SYNTHESIS, BIOLOGICAL EVALUATION, QSAR AND DOCKING STUDIES OF 2-AMINO-5-(SUBSTITUTED)PHENYL-1,3,4-THIADIAZOLES

INDIAN DRUGS ◽  
2015 ◽  
Vol 52 (09) ◽  
pp. 5-12
Author(s):  
S. S Mahajan ◽  
◽  
A. D. Gaitonde
Keyword(s):  
Analgesic Activity ◽  
Docking Studies ◽  
Biological Evaluation ◽  
Qsar Studies ◽  
Paw Oedema ◽  
Cox 2 ◽  
Anti Inflammatory ◽  
Analgesic Activities ◽  
Rat Paw ◽  
Rat Paw Oedema

Ten compounds from the series of 2-amino-5-(substituted)phenyl-1,3,4-thiadiazoles were synthesized and evaluated for anti-inflammatory and analgesic activities. Their structures were characterized by infrared spectroscopy and confirmed by 1H NMR spectroscopy. Anti-inflammatory activity was carried out by carrageenan-induced rat paw oedema method using indomethacin as standard. Analgesic activity was performed by acetic-acid induced writhing method in mice using aspirin as standard. The QSAR studies were performed for the analgesic activity using the software ‘Strike’ from Schrodinger. Docking studies were carried out for COX-2 inhibition using the software ‘Glide’ from Schrodinger. The compounds were obtained in good yields and possessed good anti-inflammatory and analgesic activities. Various physicochemical parameters, contributing towards analgesic activity were identified from the QSAR studies. The Glide Scores were more or less correlated with the anti-inflammatory and analgesic activities of compounds.

scholarly journals Synthesis and Evaluation of New Coumarin Derivatives as Antioxidant, Antimicrobial, and Anti-Inflammatory Agents

Molecules ◽  
2020 ◽  
Vol 25 (14) ◽  
pp. 3251 ◽  
Author(s):  
Hanan M. Alshibl ◽  
Ebtehal S. Al-Abdullah ◽  
Mogedda E. Haiba ◽  
Hamad M. Alkahtani ◽  
Ghada E.A. Awad ◽  
...  
Keyword(s):  
Significant Inhibition ◽  
Coumarin Derivatives ◽  
Paw Oedema ◽  
Cox 2 ◽  
Anti Inflammatory ◽  
Rat Paw ◽  
Orally Active ◽  
Rat Paw Oedema ◽  
Sulfonamide Compound

New pyranocoumarin and coumarin-sulfonamide derivatives were prepared and evaluated for their antioxidant, antimicrobial, and/or anti-inflammatory activities. Coumarin-sulfonamide compounds 8a–d demonstrated significant antioxidant activity, while 7c,d, 8c,d, and 9c,d exhibited antimicrobial activity equal to or higher than the standard antimicrobials against at least one tested microorganism. Regarding the anti-inflammatory testing, pyranocoumarins 2b, 3a,b and 5c and coumarin-sulfonamide compound 9a showed more potent antiproteinase activity than aspirin in vitro; however, five compounds were as potent as aspirin. The anti-inflammatory activity of the promising compounds was further assessed pharmacologically on formaldehyde-induced rat paw oedema and showed significant inhibition of oedema. For in vitro COX-inhibitory activity of coumarin derivatives, pyranocoumarin derivative 5a was the most selective (SI = 152) and coumarin-sulfonamide derivative 8d was most active toward COX-2 isozyme. The most active derivatives met the in silico criteria for orally active drugs; thus, they may serve as promising candidates to develop more potent and highly efficient antioxidant, antimicrobial, and/or anti-inflammatory agents.

