- Demonstrating the role of anchoring functionality in interfacial electron transfer dynamics in the newly synthesized BODIPY-TiO2 nanostructure composite
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New BODIPY derivatives (dyes 1 and 2) with either catechol or resorcinol functionality, respectively, for anchoring to nanostructured (NS) TiO2 surfaces were synthesized. Extended conjugation at one of the two pyrrole rings at the C3 position helped us to achieve the desired control in tuning the optical and redox properties of the BODIPY based dye molecules. Relative emission quantum yields (Φem1 = ~52 ± 2% and Φem2 = 54 ± 2%) were found to be much higher in a polar aprotic solvent (acetonitrile) and substantially lower for dye 1 in a polar protic solvent. Steady state optical absorption studies revealed the formation of a strong charge transfer complex between dye 1 and NS-TiO2, while this interaction was much weaker for dye 2. Transient absorption studies were carried out for 1/NS-TiO2 and 2/NS-TiO2 systems following excitation with a laser source of 400 nm to understand the charge transfer dynamics. The results of the transient absorption spectral studies helped us to elucidate the role of anchoring functionality in influencing the dynamics of interfacial electron transfer and charge recombination processes on an ultrafast timescale.
- Aute, Sunil,Maity, Partha,Das, Amitava,Ghosh, Hirendra N.
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Read Online
- Synthesis, evaluation and molecular modelling of piceatannol analogues as arginase inhibitors
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Arginase is involved in a wide range of pathologies including cardiovascular diseases and infectious diseases whilst it is also a promising target to improve cancer immunotherapy. To date, only a limited number of inhibitors of arginase have been reported. Natural polyphenols, among them piceatannol, are moderate inhibitors of arginase. Herein, we report our efforts to investigate catechol binding by quantum chemistry and generate analogues of piceatannol. In this work, we synthesized a novel series of amino-polyphenols which were then evaluated as arginase inhibitors. Their structure-activity relationships were elucidated by deep quantum chemistry modelling. 4-((3,4-Dihydroxybenzyl)amino)benzene-1,2-diol3tdisplays a mixed inhibition activity on bovine and human arginase I with IC50(Ki) values of 76 (82) μM and 89 μM, respectively.
- Cardey, B.,Desingle, C.,Foley, S.,Girard, C.,Grzybowski, M.,Harakat, D.,Muller, J.,Pomper, P.,Pudlo, M.,Ramseyer, C.,Zedet, A.
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p. 559 - 568
(2020/06/04)
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- Discovery and Development of S6821 and S7958 as Potent TAS2R8 Antagonists
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In humans, bitter taste is mediated by 25 TAS2Rs. Many compounds, including certain active pharmaceutical ingredients, excipients, and nutraceuticals, impart their bitter taste (or in part) through TAS2R8 activation. However, effective TAS2R8 blockers that can either suppress or reduce the bitterness of these compounds have not been described. We are hereby reporting a series of novel 3-(pyrazol-4-yl) imidazolidine-2,4-diones as potent and selective TAS2R8 antagonists. In human sensory tests, S6821 and S7958, two of the most potent analogues from the series, demonstrated efficacy in blocking TAS2R8-mediated bitterness and were selected for development. Following data evaluation by expert panels of a number of national and multinational regulatory bodies, including the US, the EU, and Japan, S6821 and S7958 were approved as safe under conditions of intended use as bitter taste blockers.
- Fotsing, Joseph R.,Darmohusodo, Vincent,Patron, Andrew P.,Ching, Brett W.,Brady, Thomas,Arellano, Melissa,Chen, Qing,Davis, Timothy J.,Liu, Hanghui,Servant, Guy,Zhang, Lan,Williams, Mark,Saganich, Michael,Ditschun, Tanya,Tachdjian, Catherine,Karanewsky, Donald S.
