- Unravelling the allosteric targeting of phgdh at the act-binding domain with a photoactivatable diazirine probe and mass spectrometry experiments
-
The serine biosynthetic pathway is a key element contributing to tumor proliferation. In recent years, targeting of phosphoglycerate dehydrogenase (PHGDH), the first enzyme of this pathway, intensified and revealed to be a promising strategy to develop ne
- Dochain, Simon,Feron, Olivier,Frédérick, Rapha?l,Ravez, Séverine,Spillier, Quentin,Thabault, Léopold,Vertommen, Didier
-
supporting information
(2021/06/28)
-
- GEM-DISUBSTITUTED HETEROCYCLIC COMPOUNDS AND THEIR USE AS IDH INHIBITORS
-
The present invention relates to certain gem-disubstituted heterocyclic compounds, which modulate the activity of Isocitrate Dehydrogenase (IDH). The compounds of this invention are therefore useful in treating diseases caused by mutated IDH1 and/or mutat
- -
-
Page/Page column 63
(2021/05/15)
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- Stereoselective Bioreduction of Telluro-Acetophenones to Optically Active Hydroxy Tellurides
-
Organotellurium compounds exhibit a broad range of useful applications in organic synthesis, materials science and medicinal chemistry fields. Despite their increasing applicability, the synthesis of enantiomerically pure organotellurium compounds remains nowadays scarcely reported in the literature. Herein, the chemical synthesis and biocatalyzed reductions of a set of telluro-acetophenones using both (R) and (S)-selective alcohol dehydrogenases (ADHs) is described for the first time, obtaining enantiomerically enriched hydroxy tellurides with excellent selectivities under very mild reaction conditions. On the one hand, enantiopure para-substituted (S)-hydroxy tellurides were obtained using the Ras-ADH (77–95 % conversion) and ADH-A (52–75 %), the ADH-A leading to the enantiopure (S)-hydroxy tellurides substituted at the meta-position (69–75 %). On the other hand, the evo-1.1.200 displayed high selectivity towards the preparation of optically alcohols with substitutions at the para-position of the aromatic ring (60–68 % conversion and 92–97 % ee), while the Lb-ADH led to the best results when reducing bulky ketones at the meta-position (79–82% conversion and 88–99 % ee).
- Bandeira, Pamela Taisline,Gotor-Fernández, Vicente,Piovan, Leandro
-
-
- Tetrahedral Silicon-Centered Dibenzoylmethanatoboron Difluorides: Synthesis, Crystal Structure, and Photophysical Behavior in Solution and the Solid State
-
Four tetrahedral silicon-centered derivatives of dibenzoylmethanatoboron difluoride (DBMBF2) were synthesized and characterized. Their structural and optical features both in solution and the solid state were investigated by using X-ray crystal
- Kononevich, Yuriy N.,Temnikov, Maxim N.,Korlyukov, Alexander A.,Volodin, Alexander D.,Dorovatovskii, Pavel V.,Sazhnikov, Viacheslav A.,Safonov, Andrey A.,Ionov, Dmitriy S.,Ivanov, Anatoly A.,Surin, Nikolay M.,Svidchenko, Evgeniya A.,Muzafarov, Aziz M.
