Synthesis, characterization, in vitro antimicrobial, and U2OS tumoricidal activities of different coumarin derivatives (original) (raw)
Related papers
Journal of Heterocyclic Chemistry, 2018
Various new substituted and fused coumarin analogues have been synthesized via different synthetic pathways. Among which are variable substituted coumarin derivatives bearing either biologically active side chains or rings at 5, 6, and 3 positions of the coumarin nucleus as indicated in compounds 10, 12, 13, 16-19, 21, 23-32, 38, and 42-45. In addition, different pyranocoumarin derivatives either substituted as in compounds 2, 3, and 6 or fused as compounds 33-36, pyranoxanthene analogues such as compounds 4 and 46, coumarinotriazolothiadiazine derivative 8, coumarinonaphthodiazocin analogue 39 and coumarinopyrazolone derivative 40 were synthesized. Thirty-eight of the synthesized compounds were subjected to in vitro anticancer screening against mammalian liver carcinoma HepG2 and breast carcinoma MCF7 cell lines using Cisplatin as a standard reference. The anticancer activity screening results revealed that, among the tested compounds, compounds 16, 40, and 43 bearing 4-chlorophenyl-2-aminopyridine-3carbonitrile attached to C 6 position, fused pyrazolone ring or attached to 4-chlorophenyl-2-oxodihydropyridine-3-carbonitrile at C 3 position of the coumarin nucleus, respectively, exhibited moderate to strong activity against both cell lines.
Antibacterial and Antitumor Potentials of Some Novel Coumarins
2022
The growing rise of resistance developed by highly contagious microorganisms and malignant cells is a frightening threat to mankind. The search for novel bioactive molecules and their biological potentials may replenish our armory with weapons capable of combating this danger. The Bargellini reaction was used to convert hymecromone into a new Bargellini-based molecule, however its applicability to further functionalize hydroxycoumarins has not been reported. The latter was reacted with a variety of halophenols to produce the N1-N12 congeners. By looking at and studying the spectrum charts of the produced compounds, the molecular structures were clearly recognized. The antitumor and antibacterial potentials of the produced compounds were evaluated. The first potential was tested using an MTT-based experiment versus 6 malignant tumor cells, namely MCF-7, SK-OV-3, HeLa, KYSE-30, AMN3, and SKG. A broth-dilution test was used to assess the antibacterial potential versus 6 gram-negative b...
Synthesis and Pharmacological Evaluation of Novel Coumarin Derivatives
International Journal of Research in Pharmaceutical Sciences, 2020
The current work focuses on new architecture, synthesis of coumarinoxadiazole hybrid derivative products as both these (coumarin ring and oxadiazole) have a wide variety of biological behavior, Compounds containing the nucleus of coumarin (2H-1-benzopyran-2-one) are an interesting class of hetero cycles which hold an important role in the ield of natural ingredients and synthetic organic chemistry. It has been exciting medicinal chemists to study native coumarins or synthetic analogs for their application for decades. And they can be further modi ied to synthesize more effective and potent drugs. Compounds have been characterized by spectrophotometry of physicochemical properties and their structures veri ied by infrared spectroscopy (FTIR) and nuclear magnetic resonance (1H-NMR) Such new derivatives of coumarinyl-oxadiazole was quali ied to estimate the lethal dose, anticancer, anticoagulant and antioxidant activity. Their pharmacological properties depend on their pattern of substitution, compound S4F proved signi icant anticoagulant activity in concentration (50, 100, 200 mg/ml) similar for heparin, and monitor the coagulation effect on plasma, while compound S 4 CO give signi icant anticancer activity against MCF-7 a breast cancer cell. Speci ic compounds have strong antioxidants with the effective action of radical scavengers; the S4Cl compound with IC50 1.49 is the most potent antioxidant activity note. Basically, all the formulations tested reported satisfactory behavior. The review shows that varieties of coumarin derivatives have synthesized and shown anti-cancer, antioxidant and anti-coagulant potentials. These derivatives synthesis and its biological assay can be further modi ied in the future to improve the anti-cancer, anti-oxidant and anticoagulant potentials of the versatile coumarin nucleus.
