- Photo-switchable nanoporous silica supports for controlled drug delivery
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A photo-responsive ligand 7-[(3-triethoxysilyl)propoxy]coumarin (C) was grafted on the surface of a mesoporous silica SBA-12 material. The obtained functionalized support SBA-12_C was used as an effective light-controlled storage/release system of the anti-inflammatory drug naproxen. Irradiation with UV light at 365 nm induces the photo-dimerization of the coumarin on the surface, giving a dimer connected by a cyclobutane ring, leading to pore closure. However, irradiation with UV light of a shorter wavelength, 254 nm, leads to the cleavage of the dimers, opening of the pores, and the guest drug molecules can be released from the pores. The release of the drug was studied in two types of media, a simulated body fluid at pH = 7 and a simulated gastric fluid at pH = 2. The prepared materials were characterized by high resolution transmission electron microscopy (HR-TEM), nitrogen adsorption/desorption, infrared spectroscopy (FT-IR), thermoanalytical methods (TG/DTA) and liquid and solid-state NMR spectroscopy. The amount of released drug was monitored by HPLC chromatography at defined time intervals. The samples with pores closed by coumarin dimers were tight enough to show premature release of the drug from the sample. After light-driven pore opening, the amounts of released naproxen from coumarin modified mesoporous silica were different, depending on the pH conditions of the release media.
- Zeleňák, Vladimír,Beňová, Eva,Almá?i, Miroslav,Halamová, Dá?a,Hornebecq, Virginie,Hronsky, Viktor
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- A novel class of inhibitors for steroid 5α-Reductase: Synthesis and evaluation of umbelliferone derivatives
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A series of umbelliferone derivatives was prepared and their 5α-reductase type 1 inhibitory activities were evaluated in cell culture systems. Our studies have identified a new series of potent 5α-reductase type 1 inhibitors and provided the basis for further development for the treatment of human endocrine disorders associated with overproduction of DHT by 5α-reductase type 1. The preliminary structure-activity relationship was described to elucidate the essential structural requirements.
- Fan, Gao-jun,Mar, Woongchon,Park, Man Ki,Wook Choi, Eun,Kim, Kinam,Kim, Sanghee
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- SESEBRINIC ACID, A CINNAMIC ACID DERIVATIVE FROM SESELI SIBIRICUM
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A new cinnamic acid, sesebrinic acid, was isolated from the aerial parts of Seseli sibiricum; its structure was elucidated by chemical and spectral data and hemisynthesis.A number of its analogues were also synthesized. - Key Word Index: Seseli sibiricum; Umbelliferae; coumarins; sesebrinic acid; synthesis.
- Banerjee, Sunil K.,Mukhopadhyay, Sibabrata,Gupta, Bishan D.,Singh, Kuber,Raj, Som
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- A minor structure modification serendipitously leads to a highly carbapenemase-specific fluorogenic probe
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Reported herein is a fluorogenic probe for the detection of carbapenemase activity. This reagent features carbapenem as an enzyme recognition motif and a carbon-carbon double bond between carbapenem and the fluorophore, exhibiting high specificity to all carbapenemases, including metallo carbapenemases and serine carbapenemases, over other β-lactamases.
- Wang, Jie,Xie, Hexin,Xu, Weipan,Xue, Shuyuan,Yu, Tao
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- Realizing both selective adsorption and efficient regeneration using adsorbents with photo-regulated molecular gates
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A new generation of smart adsorbents was designed by grafting photo-responsive molecules onto the pore entrances of mesoporous silica. These molecules act as the gates of the mesopores, which are reversibly closed/opened upon light irradiation. Our smart adsorbents thus realize both selective adsorption and efficient desorption, which is highly expected for adsorption but impossible for traditional adsorbents with fixed pore entrances.
- Zhu, Jing,Ding, Jia-Jia,Liu, Xiao-Qin,Tan, Peng,Sun, Lin-Bing
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- Multi-cycle reversible control of gas permeability in thin film composite membranesviaefficient UV-induced reactions
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This communication presents a new, UV-induced mechanism to reversibly control the permeability of ultra-thin polymer coatings. Photoreversible [2+2] cycloaddition reactions were utilised to adjust the crosslinking degree and glass transition temperature of a coating. Consequently, a 300%, reversible change in the coating's oxygen permeability was achieved without loss of performance. Ultimately, the findings demonstrate the capability of using low UV doses to reversibly and efficiently regulate mass transport through ultra-thin coatings fabricated in a facile manner.