-
p. 1111 - 1119
(2020/04/07)
-
- Chemo- and Stereoselective Synthesis of Fluorinated Amino Alcohols through One-pot Reactions using Alcohol Dehydrogenases and Amine Transaminases
-
A series of amino alcohols have been prepared in a chemo-, diastereo- and enantioselective fashion starting from the corresponding (het)aryl diketones, avoiding tedious chemical protection and deprotection steps. Different alcohol dehydrogenases have been
- González-Martínez, Daniel,Gotor, Vicente,Gotor-Fernández, Vicente
-
supporting information
p. 5398 - 5410
(2020/10/06)
-
- Synthesis, Antioxidant Activity and Cytotoxicity of N-Functionalized Organotellurides
-
The use of antioxidants is the most effective means to protect the organism against cellular damage caused by oxidative stress. In this context, organotellurides have been described as promising antioxidant agents for decades. Herein, a series of N-functionalized organotellurium compounds has been tested as antioxidant and presented remarkable activities by three different in vitro chemical assays. They were able to reduce DPPH[rad] radical with IC50 values ranging from 5.08 to 19.20 μg mL?1, and some of them also reduced ABTS[rad]+ radical and TPTZ-Fe3+ complex in ABTS[rad]+ and FRAP assays, respectively. Initial structure-activity relationship discloses that the nature of N-substituent strongly influenced both activity and cytotoxicity of the studied compounds. Furthermore, radical scavenging activities of N-functionalized organotellurides have been compared with those of their selenilated congeners, demonstrating that the presence of tellurium atom has an essential role in antioxidant activity.
- Bandeira, Pamela T.,Dalmolin, Mara C.,de Oliveira, Mariana M.,Nunes, Karine C.,Garcia, Francielle P.,Nakamura, Celso V.,de Oliveira, Alfredo R.M.,Piovan, Leandro
-
supporting information
p. 410 - 415
(2019/01/04)
-
- Molybdenum-catalyzed diastereoselective anti-dihydroxylation of secondary allylic alcohols
-
In this protocol, we report a Mo-catalyzed anti-dihydroxylation of secondary allylic alcohols, providing a general method for the preparation of 1,2,3-triols bearing up to three continuous stereocenters with excellent diastereocontrol. The mechanistic studies reveal that this dihydroxylation reaction consists of two steps and up to excellent diastereomeric ratios of the final triol products can be achieved due to the high level of both diastereocontrol in the initial epoxidation and regiocontrol in the following hydrolysis in situ.
- Su, Shixia,Wang, Chuan
-
supporting information
p. 2436 - 2440
(2019/03/29)
-
- Diacetal Ditellurides as Highly Active and Selective Antiparasitic Agents toward Leishmania amazonensis
-
Leishmaniasis is a neglected tropical disease and a public health concern in at least 98 countries, affecting mainly the poorest populations. Pharmaceuticals and chemotherapies available for leishmaniasis treatment have several limitations, which clearly justify the efforts to find new potential antileishmanial drugs. In this context, antiprotozoal activities toward different Leishmania species have been reported for hypervalent tellurium compounds, which motivated us to investigate, for the first time, the leishmanicidal properties of some nonhypervalent diaryl ditellurides. Thus, this work describes in vitro activity against Leishmania amazonensis and the cytotoxicities of diaryl ditellurides. Ditelluride LQ7 revealed a strong leishmanicidal activity on promastigotes and amastigotes at submicromolar levels (IC50 = 0.9 ± 0.1 and 0.5 ± 0.1 μmol L-1, respectively) and presented selectivity indexes greater than those of reference drug miltefosine. This preliminary study suggests that diaryl ditellurides may be promising scaffolds for the development of new agents for leishmaniasis treatment.
- Bandeira, Pamela T.,Souza, Jo?o Pedro A.,Scariot, Débora B.,Garcia, Francielle P.,Nakamura, Celso V.,De Oliveira, Alfredo R. M.,Piovan, Leandro
-
supporting information
p. 806 - 810
(2019/05/06)
-
- Achieving Enantioselectivity in Difficult Cyclohexa-1,3-diene Diels-Alder Reactions with Sulfur-Stabilized Silicon Cations as Lewis Acid Catalysts
-
A novel cationic silicon-sulfur Lewis pair with a chiral H8-binaphthyl backbone is reported. It catalyzes otherwise sluggish Diels-Alder reactions of cyclohexa-1,3-diene and chalcone derivatives in good yields and decent enantioselectivities (up to 81% ee). The enantioinduction is highest with a [1,1′-biphenyl]-4-yl substituent at the carbonyl carbon atom. This moiety can be later converted into a carboxyl group by Baeyer-Villiger oxidation. The same oxidant also epoxidizes the double bond in the cycloadduct, and the epoxide engages in a lactonization with the carboxylic acid. Synthetically interesting hexahydro-3,6-methanobenzofuran-2(3H)-one skeletons are obtained in one pot.