International research journal of pharmacy, 2018
Coumarins and their analogs were found to be better antitumoral agents and still active against human retroviral invading system. This property could be ameliorated by coupling of few active groups to the parental molecule for enhancing its frequency of biofunctional diversity and multi spectrum characteristic, such an endeavor was done by 2-Oxo-2H-chromene-3-carboxylic acid phenylamide analogs. The structure were well characterized. Further the antimicrobial activity was examined by disc diffusion method and based on the minimum inhibitory concentration (MIC) values obtained the molecules were approximately 70% as active as the positive control especially halogenated compounds showed promising result. Even their free radical scavenging activity was considerably as good as 20% to that of ascorbic acid. Present research on coumarin analogs necessitate novel ideas in synthetic chemistry therein concerning the development of innovative synthetic strategies that could help in drug design.
SYNTHESIS, REACTIVITY, ANTI-OXIDANT AND CYTOTOXICITY EVALUATION OF SOME COUMARIN DERIVATIVES
EUROPEAN JOURNAL OF PHARMACEUTICAL AND MEDICAL RESEARCH, 2018
In the present work 3-amino-8-methoxy coumarin was prepared either by microwave irradiation or by convential method. It was used as a key starting material for the synthesis of triazole thione (8), Schiffs’ bases (10), thiazolone (11a-d), pyrimidinethione (13), aminothiazole (15) and isoxazole (18) derivatives through its reaction with different reagents. The structures of the newly synthesized compounds were elucidated on the basis of their elemental analysis and by using different spectroscopic methods. The free radical scavenging activity of some newly synthesized derivatives was determined by measuring their interaction with the stable free radical DPPH and some compounds have shown encouraging antioxidant activity. Also, they were screened for their in-vitro cytotoxicity against two human cancer cell lines namely HEIA cells (human cervical carcinoma) and A-549 cells (human lung cancer cell line). The IC50 values (the sample concentration that produces 50% reduction in cell growth) in μg/mL showed that some of the tested compounds exhibited significant cytotoxic effect.
Medicinal Chemistry Research, 2012
Coumarin is a naturally occurring oxygen heterocyclic having multifarious medicinal properties, hence used as a lead compound for designing new potent analogs. Based on the X-ray crystal structure of complexes of inhibitors containing coumarin nucleus with human NAD(P)H:quinone oxidoreductase-1 and human phosphodiesterase 4B enzymes, some novel coumarin derivatives have been designed as probable inhibitors specifically for pancreatic cancer. These two enzymes are overexpressed in various tumors, the former specifically in pancreatic cancer. The computational analysis by e-pharmacophore and docking studies suggested that specific groups at position 8 of 4-methyl-7-hydroxycoumarin have anticancer activity against skin cancer in mice and can enhance the anti-tumor activity. The chemical syntheses of 4-methyl-7-hydroxycoumarin and its 8-formyl derivative were carried out using Pechmann's condensation followed by Duffs reaction. Treatment of the 8-formyl derivative with nine different N,N-di substituted cyanoacetamides in the presence of piperidine afforded the corresponding nine new 8-substituted-4-methyl-7-hydroxycoumarin derivatives. These compounds were characterized by IR, 1 H, 13 C NMR, mass spectra and elemental analysis. Intriguingly, molecular docking suggested a remarkable binding pose for all the nine coumarin derivatives visa -vis coumarin itself, opening further options for designing inhibitors for tumor suppression. From the docking simulation study, it was concluded that the derived coumarin derivatives are active against more than one proteins and most importantly addition of substituents at the 8th position of 4-methyl-7hydroxycoumarin support the possibility of new coumarin derivatives having comparatively higher binding affinity and therefore more potent inhibitors.
