Relevant bibliographies by topics / Hydroxycoumarins

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  1. Journal articles
  2. Dissertations / Theses
  3. Book chapters
  4. Conference papers

Academic literature on the topic 'Hydroxycoumarins'

Author: Grafiati
Published: 4 June 2021
Last updated: 27 April 2022

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Journal articles on the topic "Hydroxycoumarins"

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Bhuyan, Pulak, Sinki Kolita, Leema Dutta, and Pankaj Das. "One-Pot Synthesis of Unsymmetrical Bis(4-Hydroxycoumarin-3-yl)methanes." Synlett 28, no. 17 (July 13, 2017): 2291–94. http://dx.doi.org/10.1055/s-0036-1589065.

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Unsymmetrical bis(4-hydroxycoumarin-3-yl)methane derivatives have been synthesized from 4-hydroxycoumarins, aldehydes, and secondary amines via 3-(aminoalkyl)-4-hydroxycoumarin intermediates, followed by substitution.
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Traven, Valery F., Larisa I. Vorobjeva, Tatjana A. Chibisova, Edward Andrew Carberry, and Noelle Jean Beyer. "Electronic absorption spectra and structure of hydroxycoumarin derivatives and their ionized forms." Canadian Journal of Chemistry 75, no. 4 (April 1, 1997): 365–76. http://dx.doi.org/10.1139/v97-042.

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Electronic absorption spectra of 18 hydroxycoumarin derivatives and their ionized forms have been studied. Close agreement between experimental and the PPP CI calculated electron absorption band energies has been found in most cases. Strong polarization of the carbonyl function of the pyrone ring in the 7-hydroxycoumarin derivatives, H-bonding between the hydroxyl group and neighboring substituent in the ortho-substituted hydroxycoumarins, as well as their tautomeric transformations, have been suggested in the discussion of the electronic absorption spectra of the hydroxycoumarin derivatives. In accord also with calculational results, ionization of the hydroxyl function leads to a bathochromic shift of the longest-wavelength absorption bands in the spectra of 7-hydroxycoumarin derivatives. The ionization has no effect on the electronic absorption of the 4-hydroxycoumarin derivatives. Relative stabilities of the tautomeric forms of hydroxycoumarin derivatives and their ionized forms have also been compared by MNDO calculations. Keywords: hydroxycoumarins, intramolecular H-bonding, ionization, electronic absorption spectra, keto–enol tautomerism.
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Anary-Abbasinejad, Mohammad, Hossein Anaraki-Ardakani, Azimeh Saidipoor, and Mahmood Shojaee. "Synthesis of 3-[(acetylamino)(aryl)methyl]-4-Hydroxycoumarins." Journal of Chemical Research 2007, no. 9 (September 2007): 535–37. http://dx.doi.org/10.3184/030823407x247785.

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One-pot, three-component reaction between aryl aldehydes, 4-hydroxycoumarin, and acetonitrile in the presence of chlorosulfonic acid affords 3-[(acetylamino)(aryl)methyl]-4-hydroxycoumarins in excellent yields.
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Wu, Nan, Xinnian Li, Xin Xu, and Daqing Shi. "Synthesis of 3,3′-arylmethylidenebis-4-hydroxycoumarin derivatives catalysed by KF-montmorillonite." Journal of Chemical Research 2007, no. 10 (October 2007): 561–62. http://dx.doi.org/10.3184/030823407x255551a.

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3,3′-Arylmethylidenebis-4-hydroxycoumarins derivatives have been synthesised in good yields by the Michael addition reaction of aromatic aldehydes with 4-hydroxycoumarin in DMF catalysed by KF-montmorillonite.
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Anary-Abbasinejad, Mohammad, Khadijeh Charkhati, and Alireza Hassanabadi. "Stereoselective synthesis of 3-[2-(dialkoxyphosphoryl)-1,2-dialkoxycarbonyl-ethyl]-4-hydroxycoumarins by reaction between trialkyl phosphites, dialkyl acetylenedicarboxylates and 4-hydroxycoumarin." Journal of Chemical Research 2009, no. 5 (May 2009): 319–21. http://dx.doi.org/10.3184/030823409x450435.

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A three-component reaction between trialkyl phosphites, dialkyl acetylenedicarboxylates and 4-hydroxycoumarin is described as a simple and efficient route for the synthesis of 3-[2-(dialkoxyphosphoryl)-1,2-dialkoxycarbonyl-ethyl]-4-hydroxycoumarins in high yields.
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Yoon, Jeong A., and Young Taek Han. "Efficient Synthesis of Pyrido[3,2-c]coumarins via Silver Nitrate Catalyzed Cycloisomerization and Application to the First Synthesis of Polyneomarline C." Synthesis 51, no. 24 (September 30, 2019): 4611–18. http://dx.doi.org/10.1055/s-0037-1610730.