- Shaykhutdinova, Polina,Oestreich, Martin
-
supporting information
p. 7029 - 7033
(2018/11/24)
-
- Straightforward microwave-assisted synthesis of organochalcogen amines by reductive amination
-
Organoselenium and organotellurium amines have been shown to present a broad range of interesting properties for both synthetic and biological applications. Despite the current interest in this class of compounds, only few methods to access organochalcogen amines are described in literature, most which involve restrictive conditions associated with displacement reaction, metal-assisted reactions or enzymatic approach. In general, these methods produce organochalcogen amines in poor yields, by long reactions that require protective groups. In this regard, a set of aryl chalcogen (Se, Te) amines were prepared by reductive amination employing a microwave-assisted one-pot protocol. This approach offered a convenient and versatile method to synthesize primary and secondary organochalcogen amines with significantly short time reactions (5–10 min) and satisfactory yields (40–89%).
- Dalmolin, Mara C.,Bandeira, Pamela T.,Ferri, Matheus S.,de Oliveira, Alfredo R.M.,Piovan, Leandro
-
-
- Carbonyl group protection method
-
The invention belongs to the technical field of methods for protection of groups in organic chemistry reaction, and particularly discloses a carbonyl group protection method. The response equation is shown in the description, wherein R1 and R2 are alkyl,
- -
-
Paragraph 0067; 0068
(2017/02/09)
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- Oxadiazole-substituted naphtho[2,3-b]thiophene-4,9-diones as potent inhibitors of keratinocyte hyperproliferation. Structure?activity relationships of the tricyclic quinone skeleton and the oxadiazole substituent
-
Novel analogues of oxadiazole-substituted naphtho[2,3-b]thiophene-4,9-diones were synthesized in which the tricyclic quinone skeleton was systematically replaced with simpler moieties, such as structures with fewer rings and open-chain forms, while the oxadiazole ring was maintained. In addition, variants of the original 1,2,4-oxadiazole ring were explored. Overall, the complete three-ring quinone was essential for potent suppression of human keratinocyte hyperproliferation, whereas analogous anthraquinones were inactive. Also, the oxadiazole ring per se was not sufficient to elicit activity. However, rearrangement of the heteroatom positions in the oxadiazole ring resulted in highly potent inhibitors with compound 24b being the most potent analogue of this series showing an IC50 in the nanomolar range. Furthermore, experiments in isolated enzymatic assays as well as in the keratinocyte-based hyperproliferation assay did not support a major role of redox cycling in the mode of action of the compounds.
- Basoglu, Atila,Dirkmann, Simone,Zahedi Golpayegani, Nader,Vortherms, Silke,Tentrop, Jan,Nowottnik, Dominica,Prinz, Helge,Fr?hlich, Roland,Müller, Klaus
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supporting information
p. 119 - 132
(2017/04/14)
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- New Fluorescence Domain "excited Multimer" Formed upon Photoexcitation of Continuously Stacked Diaroylmethanatoboron Difluoride Molecules with Fused π-Orbitals in Crystals
-
The crystal-packing structures of seven derivatives of diaroylmethanatoboron difluoride (1 a-gBF2) are characterized by no overlap of the π-conjugated main units of two adjacent molecules (typeI), overlap of the benzene ring π-orbitals of two adjacent molecules (typeII), and overlap of the benzene and dihydrodioxaborinine rings π-orbitals of adjacent molecules (typeIII). The crystal-packing structures govern the fluorescence (FL) properties in the crystalline states. The FL domain that is present in typeI crystals, in which intermolecular orbital interactions are absent, leads to excited monomer-like FL properties. In the case of the typeII crystals, the presence of intermolecular overlap of the benzene rings π-orbitals generates new FL domains, referred to as "excited multimers", which possess allowed S0-S1 electronic transitions and, as a result, similar FL lifetimes at longer wavelengths than the FL of the typeI crystals. Finally, intermolecular overlap of the benzene and dihydrodioxaborinine ring π-orbitals in the typeIII crystals leads to "excited multimer" domains with forbidden S0-S1 electronic transitions and longer FL lifetimes at similar wavelengths as that in typeI crystals.