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p. 4957 - 4977
(2020/05/25)
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- Design, synthesis, and evaluation of curcumin derivatives as Nrf2 activators and cytoprotectors against oxidative death
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Activation of nuclear factor erythroid-2-related factor 2 (Nrf2) has been proven to be an effective means to prevent the development of cancer, and natural curcumin stands out as a potent Nrf2 activator and cancer chemopreventive agent. In this study, we synthesized a series of curcumin analogs by introducing the geminal dimethyl substituents on the active methylene group to find more potent Nrf2 activators and cytoprotectors against oxidative death. The geminally dimethylated and catechol-type curcumin analog (compound 3) was identified as a promising lead molecule in terms of its increased stability and cytoprotective activity against the tert-butyl hydroperoxide (t-BHP)-induced death of HepG2 cells. Mechanism studies indicate that its cytoprotective effects are mediated by activating the Nrf2 signaling pathway in the Michael acceptor- and catechol-dependent manners. Additionally, we verified by using copper and iron ion chelators that the two metal ion-mediated oxidations of compound 3 to its corresponding electrophilic o-quinone, contribute significantly to its Nrf2-dependent cytoprotection. This work provides an example of successfully designing natural curcumin-directed Nrf2 activators by a stability-increasing and proelectrophilic strategy.
- Tu, Zhi-Shan,Wang, Qi,Sun, Dan-Dan,Dai, Fang,Zhou, Bo
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- Resveratrol derivative containing fluorine group, and preparation method and application
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The invention belongs to the technical field of medicines and discloses a resveratrol derivative containing a fluorine group, and a preparation method and an application. The resveratrol derivative has the structural characteristics as shown in a general
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Paragraph 0096; 0101; 0102
(2017/09/01)
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- Novel multifunctional dopamine D2/D3receptors agonists with potential neuroprotection and anti-alpha synuclein protein aggregation properties
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Our ongoing drug development endeavor to design compounds for symptomatic and neuroprotective treatment of Parkinson's disease (PD) led us to carry out a structure activity relationship study based on dopamine agonists pramipexole and 5-OHDPAT. Our goal was to incorporate structural elements in these agonists in a way to preserve their agonist activity while producing inhibitory activity against aggregation of α-synuclein protein. In our design we appended various catechol and related phenol derivatives to the parent agonists via different linker lengths. Structural optimization led to development of several potent agonists among which (?)-8a, (?)-14 and (?)-20 exhibited potent neuroprotective properties in a cellular PD model involving neurotoxin 6-OHDA. The lead compounds (?)-8a and (?)-14 were able to modulate aggregation of α-synuclein protein efficiently. Finally, in an in vivo PD animal model, compound (?)-8a exhibited efficacious anti-parkinsonian effect.
- Luo, Dan,Sharma, Horrick,Yedlapudi, Deepthi,Antonio, Tamara,Reith, Maarten E.A.,Dutta, Aloke K.
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p. 5088 - 5102
(2016/10/22)
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- Caffeic acid derivatives in the treatment of leucoderma application (by machine translation)
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The invention provides a coffee acid derivatives, the caffeic acid and derivatives with ester bond with the EGC connect into a prodrug, through the coffee acid and the EGC joint play activity, bioavailability is high, good treatment effect to vitiligo. (by machine translation)
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Paragraph 0052; 0053; 0060; 0061
(2016/10/27)
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- The design, synthesis and biological evaluation of pro-EGCG derivatives as novel anti-vitiligo agents
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With the aim of overcoming the instability and poor membrane permeability of epigallocatechin-3-gallate (EGCG), a series of prodrugs of EGCG and its derivatives (pro-EGCGs) were designed and synthesized, and their protective effect on melanocytes against
- Wang, Siyu,Jin, Rong,Wang, Ruiquan,Hu, Yongzhou,Dong, Xiaowu,Xu, Ai e
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p. 106308 - 106315
(2016/11/23)
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- Synthesis, characterization, and antioxidant activity of Zn2+ and Cu2+ coordinated polyhydroxychalcone complexes
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Four new metal complexes [Cu(ISO)2], [Cu(BUT)2] and [Zn(ISO)2], [Zn(BUT)2] of the polyhydroxychalcones (isoliquiritigenin and butein) are synthesized, structurally characterized and their antioxidant activity is investigated. The formation of the complexes [Cu(ISO)2] and [Zn(ISO)2] is followed by Job’s plot using NMR titration. The resulting compounds are characterized by mass spectrometry, IR spectroscopy, and elemental analysis. Studies on the radical scavenging activity are performed using DPPH as substrate. The results showed that the antioxidant activities of isoliquiritigenin and butein are enhanced after binding to copper or zinc. Graphical abstract: [Figure not available: see fulltext.]