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Herein, we report an efficient method for the synthesis of the pyrido[3,2-c]coumarin scaffold, one of the privileged heterocycle-fused coumarin scaffolds, via a AgNO3-catalyzed cycloisomerization of 4-(propynylamino)coumarins obtained from diverse 4-hydroxycoumarins. This concise method affords pyrido[3,2-c]coumarin analogues bearing diverse substituents on the benzene or pyridine ring in moderate to good yields. Moreover, this methodology was extended to the facile synthesis of polyneomarline C, a natural pyrido[3,2-c]coumarin derivative isolated from the Chinese herbal medicine Polyalthia nemoralis A. DC., in three steps and in 26% overall yield from the known 4-hydroxycoumarin.
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Kostova, Ivanka. "Hydroxycoumarins fromFraxinus ornusBark." Planta Medica 58, no. 05 (October 1992): 484. http://dx.doi.org/10.1055/s-2006-961529.

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Timonen, Juri, Paula Aulaskari, Pipsa Hirva, and Pirjo Vainiotalo. "Negative Ion Electrospray Ionization Mass Spectrometry and Computational Studies on Substituted 7-Hydroxycoumarins." European Journal of Mass Spectrometry 15, no. 5 (October 2009): 595–603. http://dx.doi.org/10.1255/ejms.1019.

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Twenty-two substituted 7-hydroxycoumarins were studied by negative ion electrospray ionization collision-induced dissociation (CID) mass spectrometry. Fragmentation pathways were also investigated by computation method using the B3LYP density functional theory. In general, the most important fragmentations of the 7-hydroxycoumarin [M – H]− ions were the elimination of CO2 and CO which agreed with the calculated energies of the proposed fragmentation reactions. In most cases, methyl group elimination was also favorable. Methyl group elimination occurred in three different ways, the most interesting being hydrogen rearrangement from a neighboring alkyl group to a ring carbon, which led to a benzyl radical formation. In some cases, CH2CO elimination was observed as well. Isomeric compounds gave rise to different CID spectra.
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Sizov, A. Yu, A. F. Kolomiets, and A. F. Fokin. "3-Polyfluoroalkylthio-4-hydroxycoumarins." Journal of Fluorine Chemistry 58, no. 2-3 (August 1992): 342. http://dx.doi.org/10.1016/s0022-1139(00)80807-6.

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Huitink, Geraldine M. "Studies of 7-hydroxycoumarins." Talanta 35, no. 12 (December 1988): 973–76. http://dx.doi.org/10.1016/0039-9140(88)80231-5.

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Dissertations / Theses on the topic "Hydroxycoumarins"

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Alhalaseh, Lidia. "Phytochemistry of hydroxycoumarins from Manihot esculenta Euphorbiaceae (cassava)." Thesis, University of Bath, 2017. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.725401.

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This is an interdisciplinary research project on cassava (Manihot esculenta Crantz, Euphorbiaceae) ultimately working towards producing cassava roots which are long-lasting, free of post-harvest physiological deterioration (PPD). It aims to contribute to ensuring food security. In cassava, scopoletin and its -glycoside scopolin are considered phytoanticipants, not phytoalexins, due to their increasing accumulation during the PPD process compared to their barely detectable levels in fresh roots. Starting with a focussed literature review on the potential of cassava, contrasted with its limitations on harvesting due to PPD, and biosynthesis along the phenylpropanoid pathway of key hydroxycoumarins, e.g. scopoletin and esculetin, the associated gaps in our current knowledge have been set out. Whether scopoletin is biosynthesized de novo from L-phenylalanine in response to stress, or whether stress prompts its release from the corresponding glycoside is unknown. Therefore, assessing hydroxycoumarin biosynthesis and quantifying their accumulation patterns have been undertaken in wild-type and transgenic plants in order to elucidate the divergence in scopoletin biosynthetic pathways. The identification of key genes on each pathway leading to scopoletin in cassava, and then exploring their functional identities using the model plant A. thaliana and genetically engineered E. coli, where the genes were isolated, cloned, and expressed, were also undertaken. Transgenic A. thaliana lines with no activity of the key enzymes on the proposed pathway, namely F6ʹH1, CCoAOMT, and EOMT, were developed. Competition feeding experiments using stable isotopically labelled potential biosynthetic intermediates showed the incorporation of labelled ferulate into scopoletin in transgenic A.t-F6´H1 and M.e-F6´H. This confirmed the activity of other hydroxylase enzymes rather than F6´H1 in the ortho-hydroxylation steps. The hydroxycoumarins of interest were isolated, characterized, and quantified in the wild type and mutant lines using chromatographic and spectroscopic techniques, mainly NMR, HR-MS, and LC-MS. Taken together, a significant contribution to knowledge about hydroxycoumarin biosynthesis has been made.
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Boulven, Manon. "Conception, synthèse et évaluation biologique de nouveaux composés hétérocycliques anticoagulants à usage rodonticide." Thesis, Lyon, 2016. http://www.theses.fr/2016LYSEI106.

