ABSTRACT
Series of novel coumarin derivatives [I (a-d) and II (a-d)] were successfully synthesized and their structures were determined based on infrared 1H-nuclear magnetic resonance (NMR), HRMS, and single crystal X-ray crystallography. Additionally, the new synthesized compounds were evaluated to identify the molecular characteristics that contribute to their cytotoxicity, which was tested against SK-LU-1, SPC-A-1 and 95D human lung cancer cell lines, using the MTT assay. The results of this study showed that compounds Ic, Id, IIc, and IId exhibited an efficient percentage of inhibition of cell proliferation.
Subject(s)
Humans , Antineoplastic Agents/pharmacology , Coumarins/pharmacology , Lung Neoplasms/drug therapy , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Coloring Agents , Coumarins/chemical synthesis , Coumarins/chemistry , Crystallography, X-Ray/methods , Drug Screening Assays, Antitumor , Lung Neoplasms/pathology , Magnetic Resonance Spectroscopy/methods , Reference Values , Reproducibility of Results , Tetrazolium Salts , ThiazolesSubject(s)
Humans , Coumarins/pharmacology , Monoamine Oxidase Inhibitors/pharmacology , Monoamine Oxidase/metabolism , Coumarins/chemistry , Coumarins/chemical synthesis , Dose-Response Relationship, Drug , Enzyme Activation/drug effects , Models, Molecular , Molecular Structure , Monoamine Oxidase Inhibitors/chemistry , Monoamine Oxidase Inhibitors/chemical synthesis , Structure-Activity RelationshipABSTRACT
A series of new 7-[2-[3-alkyl/aryl-4-arylthiazol-2[3H]-ylidene]hydrazono]propoxy]-4-methyl-2H-chromen-2-ones, [6-9a-e], was prepared by the reaction of appropriate N-alkyl/aryl-2-[1-[4-methyl-2-oxo-2H-chromen-7yloxy]propan-2-ylidene]hydrazine carbothioamides [4a-d] and phenacyl bromides [5a-e]. The purity of all new compounds was checked by TLC and elucidation of their structures was confirmed by IR, [1]H NMR, and mass spectrometry along with elemental microanalyses. All the target compounds were evaluated for their possible antimicrobial activity. Most of the tested compounds showed weak to moderate antibacterial activity against most of the bacterial strains used in comparison with gatifloxacin as a reference drug. The most active compounds were 6b, 6c, 7b, 8b, 8c, and 9c against B. cereus, E. coli and S. marcescens. Results of antifungal activity revealed that all compounds showed weak to moderate activity against S. brevicaulis, while ketoconazole as a reference drug was completely inactive. Compounds 6a, 6b, 6c, 6e and 7b were even more active than ketoconazole against F. oxysporum
Subject(s)
Coumarins/chemical synthesis , Anti-Infective Agents , Mass Spectrometry/statistics & numerical data , Infrared Rays , Escherichia coli/drug effects , Bacillus cereus/drug effectsABSTRACT
New series of coumarin derivatives was synthesized and evaluated as antitumor agents against breast cancer in human cell line [MCF 7]. The key compound 8-acetyl-7-hydroxy-4-methyl coumarin [1] was synthesized and condensed with phenyl hydrazine to form the hydrazone derivative 2. Also, 1 condensed with different alkylating agents to give the corresponding sulphonyl derivatives 3a, b which further condensed with 2,4-dinitrophenyihydrazine to give the corresponding hydrazones 4a,b. One pot reaction of 5 with different aldehydes, ethylcyanoacetate and ammoniumacetate gave pyridone derivatives 6a-e. Also. compound 5 condensed with different aldehydes then cyclized to give the pyrazoline derivatives 9a,b and 10a,b. While, on condensation of 5 with thiosemicarbazide derivatives followed by cyclization the resulting product, gave the oxathiazoline 12 and thiazolidine 13. Some of these newly synthesized compounds showed noderate activity against breast carcinoma cell line[MCF7] in human
Subject(s)
Coumarins/chemical synthesis , Cytotoxins/chemical synthesis , Breast Neoplasms/therapy , PyridonesABSTRACT
