Synthesis and evaluation of anti-inflammatory and analgesic activity of 3-[(5-substituted-1,3,4-oxadiazol-2-yl-thio)acetyl]-2H-chromen-2-ones

Ingale, Nista; Maddi, Veeresh; Palkar, Mahesh B.; Ronad, Pradeepkumar; Mamledesai, Shivalingrao; Vishwanathswamy, A.H.M.; Satyanarayana, D.

doi:10.1007/s00044-010-9494-z

Cited by 34 publications

(8 citation statements)

References 18 publications

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“…(The scheme was redrawn from literature.) [33][34][35][36][37][38][39][40][41] ChemistrySelect ChemistrySelect formation of 1,3-thiazolidine-2,4-dione-coumarin compounds (21) in potassium carbonate and dimethylformamide solution in reasonable-to-good yields (Scheme 3). [41] The antioxidant, anti-inflammatory and antidiabetic activity of synthesized compounds were evaluated and in cases for R = 4-Cl, 3-Br, 3-OC 2 H 5 -4-OH displayed the best activities in vivo.…”

Section: Nucleophilic Substitutions Of 3-bromoacetylcoumarinmentioning

confidence: 99%

“…For instance, the reaction of 3‐bromoacetylcoumarin ( 2 ) with heterocyclic amines under reflux conditions formed amino acetyl compounds ( 3 ) in good yields [33] . A series of oxadiazol‐2‐ylthio‐acetyl‐2 H ‐chromen‐2‐ones ( 5 ) were made in reasonable‐to‐good yields by the condensation of 3‐bromoacetylcoumarin ( 2 ) and oxadiazolyl‐2‐thione ( 4 ) with sodium ethoxide as a catalyst under reflux conditions in ethanol [34] . Compounds 5 were evaluated in vivo for acute anti‐inflammatory and analgesic activities at a dosage of 200 mg/kg bw and considerable anti‐inflammatory and analgesic activity were reported (c, e, f and h) [34] …”

Section: Nucleophilic Substitutions Of 3‐bromoacetylcoumarinmentioning

confidence: 99%

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3‐Bromoacetylcoumarin, a Crucial Key for Facial Synthesis of Biological Active Compounds

et al. 2022

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Compounds containing the coumarin scaffold are widely used in the pharmaceutical and medicinal industries. The biological activities of coumarin containing derivatives make the attractive for the develop new drugs. Different methods and techniques are developed to synthesize new drugs using coumarin as a starting material. This review summarized various methods, techniques and reaction conditions for synthesis of coumarins containing compounds from 3‐bromoacetylcoumarin. A total of 79 coumarin intermediates and products are reported herein. The different reactions include nucleophilic substitutions, one‐pot and multi‐step synthesis for preparation of coumarin containing compounds through different mechanisms and the outcomes achieved through such reactions are discussed. The prepared compounds showed a range of activities resulting in antifungal, antimicrobial, anti‐inflammatory, antidiabetic and cholinesterase inhibitors. The nucleophilic substitution reactions involving urea related compounds, followed by intramolecular cyclization lead to imidazole and thiazole moieties, which exhibit antibacterial activities. It is hoped that this review provides useful insight for researchers engaged in this field to expand the knowledge gained in this area.

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Section: Nucleophilic Substitutions Of 3-bromoacetylcoumarinmentioning

confidence: 99%

Section: Nucleophilic Substitutions Of 3‐bromoacetylcoumarinmentioning

confidence: 99%

3‐Bromoacetylcoumarin, a Crucial Key for Facial Synthesis of Biological Active Compounds

et al. 2022

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“…Inflammation is a physiological reactionwhich involves cellular and biochemical responses, which is not only symptom for common diseases but also known to be an early phase for some serious diseases such as alzheimer's disease, cancer, heart vascular diseases [ 1 ] etc. Nonsteroidal anti-inflammatory drugs (NSAIDs) like ketoprofen, ibuprofen, aceclofenac, and so forth under current clinical usage for the treatment of inflammation, algesia and pyresis [ 2 ] are associated with major drawbacks of gastrointestinal disorders like dyspepsia, gastric ulcers, and so forth, due to the direct contact of free carboxylic group with the gastric mucosa [ 3 , 4 ] and due to decrease in production of prostaglandins in tissue [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

