Synthesis and SAR Evaluation of Mercapto Triazolobenzothiazole

2021 ◽  
Vol 18 (4) ◽  
pp. 362-374
Author(s):  
Mamatha S.V ◽  
S.L. Belagali ◽  
Mahesh Bhat
Keyword(s):  
Antibacterial Activity ◽  
Biological Activities ◽  
Antibacterial Activities ◽  
Biological Properties ◽  
Biological Evaluation ◽  
Step Method ◽  
Good Antibacterial Activity ◽  
Anti Inflammatory ◽  
Mic Value

Background: Benzothiazoles possess a vast sphere of biological activities including anti- inflammatory, antibacterial activities whereas triazoles display various pharmacological properties including antimicrobial and antitubercular activities. Hence, triazole conjugated benzothiazole side-chain anticipating their interesting biological properties has been focused upon. Objective: The objective of the current work is synthesis and biological evaluation of a new series of benzothiazole appended triazole derivatives. Methods: The target compounds were prepared via a multi-step method involving the treatment of 2-amino benzothiazole with hydrazine followed by cyclization with carbon disulfide to give the corresponding triazol-2-thiol derivatives and then alkylation of these derivatives. All the synthesized compounds were characterized by FT-IR, Mass, 1H and 13C NMR spectra and were screened for their antibacterial, antioxidant, anti-inflammatory and anti-tubercular (anti-TB) activities in vitro. These molecules were also docked into the enoyl acyl carrier reductase (Inha, PDB ID-1ZID) in silico. Results: While all the synthesized compounds were active against M. tuberculosis at 50 μg/ml, the pyrrolidine and piperidine appended benzothiazolyltriazoles showed the superior activity (MIC values 12.5 to 1.6 μg/ml). Compound 5a (5-CH3 with piperidine), 5b (7-CH3 with piperidine) and 7b (7-CH3 with pyrrolidine) showed good antibacterial activity against Staphylococcus aureus with MIC value 31.25μg/ml, while compounds 7a (5-CH3 with pyrrolidine), 6b (7-CH3 with morpholine) and 8c (7-Br with pyridine) exhibited good antibacterial activity against E-coli with MIC value 62.5μg/ml. Compounds 7b (7-CH3 with pyrrolidine) and 5c (7-Br with piperidine) showed good anti-oxidant activities with IC50 values 93.25 and 82.25, respectively. Notably, these compounds were non-toxic to the normal cells even at high concentrations with IC50 value 238μg/ml. Conclusion: The compound 7b, a benzothiazolyltriazole having a pyrrolidine group (five membered ring) attached to two CH2 groups and methyl substituent at 7th position of the benzothiazole ring emerged as a novel and promising hit molecule that showed anti-TB, antimicrobial and antiinflammatory activities in vitro.

Biological Evaluation of Some Selected Cyclic Imides: Mitochondrial Effects and in vitro Cytotoxicity

2004 ◽  
Vol 59 (9-10) ◽  
pp. 663-672 ◽  
Author(s):  
Silvia Regina Tozado Prado ◽  
Valdir Cechinel-Filho ◽  
Fátima Campos Buzzi ◽  
Rogério Corrêa ◽  
Silvia Maria Correia Suter Cadena ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Cell Viability ◽  
Cell Line ◽  
Biological Activities ◽  
General Structure ◽  
Peritoneal Macrophages ◽  
Biological Evaluation ◽  
Rat Liver Mitochondria ◽  
Cyclic Imides

Abstract Cyclic imides such as succinimides, maleimides, glutarimides, phthalimides and their derivatives contain an imide ring and a general structure -CO-N(R)-CO- that confers hydrophobicity and neutral characteristic. A diversity of biological activities and pharmaceutical uses have been attributed to them, such as antibacterial, antifungal, antinociceptive, anticonvulsant, antitumor. In spite of these activities, much of their action mechanisms at molecular and cellular levels remain to be elucidated. We now show the effects of several related cyclic imides: maleimides (S2, S2.1, S2.2, S3), glutarimides (S4, S5, S6), 4-aminoantipyrine derivatives (L1, F1, AL1, F1.14, F1.2) and sulfonated succinimides (RO1, FA, FE, FD, MC, DMC) on isolated rat liver mitochondria, B16-F10 melanoma cell line, peritoneal macrophages and different bacterial streams. The effects on mitochondrial respiratory parameters, cell viability and antibacterial activity were also evaluated. The results indicated that S3, S5 and S6 caused an increased oxygen consumption in the presence of ADP (state III) or its absence (state IV), while all other compounds decreased those parameters at different degrees of inhibition. All the compounds decreased the respiratory control coefficient (RCC). Loss of cell viability of peritoneal macrophages and the B16- F10 cell line was observed, L1 and S2.1 being more effective. S1, S2, S3, L1 and F1 compounds showed antibacterial activity at experimental concentrations.