- Sulpizio, Chiara,Müller, Simon T. R.,Zhang, Qi,Brecker, Lothar,Rompel, Annette
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p. 1871 - 1881
(2016/10/22)
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- Toward chelerythrine optimization: Analogues designed by molecular simplification exhibit selective growth inhibition in non-small-cell lung cancer cells
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A series of novel chelerythrine analogues was designed and synthesized. Antitumor activity was evaluated against A549, NCI-H1299, NCI-H292, and NCI-H460 non-small-cell lung cancer (NSCLC) cell lines in vitro. The selectivity of the most active analogues a
- Yang, Rosania,Tavares, Maurício T.,Teixeira, Sarah F.,Azevedo, Ricardo A.,Pietro, Diego,Fernandes, Thais B.,Ferreira, Adilson K.,Trossini, Gustavo H.G.,Barbuto, José A.M.,Parise-Filho, Roberto
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p. 4600 - 4610
(2016/09/13)
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- A PROCESS FOR THE PREPARATION PUERARIAFURAN
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The present invention relates to a chemical method for producing puerariafuran, which is separated from Pueraria thunbergiana having various physiological activities, and derivatives thereof. The chemical method for producing puerariafuran and derivatives
- -
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Paragraph 0049; 0085; 0091-0092
(2016/12/22)
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- First synthesis and anti-inflammatory effects of puerariafuran and its derivatives
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The total synthesis of puerariafuran and its derivatives was achieved for the first time by the direct reaction between substituted α-bromoacetophenones and resorcinol. The reaction was mediated by neutral alumina and was fully regio-controlled. Subsequen
- Yoon, Hyun-Ho,Kim, Jin-Kyung,Jun, Jong-Gab
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p. 571 - 577
(2015/05/05)
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- Biomimetic Total Synthesis of Santalin Y
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A biomimetic total synthesis of santalin Y, a structurally complex but racemic natural product, is described. The key step is proposed to be a (3+2) cycloaddition of a benzylstyrene to a "vinylogous oxidopyrylium", which is followed by an intramolecular F
- Strych, Sebastian,Journot, Guillaume,Pemberton, Ryan P.,Wang, Selina C.,Tantillo, Dean J.,Trauner, Dirk
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supporting information
p. 5079 - 5083
(2015/04/27)
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- NEUROPROTECTIVE AGENTS FOR TREATMENT OF NEURODEGENERATIVE DISEASES
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A compound having formula I is useful for treating a neurodegenerative disease: I, R1 is an C1-12 organyl group; is a C1-12 heterocyclic ring system containing 5 to 12 ring atoms and up to three heteroatoms individually selected from the group consisting of N, O, S, and Se; R2 are C1-12 organyl groups; R7, R8 are each independently, hydrogen (H), hydroxyl, oxo (i.e., carbonyl), C1-8 alkyl, C1-8 alkoxyl, C2-8 alkenyl, C2-10 alkynyl, C5-7 cycloalkyl, C5-7 cycloalkenyl, halo, C1-4 aldehyde, or -NR4q where R4 is H, C1-8 alkyl, C2-8 alkenyl, C4-8 cycloalkyl, C4-8 cycloalkenyl, or C6-10 aryl; o is 0, 1, 2, 3, or 4; A is a C6-12 aryl group, C5-12 heteroaryl group, or an optionally substituted 3-hydroxypyridin- 4(1H)-one; p is an integer from 1 to 6; and Zm is absent or a divalent linking moiety; and m is an integer representing the number of time Z is repeated.
