Induced Rat Paw Edema Test Research Articles

Synthesis and in silico ADMET evaluation of new thiazole and thiazolidine-4-one derivatives as non-ulcerogenic analgesic and anti-inflammatory agents

A series of 1,3-thiazoline-4-one derivatives bearing 2-phenoxyphenyl moiety, were synthesized as potential new analgesic and anti-inflammatory agents. The structures were confirmed by FT-IR, NMR, and Mass spectra. The abdominal constriction (writing) test was selected to evaluate analgesic activity and results showed that nearly all of them were active, and the most potent was 10m with 96% inhibition when compared to the control. The best compounds were selected to investigate the anti-inflammatory activity by carrageenan induced rat paw edema test. The results showed that compounds 8 and 10h were active from the 2nd to 5th hours of assessment. The ulcerogenic evaluation of two selected compounds showed that they are comparable with the vehicle control group and without any ulcerogenic effect potential. The target compounds showed an acceptable in silico ADME profile.

Novel Thiazolotriazolone Derivatives: Design, Synthesis, In Silico Investigation, Analgesic and Anti‐inflammatory Activity

AbstractA group of new thiazolo[3,2‐b][1,2,4]triazol‐6(5H)‐one fenamate‐like derivatives designed by using hybrid strategy in order to explore analgesic/anti‐inflammatory activity of the hybrid structures. Some of the synthesized analogs showed comparable activities with mefenamic acid in abdominal constriction test and carrageenan induced rat paw edema test. 5‐(4‐nitrobenzylidene)‐2‐(2‐(2‐chlorophenoxy)phenyl)thiazolo[3,2‐b][1,2,4]triazol‐6(5H)‐one (8 e) and 5‐(3,5‐di‐tert‐butyl‐4‐hydroxybenzylidene)‐2‐(2‐(2‐chlorophenoxy)phenyl)thiazolo[3,2‐b][1,2,4]triazol‐6(5H)‐one (8 k) were determined as the most active agents with 53.1 and 49.3 percent of inhibition after 4 hrs of ip administration respectively. Flexible docking investigation indicated that the designed molecules interacted with cyclooxygenase 1 and 2 (COX‐1 and COX‐2) active sites. Moreover, the results suggest that thiazolo[3,2b][1,2,4]triazol‐6(5H)‐one moiety has the same effect as mefenamic acid COOH group over COX‐1,2 with a significant low or no ulcerogenic activity. Furthermore, the energetically favorable conformer Z, revealed as the active structural conformation due to the less steric hindrance. Based on the predicted ADME properties of high potent anti‐inflammatory agents, it is proposed that the applied modifications promote the rational drug design of novel analgesic and anti‐inflammatory candidates.

Preparation and evaluation of herbo-mineral topical emulgel formulation in bovine clinical mastitis