scholarly journals Anti-periodontal Pathogen and Anti-inflammatory Activities of Oxyresveratrol

2013 ◽  
Vol 8 (5) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Waranyoo Phoolcharoen ◽  
Sireerat Sooampon ◽  
Boonchoo Sritularak ◽  
Kittisak Likhitwitayawuid ◽  
Jintakorn Kuvatanasuchati ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Pathogenic Bacteria ◽  
Biological Activities ◽  
Mrna Level ◽  
Periodontal Pathogen ◽  
Enzyme Linked Immunosorbent Assay ◽  
Minimal Bactericidal Concentration ◽  
Potential Candidate ◽  
Anti Inflammatory

Oxyresveratrol, a compound in the heartwood of Artocarpus lakoocha Roxb and other medicinal plants, has been shown to have various biological activities. However, these have not been studied in periodontal research. In this study, we investigated whether oxyresveratrol has antibacterial activity against the predominant perio-pathogenic bacteria Porphyromonas gingivalis and Aggregatibacter actinomycetemcomitans. Moreover, the anti-inflammatory properties of oxyresveratrol were studied in LPS-stimulated human periodontal ligament (hPDL) cells. The antibacterial activity of oxyresveratrol on P. gingivalis and A. actinomycetemcomitans was initially evaluated using a disc diffusion test. The anti-bacterial strength of oxyresveratrol was then assessed in vitro by determining the minimal inhibitory concentration (MIC) and the minimal bactericidal concentration (MBC). Furthermore, the effects of oxyresveratrol on the LPS-induced production of inflammatory mediators were measured in hPDL cells. The levels of cytokine mRNA and protein expression were determined using reverse transcriptase-polymerase chain reaction (RT-PCR) and enzyme-linked immunosorbent assay (ELISA), respectively. Our results showed that oxyresveratrol exhibited antibacterial activities against P. gingivalis with MIC and MBC values of 0.07 mg/mL and 0.16 mg/mL, respectively. The MIC and MBC values against A. actinomycetemcomitans were 0.08 mg/mL and 0.16 mg/mL, respectively. When examining inflammatory stimulation, LPS treatment strongly induced the expression of pro-inflammatory cytokines in hPDL cells. However, pre-treatment with oxyresveratrol significantly inhibited the expression of IL-6 and IL-8 at both the mRNA and protein levels. The IL-1β mRNA level was suppressed by oxyresveratrol, but the level of secreted IL-1β protein was not detectable using ELISA. The results of the present study indicate that oxyresveratrol is a potential candidate for use as an anti-periodontitis agent because of its anti-bacterial activity against the main oral pathogens related to periodontal disease and its anti-inflammatory activity in LPS-stimulated hPDL cells.

scholarly journals Phytochemical Characterization and Biological Evaluation of the Aqueous and Supercritical Fluid Extracts from Salvia sclareoides Brot

2017 ◽  
Vol 15 (1) ◽  
pp. 82-91
Author(s):  
Daniela Batista ◽  
Pedro L. Falé ◽  
Maria L. Serralheiro ◽  
Maria-Eduarda Araújo ◽  
Catarina Dias ◽  
...  
Keyword(s):  
Linoleic Acid ◽  
Supercritical Fluid ◽  
Antioxidant Properties ◽  
Biological Properties ◽  
Biological Evaluation ◽  
Cyclooxygenase 1 ◽  
Wide Range ◽  
Anti Inflammatory ◽  
Β Carotene