- Alrayyes, Abdalrahman U.,Low, Ze-Xian,Wang, Huanting,Saito, Kei
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- A fluorogenic assay for transketolase from Saccharomyces cerevisiae
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In order to generate transketolase (TK) with new or improved properties by in vitro evolution, an efficient screening system is an absolute prerequisite for identifying the evolved enzyme variants. We report here an assay allowing us to detect wild type TK activity in vitro by fluorescence. We examined the use of the fluorogenic compound 1 as donor substrate of TK, which is itself non fluorescent but releases a fluorescent product: umbelliferone.
- Sevestre, Aurélie,Hélaine, Virgil,Guyot, Ghislain,Martin, Christine,Hecquet, Laurence
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- A new synthesis of angelicin from 7-hydroxycoumarin via c-propenation-o-vinylation and ring-closing metathesis
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A new and concise method for the synthesis of angelicin was described. 7-Hydroxycoumarin was converted into angelicin in good overall yields via the process of c-propenation-o-vinylation and ring-closing metathesis (RCM).
- Tsai, Tzu-Wei,Wang, Eng-Chi
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- Photoresponsive cellulose paper as a molecular printboard for covalent printing
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This contribution unveils and defines the concept of covalent printing onto cellulose paper through the support of a simple and efficient strategy. A photoresponsive cellulose paper bearing disulfide functional groups was created as a molecular printboard for spatio-temporal writing through thiol-X ligation of functional inks upon light irradiation. This strategy using molecular inks in a modular way culminated with the creation of patterns with a high resolution. Hidden covalent writing to the naked eyes was developed through the use of coumarin-based inks while the use of colored inks containing a rhodamine backbone established an uncovered pH-responsive covalent printing, both strategies can potentially find applications in the formation of anti-counterfeiting devices.
- Rull-Barrull,D'Halluin,Le Grognec,Felpin
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- On the possibility of tuning molecular edges to direct supramolecular self-assembly in coumarin derivatives through cooperative weak forces: Crystallographic and hirshfeld surface analyses
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Four organic compounds based on substituted coumarin derivatives (1 - 4) have been synthesized and characterized by X-ray structural studies with a detailed analysis of Hirshfeld surface and fingerprint plots facilitating a comparison of intermolecular interactions in building different supramole-cular architectures. The X-ray study reveals that in the molecular packing C - H · · ·O, π · · · π, and carbonyl (lone pair) · · · π interactions cooperatively take part. The recurring feature of the self-assembly in all the compounds is the appearance of the molecular ribbon through weak hydrogen bonding. These hydrogen bonded ribbons further stacked into molecular layers by π · · · π forces. The mode of cooperativity of the weak C - H · · · O and π · · · π forces is such that they operate in mutuallyperpen-dicular directions - hydrogen bonding in the plane of the molecule at their edges and π-stacking perpendicular to the molecular plane. Investigation of intermolecular interactions and crystal packing via Hirshfeld surface analyses reveals that more than two-thirds of the close contacts are associated with weak interactions. Hirshfeld surface and breakdown of the corresponding fingerprint plots of four coumarin structures clearly quantify the interactions within the crystal structures, revealing significant similarities in the interactions experienced by each compound. The binding energies associated with the weak interactions have been estimated using density functional theory calculations.
- Seth, Saikat Kumar,Sarkar, Debayan,Jana, Atish Dipankar,Kar, Tanusree
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- A novel fluorescent functional monomer as the recognition element in core-shell imprinted sensors responding to concentration of 2,4,6-trichlorophenol
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We have demonstrated a fluorescent functional monomer instead of the traditional functional monomers for molecularly imprinted sensors. The sensors were firstly used to selectively detect 2,4,6-trichlorophenol (2,4,6-TCP) by solid fluorescence detection without a dispersion solution. Moreover, the selectivity and anti-interference ability of the SiO2@dye-FMIPs sensor meet the requirements of a fluorescent sensor. The novel fluorescent monomer introduced into MIP is no longer just a fluorophore without recognizing ability. The fluorescence intensity of SiO2@dye-FMIPs showed a linear response to 2,4,6-TCP concentration in the range of 0-100 nM with a detection limit of 0.0534 nM. We could also demonstrate that such a system can not only get rid of the confines of traditional functional monomers and detection manner, but also improved the applications of MIPs sensors in sensing systems.