The present study was conducted to prepare and evaluate the herbo-mineral emulgel formulation containing Curcuma longa, Datura metel, Aloe vera and and calcium hydroxide against bovine clinical mastitis. Extracts of selected plants were screened for phytochemicals. In Vitro antimicrobial screening of herbal extracts against isolated bacterial strains was performed by Agar disc-diffusion method. In Vitro antimicrobial activities of polyherbals (Curcuma longa, Datura metel and Aloe vera) and gentamicin sulphate (antibiotic agent) against Staphylococcus aureus, Streptococcus agalactiae and Escherichia coli isolates, alone and in combination were evaluated by minimum and fractional inhibitory concentrations study. Oil-in-water herbo-mineral emulsion was prepared using Cremophor EL and Tween 20. The optimized herbo-mineral emulsion was developed into emulgel using Carbopol 940 as a gelling agent and triethanolamine as alkalizer. Herbo-mineral emulgel formulations were evaluated for its pH, appearance, homogenecity, viscosity, spreadability, ex vivo permeation and stability. In vivo anti-inflammatory assay was done by carrageenan induced rat paw edema test. Acute dermal irritation study was conducted in rabbits. Clinical study was conducted in lactating cows to evaluate the efficacy herbo-mineral emulgel formulation against clinical mastitis. The phytochemicals screening showed the presence of alkaloids, flavonoids, glycosides, phenols, tannins, terpenoids, phlobatannins, saponins and carbohydrate compounds. Minimum and fractional inhibitory concentrations study showed that polyherbals in combination with gentamicin sulphate were able to provide stable synergistic therapeutic outcomes with higher efficacy in combating mastitis causing organisms in bovines. Based on In Vitro antimicrobial study, the extracts of Aloe vera, Datura metel, Curcuma longa and calcium hydroxide were taken in the ratio of 2:1:1:0.3 for the final formulation. The pH of emulgel (6.25± 0.30) was found to be in accordance with the range of udder skin pH. Herbo-mineral emulgel also illustrated efficient permeation (79.20 μL/cm2) through skin in 12 h. Viscosity (5720±85 cp), spreadability (10.02 ±0.12 g.cm/sec) indicated its suitability for topical application. Antimicrobial evaluation of polyherbal emulgel revealed broader zones of growth inhibitions against E.coli (16.35±0.58mm), S. aureus (19.23±1.05mm) and S. agalactiae (19.88±0.67mm). In vivo anti-inflammatory study showed that the anti-inflammatory effect of the herbo-mineral emulgel was significantly higher than the effect of Valdecoxib gel formulation and herbo-mineral formulation. Moreover, herbo-mineral emulgel was also found to be non-irritant. These parameters were consistent over 6 months. The Somatic cell counts and bacterial load in milk was significantly reduced in cows treated with herbo-mineral emulgel formulation. The results of clinical study indicated that the combined treatment i.e. herbo-mineral emulgel formulation topically along with systemic administration of gentamicin sulphate continuously for 5 days was most effective in the treatment of clinical mastitis as compared to herbo-mineral emulgel treatment alone or gentamicin sulphate treatment alone. From this study, it can also be concluded that the emulgel turned out to be a promising topical delivery of herbo-mineral containing Curcuma longa, Datura metel, Aloe vera and calcium hydroxide with enhanced therapeutic efficacy against clinical mastitis. Further, the herbo-mineral emulgel formulation will be an efficient and economically affordable formulation in the field to treat clinical mastitis immediately by farmers itself before getting help of veterinarians

COMPARATIVE STUDY ON ANTI-INFLAMMATORY SYNERGISTIC ACTIVITY OF LORNOXICAM USING TURMERIC OIL IN TDDS

The present research work was an attempt to develop, evaluate matrix-type transdermal therapeutic system containing lornoxicam with hydrophilic polymer (HPMC E-5) and turmeric oil (leaf extract) by the solvent evaporation technique. The turmeric oil has been used for two reasons, one is to see whether it act as natural penetration enhancer (replacing chemical enhancers) and also to compare the anti-inflammatory synergism between the drug and the oil itself. The anti-inflammatory activity of turmeric oil has been well documented. The physicochemical compatibility of the drug, polymers and oil was studied by infrared spectroscopy. The results suggested no physicochemical incompatibility between them. Five transdermal patch formulations (F1 to F5) consists of HPMC E5 (300 mg fixed) and turmeric oil in the concentrations 3%, 4%, 5%, 6% and 7% respectively were prepared. All formulations carried 10% w/v of Polyethylene glycol as plasticizer in dichloromethane and methanol (4:1) as solvent system. The prepared transdermal patches were evaluated for in vitro release, moisture absorption, moisture loss and mechanical properties. The diffusion studies were performed by using modified Franz diffusion cells. The formulation, F3 showed maximum release 97.56% as compared to patch without any penetration enhancer (58.83%).The synergistic activity has been determined by Carrageenan induced rat paw edema test and the results have confirmed the synergistic activity between the drug and turmeric oil. The developed transdermal patches may increase the efficacy of lornoxicam for the therapy of arthritis and other painful muscular conditions.
 Keywords: Transdermal system, HPMC, Turmeric oil, penetration enhancer, Synergistic activity.

Microwave-Assisted Synthesis, In Vivo Anti-Inflammatory and In Vitro Anti-Oxidant Activities, and Molecular Docking Study of New Substituted Schiff Base Derivatives