- -
-
Paragraph 000130
(2014/06/23)
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- Synthesis and structure-activity relationship study of substituted caffeate esters as antinociceptive agents modulating the TREK-1 channel
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The TWIK-related K+ channel, TREK-1, has recently emerged as an attractive therapeutic target for the development of a novel class of analgesic drugs. It has been reported that TREK-1 -/- mice were more sensitive than wild-type mice to painful stimuli, suggesting that activation of TREK-1 could result in pain inhibition. Here we report the synthesis of a series of substituted caffeate esters (12a-u) based on the hit compound CDC 2 (cinnamyl 3,4-dihydroxyl-α-cyanocinnamate). These analogs were evaluated for their ability to modulate TREK-1 channel by electrophysiology and for their in vivo antinociceptive activity (acetic acid induced-writhing assay) leading to the identification a series of novel molecules able to activate TREK-1 and displaying potent analgesic activity in vivo.
- Rodrigues, Nuno,Bennis, Khalil,Vivier, Delphine,Pereira, Vanessa,Chatelain, Franck C.,Chapuy, Eric,Deokar, Hemantkumar,Busserolles, Jér?me,Lesage, Florian,Eschalier, Alain,Ducki, Sylvie
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supporting information
p. 391 - 402
(2014/03/21)
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- Biomimetic synthesis of santalin a,b and santarubin a,b, the major colorants of red sandalwood
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Better late than never! Almost 200 years after Pelletier's pioneering studies on the chemical constituents of red sandalwood, the major santalins and santarubins have been synthesized. This efficient approach integrates a Knochel isoflavonoid synthesis with Friedel-Crafts allylations or olefin metatheses, and a final biomimetic reaction cascade that furnishes the venerable benzoxanthenone dyes in a single operation (see scheme). Copyright
- Strych, Sebastian,Trauner, Dirk
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supporting information
p. 9509 - 9512
(2013/09/23)
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- Molecular docking studies of (1E,3E,5E )-1,6-bis(substituted phenyl)-hexa-1,3,5-triene and 1,4-bis(substituted trans-styryl)benzene analogs as novel tyrosinase inhibitors
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We simulated the docking of the tertiary structure of mushroom tyrosinase with our compounds. From the structure-tyrosinase inhibitory activity relationship, it is notable that compounds 4, 8 and 11 showed similar or better activity rates than kojic acid which was used as a positive control. Compounds 17, 21, and 23 among benzene analogs that possess the same substituent showed significantly lower tyrosinase inhibitory effects. Therefore, we have confirmed that among the compounds showing better tyrosinase inhibitory effects than kojic acid, the compounds with triene analogs have better tyrosinase inhibitory effect than the compounds with benzene analogs. Docking simulation suggested the mechanism of compounds by several key residues which had possible hydrogen bonding interactions. The pharmacophore model underlined the features of active compounds, 4,4′-((1E,3E,5E )-hexa-1,3,5-triene-1,6-diyl)diphenol, 5,5′-((1E,3E,5E )-hexa-1,3,5-triene-1,6-diyl)bis(2-methoxy-phenol), and 5,5′-((1 E,3E,5E )-hexa-1,3,5-triene-1,6-diyl)dibenzene-1,3-diol among triene derivatives which had several hydrogen bond groups on both terminal rings. The soundness of the docking results and the agreement with the pharmacophores suggest that it can be conveniently exploited to design inhibitors with an improved affinity for tyrosinase.
- Ha, Young Mi,Lee, Hye Jin,Park, Daeui,Jeong, Hyoung Oh,Park, Ji Young,Park, Yun Jung,Lee, Kyung Jin,Lee, Ji Yeon,Moon, Hyung Ryong,Chung, Hae Young
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- Regiocomplementary synthesis of fluorinated bridged biphenyls
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Complementary synthesis of two kinds of fluorinated bridged biphenyls has been developed by the combination of oxidative carbon-carbon bond formation and deoxyfluorination. Georg Thieme Verlag Stuttgart · New York.
- Nemoto, Hiroyuki,Takubo, Keita,Shimizu, Kazuki,Akai, Shuji
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supporting information; experimental part
p. 1978 - 1984
(2012/10/07)
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- Ambivalent adhesives: Combining biomimetic cross-linking with antiadhesive Oligo(ethylene glycol)
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Oligo(ethylene glycol) (OEG) and poly(ethylene glycol) (PEG) exhibit several desirable properties including biocompatibility and resistance to fouling by protein adsorption. Still needed are surgical glues and orthopedic cements, among several other mater
- Matos-Perez, Cristina R.,Wilker, Jonathan J.