AbstractPlants belonging to the genus Salvia (Lamiaceae) are known to have a wide range of biological properties. In this work, extracts obtained from the aerial parts of Salvia sclareoides Brot. were evaluated to investigate their chemical composition, toxicity, bioactivity, and stability under in vitro gastrointestinal conditions. The composition of the supercritical fluid extract was determined by GC and GC-MS, while the identification of the infusion constituents was performed by HPLC-DAD and LC-MS. The in vitro cytotoxicity of both extracts (0-2 mg/mL) was evaluated in Caco-2 cell lines by the MTT assay. The anti-inflammatory and anticholinesterase activities were determined through the inhibition of cyclooxygenase-1 and acetylcholinesterase enzymes, while β-carotene/linoleic acid bleaching test and the DPPH assays were used to evaluate the antioxidant activity. The infusion inhibited cyclooxygenase-1 (IC50 = 271.0 μg/mL), and acetylcholinesterase (IC50 = 487.7 μg/ mL) enzymes, also demonstrated significant antioxidant properties, as evaluated by the DPPH (IC50 = 10.4 μg/mL) and β-carotene/linoleic acid (IC50 = 30.0 μg/mL) assays. No remarkable alterations in the composition or in the bioactivities of the infusion were observed after in vitro digestion, which supports the potential of S. sclareoides as a source of bioactive ingredients with neuroprotective, anti-inflammatory and antioxidant properties.

Synthesis and Biological Evaluation of Polyfluoroalkylated Antipyrines and their Isomeric O-Methylpyrazoles

2019 ◽  
Vol 15 (5) ◽  
pp. 521-536 ◽  
Author(s):  
Natalya Agafonova ◽  
Evgeny Shchegolkov ◽  
Yanina Burgart ◽  
Victor Saloutin ◽  
Alexandra Trefilova ◽  
...  
Keyword(s):  
Biological Activities ◽  
Biological Evaluation ◽  
Antipyretic Activity ◽  
Starting Point ◽  
Anti Inflammatory ◽  
Analgesic Activities ◽  
Synthesis And Biological Evaluation ◽  
Cox 1

Background: Formally belonging to the non-steroidal anti-inflammatory drug class pyrazolones have long been used in medical practices. Objective: Our goal is to synthesize N-methylated 1-aryl-3-polyfluoroalkylpyrazolones as fluorinated analogs of antipyrine, their isomeric O-methylated derivatives resembling celecoxib structure and evaluate biological activities of obtained compounds. Methods: In vitro (permeability) and in vivo (anti-inflammatory and analgesic activities, acute toxicity, hyperalgesia, antipyretic activity, “open field” test) experiments. To suggest the mechanism of biological activity, molecular docking of the synthesized compounds was carried out into the tyrosine site of COX-1/2. Conclusion: The trifluoromethyl antipyrine represents a valuable starting point in design of the lead series for discovery new antipyretic analgesics with anti-inflammatory properties.

scholarly journals SYNTHESIS AND EVALUATION OF ANTI-INFLAMMATORY AND ANTIBACTERIAL ACTIVITIES OF SOME 1, 2-BENZISOXAZOLE DERIVATIVES

2016 ◽  
Vol 8 (4) ◽  
pp. 64 ◽  
Author(s):  
Sarath Sasikumar ◽  
Haripriya M. ◽  
Anjali T.
Keyword(s):  
Antibacterial Activity ◽  
Diclofenac Sodium ◽  
Analytical Techniques ◽  
Antibacterial Activities ◽  
Inflammatory Activity ◽  
Antibacterial Drug ◽  
Standard Drug ◽  
Good Antibacterial Activity ◽  
Anti Inflammatory ◽  
And Staphylococcus Aureus

Objective: A series of 1, 2-Benzisoxazole derivatives were synthesized and characterized by various analytical techniques like Melting point, Rf, FTIR, and NMR spectra.Methods: Structures of the compounds were elucidated and evaluated for anti-inflammatory activity by HRBC membrane stabilization method, antibacterial activity against Escherichia coli and Staphylococcus aureus by cup plate method.Results: The compounds 4a and 4e showed good anti-inflammatory activity compared with standard drug Diclofenac sodium and compounds 4b and 4d showed good antibacterial activity on compared with standard drug Gentamycin.Conclusion: These compounds may serve as future leads for anti-inflammatory and antibacterial drug discovery.

scholarly journals Room Temperature Synthesis and Antibacterial Activity of New Sulfonamides Containing N,N-Diethyl-Substituted Amido Moieties

2012 ◽  
Vol 2012 ◽  
pp. 1-13 ◽  
Author(s):  
Olayinka O. Ajani ◽  
Oluwole B. Familoni ◽  
Feipeng Wu ◽  
Johnbull O. Echeme ◽  
Zheng Sujiang
Keyword(s):  
Antibacterial Activity ◽  
Mass Spectra ◽  
Room Temperature ◽  
Biological Activities ◽  
Chemical Structures ◽  
Wide Range ◽  
Synthetic Routes ◽  
Mic Value ◽  
C Nmr