In view of considerable interest in the design and synthesis of new heterocyclic compounds with promising biological activities for medical and biological applications, a series of eight imine derivatives have been synthesized through microwave-assisted Schiff base formation by reacting 2-(4-methoxyphenyl)acetohydrazide (3) and 4-amino-3-(4-methoxybenzyl)-1H-1,2,4-triazole-5(4H)-thione (6) with various substituted aldehydes. Structures of the newly synthesized compounds were characterized by FT-IR, 1H NMR and 13C NMR spectral analysis. All the synthesized derivatives were screened for their in vivo anti-inflammatory and in vitro anti-oxidant activities using carrageenan induced rat paw edema test and DPPH free radical scavenging assay, respectively. In addition, molecular docking experiment was also performed to check the actual binding affinity of ligand against target protein. Compounds 4a, 4c, 7a, and 7c screened as potent anti-inflammatory drugs significantly lowered the volume of rat paw edema (P < 0.05). In case of anti-oxidant assay, compound 7a with ferrocenyl group as substituent R and 3,4-disubstitued 1,2,4-triazole as side coupled group exhibited IC50 value of 7.2 ± 2.7 μg/mL comparable with that of the reference ascorbic acid (2.61 ± 0.29 μg/mL) and was the most active compound among the series. However, no prominent results were obtained in case of aralkanoic acid hydrazide substituted Schiff base derivatives 4a – 4d. It is believed that the synthesized Schiff base derivatives can be used for the development of potent anti-inflammatory and anti-oxidant drugs with considerable advantages of convenient synthetic strategy possessing high product yield, short reaction time, and convenient handling. The molecular docking results were found in good correlation with experimental IC50 values.

Isolation and Characterization of Bioactive Moiety from Leaf Extract of Ipomoea mauritiana and Evaluation of Anti-Inflammatory Activity by Carrageenan Induced Rat Paw Edema Test

Ipomoea mauritiana Jacq. is a member of family Convolvulaceae and commonly called as Ksheervidari is widely used in various traditional medicines for the treatment of many diseases. In the present work the column fractions of leaf extracts of I. mauritiana obtained by Soxhlet exrtaction was subjected to TLC, column chromatography, HPLC and liquid chromatography and mass spectroscopy (LC-MS). The compounds like caffeic acid and β-amyric acetate were tentatively identified to be present in one of the purified fraction. The column fraction was also tested for anti-inflammatory activity by carrageenan induced rat paw edema assay. The column fraction tested showed a very good anti inflammatory activity.

Phytochemical and Biological Evaluations of Methanolic Extract of Amaranthus graecizans subsp. silvestris (Vill.) Brenan

Amaranthus graecizans subsp. silvestris (AMGRS) has traditionally been used a folk medicine in the treatment of inflammation, gonorrhea and piles without scientific evidence. Therefore, methanolic (MeOH) extract of AMGRS was studied for anti-nociceptive, anti-inflammatory and enzymatic inhibition activities in addition to phytochemical screening to ascertain the realism of the folk claims. Anti-nociceptive activity was screened by hot plate test, tail immersion test and acetic acid-induced abdominal writhing in mice with different doses of MeOH extract of AMGRS i.e. 100, 300 and 600 mg/kg. Anti-inflammatory activity was evaluated using carrageenan-induced paw edema model in rats with different doses of MeOH extract of AMGRS i.e. 100, 300 and 600 mg/kg. While, anticholinesterase and protease inhibition was carried to screen MeOH extract for its relevant therapeutic uses. Hot plate technique and tail immersion method demonstrated dose related antinociceptive response starting from 300 mg/kg to maximum effect seen at 600 mg/kg dose. Acetic acid induced writing produced 47% pain protection during 1st phase (0-15 minutes) at 600 mg/kg dose. Likewise, carrageenan induced rat paw edema test showed 42% reduction in edema at 4th h after oral administration of dose (600 mg/kg). The MeOH extract showed mild anticholinesterase inhibition (24.29±0.57) while exhibited significant protease inhibition activity (60.52±0.18). The present investigation suggests that this plant possesses substantial anti-nociceptive, anti-inflammatory and protease inhibition activities.

In vivo anti-inflammatory activity and docking study of newly synthesized benzimidazole derivatives bearing oxadiazole and morpholine rings

In search of potential therapeutics for inflammatory disease, we report herein the synthesis, characterization and anti-inflammatory activities of a new series of 1-{(5-substituted-1,3,4-oxadiazol-2-yl)methyl}-2-(morpholinomethyl)-1H-benzimidazoles (5a-r). The anti-inflammatory activity of the compounds was evaluated using carrageenan induced rat paw edema test. Some compounds showed excellent anti-inflammatory activity in carrageenan induced rat paw edema test. 1-{(5-(2-Chlorophenyl)-1,3,4-oxadiazol-2-yl)methyl}-2-(morpholinomethyl)-1H-benzimidazole (5g) showed maximum anti-inflammatory (74.17±1.28% inhibition) with reduced ulcerogenic and lipid peroxidation profile and also showed significant COX-2 inhibition with IC50 values of 8.00μM. Compounds 5o and 5q were also found to exhibit good COX-2 inhibition with IC50 values of 11.4 and 13.7μM concentrations. Molecular docking study showed that morpholine and oxadiazole rings linked to the benzimidazole nucleus play an important role in binding with the COX-2.