Synthesis of novel thiadiazole derivatives as selective COX-2 inhibitors

MedChemComm ◽  
2016 ◽  
Vol 7 (12) ◽  
pp. 2309-2327 ◽  
Author(s):  
Fatma A. Ragab ◽  
Helmi I. Heiba ◽  
Marwa G. El-Gazzar ◽  
Sahar M. Abou-Seri ◽  
Walaa A. El-Sabbagh ◽  
...  
Keyword(s):  
Paw Oedema ◽  
Analgesic Agents ◽  
Thiadiazole Derivatives ◽  
Cox 2 ◽  
Anti Inflammatory ◽  
Rat Paw ◽  
Cox 2 Inhibitors ◽  
Rat Paw Oedema

A novel series of thiadiazole derivatives were designed and synthesized for evaluation as selective COX-2 inhibitors in vitro and were investigated in vivo as anti-inflammatory and analgesic agents against carrageenan-induced rat paw oedema model in irradiated rats.

scholarly journals Anti-Inflammatory, Analgesic Evaluation and Molecular Docking Studies of N-Phenyl Anthranilic Acid-Based 1,3,4-Oxadiazole Analogues

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Suman Bala ◽  
Sunil Kamboj ◽  
Vipin Saini ◽  
D. N. Prasad
Keyword(s):  
Molecular Docking ◽  
Analgesic Activity ◽  
Anthranilic Acid ◽  
Docking Studies ◽  
Immersion Method ◽  
Molecular Docking Studies ◽  
Rat Paw Edema ◽  
Cox 2 ◽  
Anti Inflammatory ◽  
Rat Paw

A novel series of N-phenyl anthranilic acid-based 1,3,4-oxadiazoles were prepared (4a–h) and subjected to anti-inflammatory, analgesic activity and molecular docking studies to target cyclooxygenase-2 enzyme. 1,3,4-Oxadiazole derivatives were screened for anti-inflammatory activity in carrageenan-induced rat paw edema and analgesic activity by tail immersion method. In synthesized compounds, the free carboxylic group, which is responsible for gastric side effects, was derivatized by heterocyclic 1,3,4-oxadiazole bioactive core, which showed good interaction with COX-2 receptor with good docking score. Among all the synthesized compounds,4eand4fhave emerged out as potential COX-2 inhibitors.

scholarly journals Synthesis, characterization and pharmacological evaluation of substituted phenoxy acetamide derivatives

2015 ◽  
Vol 69 (4) ◽  
pp. 405-415 ◽  
Author(s):  
Priyanka Rani ◽  
Dilip Pal ◽  
Rahul Hegde ◽  
Syed Hashim
Keyword(s):  
Analgesic Activity ◽  
Diclofenac Sodium ◽  
Inflammatory Activity ◽  
The Novel ◽  
Standard Drug ◽  
Antipyretic Activity ◽  
Paw Oedema ◽  
Anti Inflammatory ◽  
Rat Paw ◽  
Rat Paw Oedema

A novel series of 2-(substituted phenoxy)-N-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)acetamide and N-(2-bromocyclohexyl)-2-(substituted phenoxy)acetamide derivatives having cyclohexyl nucleus as common in both types were synthesized and assessed for their anti-inflammatory activity by a carrageenan induced rat paw oedema method, analgesic activity by Eddy?s hot plate method and antipyretic activity by brewer?s yeast induced pyrexia method. All the novel derivatives have been synthesized by the reaction of camphor and similar ketone having cyclohexane nucleus (e.g. 2-bromocyclohexanone) with ammonium carbonate and formic acid resulting in the formation of aromatic amines (1a-b). These amines on further chloroacetylation with chloroacetylchloride give compounds (2a-b). Compounds (2a-b) are converted to 2-(substituted phenoxy)-N-(1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl) acetamide and N-(2-bromocyclohexyl)-2-(substituted phenoxy)acetamide derivatives on treatment with substituted phenol. Among the series 3a-f, 3i, 3k, 3l compounds showed significant anti-inflammatory activity as compared to the standard drug diclofenac sodium and also compound 3a-f, 3h, 3j, 3k exhibit significant analgesic activity as compared to the standard drug. Compounds 3a-f and 3k showed antipyretic activity nearly to the standard drug indomethacin. Compounds 3a-f and 3k possess anti-inflammatory, analgesic and antipyretic activities near to the standard.

scholarly journals Synthesis of N-((2-Substituted Phenyl)-4, 5-Diphenyl-1H-Imidazol1yl)(Phenyl)Methyl) substituted amine derivatives, spectral characterization and their pharmacological evaluation

2011 ◽  
Vol 1 (5) ◽  
pp. 184-190 ◽  
Keyword(s):  
Aromatic Aldehyde ◽  
Analgesic Activity ◽  
Elemental Analysis ◽  
Spectral Characterization ◽  
Hot Plate ◽  
Pharmacological Evaluation ◽  
Paw Oedema ◽  
Anti Inflammatory ◽  
Rat Paw ◽  
Rat Paw Oedema