- Ren, Baixiang,Qi, Huan,Li, Xiuying,Liu, Lihui,Gao, Lin,Che, Guangbo,Hu, Bo,Wang, Liang,Lin, Xue
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- Controlled In-Cell Generation of Active Palladium(0) Species for Bioorthogonal Decaging
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Owing to their bioorthogonality, transition metals have become very popular in the development of biocompatible bond-cleavage reactions. However, many approaches require design and synthesis of complex ligands or formulation of nanoparticles which often perform poorly in living cells. This work reports on a method for the generation of an active palladium species that triggers bond-cleaving reactions inside living cells. We utilized the water-soluble Na2PdCl4 as a simple source of PdII which can be intracellularly reduced by sodium ascorbate to the active Pd0 species. Once generated, Pd0 triggers the cleavage of allyl ether and carbamate caging groups leading to the release of biologically active molecules. These findings do not only expand the toolbox of available bioorthogonal dissociative reactions but also provide an additional strategy for controlling the reactivity of Pd species involved in Pd-mediated bioorthogonal reactions.
- Bernardes, Gon?alo J. L.,Day, Jason,Domingos, Josiel B.,Jiménez-Moreno, Ester,Kon?, Juraj,Latocheski, Eloah,Pérez, Laura Rodríguez,Sabatino, Valerio
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supporting information
(2022/01/11)
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- Synthesis and biological evaluation of novel coumarin derivatives in rhabdoviral clearance
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Diseases caused by rhabdoviruses have had a huge impact on the productive lives of the entire human population. The main problem is the lack of drugs for the treatment of this family of viruses. Infectious hematopoietic necrosis virus (IHNV), the causative agent of IHN, is a typical rhabdovirus which has caused huge losses to the salmonid industry. Therefore, in this study, IHNV was studied as a model to evaluate the antiviral activity of 35 novel coumarin derivatives. Coumarin A9 was specifically selected for further validation studies upon comparing the half maximum inhibitory concentration (IC50) of four screened candidate derivatives in epithelioma papulosum cyprinid (EPC) cells, as it exhibited an IC50 value of 2.96 μM against IHNV. The data revealed that A9 treatment significantly suppressed the virus-induced cytopathic effect (CPE) in EPC cells. In addition, A9 showed IC50 values of 1.68 and 2.12 μM for two other rhabdoviruses, spring viremia of carp virus and micropterus salmoides rhabdovirus, respectively. Furthermore, our results suggest that A9 exerts antiviral activity, but not by destroying the virus particles and interfering with the adsorption of IHNV. Moreover, we found that A9 had an inhibitory effect on IHNV-induced apoptosis in EPC cells, as reflected by the protection against cell swelling, formation of apoptotic bodies, and loss of cell morphology and nuclear division. There was a 19.05 % reduction in the number of apoptotic cells in the A9 treatment group compared with that in the IHNV group. In addition, enzyme activity assays proved that A9 suppressed the expression of caspase 3, 8 and 9. These results suggested that A9 inhibit viral replication, to some extent, by blocking IHNV-induced apoptosis. In an in vivo study, A9 exhibited an anti-rhabdovirus effect in virus-infected fish by substantially enhancing the survival rate. Consistent with the above results, A9 repressed IHNV gene expression in virus-sensitive tissues (brain, kidney and spleen) in the early stages of virus infection. Importantly, the data showed that horizontal transmission of IHNV was reduced by A9 in a static cohabitation challenge model, especially in fish that underwent bath treatment, suggesting that A9 might be a suitable therapeutic agent for IHNV in aquaculture. Therefore, coumarin derivatives can be developed as antiviral agents against rhabdoviruses.