Sulfonamide drugs which have brought about an antibiotic revolution in medicine are associated with a wide range of biological activities. We have synthesized a series of α-tolylsulfonamide, 1–11 and their substituted N,N-diethyl-2-(phenylmethylsulfonamido) alkanamide derivatives, 12–22 in improved and excellent yields in aqueous medium at room temperature through highly economical synthetic routes. The chemical structures of the synthesized compounds 1–22 were confirmed by analytical and spectral data such as IR, 1H- and 13C-NMR, and mass spectra. The in vitro antibacterial activity of these compounds along with standard clinical reference, streptomycin, was investigated on two key targeted organisms. It was observed that 1-(benzylsulfonyl)pyrrolidine-2-carboxylic acid, 2 emerged as the most active compound against Staphylococcus aureus at MIC value of 1.8 μg/mL while 4-(3-(diethylamino)-3-oxo-2-(phenylmethylsulfonamido) propyl)phenyl phenylmethanesulfonate, 22 was the most active sulfonamide scaffold on Escherichia coli at MIC value of 12.5 μg/mL.

scholarly journals Isolation and Biological Properties of the Natural Flavonoids Pectolinarin and Pectolinarigenin—A Review

Antibiotics ◽  
2020 ◽  
Vol 9 (7) ◽  
pp. 417
Author(s):  
Thamere Cheriet ◽  
Balkeis Ben-Bachir ◽  
Oumelkhir Thamri ◽  
Ramdane Seghiri ◽  
Ines Mancini
Keyword(s):  
Medicinal Plants ◽  
Fruits And Vegetables ◽  
Biological Properties ◽  
Biological Evaluation ◽  
Biological Agent ◽  
Antitumor Activities ◽  
Anti Inflammatory ◽  
Antidiabetic Effects

Flavonoids are metabolites widely distributed in plants and commonly present in foods, such as fruits and vegetables. Pectolinarin, which belongs to the flavone subclass, has attracted considerable attention due to its presence in many medicinal plants. It has turned out to be a good biological agent especially due to its antioxidant, anti-inflammatory, antidiabetic, and antitumor activities, evaluated both in vitro and in vivo. Its aglycone, the metabolite pectolinarigenin, is also known for a series of biological properties including anti-inflammatory and antidiabetic effects. In the first overview on the two metabolites here presented, their collection, isolation and the results of their biological evaluation are reported.

scholarly journals Investigation of the Biological Activities and Characterization of Bioactive Constituents of Ophiorrhiza rugosa var. prostrata (D.Don) & Mondal Leaves through In Vivo, In Vitro, and In Silico Approaches

Molecules ◽  
2019 ◽  
Vol 24 (7) ◽  
pp. 1367 ◽  
Author(s):  
Md. Adnan ◽  
Md. Nazim Uddin Chy ◽  
A.T.M. Mostafa Kamal ◽  
Md Azad ◽  
Arkajyoti Paul ◽  
...  
Keyword(s):  
Biological Activities ◽  
Gastrointestinal Transit ◽  
Ethanol Extract ◽  
Indigenous Communities ◽  
Antibacterial Activities ◽  
Significant Inhibition ◽  
Bioactive Constituents ◽  
Anti Inflammatory

Ophiorrhiza rugosa var. prostrata is one of the most frequently used ethnomedicinal plants by the indigenous communities of Bangladesh. This study was designed to investigate the antidiarrheal, anti-inflammatory, anthelmintic and antibacterial activities of the ethanol extract of O. rugosa leaves (EEOR). The leaves were extracted with ethanol and subjected to in vivo antidiarrheal screening using the castor oil-induced diarrhea, enteropooling, and gastrointestinal transit models. Anti-inflammatory efficacy was evaluated using the histamine-induced paw edema test. In parallel, in vitro anthelmintic and antibacterial activities were evaluated using the aquatic worm and disc diffusion assays respectively. In all three diarrheal models, EEOR (100, 200 and 400 mg/kg) showed obvious inhibition of diarrheal stool frequency, reduction of the volume and weight of the intestinal contents, and significant inhibition of intestinal motility. Also, EEOR manifested dose-dependent anti-inflammatory activity. Anthelmintic action was deemed significant (P < 0.001) with respect to the onset of paralysis and helminth death. EEOR also resulted in strong zones of inhibition when tested against both Gram-positive and Gram-negative bacteria. GC-MS analysis identified 30 compounds within EEOR, and of these, 13 compounds documented as bioactive showed good binding affinities to M3 muscarinic acetylcholine, 5-HT3, tubulin and GlcN-6-P synthase protein targets in molecular docking experiments. Additionally, ADME/T and PASS analyses revealed their drug-likeness, likely safety upon consumption and possible pharmacological activities. In conclusion, our findings scientifically support the ethnomedicinal use and value of this plant, which may provide a potential source for future development of medicines.