Therapeutic Potential of Hydrazones as Anti-Inflammatory Agents

Kajal

Bala

Sharma

et al. 2014

International Journal of Medicinal Chemistry

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Hydrazones are a special class of organic compounds in the Schiff base family. Hydrazones constitute a versatile compound of organic class having basic structure (R1R2C=NNR3R4). The active centers of hydrazone, that is, carbon and nitrogen, are mainly responsible for the physical and chemical properties of the hydrazones and, due to the reactivity toward electrophiles and nucleophiles, hydrazones are used for the synthesis of organic compound such as heterocyclic compounds with a variety of biological activities. Hydrazones and their derivatives are known to exhibit a wide range of interesting biological activities like antioxidant, anti-inflammatory, anticonvulsant, analgesic, antimicrobial, anticancer, antiprotozoal, antioxidant, antiparasitic, antiplatelet, cardioprotective, anthelmintic, antidiabetic, antitubercular, trypanocidal, anti-HIV, and so forth. The present review summarizes the efficiency of hydrazones as potent anti-inflammatory agents.

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“…Further, Bhandari et al, (2008) reported the synthesis and pharmacological evaluations (antiinflammatory, analgesic, and ulcerogenicity) of novel Schiff bases derived from 2-[(2,6-dichloroanilino) phenyl] acetic acid (Diclofenac). Based on the above mentioned facts and in continuation of our research program (Palkar et al, 2014;Ingale et al, 2012;Khode et al, 2009;Gadad et al, 2008) on the synthesis of novel therapeutic antiinflammatory agents, we herein report the synthesis and spectral studies of series of novel Schiff base analogs derived from a versatile phenylalanine scaffold (2a-j). These compounds exhibited an interesting anti-inflammatory and analgesic activity profile with significant reduction in their ulcerogenic effect.…”

Section: Introductionmentioning

confidence: 99%

Novel series of phenylalanine analogs endowed with promising anti-inflammatory activity: synthesis, pharmacological evaluation, and computational insights

et al. 2014

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A novel series of methyl-2-(substituted benzylideneamino)-3-phenyl propionate (2a-j) derivatives have been synthesized. The title compounds (2a-j) were screened for in vivo acute anti-inflammatory and analgesic activities at a dose of 200 mg/kg b.w. Compound 2e exhibited the most promising and significant anti-inflammatory profile while compounds 2b, 2h, 2i, and 2j showed moderate to good inhibitory activity at 2nd and 4th h, respectively. These compounds were also found to have considerable analgesic activity (acetic acid-induced writhing model) and antipyretic activity (yeast-induced pyrexia model). In addition, the tested compounds were also found to possess less degree of ulcerogenic potential as compared to the standard NSAIDs. The synthesized compounds were further evaluated for their inhibitory activity against cyclooxygenase enzyme (COX-1/COX-2), by in vitro colorimetric COX (ovine) inhibitor screening assay method. The results revealed that the compounds 2b, 2e, 2h, 2i, and 2j exhibited selective and effective inhibition against COX-2. In an attempt to understand the ligand-protein interactions in terms of their binding affinity, docking studies were also performed using Molegro Virtual Docker (MVD-2013, 6.0) for the title compounds. It was observed that the binding affinities calculated were in agreement with the experimental IC 50 values.

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Synthesis and evaluation of anti-inflammatory and analgesic activity of 3-[(5-substituted-1,3,4-oxadiazol-2-yl-thio)acetyl]-2H-chromen-2-ones

Cited by 34 publications

References 18 publications

3‐Bromoacetylcoumarin, a Crucial Key for Facial Synthesis of Biological Active Compounds

3‐Bromoacetylcoumarin, a Crucial Key for Facial Synthesis of Biological Active Compounds

Therapeutic Potential of Hydrazones as Anti-Inflammatory Agents

Novel series of phenylalanine analogs endowed with promising anti-inflammatory activity: synthesis, pharmacological evaluation, and computational insights

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