- Chen, Jiong,Hu, Yang,Liu, Lei,Qiu, Tianxiu,Shan, Lipeng
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supporting information
(2021/08/10)
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- Photo-switchable membranes constructed from graphene oxide/star-PDMS nanocomposites for gas permeation control
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A novel, photo-responsive membrane based on a star-shaped polydimethylsiloxane (PDMS) polymer and graphene-based nanosheets was for the first time designed and fabricated for controlling gas permeation. The sub-60 nm thick membrane exhibited continuous photo-reversible gas permeance control when irradiated with UV light of variable wavelengths. By optimising the nanosheet loading and nanosheet-polymer interface, the defect-free membrane demonstrated a satisfactory gas separation performance towards CO2and C3H8, allowing the membrane to potentially be useful as a photoresponsive coating for applications such in modern plant cultivation technologies. The effect of the nanosheets on the photo-triggering mechanism, a [2 + 2] cycloaddition reaction, was investigated, which revealed that the presence of the nanosheets improved the polymerisation reaction, but hindered the de-polymerisation reaction. Overall, this work provides a new opportunity for the production and investigation of a new class of photo-responsive two-dimensional nanocomposite membranes for highly controlled molecular/ion sieving.
- Alrayyes, Abdalrahman U.,Hu, Yaoxin,Tabor, Rico F.,Wang, Huanting,Saito, Kei
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supporting information
p. 21167 - 21174
(2021/10/05)
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- Design, synthesis and biological evaluation of O-alkyl umbelliferone derivatives as pancreatic lipase inhibitors
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A series of coumarin derivatives were synthesised through O-alkylation of umbelliferone. These derivatives were screened for their pancreatic lipase (PL) inhibitory potential. The PL inhibitory effect of compounds with various benzyl and long chain alkyl substituents on umbelliferone were analysed. The compound 1g, having the geranyl substituent was found to have better PL inhibitory potential with an IC50 of 21.64 M. The compounds 1a-j were subjected to molecular docking into the crystal structure of human PL. The molecular docking results are in correlation with the in vitro PL inhibition activity, wherein compound 1g showed a higher MolDock score of -122.12 kcal/mol. The long chain alkyl groups were found to have PL inhibition due to additional interactions with lid domain amino acids (Phe215, Tyr114, Phe77), as revealed by molecular docking study.
- Yadav, Nisha,Auti, Prashant,George, Ginson,Paul, Atish T.
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p. 1265 - 1271
(2020/12/04)
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- Highly regioselective O-allylation of phenol derivatives using MMZCu(I)Y catalyst
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A clean and effective method has been developed for the regioselective of O-allylation of phenol derivatives using a recyclable Cu(I)-exchanged multi-size porous material. Ease of preparation of catalyst through simple solid-state exchange and its compatibility in producing excellent amount of O-allylated products and a plausible mechanistic pathway for the regioselectivity are highlighted. This reported procedure is not requiring any external stabilizing ligand for Cu(I) species and further purification of products.
- Thangapriya, Cheirmakani,Ilaamirthamani, Simsonrubarathinam,Kumarraja, Mayilvasagam
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p. 361 - 367
(2019/12/11)
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- Combined molecular modeling and cholinesterase inhibition studies on some natural and semisynthetic O-alkylcoumarin derivatives
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Coumarins of synthetic or natural origins are an important chemical class exerting diverse pharmacological activities. In the present study, 26 novel O-alkylcoumarin derivatives were synthesized and have been tested at 100 μM for their in vitro inhibitory potential against acetylcholinesterase (AChE) and butyrlcholinesterase (BChE) targets which are the key enzymes playing role in the pathogenesis of Alzheimer's disease. Among the tested coumarins, none of them could inhibit AChE, whereas 12 of them exerted a marked and selective inhibition against BChE as compared to the reference (galanthamine, IC50 = 46.58 ± 0.91 μM). In fact, 10 of the active coumarins showed higher inhibition (IC50 = 7.01 ± 0.28 μM – 43.31 ± 3.63 μM) than that of galanthamine. The most active ones were revealed to be 7-styryloxycoumarin (IC50 = 7.01 ± 0.28 μM) and 7-isopentenyloxy-4-methylcoumarin (IC50 = 8.18 ± 0.74 μM). In addition to the in vitro tests, MetaCore/MetaDrug binary QSAR models and docking simulations were applied to evaluate the active compounds by ligand-based and target-driven approaches. The predicted pharmacokinetic profiles of the compounds suggested that the compounds reveal lipophilic character and permeate blood brain barrier (BBB) and the ADME models predict higher human serum protein binding percentages (>50%) for the compounds. The calculated docking scores indicated that the coumarins showing remarkable BChE inhibition possessed favorable free binding energies in interacting with the ligand-binding domain of the target. Therefore, our results disclose that O-alkylcoumarins are promising selective inhibitors of cholinesterase enzymes, particularly BChE in our case, which definitely deserve further studies.