Preparation and evaluation of solid lipid nanoparticles based nanogel for dermal delivery of meloxicam

The aim of the current investigation was to prepare and investigate the potential of solid lipid nanoparticles based gel (SLN-gel) for the dermal delivery of meloxicam (MLX). The meloxicam loaded SLN (MLX-SLN) gel was developed and characterized by means of photon correlation spectroscopy, rheometry, and differential scanning calorimetry to determine the physicochemical properties. The behavior of SLN gel on rat skin was evaluated in vitro using Franz diffusion cells to determine the skin permeation and penetration characteristics, in vivo on mice to determine the skin tolerance by histopathological examinations. The anti-inflammatory potential of SLN gel was assessed by carrageenan induced rat paw edema test. Biophysical studies including differential scanning calorimetry (DSC) and Fourier transform infrared spectroscopy (FTIR) were undertaken to study the interaction between the SLN gel and skin. MLX-SLN gel with nanometric particle size exhibited the controlled release abilities and simultaneously the potential to transport the drug to various skin layers. SLN gel displayed viscoelastic properties with predominantly elastic behavior and exhibited plastic flow. Biophysical studies elucidated the interaction between the SLN gel and stratum corneum (SC) lipids, and proposed the lipid bilayer fluidization as the possible mechanism for the increased penetration of meloxicam into skin. The nano-gel system showed marked anti-inflammatory activity and excellent skin tolerability. It can be concluded that SLN gel may be a promising delivery system for MLX in the treatment of inflammatory disorders.

Bioavailability Studies of Ketorolac Tromethamine Fast Dissolving Tablets Prepared By Direct Compression Method

This study was concerned with the investigation of acute pharmacological responses (pharmacodynamics) including analgesic and anti-inflammatory effects of ketorolac tromethamine fast dissolving tablets prepared by direct compression method using 3% croscarmellose sodium as a superdisintegrant by applying tail flick test and carragenan induced rat paw edema test respectively. Also, the work aimed to develop a sensitive LC-MS/MS method for simultaneous determination of ketorolac tromethamine in human plasma samples released from fast dissolving tablets. Also, to estimate whether the prepared tablet dosage form increases the bioavailability of ketorolac tromethamine in the body compared to marketed conventional tablet. From this study, it could be inferred that ketorolac tromethamine fast dissolving tablets (G5) containing (3% corscarmellose sodium as a superdisintegrant, 30% Avicel pH102, 5% aspartame, 1% talc, 1% magnesium stearate, and mannitol Q.S.) and prepared by direct compression method could be considered as a promising formula to enhance bioavilability of the drug. Keyword: Ketorolac tromethamine fast dissolving tablet , Tail flick, Rat paw edema and bioavialbility

Synthesis of novel Naphthalene COX inhibitors for anti-inflammatory activity

Micropropagation and shoot regeneration of Cistus creticus ssp. CreticusPanagiotis Madesis, Elpiniki Konstantinidou, Athanasios Tsaftaris, Irini Nianiou-Obeidat

Antioxidant, Anti-Glycation and Anti-Inflammatory Activities of Phenolic Constituents from Cordia sinensis

Nine compounds have been isolated from the ethyl acetate soluble fraction of C. sinensis, namely protocatechuic acid (1), trans-caffeic acid (2), methyl rosmarinate (3), rosmarinic acid (4), kaempferide-3-O-β-D-glucopyranoside (5), kaempferol-3-O-β-D-glucopyranoside (6), quercetin-3-O-β-D-glucopyranoside (7), kaempferide-3-O-α-L-rhamnopyranosyl (1→6)-β-D-glucopyranoside (8) and kaempferol-3-O-α-L-rhamno-pyranosyl (1→6)-β-D-glucopyranoside (9), all reported for the first time from this species. The structures of these compounds were deduced on the basis of spectroscopic studies, including 1D and 2D NMR techniques. Compounds 1–9 were investigated for biological activity and showed significant anti-inflammatory activity in the carrageen induced rat paw edema test. The antioxidant activities of isolated compounds 1–9 were evaluated by the DPPH radical scavenging test, and compounds 1, 2, 4 and 7–9 exhibited marked scavenging activity compared to the standard BHA. These compounds were further studied for their anti-glycation properties and some compounds showed significant anti-glycation inhibitory activity. The purity of compounds 2–5, 8 and 9 was confirmed by HPLC. The implications of these results for the chemotaxonomic studies of the genus Cordia have also been discussed.

