- The preparation and structures of several cross-conjugated allenes ("allenic dendralenes")
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The cross-conjugated allenes ("allenic dendralenes") 2-allenylbuta-1,3-diene (2), 1,1-divinylallene (3, prepared here as the methyl derivative 49), and 1,1-diallenylethene (4) are prepared either by S N2′-substitution processes from appropriate allenic or acetylenic precursors or by base-catalyzed isomerizations of propargylic substrates. Thermal elimination/isomerization routes to these highly unsaturated hydrocarbons require reaction conditions under which these allenes undergo secondary transformations. The new oligoolefins, the structures of which have been calculated by MP2 methods, are interesting substrates for addition and isomerization reactions. The phenomenon of cross-conjugation is extended to allenes; the resulting oligoolefins are predicted to become useful dienes for multiple-Diels-Alder additions allowing the rapid construction of complex carbon frameworks.
- Lehrich, Friedhelm,Hopf, Henning,Grunenberg, Joerg
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scheme or table
p. 2705 - 2718
(2011/06/25)
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- A scalable synthesis of MN-447, an antagonist for integrins αvβ3 and αIIbβ 3
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(2S)-Benzeneslfonylamino-3-[3-methoxy-4-{4-(1,4,5,6-tetrahydropyrimidin-2- ylamino)piperidin-1-yl}benzoylamino]propionic acid, MN-447, is a potent antagonist of the integrins αvβ33 and αIIbβ3 Herein, we report a novel synthetic protocol that produces MN-447 in an overall yield of 45%. This protocol, when compared with the original synthetic route for MN-447, is more cost-effective, requires fewer steps, does not require chromatographic purification of intermediates and MN-447, and increases the overall yield by 35%. This report focuses on the synthetic strategies that were developed for this protocol. Now, the large quantities of MN-447 that are needed for preclinical and toxicological studies can be readily obtained.
- Ishikawa, Minoru,Tsushima, Masaki,Kubota, Dai,Yanagisawa, Yumiko,Hiraiwa, Yukiko,Kojima, Yasuo,Ajito, Keiichi,Anzai, Naomichi
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p. 596 - 602
(2013/01/03)
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- Novel double para-phenylenediamines joined by a linker arm substituted with at least one group chosen from hydroxyl, alkoxy, and/or amino groups and method of dyeing keratinous fibers
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Disclosed herein is a novel family of double para-phenylenediamines joined by a linker arm comprising at least one substituent chosen from hydroxyl, alkoxy, and/or amino substituents. Also disclosed herein is a dyeing composition comprising, in a medium s
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Page/Page column 9
(2008/06/13)
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- SYNTHESIS OF CHLORINS AND PHORBINES WITH ENHANCED RED SPECTRAL FEATURES
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The present invention provides compounds of the general Formula DI: along with methods of making such compounds, formulations containing the same, and methods of using the same (e.g., in photodynamic therapy, for the production of solar cells, etc.).
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Page/Page column 124
(2008/06/13)
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- Large-scale synthesis of "Cpep" RNA monomers and their application in automated RNA synthesis
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Small interfering RNAs (siRNA) are the latest candidates for oligonucleotide-based therapeutics. Should siRNA be successful in clinical trials, a huge demand for synthetic RNA is anticipated. We believe that 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl (Cpep
- Pon,Yu,Prabhavalkar,Mishra,Kulkarni,Sanghvi
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p. 777 - 781
(2007/10/03)
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- Synthesis of 1,5-bis(triphenylphosphonium)pentan-3-ol dichloride and its application to the preparation of 1,7-di(pyridin-3-yl)heptan-4-ol
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The preparation of 1,7-di(pyridin-3-yl)-heptan-4-ol (1), an important intermediate in the synthesis of a series of novel cancer multidrug resistance (CMR) chemosensitizers, has been accomplished in high overall yield via the new bis-Wittig reagent 1,5-bis(triphenylphosphonium)pentan-3-ol dichloride (6), that can also be used in the preparation of other members of the class of CMRs.