- Sakai, Atsushi,Ohta, Eisuke,Yoshimoto, Yuichi,Tanaka, Mirai,Matsui, Yasunori,Mizuno, Kazuhiko,Ikeda, Hiroshi
-
supporting information
p. 18128 - 18137
(2015/12/24)
-
- Synthesis of polyfunctional secondary amines by the addition of functionalized zinc reagents to nitrosoarenes
-
Addition of functionalized aryl, heteroaryl or adamantyl zinc reagents to various nitroso-arenes in the presence of magnesium salts and LiCl in THF produces after a reductive work-up with FeCl2 and NaBH4 in ethanol the corresponding polyfunctional secondary amines in high yields. This journal is
- Dhayalan, Vasudevan,S?mann, Christoph,Knochel, Paul
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p. 3239 - 3242
(2015/06/01)
-
- Anti-Markovnikov Hydroamination of Homoallylic Amines
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The development of an anti-Markovnikov-selective hydroamination of unactivated alkenes is a significant challenge in organometallic chemistry. Herein, we present the rhodium-catalyzed anti-Markovnikov-selective hydroamination of homoallylic amines. The proximal Lewis basic amine serves to promote reactivity and enforce regioselectivity through the formation of the favored metallacycle, thus over-riding the inherent reactivity of the alkene. The scope of both the amine nucleophiles and homoallylic amines that participate in the reaction is demonstrated.
- Ensign, Seth C.,Vanable, Evan P.,Kortman, Gregory D.,Weir, Lee J.,Hull, Kami L.
-
supporting information
p. 13748 - 13751
(2016/01/15)
-
- Asymmetric hydrogenation of α,β-unsaturated nitriles with base-activated iridium N,P ligand complexes
-
Although many chiral catalysts are known that allow highly enantioselective hydrogenation of a wide range of olefins, no suitable catalysts for the asymmetric hydrogenation of α,β-unsaturated nitriles have been reported so far. We have found that Ir N,P ligand complexes, which under normal conditions do not show any reactivity towards α,β-unsaturated nitriles, become highly active catalysts upon addition of N,N- diisopropylethylamine. The base-activated catalysts enable conjugate reduction of α,β-unsaturated nitriles with H2 at low catalyst loadings, affording the corresponding saturated nitriles with high conversion and excellent enantioselectivity. In contrast, alkenes lacking a conjugated cyano group do not react under these conditions, making it possible to selectively reduce the conjugated C=C bond of an α,β-unsaturated nitrile, while leaving other types of C=C bonds in the molecule intact.
- Mueller, Marc-Andre,Pfaltz, Andreas
-
supporting information
p. 8668 - 8671
(2014/08/18)
-
- Development of novel silicon-containing inverse agonists of retinoic acid receptor-related orphan receptors
-
Retinoic acid receptor (RAR)-related orphan receptors (RORs) regulate a variety of physiological processes, including hepatic gluconeogenesis, lipid metabolism, circadian rhythm and immune function. The RAR agonist: all-trans retinoic acid was reported to be an RORβ inverse agonist, but no information is available regarding ROR activity of its synthetic analogue Am580. Therefore, we screened Am580 and some related tetramethyltetrahydronaphthalene derivatives and carried out structural development studies, including substitution of carbon atoms with silicon, with the aim of creating a potent ROR transcriptional inhibitor. The phenyl amide disila compound 22 showed the most potent ROR-inhibitory activity among the compounds examined. Its activity towards RORα, RORβ and RORγ was increased compared to that of Am580. The IC50 values for RORα, RORβ and RORγ are 1.3, >10 and 4.5 μM, respectively.