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A ce jour, les anticoagulants commerciaux souffrent de deux inconvénients majeurs : leur rémanence avec, pour certains d’entre eux, une demi-vie hépatique proche des 300 jours causant des intoxications secondaires sur les prédateurs des rongeurs, ainsi que le développement de nombreuses mutations génétiques causé par l’utilisation intensive de ces composés, rendant inopérant l’utilisation de certains AVKs commerciaux. Face à ce constat, l’Union Européenne envisage d’interdire l’utilisation de tels composés. La mission prioritaire est donc de trouver un anticoagulant capable de gérer les populations de rongeurs sans affecter leurs prédateurs. Les recherches mises en avant par Adrien Montagut (Thèse 2011-2014) ont permis d’aboutir à une structure type d’anticoagulants, dérivés de la 4-hydroxycoumarine. Actuellement, AMR361 a été testé in vitro sur l’ensemble des mutations de VKORC1 et in vivo sur rats sauvages, et constitue le premier AVK développé qui répond à l’ensemble des caractéristiques du cahier des charges initial. La première partie de mon projet de thèse consistait à compléter l’étude biologique sur le noyau 4-hydroxycoumarine en amenant de la diversité fonctionnelle sur la position para du noyau aromatique. D’un point de vue biologique, l’allongement du bras espaceur sur la chaîne latérale par l’utilisation de fonctions telles que les amides ou amides inversés ou l’introduction d’un groupement diméthyle sur le pont méthylène ont été étudiés afin d’analyser les paramètres d’efficacité et de rémanence. Cependant, la plupart des composés synthétisés appartenant à la famille des 4-hydroxycoumarines font déjà l’objet d’un brevet déposé par l’entreprise Liphatech en 1999. L’étude de nouveaux noyaux, dont certains sont analogues à la 4-hydroxycoumarine, de même que la fonctionnalisation du noyau 4-hydroxycoumarine sur la partie aromatique, a permis l’accès à des structures plus diverses. Ces perspectives originales pour l’innovation ont été introduites pour contourner les brevets déjà existants
To date, commercial anticoagulants suffer from two major inconveniences: their persistence causing secondary poisoning of rodent predators and the development of many genetic mutations caused by the intensive use of these compounds. As a result, the European Union plans to prohibit the use of such compounds. Consequently, the priority task is to find an anticoagulant that can control the rodent populations without affecting their predators. The research of Dr. Adrien Montagut (PhD, 2011-2014) have led to the structure type of an anticoagulant derived from 4-hydroxycoumarin. Currently, AMR361 was tested in vitro on all VKORC1 mutations and in vivo on wild rats. It is the first AVK developed that responds to all the characteristics of the initial specification. The first part of my PhD was to complete the biological study on 4-hydroxycoumarin core by bringing functional diversity on the para position of the aromatic ring. From a biological point of view, the lengthening of the spacer arm on the side chain by use of various functions or the introduction of a dimethyl group on the methylene bridge were studied in order to analyze the effectiveness and persistence parameters. However, most of the synthesized compounds belonging to the family of 4-hydroxycoumarins are already described in a patent filed by Liphatech company in 1999. The study of new cores which are similar to the 4-hydroxycoumarin or the functionalization of the aromatic part of the 4-hydroxycoumarin has provided access to more diverse structures. These original possibilities for innovation have been introduced to circumvent existing patents
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Montagut-Romans, Adrien. "Réactivité et pharmacomodulation de la 4-hydroxycoumarine : conception, synthèse et évaluation biologique de nouvelles molécules rodonticides éco-compatibles." Thesis, Lyon 1, 2014. http://www.theses.fr/2014LYO10028.