- Orhan, Ilkay Erdogan,Senol Deniz, F. Sezer,Salmas, Ramin Ekhteiari,Durdagi, Serdar,Epifano, Francesco,Genovese, Salvatore,Fiorito, Serena
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p. 355 - 362
(2018/12/13)
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- Natural and semisynthetic oxyprenylated aromatic compounds as stimulators or inhibitors of melanogenesis
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It has been very recently shown how naturally occurring oxyprenylated coumarins are effective modulators of melanogenesis. In this short communication we wish to generalize the potentialities as skin tanning or whitening agents of a wider panel of natural and semisynthetic aromatic compounds, including coumarins, cinnamic and benzoic acids, cinnamaldehydes, benzaldehyde, and anthraquinone derivatives. A total number of 43 compounds have been tested assaying their capacity to inhibit or stimulate melanin biosynthesis in cultured murine Melan A cells. The wider number of chemicals herein under investigation allowed to depict a detailed structure-activity relationship, as the following: (a) benzoic acid derivatives are slightly pigmenting agent, for which the effect is more pronounced in compounds with longer O-side chains; (b) independently from the type of substitution, cinnamic acids are able to increase melanin biosynthesis, while benzaldehydes are able to decrease it; (c) coumarins with a 3,3-dimethylallyl or shorter skeletons as substituents in position 7 are tanning agents, while coumarins with farnesyloxy groups are whitening ones; (d) double oxyprenylation in position 6 and 7 and 3,3-dimethylallyl or geranyl skeletons have slight depigmenting capacities, while farnesyl skeletons tend to marginally increase the tanning effect; (e) the presence of electron withdrawing groups (acetyl, COOH, and -Cl) and geranyl or farnesyl oxyprenylated chains respectively in positions 3 and 7 of the coumarin nucleus lead to a whitening effect, and finally (f) oxyprenylated anthraquinones have only a weak depigmenting capacity.
- Genovese, Salvatore,Epifano, Francesco,Medina, Philippe de,Caron, Nicolas,Rives, Arnaud,Poirot, Marc,Poirot, Sandrine Silvent,Fiorito, Serena
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p. 181 - 190
(2019/03/23)
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- Collection of alkenylcoumarin derivatives as Taq DNA polymerase inhibitors: SAR and in silico simulations
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Using a feasible method, we generated a small focused library of structurally related alkenylcoumarins. These compounds were evaluated as potential antitumoral agents against Taq DNA polymerase. 6-(pent-4-enyloxy)-coumarin (7) IC50 = 48.33 ± 2.85 μM was defined as a small molecule able to disturb DNA replication. Docking and Molecular Dynamic Simulations suggest an active-site binding. Structure/activity relationship was reasonably established. Compound 7 represents a potential structure for further studies in the development of new anti-cancer DNA/polymerase binding agents.
- Bruna-Haupt, Ezequiel,Garro, Hugo A.,Gutiérrez, Lucas,Pungitore, Carlos R.
