weak antibacterial activity.

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“…16) Furthermore, a lot of 3(2H)-pyridazinone derivatives have been reported as analgesic and anti-inflammatory agents without gastrointestinal side effect. 14,17,18) In the same direction, we planned to design new pyridazinone scaffolds as potential anti-inflammatory agents (Fig. 2).…”

mentioning

confidence: 99%

Synthesis and Biological Evaluation of New Heteroaryl Carboxylic Acid Derivatives as Anti-inflammatory-Analgesic Agents

Abouzid

Khalil

Ahmed

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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A series of nicotinic acid derivatives structurally related to niflumic acid and certain pyridazine-containing compounds have been synthesized and characterized by analytical and spectral data. All compounds were screened for their potential analgesic and anti-inflammatory activities. The compounds which displayed analgesic and anti-inflammatory activities were tested for ulcerogenicity and screened for in vivo inhibition of certain inflammatory cytokines such as tumor necrosis factor-alpha (TNF-α), interleukin-6 (IL-6), and cyclooxygenase-2 (COX-2). Compounds 1c, 2a, 2b, and 5a have shown potent analgesic and anti-inflammatory activities.

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Synthesis, Analgesic, and Anti-Inflammatory Activities of [6-(3,5-Dimethyl-4-Chloropyrazole-1-yl)-3(2H)-Pyridazinon-2-yl]Acetamides

Cited by 53 publications

References 20 publications

Utilization of Cyanoacetohydrazide and Oxadiazolyl Acetonitrile in the Synthesis of Some New Cytotoxic Heterocyclic Compounds

Utilization of Cyanoacetohydrazide and Oxadiazolyl Acetonitrile in the Synthesis of Some New Cytotoxic Heterocyclic Compounds

Synthesis and antinociceptive-antimicrobial activities of some new amide derivatives of 3,5-di/-and 1,3,5-trimethylpyrazoles

Synthesis and Biological Evaluation of New Heteroaryl Carboxylic Acid Derivatives as Anti-inflammatory-Analgesic Agents

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