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L'usage des pesticides au sein de l'Union européenne est de plus en plus réglementé, et les rodonticides actuellement disponibles sur le marché sont responsables de nombreuses intoxications secondaires chez les prédateurs des rongeurs. Il est donc crucial aujourd'hui de trouver une alternative plus écologique aux molécules commerciales. Les travaux de recherches décrits dans cette thèse s'inscrivent dans ce contexte et présentent la mise au point de nouvelles voies d'accès à des structures coumariniques et leurs études biologiques. La molécule anticoagulante ciblée se devait d'être active sur rats sensibles et résistants, et d'avoir une rémanence faible dans l'organisme. Les synthèses chimiques ont été menées conjointement avec les tests biologiques, conduisant l'ensemble des études de façon convergente vers la production d'un lead. Trois nouveaux outils moléculaires ont été mis au point et ont permis la synthèse et l'évaluation d'un grand nombre de candidats. Les deux premières en catalyse homogène, sous micro-onde, ont permis de réduire le temps réactionnel nécessaire à la synthèse de 4-hydroxycoumarine substituée sur le carbone 3. La troisième méthodologie conduit par une approche séquentielle aux mêmes types de composés à l'échelle du gramme. Cette dernière ouvre également la porte à de nombreuses possibilités réactionnelles permettant d'envisager plus de diversité. Toutes les molécules ont été évaluées in vitro, sur différentes souches d'enzymes VKORC1 et ont offert une meilleure compréhension des interactions enzyme/inhibiteur. Après cette première évaluation, des tests in vivo ont été conduits sur une sélection de composés, et ont apporté des informations cruciales sur les relations structure/activité in vivo et structure/rémanence. Le meilleur composé synthétisé à ce jour semble répondre parfaitement aux différentes contraintes liées au cahier des charges établi initialement qui se basait sur une approche singlefeeding. Une stratégie multifeeding est aujourd'hui envisagée afin de mieux correspondre à la réalité du terrain. Sur la base de celle-ci, le nombre de composés décrit dans ce manuscrit potentiellement utilisable en tant que rodonticide se retrouve largement augmenté
To reduce the ecological impact of pesticides in UE many new legislations were put in place, in other hand, most of secondary intoxications of rodent's predators are due to rodenticides available on the market. That why it’s crucial to find alternative rodenticide more eco-friendly. This work describes optimization of new coumarinics compounds synthesis and their biological studies. The new anticoagulant should be active on wild and mutant rat, and must have a low hepatic persistence in the rat body. Organic syntheses were driven with biological studies and have converged to discover the lead. Three different new molecular tools were optimized and have allowed the synthesis and the evaluation of a large number of candidates. The first two through homogeneous catalysis by using micro-waves have reduced the time needed for the alkylation of 4-hydroxycoumarin on the carbon 3. The third methodology allows the synthesis of same kind of compounds in large scale. This methodology opens news potentials reactions to add structural diversity. All the molecules were evaluated in vitro on different types of VKORC1 and have participated to a better understanding of the enzyme/inhibitor interactions. After this first evaluation, in vivo tests were performed on a selection of candidates, and have brought a crucial structural relationship between structure and in vivo persistence/activity. The best compound produced by now seems to answer at all specifications established linked to the single-feeding strategy. Multiple-feeding strategy is today planned to better correspond to the field reality. On the base of this one the number of candidates usable as rodenticides is increased
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Bayoumi, Soad Abdel Latief Hassan. "Molecular genetic analysis of secondary metabolite biosynthesis in cassava as an economic and nutritious plant." Thesis, University of Bath, 2008. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.512260.

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Cassava (Manihot esculenta Crantz Family Euphorbiaceae) is an important tropical food crop. However, harvested cassava roots have a shelf-life of only days due to post-harvest physiological deterioration (PPD). Within 1-3 days of harvesting, the roots show blue-black vascular streaking and are unpalatable. PPD includes altered gene expression and the accumulation of hydroxycoumarin secondary metabolites, e.g. scopoletin and esculetin, and their respective glucosides scopolin and esculin. In this research several important aspects of the biosynthesis of these phytochemically important hydroxycoumarins were resolved. Stable isotopically labelled intermediates on the postulated biosynthetic pathways of scopoletin were fed to cassava cubes and PPD was allowed to occur. Ethanolic extracts of these deteriorated roots were separated (HPLC) and analysed (HRESI-MS). Incorporation (in both scopoletin and scopolin) of only 3 deuterons from E-cinnamic-2,3,2',3',4',5',6'-d7 and E-cinnamic-3,2',3',4',5',6'-d6 is strong support that the E-Zisomerisation step is enzymatic and not photochemical. There are three hypothetical pathways for the biosynthesis of scopoletin via: 2',4'-dihydroxycinnamate, caffeate, or ferulate. High incorporation of label from p-coumaric-2-13C, caffeic-2-13C and ferulic-2-13C acids was observed into labelled scopoletin and scopolin while there was only a small incorporation from 18O-umbelliferone and 18O-esculetin. We conclude that the major biosynthetic pathway to scopoletin and scopolin is via ferulic acid. C18O2-enrichment of E-cinnamic and ferulic acids and feeding gave scopoletin containing only one 18O-labelled oxygen atom. Therefore the lactonisation step is through o-hydroxylation and not via a postulated spirolactone-dienone intermediate. These results were confirmed by feeding experiments in an atmosphere of 18O2-air which showed that the major isotopic peak was 18O3-enriched scopoletin. Three glucosyltransferases were isolated and identified from a cassava PPDrelated cDNA library. These genes are expressed in the cassava storage root during PPD and they are also expressed in the fresh root. While one of these glucosyltransferases was novel, two had previously been isolated from cassava cotyledons.
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Fergusson, D. "The effects of 4-hydroxycoumarin anticoagulant rodenticides on birds and the development of techniques for non-destructively monitoring their ecotoxicological effect." Thesis, University of Reading, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.239503.