- Toyama, Hirozumi,Nakamura, Masaharu,Nakamura, Masahiko,Matsumoto, Yotaro,Nakagomi, Madoka,Hashimoto, Yuichi
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p. 1948 - 1959
(2014/03/21)
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- Directing-group-assisted copper-catalyzed olefinic trifluoromethylation of electron-deficient alkenes
-
Assistance provided: The directing group in the title reaction not only activates the substrates but also allows the stereospecific formation of cis-trifluoromethylated products. The reaction is operationally simple and tolerates a wide variety of functional groups, thus providing an efficient method for the stereoselective synthesis of β-CF3-functionalized acrylamide derivatives. Copyright
- Feng, Chao,Loh, Teck-Peng
-
supporting information
p. 122414 - 122417
(2013/12/04)
-
- Triphenylbutanamines: Kinesin spindle protein inhibitors with in vivo antitumor activity
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The human mitotic kinesin Eg5 represents a novel mitotic spindle target for cancer chemotherapy. We previously identified S-trityl-l-cysteine (STLC) and related analogues as selective potent inhibitors of Eg5. We herein report on the development of a series of 4,4,4-triphenylbutan-1-amine inhibitors derived from the STLC scaffold. This new generation systematically improves on potency: the most potent C-trityl analogues exhibit Kiapp ≥ 10 nM and GI50 ≈ 50 nM, comparable to results from the phase II clinical benchmark ispinesib. Crystallographic studies reveal that they adopt the same overall binding configuration as S-trityl analogues at an allosteric site formed by loop L5 of Eg5. Evaluation of their druglike properties reveals favorable profiles for future development and, in the clinical candidate ispinesib, moderate hERG and CYP inhibition. One triphenylbutanamine analogue and ispinesib possess very good bioavailability (51% and 45%, respectively), with the former showing in vivo antitumor growth activity in nude mice xenograft studies.
- Wang, Fang,Good, James A. D.,Rath, Oliver,Kaan, Hung Yi Kristal,Sutcliffe, Oliver B.,MacKay, Simon P.,Kozielski, Frank
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supporting information; experimental part
p. 1511 - 1525
(2012/04/10)
-
- Synthesis and evaluation of photoreactive probes to elucidate iodide efflux in thyrocytes
-
Four photoreactive analogues of 3-biphenyl-4′-yl-5,6-dihydroimidazo[2,1-b]thiazole were prepared and evaluated as iodide sequestering agents in sodium iodide symporter-expressing cells. One of these new photoactivatable compounds retained biological activ
- Derbré, Séverine,Lecat-Guillet, Nathalie,Pillon, Florence,Ambroise, Yves
-
scheme or table
p. 825 - 827
(2009/08/07)
-
- Chemo- and enantioselective routes to chiral fluorinated hydroxyketones using ketoreductases
-
Chiral fluorinated hydroxyketones were synthesized with excellent ee (>98%) and yield by a chemo- and stereoselective reduction of prochiral methyl/trifluoromethyl diketones using commercially available ketoreductase enzymes. By using p- and m-trifluoroac
- Grau, Brendan T.,Devine, Paul N.,DiMichele, Lisa N.,Kosjek, Birgit
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p. 4951 - 4954
(2008/03/28)
-
- Reductive cleavage of acetals and ketals with 9-borabicyclo[3.3.1]nonane
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The reductive cleavage of benzaldehyde acetals and acetophenone ketals with the air-stable crystalline 9-borabicyclo[3.3.1]-nonane dimer provides monobenzylated ether derivatives of diols and 1,2-oxygen-transposed β-phenethyl alcohols, respectively. The boron moiety is effectively recovered through simple procedures which involve convenient air-stable reagents and boron byproducts. The process is particularly selective for 1,3-diols giving the more substituted monobenzyl ether derivatives exclusively. With acetophenone ketals both reduction and elimination occur, permitting 9-BBN-H to hydroborate the resulting styrene to produce 1,2-oxygen-transposed β-phenethyl alcohols cleanly. Potential applications of this new process were illustrated with the synthesis of the hallucinogen, mescaline, and the analgesic, ibufenac.