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p. 1432 - 1442
(2018/03/12)
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- Interaction of 7-Alkoxycoumarins with the Aryl Hydrocarbon Receptor
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The aryl hydrocarbon receptor (AhR) is a transcription factor activated by a vast array of natural and synthetic ligands. It plays a pivotal role in numerous physiological and pathological responses, such as cell proliferation and differentiation, induction of xenobiotic metabolizing enzymes, response to environmental toxins, and several others. In this study, we investigated the ability of some natural compounds (oxyprenylated ferulic acid and umbelliferone derivatives) and their semisynthetic analogues (e.g., differently substituted 7-Alkoxycoumarins) to activate AhR, using a reporter luciferase assay. Among them, we found that 7-isopentenyloxycoumarin was the best AhR activator. Boropinic acid, 7-but-2′-enyloxycoumarin, 7-(2′,2′-dimethyl-n-propyloxy)coumarin, 7-benzyloxycoumarin, and 7-(3′-hydroxymethyl-3′-methylallyloxy)coumarin were also active, although to a lesser extent. All the compounds were also analyzed for their ability to inhibit AhR activation, using a reference ligand, 6-formylindolo[3,2-b]carbazole. Data recorded in the present investigation pointed out the importance of a 3,3-dimethylallyloxy side chain attached to the coumarin ring core as a key moiety for AhR activation.
- Gargaro, Marco,Epifano, Francesco,Fiorito, Serena,Taddeo, Vito Alessandro,Genovese, Salvatore,Pirro, Matteo,Turco, Antonella,Puccetti, Paolo,Schmidt-Weber, Carsten B.,Fallarino, Francesca
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p. 1939 - 1943
(2017/06/28)
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- Synthesis and immunopotentiating activity of novel isoxazoline functionalized coumarins
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A novel series (13) of isoxazoline functionalized coumarins was synthesized through 1,3-dipolar cyclization of nitrile oxides with Allylated coumarins. Synthesis of effective and target selective immunostimulators through conjugation of diversely substitu
- Ismail, Tabasum,Shafi, Syed,Singh, Swarn,Sidiq, Tabasum,Khajuria, Anamika,Rouf, Abdul,Yadav, Mahipal,Saikam, Varma,Singh, Parvinder Pal,Alam, Mohammad Sarwar,Islam, Nasarul,Sharma, Kalicharan,Kumar, Halmuthur Mahabalarao Sampath
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- A prochelator with a modular masking group featuring hydrogen peroxide activation with concurrent fluorescent reporting
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Metal chelators masked with protecting groups for targeted release have the potential to conditionally modulate cellular metals. We report a new route to prepare cis-cinnamate protecting groups that enabled development of a prochelator with chemical stimulus response, fluorescent reporting and active compound release in a single structure. the Partner Organisations 2014.
- Franks, Andrew T.,Franz, Katherine J.
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supporting information
p. 11317 - 11320
(2014/11/07)
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- Inhibitory effects of 6-alkoxycoumarin and 7-alkoxycoumarin derivatives on lipopolysaccharide/interferon γ-stimulated nitric oxide production in RAW264 cells
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Coumarin and its derivatives are well known for their anti-inflammatory and anti-oxidative effects. In this study, we synthesized 32 coumarin derivatives from commercially available 6-hydroxycoumarin (6HC) and 7-hydroxycoumarin (7HC) and examined their ef
- Adfa, Morina,Itoh, Tomohiro,Hattori, Yosuke,Koketsu, Mamoru
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experimental part
p. 963 - 966
(2012/09/21)
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- Synthesis and anthelmintic activity of osthol analogs against Dactylogyrus intermedius in goldfish
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In an attempt to develop novel anthelmintic agents, our previously isolated osthol was used as lead structures for further optimization. In our research, a series of coumarin analogs, prepared from 7-hydroxy coumarin or 7-hydroxy-4-methyl coumarin, have been evaluated for their anthelmintic activities. In all of the compounds, 6 and 7 were first synthesized, and their structures were identified based on NMR and MS values. Among the candidates, 8-allyl-7-allyloxycoumarin showed better anthelmintic activity than other compounds against Dactylogyrus infestation with EC50 value of 1.81 mg/L. The quantitative structure-activity relationship (QSAR) of 16 osthol analogs with anthelmintic activity expressed as pEC50 and toxicity to goldfish expressed pLC50, such results can offer useful theoretical references for future experimental works.
- Liu, Guang-Lu,Hao, Bing,Liu, Shao-Peng,Wang, Gao-Xue
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p. 582 - 590
(2012/09/11)
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- CARBONIC ANHYDRASE INHIBITORS WITH ANTIMETASTATIC ACTIVITY
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Compositions for the treatment of cancer comprising coumarin and thiocoumarin derivatives of Formulas I- XII are disclosed. Said derivatives preferentially inhibit carbonic anhydrase IX and XII (which are associated with hypoxic and metastatic tumours) over inhibiting carbonic anhydrase I and II activity. The compositions therefore are suited for treatment of hypoxic or metastatic cancers due to this selective mechanism of action.
