- Unusual C7- versus Normal 5′-O-Dimethoxytritylation of 6-Arylpyrrolocytidine Analogs
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Fluorescent deoxynucleosides possessing the modified bases 6-(2-benzo[b]furyl)- and 6-(2-furyl)pyrrolocytosine (BFpC and FpC) have been synthesized along with the quencher nucleosides possessing 6-{4-[(4-dimethylamino)azo]phenyl}pyrrolocytosine (DABCYLpC) and 6-(p-nitrophenyl)pyrrolocytosine (p-NO2-PhpC) nucleobase analogs. Standard treatment of BFpC, FpC, DABCYLpC, and p-NO2-PhpC with dimethoxytrityl chloride (DMT-Cl) led to the unusual substitution on the C7 of the pyrrolocytosine skeleton. The desired 5′-O-DMT-protected nucleoside analogs were synthesized from suitably protected 5′-O-DMT cytidines. Subsequent phosphitylation smoothly afforded BFpC-, FpC-, DABCYLpC-, and p-NO2-PhpC-derived monomers suitable for standard oligonucleotide synthesis.
- Suchy, Mojmír,Ettles, Christie,Wisner, James A.,Matarazzo, Augusto,Hudson, Robert H. E.
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p. 8415 - 8425
(2016/09/28)
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- Pyrimidine or pyridine pyridine ketone compound and its preparation method and application (by machine translation)
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The invention discloses a kind of type I of the pyrimidine or pyridine pyridine ketone compound and its preparation and application, which belongs to the technical field of pharmaceutical preparation. The compounds have high-efficient and selectively inhibit the cell cycle dependent kinases (Cdks) CDK4 and CDK6 active, and then by inhibiting CDK4/CDK6 prevent tumor cell division. Therefore, the compounds of this invention can be used for CDK4 and CDK6 the involved in cell cycle control disorders result in various diseases, especially suitable for the treatment of malignant tumors. (by machine translation)
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Paragraph 0376
(2016/10/09)
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- Formation of quaternary stereogenic centers by copper-catalyzed asymmetric conjugate addition reactions of alkenylaluminums to trisubstituted enones
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Alkenylaluminums undergo asymmetric copper-catalyzed conjugate addition (ACA) to β-substituted enones allowing the formation of stereogenic all-carbon quaternary centers. Phosphinamine-copper complexes proved to be particularly active and selective compared with phosphoramidite ligands. After extensive optimization, high enantioselectivities (up to 96 % ee) were obtained for the addition of alkenylalanes to β-substituted enones. Two strategies for the generation of the requisite alkenylaluminums were explored allowing for the introduction of aryl- and alkyl-substituted alkenyl nucleophiles. Moreover, alkyl-substituted phosphinamine (SimplePhos) ligands were identified for the first time as highly efficient ligands for the Cu-catalyzed ACA. Chiral synthesis made easy: The copper-catalyzed conjugate addition of alkenylaluminum reagents to 3-substituted cyclic enones allows for the formation of all-carbon chiral quaternary centers (see scheme; CuTC=copper(I) thiophene-2-carboxylate). Chiral phosphinamine (SimplePhos) ligands were found to be highly efficient for this transformation.
- Mueller, Daniel,Alexakis, Alexandre
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supporting information
p. 15226 - 15239
(2013/11/06)
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- One-pot, two-step conversion of aldehydes to phosphonyl- and sulfonylpyrazoles using Bestmann-Ohira reagent
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A one-pot, two-step, three-component method for the conversion of commercially available aldehydes to phosphonylpyrazoles has been developed, demonstrating, for the first time, the dual reactivity of the Bestmann-Ohira reagent (BOR) in a single-pot transformation. This method, extended to the synthesis of sulfonylpyrazoles by employing BOR in the first step and a diazomethyl sulfone in the second step, is complementary, with regard to regioselectivity, to the previous methods for the synthesis of such functionalized pyrazoles.
- Kumar, Rahul,Verma, Deepti,Mobin, Shaikh M.,Namboothiri, Irishi N. N.
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supporting information; experimental part
p. 4070 - 4073
(2012/09/21)
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- DIYNE COMPOSITIONS
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A novel class of diyne compounds and diyne salts provided herein are effective and potent Olel protein inhibitors, useful for treating fungal pathogens. Compounds, fungicides and methods are provided as novel, potent and broad spectrum antifungal agents for treatment against a wide variety of fungal pathogens in humans and animals, and in the agricultural setting.
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Page/Page column 47
(2011/02/24)
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- Synthesis and activity of polyacetylene substituted 2-hydroxy acids, esters, and amides against microbes of clinical importance
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A series of novel polyacetylene substituted 2-hydroxy acids and derivatives were prepared and characterized. Alkylation of butane-2,3-diacetal (BDA) protected glycolic acid with iodoalkyl substituted polyacetylene compounds gave the corresponding diacetal protected polyacetylene substituted 2-hydroxy acids. Diacetal deprotection through acid mediated hydrolysis, transesterification or aminolysis afforded the 2-hydroxy-polyacetylenic acid, ester or amide derivatives. Twenty one of these novel compounds were tested against 10 microbes of clinical importance and several of them showed good antimicrobial activity, in particular against Pseudomonas aeruginosa.
- Kyi, Stella,Wongkattiya, Nalin,Warden, Andrew C.,O'Shea, Michael S.,Deighton, Margaret,MacReadie, Ian,Graichen, Florian H.M.
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supporting information; experimental part
p. 4555 - 4557
(2010/09/16)
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- CONJUGATED UNSATURATED COMPOUNDS
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The present invention relates to a class of conjugated unsaturated compounds, to a method of preparing such compounds, and to the polymerisation and bio-active uses of such compounds including their use as antimicrobial agents. The invention particularly relates to compounds containing three conjugated unsaturated moieties, at least two of which are yne moieties.