Fenbufen based 3-[5-(substituted aryl)-1,3,4-oxadiazol-2-yl]-1-(biphenyl-4-yl)propan-1-ones as safer antiinflammatory and analgesic agents

The synthesis of a series of 3-[5-(substituted aryl)-1,3,4-oxadiazol-2-yl]-1-(biphenyl-4-yl)propan-1-ones derived from 4-oxo-4-(biphenyl-4-yl)butanoic acid (fenbufen) is described. The structures of these compounds were supported by IR, 1H NMR, mass spectrometric data and elemental analysis. These compounds were tested for their antiinflammatory, analgesic, ulcerogenic and lipid peroxidation actions. A few compounds were found to have very good antiinflammatory activity in carrageenan induced rat paw edema test, while a fair number of compounds showed significant analgesic activity in acetic acid induced writhing test. The newly synthesized compounds showed very low ulcerogenic action with reduced malondialdehyde (MDA) content, which is one of the byproducts of lipid peroxidation. In vitro COX-1 and COX-2 isozyme inhibition studies were also performed on some of the selected compounds. Compound 4i and 4h were found to be more selective towards COX-2 as indicated by COX-2 selectivity index of 36.06 and 29.05 (COX-2 IC 50 = 1.5 μM and 1.8 μM) respectively.

Synthesis, spectroscopic, antimicrobial and anti-inflammatory studies of 5(2′-hydroxyphenyl)-3-(4-x-phenyl)pyrazolinates of copper(II) and their addition complexes with donor ligands

Complexes of copper(II) with 5(2′-hydroxyphenyl)-3-(4-x-phenyl)pyrazolines, (C15H12N2OX)2Cu [X =–H,–Cl,–CH3,–OCH3] have been synthesized with their addition complexes with 2,2′-bipyridine, 1,10-phenanthroline and triphenylphosphine. The complexes were characterized by elemental analyses, molecular weight measurement, magnetic, conductivity measurement, IR, electronic, 31P NMR, ESR and FAB mass spectra. The complexes were examined for crystalline/amorphous nature through XRD. Square-planar geometry around copper(II) is suggested with two bidentate pyrazoline ligands. In the additional complexes pyrazoline is monodentate. The bidentate and monodentate behavior of pyrazoline ligands was confirmed by IR and 31P NMR spectral data. All complexes were tested for in vitro antibacterial and antifungal activity and exhibit very good antibacterial and antifungal activity; coordination has a pronounced effect on the microbial activities. The brine shrimp bioassay was also carried out to study their in vitro cytotoxic properties. All complexes and adducts displayed potent cytotoxic activity against Artemia salina. Anti-inflammatory activity was also carried out by the carrageenan induced rat paw edema test. The complexes and adducts were found to have higher anti-inflammatory activity.

Synthesis, reactions and biological activity of 3-arylidene-5-(4-methylphenyl)-2(3H)-furanones?

3-Arylidene-5-(4-methylphenyl)-2(3H)-furanones 2a-m were prepared from 3-(4-methyl-benzoyl)propanoic acid 1 and several aromatic aldehydes. Some of the selected furanones were reacted with ammonia gas and benzylamine to give corresponding 3-arylidene-1,3-dihydro-5-(4-methylphenyl)-2H-pyrrol- 2-ones 3a-h and 3-arylidene-1-benzyl-1,3-dihydro-5-(4-methylphenyl)-2H- -pyrrol-2-ones 4a-f, respectively, which were characterized on the basis of IR, 1H-NMR, mass spectral data and elemental analysis results. These compounds were tested for their anti-inflammatory and antibacterial activities. The compounds, which showed significant anti-inflammatory activity, were further screened for their analgesic and ulcerogenic activities. Three new compounds (2e, 2h and 4d), out of twenty-seven showed very good anti-inflammatory activity in the carrageenan induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. The antibacterial activity is expressed as the corresponding MIC values.