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Page/Page column 34-65
(2012/06/15)
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- Novel Insect-Repellent Coumarin Derivatives, Syntheses, and Methods of Use
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This invention relates to novel coumarin derivative, formulations comprising same, and to methods of making and using these compounds and formulations, which are useful as repellents against insects and/or pests. The compounds also prevent illness and disease caused by insect/pest-borne vectors, and provide safer, more effective alternatives to existing repellents.
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Page/Page column 16
(2013/02/28)
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- Novel coumarins and 2-thioxo-coumarins as inhibitors of the tumor-associated carbonic anhydrases IX and XII
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A series of coumarins incorporating tert-butyl-dimethylsilyloxy- or allyoxy- moieties in positions 4-, 6 or 7 of the heterocyclic ring have been synthesized and then converted to the corresponding 2-thioxo-coumarins. Other derivatives incorporating hydrox
- Carta, Fabrizio,Maresca, Alfonso,Scozzafava, Andrea,Supuran, Claudiu T.
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experimental part
p. 2266 - 2273
(2012/05/05)
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- Synthesis and biological evaluation of fused oxepinocoumarins as free radicals scavengers
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Some fused dihydrooxepino[f]-, [g]-, and [h]coumarins were obtained from the ring-closing metathesis of the corresponding o-allyl-allyloxycoumarins under the treatment with the first generation Grubbs' catalyst. These compounds were tested in vitro for their antioxidant activity, and they present significant scavenging activity. They were also showed to inhibit in vitro soybean lipoxygenase.
- Litinas, Konstantinos E.,Mangos, Alexandros,Nikkou, Thomas E.,Hadjipavlou-Litina, Dimitra J.
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experimental part
p. 805 - 812
(2012/04/04)
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- Total synthesis of (+)-angelmarin
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(Chemical Equation Presented) An efficient 8-step enantioselective total synthesis of (+)-angelmarin, starting from commercially available umbelliferone, has been achieved. Key reactions include olefin cross-metathesis and a Shi epoxidation-cyclization sequence.
- Magolan, Jakob,Coster, Mark J.
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supporting information; experimental part
p. 5083 - 5086
(2009/10/17)
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- Application of the BHQ benzannulation reaction to the synthesis of benzo-fused coumarins
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A new approach to the synthesis of the 6H-benzo[d]naphtha[1,2-b]pyran-6-one ring system present in the gilvocarcin family of antibiotics is described. The key feature of this approach is the application of a new benzannulation strategy (the 'BHQ Reaction'
- Bull, James A.,Luján, Cristina,Hutchings, Michael G.,Quayle, Peter
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scheme or table
p. 3617 - 3620
(2009/09/30)
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- New method to prepare very stable and biocompatible fluorescent silica nanoparticles
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A new synthetic method has been developed to prepare fluorescent silica nanoparticles without employing isothiocyanated dye molecules and (3-aminopropyl)triethoxysilane (APS) for the thiourea linkage formation; the resulting fluorescent silica nanoparticl
- Ha, Shin-Woo,Camalier, Corinne E.,Beck Jr., George R.,Lee, Jin-Kyu
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supporting information; experimental part
p. 2881 - 2883
(2009/12/01)
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- SELF-INDICATING PHOTO-REPATTERNABLE HYBRID MATERIALS AND POLYMERS
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In some embodiments, the present invention is directed to a method for chemically modifying 7-substituted coumarins to produce polymerizable monomers that are used to prepare photoresponsive materials. In one embodiment, 7-hydroxy-coumarin (umbelliferone) is so modified. The present invention also relates to the photoresponsive linear polymers, copolymers, and hybrid network materials produced from the polymerizable monomers, and the method for their preparation.
