A good alternative for the synthesis of 3,4unsubstituted coumarins is the twostep wittig reaction 15. It has a sweet odor, easy to be recognized as the scent of newmown hay. The reaction proceeds under mild conditions at room temperature in the absence of any catalysts. Onepot synthesis of 4carboalkoxysubstituted benzohcoumarins. The name coumarin comes from a french term for the tonka bean, coumarou, seeds of dipteryx odorata coumarouna odorata fabaceaeleguminosae, one of the sources from which coumarin was first isolated as a natural product in 1820. A novel 3component synthesis of sulfonylated coumarins from diaryliodonium salts, arylpropynoates and sulfur dioxide is reported. Pharmacologically potentials of different substituted coumarin derivatives. Four coumarins exhibited inhibition of the 5lox pathway and had a similar structure feature containing orthodihydroxyl groups. The phytochemical coumarin 2hchromen2one is the parent of a series of natural products. Department of chemistry, indian institute of technology bombay, powai, mumbai. Except for a few rare cases, including coumarin itself which is unsubstituted, all plant coumarins contain. Natural disubstituted coumarins o r 3 o r 8 r 7 r 6 r 5 compound r 3 r 5 r 6 r 7 r 8.
Synthesis and evaluation of antiproliferative and src kinase inhibitory activities. Introduction coumarins are well recognized naturally occurring compounds which isolated and present in large number of compounds in the plant kingdom. An etoh extract of the polypore mushroom fomitopsis officinalis afforded two new naturally occurring chlorinated coumarins, which were identified as the previously synthesized compounds 6chloro4phenyl2hchromen2one 1 and ethyl 6chloro2oxo4phenyl2hchromen3carboxylate 2. They occur widely as secondary plant metabolites and are known to exhibit numerous interesting biological properties. Electronic supporting information files are available without a subscription to acs web editions. Chemical structure of coumarin and the iupac numeration of this scaffold.
Coumarins and lignans from zanthoxylum schinifolium and. A plausible mechanistic pathway for the formation of biscoumarin fused with dihydropyran ring is suggested. Coumarins coumarin 2h1benzopyran2one is a fragrant organic chemical compound in the benzopyrone chemical class, which is a colourless crystalline substance in its standard state. Effect of organic surfactant on femtosecond solvation. Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactonelike chain. Some important examples from the last years volume. A mild and simple onepot stepwise method to synthesize 3arylacetylene coumarins from alkynoates was demonstrated.
Kapdi ar, jain c, padte t, shevde u, pednekar s, et al. A series of alkynoates and phenylacetylenes were well tolerated in the optimized multicatalyti synthetic methodology in obc. Moreover, the unique and versatile oxygencontaining heterocyclic structure makes coumarin compounds occupy an important place in medicinal chemistry 22. The journal of organic chemistry 2018, 83 2, 588603. Benzogcoumarins are the most studied systems because of linear benzofusion, which results. A synthetic route for the synthesis of biscoumarin fused with dihydropyran ring via one pot multicomponent reaction using hydroxy coumarins, formyl coumarins and malononitrile as precursors is proposed.
Chapter 1 coumarins department of chemistry, sardar patel university 10 the presence of 4alkyl group decreases the stability of dibromide55. Keating gj, okennedy r 1997 the chemistry and occurrence of coumarins. Support for this is found in experiments,19 which showed that. Zanthoxylum schinifolium is an aromatic shrub, and its pericarp and leaves are widely used in culinary applications in east asian countries. Coumarins 1benzopyran2one are chemical compounds in the benzopyrone class of organic compounds found in many plants. Coumarins have been used for many practical applications, such as cosmetics, sunscreens, flavorings, laser dyes, pharmaceuticals, and wellknown anticoagulants. View the article pdf and any associated supplements and figures for a period of 48 hours. The presence of coumarin in the tonka bean, in which it occurs combined with the sugar glucose, was observed in 1820. Moreover, they mostly lead to coumarins with subsistent in the 3 or 4position 14. They are found at high levels in some essential oils, particularly cinnamon bark oil 7,000 ppm, cassia leaf oil up to 87,300 ppm and lavender oil. In addition, studies have been done regarding coumarins as bioactive agents 24, as well as supramolecular medicinal drugs, diagnostic agents and pathologic probes, and biological stains 25. It is an oral anticoagulant that inhibits vitamin k epoxide reductase, an enzyme that that recycles oxidized vitamin k.