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Page/Page column 53
(2009/10/22)
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- Stereospecific approach to α,β-disubstituted nitroalkenes via coupling of α-bromonitroalkenes with boronic acids and terminal acetylenes
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(Z)-α-Bromo-β-substituted nitroethylenes undergo facile Suzuki coupling with aryl, heteroaryl, and vinylboronic acids in the presence of Pd(PPh3)4 as catalyst to afford (E)-α,β-disubstituted nitroethylenes in high yield (up to 95%) and complete specificity. Similar coupling of α-bromonitroethylenes with terminal acetylenes (Sonogashira coupling) provides a novel route to (E)-nitroenynes. These Pd-catalyzed coupling methods offer a convenient and stereospecific entry into a diverse array of synthetically and biologically useful α,β-disubstituted nitroethylenes.
- Ganesh, Madhu,Namboothiri, Irishi N.N.
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p. 11973 - 11983
(2008/03/13)
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- Direct synthesis of heteroarylethynes via palladiumcatalyzed coupling of heteroaryl halides with ethynylzinc halides. Its application to an efficient synthesis of a thiophenelactone from chamaemelum nobile
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A variety of terminal alkynes containing a heteroaryl group can be directly and selectively synthesized by the Pd-catalyzed coupling of heteroaryl iodides or bromides with ethynylzinc halides. Various compounds of this class containing furan, thiophene, and pyridine have been prepared, and the procedure has been applied to an efficient and selective synthesis of a thiophenelactone from Chamaemelum nobile L.
- Negishi, Ei-Ichi,Xu, Caiding,Tan, Ze,Kotora, Martin
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p. 209 - 214
(2007/10/03)
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- An improved procedure for the preparation of aryl- and hetarylacetylenes
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A number of relatively volatile acetylenes RC ≡ CH (R = aryl or hetaryl) have been prepared with high yields by heating a mixture of the corresponding alcohols RC ≡ CC(CH3)2OH and paraffin oil with small amounts of powdered potassium hydroxide in vacuum. The alcohols were obtained by Pd/Cu-catalyzed cross coupling of aryl or hetaryl halides RX (X = Br, in one case I) with the commercially available HC ≡ CC(CH3)2OH.
- Mal'Kina,Brandsma,Vasilevsky,Trofimov
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p. 589 - 590
(2007/10/03)
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- Flash Vacuum Pyrolysis of Stabilised Phosphorus Ylides. Part 2. Two-step Conversion of Acid Chlorides into Acetylenic Esters and Terminal Alkynes
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The known thermal extrusion of Ph3PO from α-acyl-α-ethoxycarbonyl ylides 1 to give acetylenic esters 2 can be accomplished in excellent yield by using flash vacuum (FVP) at 500 deg C.Upon rasing the furnace temperature to 750 deg C, this reaction is accompanied by unexpected loss of the ethoxycarbonyl group to give the terminal alkynes 7 in moderate yield.A mechanism is proposed for this reaction based on isotopic labelling studies.Ten new examples of ylides 1 have been prepared for the first time.
- Aitken, R. Alan,Horsburg, Caroline E. R.,McCreadie, J. Graeme,Seth, Shirley
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p. 1727 - 1732
(2007/10/02)
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- 1-phenyl-3-aryl-2-propyne-1-one useful as calcium uptake inhibitors
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This invention relates to 1-phenyl-3-aryl-2-propyne-1-ones, the use of these compounds as calcium uptake inhibitors in leukocytes and thrombocytes, and pharmaceutical compositions containing these compounds as active ingredients, and the process of their preparation.
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- SYNTHESIS AND (13)C NMR CHARACTERIZATION OF SOME π-EXCESSIVE HETEROPOLYAROMATIC COMPOUNDS
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Several ?-excessive heteropolyaromatic compounds, which contain furan and thiophen ring and are possible antifungal agents, have been synthesized in good yields according to two general methods.The first method has been used to prepare compounds possessing thiophens linked by their 2- and 5-positions, such as the ter-aryls 2b, 2d and 2a.Two precursors of these compounds have been obtained either by the Glaser reaction, or using a novel Pd-mediated reaction.The second method, which consists of the Ni- or Pd-catalyzed heteroarylation of heteroarene halides via cross-coupling with heteroaryl Grignard reagents or zinc halides, has been used to prepare the bi-aryls 1a-e, which contain two heteroaromatic units, and the ter-aryl 2c.Compound 1e has been also prepared starting from 2-(2-thienyl)furan (1c) by selective lithiation, followed by bromination.The (13)C NMR signals of 1a-e and 2a-d have been assigned on the basis of the literature data and by relaxation measurements.Relaxation data have been also used to obtain qualitative informations on the conformational equilibria of the bi-aryls 1a, 1c and the ter-aryls 2a-d.
- Carpita, Adriano,Rossi, Renzo,Veracini, Carlo Alberto
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p. 1919 - 1930
(2007/10/02)
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- Diazoethenes: Their Attempted Synthesis from Aldehydes and Aromatic Ketones by Way of the Horner-Emmons Modification of the Wittig Reaction. A Facile Synthesis of Alkynes
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The base-promoted reaction of dimethyl (diazomethyl)phosphonate (8) with aldehydes and aryl ketones at low temperatures has been investigated.Alkynes, in modest to excellent yields, are the predominant products of these reactions, a result consistent with the intervention of diazoethenes (3).The latter appear to be unstable toward unimolecular decomposition at -78 deg C and yield nitrogen and alkylidenecarbenes (1).
- Gilbert, J. C.,Weerasooriya, U.
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p. 1837 - 1845
(2007/10/02)
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