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Page/Page column 3
(2008/06/13)
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- Artificial aldolases from peptide dendrimer combinatorial libraries
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Peptide dendrimers were investigated as synthetic models for aldolase enzymes. Combinatorial libraries were prepared with aldolase active residues such as lysine and proline placed at the dendrimer core or near the surface. On-bead selection for aldolase activity was carried out using the dye-labelled 1,3-diketone 1a, suitable for covalent trapping of enamine-reactive side-chains, and the fluorogenic enolization probe 6. Aldolase dendrimers catalyzed the aldol reaction of acetone, dihydroxyacetone and cyclohexanone with nitrobenzaldehyde. Much like enzymes, the dendrimers exhibited strong aldolase activity in aqueous medium, but were also active in organic solvent. Dendrimer-catalyzed aldol reactions reached complete conversion in 3 h at 25 °C with 1 mol% catalyst and gave aldol products with up to 65% ee. A positive dendritic effect in catalysis was observed with both lysine and proline based aldolase dendrimer catalysts. The Royal Society of Chemistry 2006.
- Kofoed, Jacob,Darbre, Tamis,Reymond, Jean-Louis
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p. 3268 - 3281
(2008/09/16)
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- Enzyme activity fingerprinting with substrate cocktails
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In the postgenomic era, emphasis is shifting from protein identification to protein functional analysis. Enzyme function can be characterized by measuring activity across series of substrates, which generates an activity profile or fingerprint. Activity f
- Goddard, Jean-Philippe,Reymond, Jean-Louis
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p. 11116 - 11117
(2007/10/03)
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- Mesoporous silica having controlled-release on-off control function, production method thereof and method using same
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The present invention provides a hexagonal mesoporous silica comprising a photo-dimerizable organic functional group provided at the entrances of the pores thereof, and a hexagonal mesoporous silica comprising a functional substance filled in the pores thereof and a dimerized organic functional group provided at the entrances of the pores to close the entrances. These hexagonal mesoporous silicas allow a substance incorporated therein to be controllably released. The present invention also provides a method of producing the mesoporous silica, and a method using the mesoporous silica to control the release of a functional substance incorporated therein.
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- Synthesis of thio- and oxo-analogues of isopsoralen
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A range of novel 5′-substituted 7-oxo and 7-thioisopsoralens were synthesized via a Claisen rearranged allyl aryl ether followed by reductive ozonolysis in the presence of a suitable solvent. In some cases dimethylthiocarbamoyl chloride was used as a protecting group and to introduce the thiol moiety.
- Clarke, Dino J,Robinson, Ross S
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p. 2831 - 2837
(2007/10/03)
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- Microwave and BF3 promoted rearrangement of allyloxycoumarins to allylcoumarins and dihydrofurocoumarins
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Allyl, crotyl, methallyl and cinamyl ethers of 4-hydroxy-, 7-hydroxy-, and 4-methyl-7-hydroxycoumarins have been efficiently synthesized and rearranged to substituted allylcoumarins under microwave irradiation. Irradiation of allylcoumarins in the presence of BF3/ether directly produced substituted dihydrofurocoumarins in good yields.
- Saidi, Mohammad R,Rajabi, Fatemeh
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p. 1805 - 1812
(2007/10/03)
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- Synthesis and Configurational Assignment of Geiparvarin: A Novel Antitumor Agent
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This report presents the first total synthesis of geiparvarin as well as assignment of configuration of the previously undefined trisubstituted olefin.A central aspect of this synthetic adventure leading to this novel antitumor agent which possesses the 3
- Jerris, Paula J.,Smith, Amos B.
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p. 577 - 585
(2007/10/02)
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- Synthesis of some photosensitizing methylangelicins, as monofunctional reagents for DNA
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angelicins methylated angelicans were synthesized for obtaining monofunctional reagents for DNA; these compounds may present some interest with regard to the development of useful drugs in photochemotheapy. The new derivatives photobind covalently to DNA, however, they are unable to produce inter-strand, cross-linkages in the macromolecule. Thephotobiological activity was tested on phage T2 and was higher for the methylated derivatives than for angelicin.
- Guiotto,Rodighiero,Pastorini,et al.
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p. 489 - 494
(2007/10/02)
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- Insect control agents
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Compounds having the formula STR1 in which one of R1 and R2 is C3 -C4 alkynoxy or C3 alkenoxy and the other is hydrogen or methoxy. The compounds have utility as insect control agents, either as insecticides or anti-juvenile hormones.
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