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p. 6634 - 6639
(2012/10/30)
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- HYDROXYL GROUP-CONTAINING METHYLSTYRENE AND POLYMERS INCORPORATING SAME
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Vulcanizates with desirable properties can be obtained from compounds incorporating polymers that include hydroxyl group-containing α-methylstyrene functionalities. The functionalities can be incorporated by using any or all of appropriate initiators, mon
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Page/Page column 21
(2011/12/14)
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- ANIONIC POLYMERIZATION INITIATORS AND PROCESSES
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A group of compounds defined by the general formula (I) can be used to anionically initiate polymerization of unsaturated monomers. In the formula, M is an alkali metal atom, R1 is an aryl group having at least one OR2 substituent gr
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Page/Page column 16
(2011/02/24)
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- HYDROXYARYL FUNCTIONALIZED POLYMERS
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Vulcanizates with desirable properties can be obtained from compounds incorporating polymers that include hydroxyl group-containing aryl functionalities. The functionalities can be incorporated by using any or all of appropriate initiators, monomers and o
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- Enantioselective, chemoenzymatic synthesis, and absolute configuration of the antioxidant (-)-gloeosporiol
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The natural antioxidant (-)-gloeosporiol, isolated as a peracetylated derivative from a culture of the fungus Colletotrichum gloeosporioides, has been enantioselectively prepared from 3,4-dihydroxybenzaldehyde by means of a chemoenzymatic synthesis. The k
- Mancilla, Gabriela,Femenía-Ríos,Grande, Manuel,Hernández-Galán,Macías-Sánchez,Collado
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experimental part
p. 8068 - 8075
(2010/11/02)
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- Synthesis of a series of caffeic acid phenethyl amide (CAPA) fluorinated derivatives: Comparison of cytoprotective effects to caffeic acid phenethyl ester (CAPE)
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A series of catechol ring-fluorinated derivatives of caffeic acid phenethyl amide (CAPA) were synthesized and screened for cytoprotective activity against H2O2 induced oxidative stress in human umbilical vein endothelial cells (HUVEC
- Yang, John,Marriner, Gwendolyn A.,Wang, Xinyu,Bowman, Phillip D.,Kerwin, Sean M.,Stavchansky, Salomon
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experimental part
p. 5032 - 5038
(2010/09/10)
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- A novel competitive class of α-glucosidase inhibitors: (E)-1-phenyl-3-(4-styrylphenyl)urea derivatives
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Competitive glycosidase inhibitors are generally sugar mimics that are costly and tedious to obtain because they require challenging and elongated chemical synthesis, which must be stereo-and regiocontrolled. Here, we show that readily accessible achiral
- Kim, Jun Young,Lee, Ji Won,Kim, Young Soo,Lee, Yuno,Ryu, Young Bae,Kim, Songmi,Ryu, Hyung Won,Curtis-Long, Marcus J.,Lee, Keun Woo,Lee, Woo Song,Park, Ki Hun
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body text
p. 2125 - 2131
(2011/12/05)
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- Total synthesis of artochamins F, H, I, and J through cascade reactions
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A concise and efficient cascade-based total synthesis of artochamins F, H, I, and J is described. The potential biogenetic connection between artochamin F, or a derivative thereof, and artochamins H, I, and J, through an unusual formal [2+2] cycloaddition
- Nicolaou,Lister, Troy,Denton, Ross M.,Gelin, Christine F.