A series of N-((2-substituted phenyl) -4,5-diphenyl-1H-imidazol-1yl)(phenyl)methyl) substituted amine derivatives TPI (I-V) were synthesized by 2-substituted 4,5-diphenyl imidazole derivatives starting from benzyl and aromatic aldehyde. All these compounds were characterized by IR, 1HNMR, mass and elemental analysis. The newly synthesized compounds were screened for analgesic and anti-inflammatory activities by hot plate and carrageenan induced rat paw oedema methods. Compounds TPI-IV and TPI-V have showed potent anti-inflammatory activity and compounds TPI-III, TPI-IV and TPI-V showed good analgesic activity

Fibrinolytic, Anti-Inflammatory and Cytotoxic Potentialities of Extracts and Chemical Constituents of Manglicolous Lichen, Graphis ajarekarii Patw. & C. R. Kulk

2020 ◽  
Vol 10 (1) ◽  
pp. 87-93 ◽  
Author(s):  
Vinay Bharadwaj Tatipamula ◽  
Girija Sastry Vedula
Keyword(s):  
Protein Denaturation ◽  
Biological Activities ◽  
Chemical Constituents ◽  
Fibrin Clot ◽  
Hydroalcoholic Extract ◽  
Paw Oedema ◽  
Anti Inflammatory ◽  
Rat Paw ◽  
Rat Paw Oedema

Background: Lichens which are betide to mangroves are termed as Manglicolous Lichens (ML). As these ML are habituated under stress conditions, they are screened for unique metabolites and biological activities. Objective: The study aimed to establish the chemical and biological profile of ML, Graphis ajarekarii. Methods: The Ethyl Acetate Extract of G. ajarekarii (EAE) was subjected to chromatographic techniques and the obtained isolates were characterized by spectroscopic analysis. The hydroalcoholic extract of G. ajarekarii (AE), EAE, isolates and Hydroalcoholic Extract of host (HE) were evaluated for fibrinolytic (fibrin clot method), in vitro (protein denaturation method) and in vivo (formalin-induced rat paw oedema assay), anti-inflammatory and cytotoxicity (MTT assay) activities. Results: Chemical investigation of the EAE led to the isolation of two known compounds namely atranorin (1) and ribenone (2), which were confirmed by spectral data. The AE and EAE gradually lysed the fibrin clot with 94.54 and 65.07%, respectively, at 24 h. The AE inhibited protein denaturation of about 88.06%, while the standard (Indomethacin) with 93.62%. Similarly, the in vivo antiinflammatory analysis of AE (200 mg/mL) showed potent reduction of rat paw oedema than the standard, whereas EAE and 1 depicted moderate depletion. In addition, the AE revealed prominence inhibition on MCF-7, DU145 and K-562 with IC50 values of 69.5, 42.5 and 38 µg/mL, respectively, whereas the HE exhibited mild inhibitory profile against fibrin clot, inflammation and cancer. Conclusion: From the results, it can be concluded that the G. ajarekarii has an aptitude to act against coagulation, inflammation and cancer cells.

scholarly journals IN SILICO DESIGN AND MOLECULAR DOCKING STUDIES OF SOME 1, 2-BENZISOXAZOLE DERIVATIVES FOR THEIR ANALGESIC AND ANTI-INFLAMMATORY ACTIVITY

2017 ◽  
Vol 9 (3) ◽  
pp. 133
Author(s):  
Sarath Sasi Kumar ◽  
Anjali T
Keyword(s):  
Molecular Docking ◽  
Acetylcholine Receptor ◽  
Nicotinic Acetylcholine Receptor ◽  
Analgesic Activity ◽  
In Silico ◽  
Docking Studies ◽  
Inflammatory Activity ◽  
Nicotinic Acetylcholine ◽  
Cox 2 ◽  
Anti Inflammatory