- Soderquist, John A.,Kock, Iveliz,Estrella, Maria E.
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supporting information
p. 1076 - 1079
(2012/12/23)
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- Reduction versus rearrangement of 6,13-dihydro-6,13-diarylpentacene-6,13- diols affording 6,13- and 13,13′-substituted pentacene derivatives
-
Pentacene has excellent semi-conducting properties but its practical use in organic thin film transistors (OTFTs) gives rise to a lot of problems caused by its sensitivity to oxygen and its very low solubility. In order to solve the problems involved in t
- Vets, Nathalie,Smet, Mario,Dehaen, Wim
-
p. 217 - 222
(2007/10/03)
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- Preparation of chiral organochalcogeno-α-methylbenzyl alcohols via biocatalysis. The role of Daucus carota root
-
A series of organochalcogeno acetophenones 3 has been submitted to the action of enzymes from Daucus carota root. Some of the chalcogeno ketones tested afforded the chiral organochalcogeno-α-methylbenzyl alcohols 4 in excellent enantiomeric excesses (>99%), under mild and environmentally friendly conditions. The stereoselectivity of the reduction is in accordance with Prelog's rule. Enzymatic kinetic resolution as alternative process was used to obtain the chiral ortho-organochalcogeno-α-methylbenzyl alcohols in excellent enantiomeric excess (>99%).
- Comasseto, Jo?o V.,Omori, álvaro T.,Porto, André L. M.,Andrade, Leandro H.
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p. 473 - 476
(2007/10/03)
-
- INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME
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Compounds of formula (I) are hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors, and are useful in therapeutic and prophylactic treatment of persons infected with hepatitis C virus.
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Page/Page column 82
(2010/02/07)
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- Traceless solid phase synthesis of 2-substituted pyrimidines using an 'off-the-shelf' chlorogermane-functionalised resin
-
The parallel solid phase synthesis of an 18-member library of 2-substituted pyrimidines is described using a chlorogermane-functionalised resin. The success of the key Pinner-type condensations between a resin-bound enaminone and an array of amidine hydrochlorides highlights the stability of arylgermane linkers (cf. arylsilanes) towards strongly basic/nucleophilic conditions.
- Spivey, Alan C.,Srikaran, Ratnasothy,Diaper, Christopher M.,Turner, David J.
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p. 1638 - 1640
(2007/10/03)
-
- Photo-Arbuzov rearrangements of 1-arylethyl phosphites: Stereochemical studies and the question of radical-pair intermediates
-
The direct UV irradiation of the 1-arylethyl phosphites 7, 8, and 9 was carried out in acetonitrile, benzene, and cyclohexane, as was the triphenylene-sensitized reaction of 9. Dimethyl 1-phenylethyl phosphite, 7, gives the photo-Arbuzov rearrangement pro
- Bhanthumnavin,Bentrude
-
p. 980 - 990
(2007/10/03)
-
- Controlled release of perfumery aldehydes and ketones by Norrish type-II photofragmentation of α-keto esters in undegassed solution
-
Alkyl or aryl α-keto esters of primary or secondary alcohols decompose upon irradiation at 350-370 nm from the intermediate triplet state into aldehydes or ketones in polar, as well as apolar solvents. The use of these keto esters as delivery systems for the controlled release of perfumery aldehydes and ketones was investigated by photoirradiation in the presence of oxygen with a Xe or UV lamp, as well as outdoor sunlight. Systematic GC/MS analysis of the irradiated solutions showed that, under these conditions, the desired Norrish type-II fragmentation of the ester side chain is the predominant reaction pathway in most of the cases. γ-H Abstraction from the alkyl side chain of alkyl keto esters, as well as an intramolecular Paterno- Buchi reaction or epoxidation of the alkene function in different citronellyl α-keto esters were identified as the most important side reactions. Some of the experimental findings have been rationalized on the basis of ab initio and density-functional calculations. (Cyclohexyl)oxoacetates and oxo(phenyl)acetates were found to be the most suitable precursors for the desired perfumery applications.