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p. 4736 - 4757
(2008/09/21)
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- COMPOSITION AND METHOD FOR CANCER TREATMENT AND PREVENTION
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Compounds, compositions, methods and kits are provided for treating, reducing the risk of, or preventing diseases and/or conditions, such as diseases associated with angiogenesis and/or abnormal cell proliferation, such as cancer. Compounds of the present
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Page/Page column 4; 18-19; Sheet 3/25; 4/25
(2008/12/04)
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- Design, synthesis, and discovery of stilbene derivatives based on lithospermic acid B as potent protein tyrosine phosphatase 1B inhibitors
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Dihydroxy stilbene derivatives were designed based on lithospermic acid B and were prepared from 4-(chloromethyl)benzoic acid. The inhibitory activities of the novel compounds against protein tyrosine phosphatase 1B (PTP1B) were evaluated. 3,4-Dihydroxy stilbene carbonyl compounds (7, 11b, 27b) inhibited PTP1B with IC50 values comparable to molybdate, while the conjugation-extended compound (15b) showed inhibition 3-fold better than preclinical RK682. The introduction of electron withdrawing groups or amides into the second phenyl ring, or extension of the conjugation into the stilbene molecule may increase stability of the generated radicals.
- Jung, Mankil,Lee, Yongnam,Park, Moonsoo,Kim, Hanjo,Kim, Heekyeong,Lim, Eunyoung,Tak, Jungae,Sim, Minjoo,Lee, Dongeun,Park, Namsoo,Oh, Won Keun,Hur, Kyu Yeon,Kang, Eun Seok,Lee, Hyun-Chul
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p. 4481 - 4486
(2008/02/13)
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- Biomimetic preparation of the racemic modifications of the stilbenolignan aiphanol and three congeners
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A chromatographically separable mixture of the racemic modification, (±)-1, of the stilbenolignan (-)-aiphanol and congeners (±)-2-4 has been generated by a silver(I)-mediated and potentially biomimetic oxidative coupling of piceatannol (5) with sinapic a
- Chand, Satish,Banwell, Martin G.
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p. 243 - 250
(2008/02/11)
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- The kulinkovich reaction in the synthesis of constrained N,N-dialkyl neurotransmitter analogues
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An intermolecular Ti(IV)-mediated cyclopropanation reaction has been used to synthesize substituted 2-phenylcyclopropylamines and constrained analogues of the neurotransmitters histamine and tryptamine. Many hydroxy- and methoxy-substituted phenylcyclopropylamines are known to inhibit monoamine oxidase and have been shown to mimic hallucinogens. These compounds were made in 1 to 5 steps from readily available starting materials.
- Faler, Catherine A.,Joullie, Madeleine M.
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p. 1987 - 1990
(2008/02/02)
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- Cascade reactions involving formal [2+2] thermal cycloadditions: Total synthesis of artochamins F, H, I, and J
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(Chemical Equation Presented) State of the artochamins: Total syntheses of artochamins F (1), H (2), I (3), and J (4; see scheme) have been achieved through a flexible and expedient strategy that features a cascade sequence involving two concurrent [3,3]
- Nicolaou,Lister, Troy,Denton, Ross M.,Gelin, Christine F.
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p. 7501 - 7505
(2008/09/17)
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- Regiocontrolled intramolecular cyclizations of carboxylic acids to carbon-carbon triple bonds promoted by acid or base catalyst
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We systematically investigated, for the first time, the relationship between regioselectivity and acid/base effects in the cyclization reactions between carboxylic acids and carbon-carbon triple bonds. We found novel acid- and base-promoted cyclizations to selectively give isocoumarin or pyran-2(2H)-one and phthalide or furan-2(5H)-one skeletons, respectively, and established a catalytic version of regioselective heterocyclic ring synthesis. Density functional theory calculations and application to a short route to thunberginol A were also described.
- Uchiyama, Masanobu,Ozawa, Hiroki,Takuma, Kazuya,Matsumoto, Yotaro,Yonehara, Mitsuhiro,Hiroya, Kou,Sakamoto, Takao
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p. 5517 - 5520
(2007/10/03)
-
- Synthesis and free radical scavenging activity of a novel metabolite from the fungus Colletotrichum gloeosporioides
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A novel metabolite (-)-1 was isolated as its peracetylated derivative, (-)-2-(3′,4′-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran (2), from a strain of the phytopathogenic fungus Colletotrichum gloeosporioides CECT 20122. The synthesis of (-)-1 was carrie
- Femenia-Rios, Marienca,Garcia-Pajon, Carlos M.,Hernandez-Galan, Rosario,Macias-Sanchez, Antonio J.,Collado, Isidro G.