Antinociceptive and anti-inflammatory activities of Pandanus fascicularis Lamk. leaves in animal models

The present study was carried out to elucidate the potential of, chloroform extract of Pandanus (P.) fascicularis Lamk (Family-Pandanaceae) leaves on antinociceptive, behavioral study and anti-inflammatory effects using various animal models The dried, powdered leaves of, P. fascicularis were extracted successively with petroleum ether (<TEX>$60\;-\;80^{\circ}C$</TEX>) and chloroform in soxhlet apparatus. The chloroform extract (yield 21.6% w/w with respected to dry powdered plant material) was selected for all experimental procedure. Two models were employed to investigate the effects on nociception, the tail immersion and hot plate method in Swiss albino mice and anti inflammatory effect were investigated by employing the carrageenan induced rat paw edema test in. adult Wister albino rats. Behavioral study was investigated by elevated plus maze method in Swiss albino mice. Results were revealed that the PFCE was found significant antinociceptive effect (P < 0.001) at the dose levels of 100, 200 and 400 mg/kg, orally in mice and produced remarkable antiinflammatory effect (P < 0.001) at the same dose levels used in the rats. Behavioral study of the PFCE has no significant anxiolysis effect when used orally. It concludes that, PFCE possessed remarkable antinociceptive effect and anti-inflammatory effect but no anxiolytic effect on animal models.

1,3,4-Oxadiazole/thiadiazole and 1,2,4-triazole derivatives of biphenyl-4-yloxy acetic acid: Synthesis and preliminary evaluation of biological properties

A series of 1,3,4-oxadiazole/thiadiazole and 1,2,4-triazole derivatives of biphenyl-4-yloxy acetic acid were synthesized in order to obtain new compounds with potential anti-inflammatory activity, analgesic activity and lower ulcerogenic potential. All compounds were evaluated for their anti-inflammatory activity by the carrageenan induced rat paw edema test method. The compounds possessing potent anti-inflammatory activity were further tested for their analgesic, ulcerogenic and antioxidant activities. Out of all tested compounds, the compounds 3, 7, 17 and 20, showed significant reduction in rat paw edema induced by carrageenan treatment. These compounds showed significant analgesic effect and at an equimolar oral doses relative to flurbiprofen were also found to be non-gastrotoxic in rats. Compound 17 was evaluated as the lead compound having more anti-inflammatory activity (81.81%) than the reference drug (79.54%), low ulcerogenic potential and protective effect on lipid peroxidation.

6-Aryl-4-Oxohexanoic Acids: Synthesis, Effects on Eicosanoid Biosynthesis,and Anti-Inflammatory In Vivo-Activities

The synthesis of a series of 6-aryl-4-oxohexanoic acids is described: This involves condensation of an appropriate aldehyde (Ia-f) and levulenic acid using catalytic amounts of piperidine and acetic acid in toluene to afford the 6-aryl-4-oxohex-5-enoic acids (IIa-f). The arylidene derivatives (IIa-d) were reduced by hydrogen at room temperature using palladium (10 %/carbon) as catalyst to produce 6-aryl-4-oxohexanoic acids (IIIa-d) as target compounds. In certain instances, the lactone derivative (IVd) was obtained as a low-melting by-product. These compounds were tested in two models used for evaluating the activity of non-steroidal anti-inflammatory drugs (NSAIDs). The first test is the effect of the synthesized compounds on arachidonic acid metabolism in vitro using human whole blood assay. The second is the in vivo carrageenan induced rat paw edema test. Compound IIe showed higher in vivo-activity compared to fenbufen at the same dose level (50mg/kg).

2‐Arylidene‐4‐(4‐phenoxy‐phenyl)but‐3‐en‐4‐olides: Synthesis, Reactions and Biological Activity.

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2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides: Synthesis, reactions and biological activity

2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides ( 1– 17) were prepared from 3-(4-phenoxy-benzoyl)propionic acid and aromatic aldehydes. Some of the selected butenolides were reacted with ammonia and benzylamine to give corresponding 3-arylidene-5-(4-phenoxy-phenyl)-2(3 H)-pyrrolones ( 18– 23) and 3-arylidene-5-(4-phenoxy-phenyl)-1-benzyl-2(3 H)-pyrrolones ( 24– 29) respectively, which were characterized on the basis of 1H-, 13C-NMR, Mass spectrometric data and elemental analysis results. These compounds were tested for anti-inflammatory and antimicrobial actions. The compounds, which showed significant anti-inflammatory activity, were screened for their analgesic and ulcerogenic activities. Five new compounds ( 5, 6, 7, 25 and 26), out of 29 showed very good anti-inflammatory activity in the carrageenan induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. Antibacterial activity against Staphylococcus aureus and Escherichia coli as well as antifungal activity against Candida albicans were expressed as the corresponding minimum inhibitory concentration (MIC) values. Compound 21, 22 and 23 showed excellent activity against C. albicans with MIC-10 μg/ml. Out of the above-mentioned compounds, 22 and 23 also showed good activity against S. aureus with MIC-20 and 15 μg/ml respectively.