- Rochat, Sabine,Minardi, Caroline,De Saint Laumer, Jean-Yves,Herrmann, Andreas
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p. 1645 - 1671
(2007/10/03)
-
- Convergence of absorption and fluorescence in cross-conjugated oligomers consisting of chalcone building blocks
-
The absorption and fluorescence spectra of two series of chalcone oligomers (1a-d) and (2a-d) are reported. Due to small or vanishing orbital coefficients (HMO calculation) within the cross-conjugated systems, the bathochromic shifts caused by the extensi
- Meier, Herbert,Aust, Harald,Ickenroth, Dirk,Kolshorn, Heinz
-
p. 529 - 535
(2007/10/03)
-
- Synthesis of novel oximes of 2-aryl-6-methoxy-3,4-dihydronaphthalene and their evaluation as inhibitors of 17α-hydroxylase-C17,20-lyase (P450 17)
-
The synthesis and biological evaluation of oximes of 2-aryl-6-methoxy-3,4-dihydronaphthalene (7a, 7b, 14a, 14b) as nonsteroidal inhibitors of 17α-hydroxylase-C17,20-lyase (P450 17, CYP 17) is described. The target compounds were synthesized and identified
- Zhuang, Yan,Hartmann, Rolf W.
-
-
- Dialkylation of acetophenones and acetophenone ethylene ketals with 1,8-bis(trimethylsilyl)-2,6-octadiene (BISTRO). Semi-empirical SCF studies of α-methoxy-α-methylbenzyl cations
-
Titanium tetrachloride mediated dialkylation of acetophenones or acetophenone ethylene ketals by 1,8-bis(trimethylsilyl)-2,6-octadiene (BISTRO) leads to a mixture of dl and meso 1-alkyl-1-phenyl-2,5-divinylcyclopentane. Better yields are observed with p-b
- Burtin, Guillaume,Pellissier, Helene,Santelli, Maurice
-
p. 2075 - 2086
(2007/10/03)
-
- Enantioselective syntheses of 2-arylpropanoic acid non-steroidal antiinflammatory drugs and related compounds
-
(S)-2-[4′-(2″-Methylpropyl)phenylpropanoic acid (ibuprofen) and (S)-2-(3′-benzoylphenyl)propanoic acid (ketoprofen) have been synthesised in high enantiomeric excess. Control of stereochemistry was achieved by a combination of Sharpless epoxidalion followed by catalytic hydrogenolysis of the introduced benzylic epoxide oxygen bond. Also, the coupling of organic compounds in the presence of palladium with enantiopure 2-(3-iodophenyl)propanoic and 2-(4-iodophenyl)propanoic acids, prepared by the methodology above, is a general method for the synthesis of optically active arylpropanoic acids.
- Hamon, David P.G.,Massy-Westropp, Ralph A.,Newton, Josephine L.