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Jhang, Jing-Fu, and 張景富. "Reactions of 4-hydroxycoumarins with 1-methyl quinolinium derivatives and their potential applications." Thesis, 2010. http://ndltd.ncl.edu.tw/handle/60528096030079638268.

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碩士
東海大學
化學系
98
An oxazabicycle derivative 5a was efficiently synthesized by coupling of 7-dimethylamino-4-hydroxycoumarin 10 with N-methyl-2-phenylquinolinium iodide 18 and to investigate its fluorescence redox-switching properties. Chemical reduction of this strongly fluorescent oxazabicycle results in the ring-opened product with a distinct decrease in emission intensity. The resulting ring-opened species can be swiftly reverted to the original ring-closed forms by DDQ oxidation. A novel coumarin and phenanthridine-fused heterocycle and an oxazaspiropyran derivative 6a were also prepared by first base-mediated condensation of coumarins 19 and N-methylquinolinium salts 15, and followed by sodium borohydride reduction. The former was found to possess redox switching properties; the later, with suitable modifications, may have the potential to function as a photochromic colorant.
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Lee, Lin-Wen, and 李玲玟. "Synthesis and antibacterial activities evaluation of 7-hydroxycoumarin and coumarin-3-carboxamide derivatives." Thesis, 2004. http://ndltd.ncl.edu.tw/handle/00138070825567486921.

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碩士
臺北醫學大學
藥學系
92
Synthesis and antibacterial activities evaluation of 7-hydroxycoumarin and coumarin-3-carboxamide derivatives Coumarin is widely distributed in plants and the coumarin derivatives are used as fluorescence dye, laser dye, food additives and medicines at present. Nowadays coumarins are an important group of organic compounds that are used as anticoagulant (dicoumarol), antiviruses, antibacterial, antifungi, antitumor, antimutagenic, anti-inflammatory and antioxidant agents. It also use as prodrug in cartilage explants. The major metabolite of coumarin is 7-hydroxy coumarin and the antiviruses effect of coumarin dimer present in previous studies. The structure of antibiotic novobiocin, chlorobiocin, and coumerymycin A1 which possess amide group on C-3 and substituted on C-7. Three serious of coumarin derivatives were synthesized from 7-hydroxy coumarin and coumarin 3-carboxylic acid in this study. First, we used 7-hydroxycoumarin and N-activated aziridines, a class of compounds important in both chemical synthesis and in chemotherapy of cancer, as starting materials to synthesize 7-hydroxycoumarin derivatives. Second, we used coumarin-3-carboxylic acid and alkyl diamine to synthesize coumarin-3-carboxamide dimer, Bis-(3-coumaric acid)-alkylene diamide. Coumarin 3-carboxylic acid amino-benzylamide was also synthesized by coumarin-3-carboxylic acid and aminobenzylamine. The physical and chemical characteristics of the synthesized compound 1-20 were measured by 1H-NMR, 13C-NMR, IR, EI Mass, HRMS spectrometry, and melting point dector. In this study, we used a new modified microplate antibiotic susceptibility test method (MMAST), which is more convenient, rapid and accurate than before. Only minute sample required for this test and the results obtained within 24 hours. Though there is no obvious antibacterial effect of the all tested compounds. The other biological evaluation will be tried again such as antiplatelet, antitumor, or antiviruses activities in the further study.
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"Protein Design and Engineering Using the Fluorescent Non-canonical Amino Acid L-(7-hydroxycoumarin-4-yl)ethylglycine." Doctoral diss., 2020. http://hdl.handle.net/2286/R.I.63009.