Synthesis of 3-acetyl-6-substituted coumarin la-c have been carried out. The reaction of 3-aeetyl-6-broniocoumarin 1b with ethyl oxalate in the presence of sodium metal afforded the corresponding 3-coumarinyl pyruvic acid derivative 2, which converted into corresponding thiazole derivatives 3. The condensation of 1a. b with thiourea in the presence of bromine afforded imidazole derivatives 4a. b and aminothiazole derivatives 5a. b. The reaction of 1e with KCN yielding carboxylic acid amide derivative 6, which converted into the corresponding pyridazine derivative 7 on treatment with hydrazine hydrate. Compound 1e condensed with malononitrile afforded ethylidene malononitrile derivative 8 and coumarinoyl ethylenyl coumarin derivative 9. While compound 1e condensed with 3- iminobutyronitrile gave pyridonaphthopyranone 10 and 9. Stirring cold solution of 1e with bromine in acetic acid to give the corresponding bromide derivative 11, which converted into propionitrile derivative 12, when refluxed when KCN solution. Also, compound 11 condensed with 3-iminobutyronitrile gave pyrrolopyridine derivative 13. Compound 12 coupled with phenyl diazonium chloride to afford acyclic azohydrazone derivative 14. Compounds 1a-e readily condensed with aromatic aldehydes to give 3-[substituted cinnamoyl]-coumarin derivatives 15a, b. The reaction of 15a with methyl isopentyl ketone in the presence of sodium acetate yielded pyridocoumarin derivative 16. The reaction of 15b with active methylene compounds namely ethyl acetoacetate, malononitrile, ethyl cyanoacetate and/or diethyl malonate in the presence of ammonium acetate gave corresponding pyronyl coumarin derivatives 17-19 respectively
Subject(s)
Coumarins/chemical synthesis , AnticoagulantsABSTRACT
Este trabalho foi desenvolvido com o objetivo de identificar os princípios tóxicos da tetrapterys multigalndulosa A. Juss. Realizou-se triagem fitoquímica nas folhas (brotos e maduras) frescas, através de marcha analítica clássica e Cromatografia em Camada Delgada (CCD) pesquisando-se os seguintes princípios ativos: heterosídeos antrasênicos, saponínicos, flavônicos, cardiotônicos, taninos (hidrolisáveis e condensados), alcalóides (terciários e quaternários), composto esteróides e cumarínicos. Os resultados obtidos mostraram na folha jovem e madura, presença de heterosídeos flavônicos e esteróides. Taninos condensados e alcalóides quaternários foram encontrados somente na folha madura.
Subject(s)
Plant Extracts/analysis , Plant Leaves/chemistry , Plant Shoots/chemistry , Plants, Toxic/chemistry , Alkaloids/chemical synthesis , Anthracenes/chemical synthesis , Cardiac Glycosides/chemical synthesis , Cardiotonic Agents/chemical synthesis , Chromatography, Thin Layer , Coumarins/chemical synthesis , Flavones/chemical synthesis , Saponins/chemical synthesis , Steroids/chemical synthesis , Tannins/chemical synthesisABSTRACT
In the present work, a novel method for the synthesis of 7-thiocarboxamidothieno [3',2',6,7] [I] benzopyran-8-one and 8-thiocarboxamidothieno [3',2',6,7] [I] benzopyran-7-one, is reported. The appropriate aldehydes were treated with cyanothioacetamide in presence of triethylamine where the products were subjected to acid hydrolysis to give the desired compounds. The chemical structures of the title compounds and their intermediates were confirmed by studying their spectral data. The biological activity of the prepared furanocoumarin sulfur analogues is under study
Subject(s)
Furans/chemical synthesis , Coumarins/chemical synthesisABSTRACT
Fusion of 6-bromo, 6,8-dibromo and 6-nitro-3-hydroxycoumarin with primary and secondary amines led to the formation of 3-aminocoumarin derivatives. Reaction of 3-hydroxycoumarin derivatives with hydrazine hydrate yielded 3-hydroazinocoumarin derivatives. Heating alpha- phenylhydrazino-beta-2-hydroxy-5-nitrocinnamic acid phenylhydrazide with acetic anhydride and hydrochloric acid gave 6-nitro-3-phenylhydrazinocoumarin