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p. 5836 - 5839
(2007/10/03)
-
- Vitamin D analogues
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The invention concerns novel bi-aromatic compounds having the formula: which are analogs of vitamin D, the process of preparing them, as well as their use in pharmaceutical compositions in human or veterinary medicine, particularly in dermatology, cancer treatment, treatment of auto-immune diseases, and in organ or tissue transplants. Cosmetic compositions and methods of use are also included.
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Page column 39
(2010/02/05)
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- The total synthesis of an aurone isolated from Uvaria hamiltonii: Aurones and flavones as anticancer agents
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The naturally occurring aurone 1, isolated from Uvaria hamiltonii, and a series of aurones analogues based structurally on known tubulin binding agents were prepared and evaluated for anticancer activity. Aurone 20 was the most active (IC50 K562 50 nM) and caused significant G2/M cell-cycle arrest.
- Lawrence, Nicholas J.,Rennison, David,McGown, Alan T.,Hadfield, John A.
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p. 3759 - 3763
(2007/10/03)
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- Catalytic asymmetric synthesis of arbutamine
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An efficient catalytic asymmetric synthesis of (R)-arbutamine has been achieved using a catalytic asymmetric nitroaldol reaction promoted by a heterobimetallic multifunctional asymmetric catalyst as a key step.
- Takaoka, Eiji,Yoshikawa, Naoki,Yamada, Yoichi M.A.,Sasai, Hiroaki,Shibasaki, Masakatsu
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p. 157 - 163
(2007/10/03)
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- Synthesis of (±)-Rosmarinic Acid Methylester
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Regioselective cleavage of the glycidic ester 3 by BF3/ether to pyruvic acid ester 4 followed by NaBH4 reduction affords the lactic acid derivative 5a which in turn can be acylated by caffeoyl chloride 8c to yield the O-protected rosmarinic acid ester 9a. Alternatively, 9a can be prepared by acylation of 5a with diethylphosphono acetyl chloride (6c) thus generating the Wadsworth-Emmons reagent 7a which is subsequently reacted with the aldehyde 1a. The analogous reaction using the silyl protected educts 7d and 1b failed to give 9d. Finally, 9a is debenzylated by BCl3 furnishing the title compound 10a in fair total yield.
- Reimann,Maas,Pflug
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p. 995 - 1008
(2007/10/03)
-
- Synthesis of 3-Acyl- and 3-Carbamoylflavones
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Routes to 3-acyl-, 3-carboxamido- and polyhydroxylated flavones have been devised by application of isoxazole methodology and Heck-Stille couplings.Reductive ring opening of 3-alkoxyisoxazoles gives β-keto carboxamides in contrast with 3-alkoxy-2-isoxazolines, which give β-hydroxy esters.
- Ellemose, Steen,Kure, Niels,Torsell, Kurt B. G.
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p. 524 - 529
(2007/10/02)
-
- Synthesis of tunichromes mm-1 and mm-2, blood pigments of the iron.Assimilating tunicate, Molgula manhattensis
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Unstable poly-phenolic pigments, tunichromes Mm-1 and Mm-2, blood pigments of the iron-assimilating tunicate, Molgula manhattensis, have been synthesized by a modified versatile route.
- Kim, Dooseop,Li, Yunyi,Horenstein, Benjamin A.,Nskanishi, Koji
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p. 7119 - 7122
(2007/10/02)
-
- SYNTHESIS OF ROOPEROL
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Rooperol, a phenolic compound bearing the pentenyne moiety, has been synthesized from simple starting materials via a nine step synthesis.A crucial step in the synthesis involves protection of the phenolic groups as the tertbutyldimethylsilyl ether deriva
- Potgieter, Maudene,Wenteler, George L.,Drewes, Siegfried E.
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p. 1101 - 1104
(2007/10/02)
-
- SYNTHESIS OF NATURAL POLYHYDROXYSTILBENES
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A synthesis of several natural polyhydroxystilbenes is described.
- Cardona, Luz,Fernandez, Isabel,Garcia, Begona,Pedro, Jose R.
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p. 2725 - 2730
(2007/10/02)
-