Synthesis of novel coumarin derivatives and its biological evaluations
Coumarins possess a number of biological activities like anticoagulant, antimicrobial, anti-inflammatory, analgesic, antioxidant, anticancer, antiviral, antimalarial etc. Coumarin belongs to a group as benzopyrones, which consists of a benzene ring joined to a pyrone nucleus. In the present study, the thirteen new coumarin derivatives are synthesized and characterized by IR and 1 H NMR spectra. These newly formed Coumarin derivatives were screened for anti-inflammatory activity by carrageenan induced rat paw edema model and antibacterial activity against Stophylococcus aureus as well as Escherichia coli by cup plate method. The synthesized coumarin derivatives were administered orally in the dose of 10 mg/kg. Ibuprofen and amoxicillin were taken as standard for anti-inflammatory and antibacterial activity respectively. The result of present investigation showed that the compounds 7, 8 & 12 showed significantly (P < 0.001) inhibition against Carrageenan induced rat paw edema, but ...
Croatica chemica acta
Four 4-hydroxycoumarin derivatives were synthesized and the structure was confirmed by NMR spectroscopy and Mass spectrometry. Tested compounds have shown significant antimicrobial activity against Bacillus subtilis subsp. spizizenii, Bacillus cereus, Staphylococcus aureus, and Staphylococcus epidermidis, and the effect of more halogens on the benzene nucleus, as well as the combination of halogen and alkyl groups, on the antimicrobial activity, was investigated. According to the docking study, these compounds can operate simultaneously on two enzymes, amylase and gyrase (1BAG and 1KZN), which are known to play an important role in bacterial life. Obtained docking study parameters for tested compounds showed an association with the in vitro results of the antimicrobial activity of these compounds. In silico tests of molecular properties of the tested compounds showed that the compounds met Lipinski's rule of five. In this paper, the ADME parameters of tested compounds were also ...
Coumarins and their derivatives are very important organic compounds; they are biologically active and widely occur in nature1,2Recent studies have been revealed that coumarin and the derivatives exhibit several other medicinal applications such as anti-coagulants, antifungal, insecticidal, hypnoticsphytoalexins, HIV protease & inhibitors3. Thus the synthesis of coumarins is of continuing interest. Potassiumdihydrogen phosphate a commercially available environmentally benign catalyst non-toxic widely used for the synthesis of the substituted coumarin4 .The scope of this catalyst has not been fully explored, but can be used as buffer, neutralizing agent. Owing to the numerous advantages associated with cheap and non-hazardous catalyst, and also realizing g the importance of coumarin herein we would like to focus the eco ?friendly method for his synthesis of derivatives of coumarin using cheaper and commercially available acid catalysts Potassium dihydrogen phosphate and also by the Knoevenagel condensation under microwave irradiation. The synthesized coumarin derivative was screened in Vitro anti-microbialefficacy testing and anti oxidant properties. In vitro anti-microbial efficacy testing was carried out by broth dilution method by broth dilution method as mentioned in ?Pharmaceutical Microbiology?. For anti-bacterial activity, MullerHinton medium was used as the nutrient media. Test bacterial species used are Escherichia coli ,(ATCC 10148), Staphylococcus aureus(NCTC 3750), Pseudomonas aeruginosa (Fisher?Immunotype IV), test fungi species used are Aspergilliusniger(ATCC 16404) and Candida albicans (ATCC 10231) in different concentrations starting from 25ppm .All the coumarin derivatives are active against the test bacteria and fungai in different concentrations. Anti-oxidant studies of all these derivatives have been carried out . These compounds were characterized by IR, NMR spectra?s. This paper focuses is to develop environmentally reactions, simple, highly efficient and high yielding protocol for the synthesis of coumarin derivatives using Potassiumdihydrogen phosphate as a catalyst. Therefore owing the importance of Potassium dihydrogen phosphate a facile catalyst used for the green synthesis of new derivatives of coumarin.