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abstract: Proteins are, arguably, the most complicated molecular machines found in nature. From the receptor proteins that decorate the exterior of cell membranes to enzymes that catalyze the slowest of chemical reactions, proteins perform a wide variety of essential biological functions. A reductionist view of proteins as a macromolecular group, however, may hold that they simply interact with other chemical species. Notably, proteins interact with other proteins, other biological macromolecules, small molecules, and ions. This in turn makes proteins uniquely qualified for use technological use as sensors of said chemical species (biosensors). Several methods have been developed to convert proteins into biosensors. Many of these techniques take advantage of fluorescence spectroscopy because it is a fast, non-invasive, non-destructive and highly sensitive method that also allows for spatiotemporal control. This, however, requires that first a fluorophore be added to a target protein. Several methods for achieving this have been developed from large, genetically encoded autofluorescent protein tags, to labeling with small molecule fluorophores using bioorthogonal chemical handles, to genetically encoded fluorescent non-canonical amino acids (fNCAA). In recent years, the fNCAA, L-(7-hydroxycoumarin-4yl)ethylglycine (7-HCAA) has been used in to develop several types of biosensors. The dissertation I present here specifically addresses the use of the fNCAA L-(7-hydroxycoumarin-4-yl)ethylglycine (7-HCAA) in protein-based biosensors. I demonstrate 7-HCAA’s ability to act as a Förster resonance energy transfer (FRET) acceptor with tryptophan as the FRET donor in a single protein containing multiple tryptophans. I the describe efforts to elucidate—through both spectroscopic and structural characterization—interactions within a 7-HCAA containing protein that governs 7-HCAA fluorescence. Finally, I present a top-down computational design strategy for incorporating 7-HCAA into proteins that takes advantage of previously described interactions. These reports show the applicability of 7-HCAA and the wider class of fNCAAs as a whole for their use of rationally designed biosensors.
Dissertation/Thesis
Doctoral Dissertation Biochemistry 2020
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Chen, Tzu Chun, and 陳姿均. "Ultrafast time-resolved fluorescence studies of Excited-State Proton Transfer Dynamics in 3-cyano-4-methyl-7-hydroxycoumarin complexes." Thesis, 2016. http://ndltd.ncl.edu.tw/handle/67587882491110745079.

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碩士
國立清華大學
化學系
104
We employed a broadband ultrafast time-resolved fluorescence (TRFL) spectrometer implemented by optical Kerr gating (OKG) to study the excited-state proton transfer (ESPT) dynamics in 3-cyano-4-methyl-7-hydroxycoumarin (3CN4MU) complexes. We chose 3CN4MU as the proton donor and two bases, triethylamine (TEA) and 1-methylimidazole (1MI), of different proton affinities (PA) as the proton acceptors. We used two solvents, ethyl acetate (EA) and toluene (TL), of different polarities to study the solvent effect in ESPT. It was conclude from by steady-state spectra that the ground-state 3CN4MU transfers a proton from its phenolic group to TEA, which possesses stronger PA. Therefore, it is difficult to study ESPT in the 3CN4MU-TEA complex. On the other hand, 3CN4MU forms ground-state hydrogen-bonded complexes with 1MI (weaker PA) which suggesting that no proton-transfer reaction occurs in the ground state. Excited states are reached by 383 nm femtosecond laser pulse excitation. The observed TRFL spectra reveal that ESPT does not occur in 3CN4MU-1MI complex in TL, due to the weak solvation effect in nonpolar solvent. On the contrary, solvation-controlled proton transfer in excited state is observed in 3CN4MI-1MI complex in polar solvent EA. We used a total fluorescence intensity function P(t) to measure the excited-state population and transition moment evolution with time during the ESPT process. The P(t) function of 3CN4MU-1MI in EA can be described by three time constants. The fast initial decay component (0.8 ps) can be assigned to first step of proton transfer, which is controlled by solvation effect. The second decay component (30 ps) is assigned to the ion-pair structural relaxation to reduce the overall free energy. In the end, the 1700 ps component is assigned to the lifetime of the excited-sate proton-transferred ion pair.
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Wu, Nien-Hsun, and 吳念勳. "Excited-State Proton Transfer Reaction in 3-Cyano-4-Methyl-7-Hydroxycoumarin Complexes Studied by Femtosecond Time-resolved Fluorescence Spectroscopy." Thesis, 2017. http://ndltd.ncl.edu.tw/handle/6xbce8.