Organo photoinduced decarboxylative alkylation of coumarins with. All typical condensation reactions for coumarin synthesis like knoevenagel, perkin, kostaneckirobinson, pechmann and reformansky reactions, have been. This transformation is solely driven by visible light and opens a new opportunity. Synthesis of coumarinbased 1,3,4oxadiazol2ylthio n. Coumarins possess a variety of biological properties, including antimicrobial, antiviral, antiinflammatory, antidiabetic, antioxidant, and enzyme inhibitory activity. The presence of lactone groups can be observed leading to changes of ph in the medium. This file contains the supporting information of the manuscript rapid synthesis of 4alkynyl coumarins and tunable electronic properties of emission solvatochromic fluorophores, selected 1h and c nmr spectra, uvvis, fluorescence spectra and linear regression analyses of lfer, and dft and tddft computational data. The structure of 3methoxycarbonyl4hydroxy coumarin has been established by xray diffraction analysis and its geometry was compared. Coumarin 2hchromen2one is a fragrant organic chemical compound in the benzopyrone chemical class, which is a colorless crystalline substance in its standard state. Coumarins are benzoalphapyrones lactones of ohydroxycinnamic acid formed via the shikimic acid pathway. It has also long been used in traditional oriental medicine for treating the common cold, stomach ache, diarrhea, and jaundice.
The name coumarin comes from a french term for the tonka bean. Simple coumarins and analogues in medicinal chemistry. General procedure for the synthesis for benzylpyrazolyl coumarin. Multicomponent synthesis and antimicrobial activity of. A read is counted each time someone views a publication summary such as the title, abstract, and list of authors, clicks on a figure, or views or downloads the fulltext. Acs synthetic biology, analytical chemistry, biochemistry, bioconjugate chemistry. The direction of the reaction of coumarin derivatives with ophenylenediamine depends on their structure, leading to 22. Department of pharmaceutical chemistry, delhi pharmaceutical sciences research university, pushp vihar, sec 3, new delhi 110017, india. Coumarins are natural products occurring in a variety of plants, including those used as traditional herbal medicines dating to as early as 1,000 b. Coumarin has a vanillalike odour, and the odour of freshly cut grass or newmown hay will be familiar to most people.
The name comes from a french term for the tonka bean, coumarou, one of the sources from which coumarin was first isolated as a natural product in 1820. Coumarins form elite classes of naturally occurring compounds, which occupy a special role in nature and interest in its chemistry continues unabated because of its usefulness as biologically active agents. A candidate must have secured 40% marks in the aggregate and studied chemistry cognate subject securing 50% marks in this subject at the b. Coumarin derivatives studied by other groups will be also taken into account, to expand the analysis of the structureactivity relationships.
Department of chemistry, saint petersburg state forest technical university, 5 institutskii per. The structure of coumarins was confirmed using spectroscopic techniques as well as elemental analysis. Furthermore, the enantiopure hexahelical coumarins exhibit strong cotton effects and lend themselves to a very high differentiation in the specific rotations and anisotropic dissymmetry factors. Pdf coumarins an important class of phytochemicals. In this study, we identified two new compounds, zanthoxyloside 1 and schinifolisatin a, along with 23 known coumarins 2. Plant secondary metabolites have played an important role in human welfare due to their great therapeutic potential. Coumarins coumarin 2hchromen2 one is a fragrant organic chemical compound in the benzopyrone chemical class, which is a colorless crystalline substance in its standard state it is found naturally in many plants families. Natural products are relatively small molecules, produced mainly by plants and microorganisms, that have a long history of uses and misuses by people, e. U mbelliferae, r utaceae, l eguminaceae,etc carribean word.
The journal of organic chemistry, accounts of chemical research, acs applied bio. Vitamin k is an activator of coagulating factors ii, vii, ix and x, so by decreasing the availability of vitamin k synthesis of these factors are decreased. An efficient annulation of phenolic acetates with acrylates in the presence of rh 2 oac 4 as catalyst and formic acid as reducing agent provides high yield of coumarin derivatives via ch bond activation. Challenges to obtain pure compounds low concentrations 610. Extraction is effected in 23 hrs and 34 washings are done. Green chemistry approaches to the synthesis of coumarin. Warfarin, the only drug listed here in this category, is a coumarin. Files available from the acs website may be downloaded for personal use only. Pdf coumarins are natural products characterized as 1,2 benzopirones widely distributed in plants, as well as, in many species of fungi and.
The addition of naoac as a base increased the yield of the products. A natural, privileged and versatile scaffold for bioactive. A synthesis of new coumarin cglycosyl derivatives the. The reaction is quite successful for both electronrich as well as electrondeficient phenolic acetates, affording coumarins with excellent regioselectivity. This catalytic system involves photosensitizerfree photocatalysis and thermocatalysis processes.
Pharmacologically potentials of different substituted. The furan ring can be recognized by using the erlich test. Thiago moreira pereira, daiana portella franco, felipe vitorio and arthur eugen kummerle affiliation. Henar martinezgarcia, in experimental organic chemistry, 2016. In hoults report, sixteen natural and synthetic coumarins were evaluated in rat peritoneal exudate leukocytes for the impact on production of throboxane b 2 and leukotriene b 4. Synthesis and antiretroviral activity of 6acetylcoumarin derivatives. Coumarins are an important type of heterocyclic compounds with diverse bioactivities. Rapid, efficient, and green synthesis of coumarin derivatives via. Moreover, the unique and versatile oxygencontaining heterocyclic structure makes coumarin compounds occupy an important place in medicinal chemistry 22, 23.
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