-
p. 12645 - 12660
(2007/10/02)
-
- OXIME DERIVATIVES
-
The invention concerns oxime derivatives of the formula I wherein R4 includes hydrogen, carboxy, carbamoyl, amino, cyano, trifluoromethyl, (1-4C)alkylamino, di(1-4C)alkylamino and (1-4C)alkyl; RS includes hydrogen, (1-4C)alkyl, (3-4C)alkeny1,(3-4C)alkynyl, (2-5C)alkanoyl, halogeno-(2-4-C)alkyl and hydroxy-(2-4C)alky1;Arl is phenylene or a hetercaryl diradical; Al is a direct link to XI, or Al is (1-4C)alkylene; XI is oxy, thio, sulphinyl or sulphonyl; Ar2 is phenylene or a heteroaryl diradical; RI is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkyny1; and R2 and R3 together form a group of the formula -A2. X2-A3- which together with the carbon atom to which A2 and A3 are attached define a ring having 5 or 6 ring atoms, wherein each of A2 and A3 is (1-3C)alkylene and X2 is oxy, thio, sulphinyl, sulphonyl or imino; or a pharmaceutically-acceptable sah thereof; processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.
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-
-
- Ester derivatives and pharmaceutical compositions containing them
-
The invention concerns ester derivatives of the formula I wherein Ar is phenyl, naphthyl, indenyl, indanyl, a 10-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from
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-
-
- Free Energy and Structure Dependence of Intramolecular Triplet Energy Transfer in Organic Model Compounds
-
A series of compounds, each containing a triplet energy donor and an acceptor separated by a rigid spacer, has been designed and synthesized.The 1,4-cyclohexanediyl moiety is employed as the spacer for the series.The rates of intramolecular triplet energy
- Sigman, Michael E.,Closs, Gerhard, L.
-
p. 5012 - 5017
(2007/10/02)
-
- Retinobenzoic Acids. 5. Retinoidal Activities of Compounds Having a Trimethylsilyl or Trimethylgermyl Group(s) in Human Promyelocytic Leukemia Cells HL-60
-
The retinoidal activities of trimethylsilyl or trimethylgermyl-containing retinobenzoic acids are discussed on the basis of differentiation-inducing activity on human promyelocytic leukemia cells HL-60.Compounds with a trimethylsilyl or trimethylgermyl gr
- Yamakawa, Takeru,Kagechika, Hiroyuki,Kawachi, Emiko,Hashimoto, Yuichi,Shudo, Koichi
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p. 1430 - 1437
(2007/10/02)
-
- Rigid rod polymers with stacked electron donor-acceptor side-chains
-
The synthesis of polymers of isocyanides having stacks of donor and acceptor functions in their side-chains is described.These side-chains are based on the betaine compounds used by Dimroth et al. for the construction of their ET scale of solve
- Beijnen, A. J. M. van,Nolte, R. J. M.,Drenth, W.
-
p. 255 - 261
(2007/10/02)
-
- Sterically Hindered Free Radicals, XIII. Wittig's Radical 4-Benzoyltriphenylmethyl and Analogous Mono-4-substituted Trityl Radicals
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The mono-4-R-triphenylmethyl radicals 1, 8b-f, R = tBu, CF3, COMe, COPh, CN, Me, or their quinonoid dimers 4, 9b-f are prepared, most of them for the first time.The degree of dissociation of the latter at 25 deg C is surprisingly high (=/ 33percent, 0.01 M), donors and acceptors being effective here likewise.ESR data are given and discussed.
- Zarkadis, Antonios K.,Neumann, Wilhelm P.,Uzick, Wolfram
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p. 1183 - 1192
(2007/10/02)
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- 1-(P-Alkanoylphenyl) alkanols and derivatives
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1-(p-alkanoylphenyl) alkanols, e.g., 1-(p-acetophenyl)-2,2-dimethylpropanol, are prepared from p-alkanoylphenyl Grignard reagents and alkyl and aryl aldehydes or acyl or aroyl halides and are useful as hypolipidemic and anti-diabetic agents.
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- α-Substituted-4-(2,2-dimethyl-1-hydroxypropyl)benzyl alcohols and esters
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α-substituted-4-(2,2-dimethyl-1-hydroxypropyl) benzyl alcohols and esters, e.g., α-methyl-4-(2,2-dimethyl-1-hydroxypropyl) benzyl alcohol, are prepared from the corresponding 1-(4-alkanoylphenyl) alkanols and derivatives and are useful as hypolipidemic ag
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