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碩士
國立清華大學
化學系所
105
We studied intermolecular excited-state proton transfer (ESPT) dynamics in hydrogen-bonded complexes of 3-cyano-4-methyl-7-hydroxycoumarin (3CN4MU) by using steady-state absorption/fluorescence spectroscopy and ultrafast time-resolved optical Kerr gating fluorescence spectroscopy. Two different proton acceptors, 1-methyl imidazole (1MI) and triethylamine (TEA), were studied, and the experiments were carried out in strong- and weak-polarity solvents. We also carried out density-functional-theory (DFT) calculations to help us interpreting the experimental results. We found that 3CN4MU-TEA complex undergoes proton transfer in its ground state in both polar and non-polar solvents. In 3CN4MU-1MI complex, the proton transfer does not occur in ground state, as confirmed by experiments and DFT calculations. Due to the lack of solvation, ESPT in 3CN4MU-1MI complex can only partially occur in non-polar solvent. However, the ESPT of 3CN4MU-1MI complex occurs in polar solvent. We used a tri-exponential decay function to fit the total fluorescence intensity function (P(t)) and the time constants are 0.6±0.3ps, 28±3ps and 2290±50ps.The fastest component is assigned to the first step of ESPT, which is a solvation-controlled step. The second component is assigned to a structural relaxation which stabilizes the ion pair. The last one is the lifetime of the ESPT complex.
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Book chapters on the topic "Hydroxycoumarins"

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Gainor, J. A., T. D. Gordon, and B. A. Morgan. "The synthesis and coupling efficiency of 7-hydroxycoumarin-4-propionic acid, a fluorescent marker useful in immobilized substrate libraries." In Peptides, 989–91. Dordrecht: Springer Netherlands, 1994. http://dx.doi.org/10.1007/978-94-011-0683-2_333.

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Pardasani, R. T., and P. Pardasani. "Molar magnetic moment of cobalt(II) complex with Schiff-base derived from 3-methylthiosemicarbazone and 5-formyl-6-hydroxycoumarin." In Magnetic Properties of Paramagnetic Compounds, Magnetic Susceptibility Data, Volume 2, 857–58. Berlin, Heidelberg: Springer Berlin Heidelberg, 2021. http://dx.doi.org/10.1007/978-3-662-62466-1_382.

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"4-Heptadecyl-7-hydroxycoumarin (4-Heptadecylumbelliferone)." In Handbook of Fluorescent Dyes and Probes, 227–28. Hoboken, NJ, USA: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781119007104.ch82.

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"3-Cyano-7-hydroxycoumarin (3-Cyanoumbelliferone)." In Handbook of Fluorescent Dyes and Probes, 141–44. Hoboken, NJ, USA: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781119007104.ch54.

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"7-Hydroxycoumarin-3-carboxylic acid succinimidyl ester." In Handbook of Fluorescent Dyes and Probes, 250–51. Hoboken, NJ, USA: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781119007104.ch88.

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"7-Hydroxycoumarin-3-carboxylic acid (Umbelliferone-3-carboxylic acid)." In Handbook of Fluorescent Dyes and Probes, 246–49. Hoboken, NJ, USA: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781119007104.ch87.

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"Pacific Blue (6,8-Difluoro-7-hydroxycoumarin-3-carboxylic acid)." In Handbook of Fluorescent Dyes and Probes, 315–16. Hoboken, NJ, USA: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781119007104.ch115.

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Kaur, Jaskiran, Paras Famta, Navneet Khurana, Manish Vyas, and Gopal L. Khatik. "Biomedical applications of 4-hydroxycoumarin as a fungal metabolite and its derivatives." In New and Future Developments in Microbial Biotechnology and Bioengineering, 209–18. Elsevier, 2020. http://dx.doi.org/10.1016/b978-0-12-821006-2.00016-9.

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MORIYA, Tetsuo, and Yoshihisa KAWAGUCHI. "AB INITIO MO CALCULATION OF THE STRUCTURE AND ENERGY LEVELS OF 7-HYDROXYCOUMARIN AND ITS TAUTOMER." In Computer Aided Innovation of New Materials, 503–5. Elsevier, 1991. http://dx.doi.org/10.1016/b978-0-444-88864-8.50109-6.

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"Commentary on and reprint of Butt HR, Allen EV, Bollman JL, A preparation from spoiled sweet clover (3,3′-methylene-bis-(4-hydroxycoumarin)) which prolongs coagulation and prothrombin time of the blood: Preliminary report of experimental and clinical studies, in Proceedings of the Staff Meeting of the Mayo Clinic (1941) 16:388–395." In Hematology, 587–96. Elsevier, 2000. http://dx.doi.org/10.1016/b978-012448510-5.50145-x.