Objective: In silico design and molecular docking of 1,2-benzisoxazole derivatives for their analgesic and anti-inflammatory activity using computational methods.Methods: In silico molecular properties of 1,2-benzisoxazole derivatives were predicted using various software’s such as Chemsketch, Molinspiration, PASS and Schrodinger to select compounds having optimum drug-likeness, molecular descriptors resembling those of standard drugs and not violating the ‘Lipinski rule of 5’. Molecular docking was performed on active site of nicotinic acetylcholine receptor (PDB: 2KSR) for analgesic activity and COX-2 (PDB: 6COX) for anti-inflammatory activity using Schrodinger under maestro molecular modelling environment.Results: From the results of molecular docking studies of 1,2-benzisoxazole derivatives, all the compounds showed good binding interactions with Nicotinic acetylcholine receptor and COX-2. Compounds 4a and 4c showed highest binding scores (-7.46 and-7.21 respectively) with nicotinic acetylcholine receptor and exhibited maximum analgesic activity. Compound 4a showed highest binding score (-7.8) with COX-2 and exhibited maximum anti-inflammatory activity.Conclusion: All the derivatives of 1,2-benzisoxazole showed good analgesic and anti-inflammatory activity as predicted using molecular docking on respective receptors.

Anti-Inflammatory Constituents of Alchornea cordifolia Leaves

2015 ◽  
Vol 19 ◽  
pp. 60-64
Author(s):  
AA Ahmadu ◽  
A Agunu ◽  
EM Abdurrahman
Keyword(s):  
Medicinal Plant ◽  
West Africa ◽  
Ethyl Acetate ◽  
Leaf Extract ◽  
Methyl Gallate ◽  
Paw Oedema ◽  
Analgesic Agents ◽  
Anti Inflammatory ◽  
Rat Paw ◽  
Rat Paw Oedema

Alchornea cordifolia (Schum and Thonn) Muell. Arg. (Euphorbiaceae) is a traditional medicinal plant widely distributed in West Africa including Nigeria.The plant has been used for ethnomedicinal purposes against wounds, ulcers, and sores. The decoction of the leaves has been reported to provide remedies for bronchial problems, rheumatic pain and cough. From the dichloromethane and ethyl acetate soluble parts of the Methanol leaf extract, two compounds namely Lup-20(29)-en-3c-ol (lupenol) and Methyl 3, 4,5-trihydroxy benzoate (Methyl gallate) were isolated and their structures elucidated. Anti-inflammatory and analgesic properties of the compounds on carrageenan-induced paw oedema and formalin-induced pain in rats showed that compound 2 significantly (P<0.05) inhibit rat paw oedema compared to the standard drugs (Piroxicam and Morphine) used, while on formalin-induced pain in rats, the same trend was observed and were both comparable to Piroxicam and morphine, the standard anti-inflammatory and analgesic agents used, respectively. Compound 1 did not show any significant anti-inflammatory activity compared to control, likewise compound 2. Thus, compound 2, Methyl trihydroxy benzoate, might be responsible for the anti-inflammatory and analgesic properties of this plant.Keywords: Alchornea cordifolia, Anti-inflammatory, Analgesic, Methyl Trihydroxy Benzoate

scholarly journals A New Cytotoxic Sesquiterpene and Three Anti-inflammatory Flavonoids from Egyptian Tanacetum Santolinoides

2007 ◽  
Vol 2 (11) ◽  
pp. 1934578X0700201 ◽  
Author(s):  
Sabrin R. M. Ibrahim ◽  
Jihan M. Badr ◽  
Khalid A. El Sayed ◽  
Diaa T. A. Youssef
Keyword(s):  
Cytotoxic Activity ◽  
Brine Shrimp ◽  
Methanolic Extract ◽  
Spectral Characteristics ◽  
Mass Spectral ◽  
Aerial Parts ◽  
Paw Oedema ◽  
Anti Inflammatory ◽  
Rat Paw ◽  
Rat Paw Oedema

A re-investigation of the methanolic extract of the aerial parts of Tanacetum santolinoides has resulted in the isolation of a new sesquiterpene, tanacetonic acid (1), along with three known methoxylated flavonoids. The structure of the isolated compounds was secured based on their IR, UV, 1D and 2D (1H-1H COSY, HSQC and HMBC) NMR spectroscopic and FAB mass spectral characteristics. The new sesquiterpene showed a significant cytotoxic activity when tested using the brine shrimp bioassay, while the three flavonoids demonstrated anti-inflammatory effects in the rat paw oedema test.

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