scholarly journals Synthesis and Biological Evaluation of Some Novel Quinoline based Chalcones as Potent Antimalarial, Anti-inflammatory, Antioxidant and Antidiabetic Agents

2020 ◽  
Vol 32 (4) ◽  
pp. 959-964
Author(s):  
Nargisbano A. Peerzade ◽  
Shravan Y. Jadhav ◽  
Raghunath B. Bhosale
Keyword(s):  
Antimalarial Activity ◽  
Biological Activities ◽  
13C Nmr Spectroscopy ◽  
Biological Evaluation ◽  
New Drugs ◽  
Antidiabetic Activity ◽  
High Yield ◽  
Excellent Activity ◽  
Anti Inflammatory

The objective of the present study was to synthesize a series of some novel quinoline based methoxy substituted chalcones and to evaluate their in vitro antimalarial, anti-inflammatory, antioxidant and antidiabetic activitites. The quinoline based chalcones was synthesized by condensation of 2-chloro-3-formyl qunoline with various methoxy substituted acetophenone in presence of NaOH. The Claisen-Schmidt condensation gave high yield of quinoline based chalcones. Synthesis of 2-chloro-3-formyl quinoline was carried out by Vilsmeir-Haack reaction on acetanilide and 4-methoxy acetanilide which on cyclization along with formylation give corresponding 2-chloro-3-formyl quinoline. The synthesized compounds were screened for in vitro antimalarial, anti-inflammatory, antioxiadant and antidiabetic activities. The structures of the synthesized compounds were characterized by infrared, 1H NMR and 13C NMR spectroscopy. Compounds 1f and 1h showed highest antimalarial activity even more than standard chloroquine diphosphate. Compound 1a showed excellent activity whereas 1c and 1d showed potent anti-inflammatory activity as compared to standard diclofenac. On the other hand, compounds 1a and 1g showed excellent antioxidant activity for 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical while compound 1a showed highest inhibition of nitic oxide free radical (NO•) and compound 1h showed highest inhibition for super oxide radical (SOR) as well as highest antidiabetic activity as compared to standard acarbose. All quinolne based chalcones were synthesized in good yields and showed potential biological activities hence they may be helpful for the designing of new drugs.

scholarly journals Antibacterial Activities andIn VitroAnti-Inflammatory (Membrane Stability) Properties of Methanolic Extracts ofGardenia coronariaLeaves

2014 ◽  
Vol 2014 ◽  
pp. 1-5 ◽  
Author(s):  
Amin Chowdhury ◽  
Shofiul Azam ◽  
Mohammed Abdullah Jainul ◽  
Kazi Omar Faruq ◽  
Atiqul Islam
Keyword(s):  
Antibacterial Activity ◽  
Antibacterial Activities ◽  
Positive Control ◽  
Membrane Stability ◽  
Deciduous Tree ◽  
Shigella Boydii ◽  
Methanolic Extracts ◽  
The Family ◽  
Anti Inflammatory

This work is carried out withGardenia coronarialeaves that belong to the family Rubiaceae, which is a small-to-medium-sized but tall, deciduous tree, 7.6–9 m high on an average. Leaves are used for the treatment of rheumatic pain and bronchitis. The leaf of the plant consists of coronalolide, coronalolic acid, coronalolide methyl ester, ethyl coronalolate acetate triterpenes (secocycloartanes), and so forth. Methanol extract from the leaves ofGardenia coronariawas completely screened for membrane stability and antibacterial activity. The lower concentrations of Methanolic leaf extract ofGardenia coronariagave good antimicrobial and anti-inflammatory activity, but higher concentrations gave relatively more projecting antibacterial activityin vitroas compared with Kanamycin. The crude drug’s anti-inflammatory effects were compared with those of Aspirin as positive control. The Methanolic extracts ofGardenia coronarialeaves possessed a broad spectrum antibacterial activity against a variety of both Gram-negative and Gram-positive organisms likeStreptococcus agalactiae,Escherichia coli,Pseudomonas aeruginosa,Bacillus cereus,Shigella sonnei,Shigella boydii, andProteus mirabilis, with a zone of inhibition from 10 to 16 mm. The extract also showed good membrane stability to be considered as having significant anti-inflammatory action.

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