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Conference papers on the topic "Hydroxycoumarins"

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Serra, Silvia, Andrea Chicca, Jürg Gertsch, Lourdes Santana, Eugenio Uriarte, and Giovanna Delogu. "Synthesis of a Series of Different Hydroxycoumarins and Their Cytotoxic Activity." In The 16th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2012. http://dx.doi.org/10.3390/ecsoc-16-01108.

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Chatterjee, Rana, Anindita Mukherjee, Grigory V. Zyryanov, and Adinath Majee. "Metal and solvent free direct C3-alkylation of 4-hydroxycoumarins with styrene." In PROCEEDINGS OF INTERNATIONAL CONFERENCE ON RECENT TRENDS IN MECHANICAL AND MATERIALS ENGINEERING: ICRTMME 2019. AIP Publishing, 2020. http://dx.doi.org/10.1063/5.0018529.

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Serra, Silvia, Eugenio Uriarte, Lourdes Santana, Ysabel Santos, Cristina Fuentes-Edfu, Giovanna Delogu, and Saleta Vazquez-Rodriguez. "Synthesis of substituted 3-aryl-4-hydroxycoumarins of expected antimicrobial activity in tenacibaculosis disease." In The 15th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2011. http://dx.doi.org/10.3390/ecsoc-15-00653.

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Matos, Maria, Claudio Olea-azar, Fernanda Perez-Cruz, Fernanda Borges, Alexandra Gaspar, Lourdes Santana, and Patricia Janeiro. "Insights into the antioxidant activity of phenolic compounds: Synthesis and electrochemical study of new series of hydroxycoumarins." In The 15th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2011. http://dx.doi.org/10.3390/ecsoc-15-00617.

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Dekamin, Mohammad G., Meysam Fallah, and Amene Yaghoubi. "Periodic mesoporous organosilica: as a novel and efficient nanocatalyst for the one-pot synthesis of 3,3'-arylmethylene-bis-4-hydroxycoumarins in water." In The 20th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2016. http://dx.doi.org/10.3390/ecsoc-20-a020.

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Kopylova, T. N., L. G. Samsonova, R. M. Gadirov, V. P. Khilya, V. V. Ishchenko, and O. V. Shablykina. "The nature of the photoprocesses in the new 7-hydroxycoumarines." In Atomic and Molecular Pulsed Lasers VII, edited by Victor F. Tarasenko. SPIE, 2007. http://dx.doi.org/10.1117/12.785624.

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Dimić, Dušan, Dejan Milenković, Edina Avdović, Goran Kaluđerović, and Jasmina Dimitrić Marković. "MOLECULAR DOCKING AND MOLECULAR DYNAMICS STUDIES OF THE INTERACTION BETWEEN COUMARIN-NEUROTRANSMITTER DERIVATIVES AND CARBONIC ANHYDRASE IX." In 1st INTERNATIONAL Conference on Chemo and BioInformatics. Institute for Information Technologies, University of Kragujevac,, 2021. http://dx.doi.org/10.46793/iccbi21.056d.

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Abstract:
Novel biologically active compounds can be obtained by the structural modification of coumarins. In this contribution, five new derivatives of 4-hydroxycoumarin with tyramine, octopamine, norepinephrine, 3-methoxytyramine, and dopamine were obtained. Their structures were optimized based on the previously obtained crystal structure of the 4-hydroxycoumarin-dopamine derivative. The special emphasis was put on the effect of various substituents on the structure of obtained compounds and intramolecular interactions governing the stability. To investigate their possible antitumor activity, molecular docking and molecular dynamics simulations were performed with Carbonic anhydrase, a prognostic factor in several cancers, and compared to the native ligand, 5-acetamido-1,3,4-thiadiazole- 2-sulfonamide. The results have shown that all of the coumarin-neurotransmitter derivatives bind to the active pocket of protein with the binding energies higher than for the native ligand. The main contributions to the binding energies were discussed. The Root Mean Square Deviation (RMSD), Root Mean Square Fluctuation (RMSF), and Radius of gyration (Rg), as results of MD simulations, were used to predict the activity of compounds towards chosen protein. The highest MD binding energies were obtained for the derivatives with dopamine and 3-methoxytyramine, with the van der Waals interaction and hydrogen bonds being the most important contributors.
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Dong, Sheying, Penghui Zhang, and Jing Li. "Microwave-Assisted Synthesis and Crystal Structure of 3',3-Benzylidene-Bis-4-Hydroxycoumarin." In 2009 Symposium on Photonics and Optoelectronics. IEEE eXpress Conference Publishing, 2009. http://dx.doi.org/10.1109/sopo.2009.5230279.

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