- Stivanello, Mariano,Leoni, Lucia,Bortolaso, Roberto
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p. 807 - 810
(2013/09/06)
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- m-SUBSTITUTED BENZOIC ACID DERIVATIVES EXHIBITING INTEGRIN ALPHA-V BETA-3 ANTAGONISM
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An object of the present invention is to provide m-substituted benzoic acid derivatives having integrin αvβ3 antagonistic activity. The derivatives according to the present invention are compounds represented by formula (I) or pharmaceutically acceptable salts or solvates thereof, which are useful for the treatment or prevention of cardiovascular diseases, angiogenesis-related diseases, cerebrovascular diseases, cancers and metastasis thereof, immunological diseases, osteopathy and other diseases: wherein A represents an optionally substituted heterocyclic group containing two nitrogen atoms, a bicylic group or the like; D represents a bond, >NR4, >CR5R6, O, S, or -NR4-CR5R6-; X represents CH or N; R7 and R8 represent hydroxyl, alkyl or the like; Q represents >C=O or the like; R9 represents hydrogen, alkyl or the like; J represents a bond or alkylene; R10 represents optionally substituted hydroxyl, amino or the like; R11 represents hydrogen, alkyl or the like; m is 0 to 5; n is 0 to 4; and p and q are each 0 to 3.
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- Stepwise versus direct long-range charge separation in molecular triads
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Trifunctional electron donor - donor - acceptor molecules are described in which photoinduced charge separation, D2 - D1 - A* → D2 - D1+ - A- , is followed by a charge migration step D
- Willemse,Piet,Warman,Hartl,Verhoeven,Brouwer
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p. 3721 - 3730
(2007/10/03)
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- Process for the synthesis of 1,7-diarly or heteroaryl-heptane-4-ols and new synthetic intermediates
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This invention offers a process for the synthesis of a compound of the formula STR1 wherein R' is a phenyl, a substituted phenyl, a heterocyclic aromatic group, a heterocyclic aromatic substituted group, a linear or branched alkyl group, or a cycloalkyl group. The invention also comprises the following compounds of a formula 1' and 2' as useful new synthesis intermediates. STR2 wherein R is a phenyl, a substituted phenyl, an alkyl, a cycloalkyl and X is Cl, Br, I, F, CH3 SO3, p--CH3 --C6 H4 --SO3.
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- Process for the synthesis of 1,7-diaryl or 1,7-heteroarylheptan-4-ols and synthetic intermediates
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This invention offers a process for the synthesis of a compound of the formula wherein R' is a phenyl, a substituted phenyl, a heterocyclic aromatic group, a heterocyclic aromatic substituted group, a linear or branched alkyl group, or a cycloalkyl group. The invention also comprises the following compounds of a formula 1' and 2'as useful new synthesis intermediates. wherein R is a phenyl, a substituted phenyl, an alkyl, a cycloalkyl and X is Cl, Br, I, F, CH3SO3, p-CH3-C6H4-SO3.
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- Synthesis and exploratory photophysical investigation of donor-bridge-acceptor systems derived from N-substituted 4-piperidones
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We report a two-step synthesis for N-aryl- and N-alkyl-substituted 4-piperidones, in which the N substituent can easily be varied.A number of intramolecular donor-acceptor systems was synthesized from these piperidones by conversion of the carbonyl functionality.The influence of the N-aryl donor on the electronic absorption and fluorescence spectra was investigated systematically.It was concluded that some systems can be used as efficient fluorescent probes with a high sensitivity for solvent polarity.
- Scherer, T.,Hielkema, W.,Krijnen, B.,Hermant, R. M.,Eijckelhoff, C.,et al.
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p. 535 - 548
(2007/10/02)
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- Phyllanthoside-Phyllanthostatin Synthetic Studies. 7. Total Synthesis of (+)-Phyllanthocin and (+)-Phyllanthocindiol
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A stereochemically linear total synthesis of (+)-phyllanthocin (5a), the aglycon methyl ester of the antineoplastic glycoside (+)-phyllanthoside (1), is described. The synthesis proceeds in 23 steps (4.5% overall yield) and affords (+)-phyllanthocin in high enantiomeric purity. The central features of the strategy include: (a) construction of aldehyde 8 via a stereoselective, intramolecular ene reaction; (b) elaboration of the spiroketal unit by a two-step tactic involving addition of a functionalized dihydropyran anion (i.e., 9) to 8, followed by a highly stereoselective spiroketalization; and (c) chemo- and stereoselective methylenation of the C(7) carbonyl group. In addition, a second-generation approach is presented, wherein an augmented spiroketalization maneuver not only establishes the C(8) spirocenter but also permits the regio- and stereocontrolled introduction of the C(11) methyl group. The latter sequence furnishes (+)-phyllanthocin in 21 steps (5.6% overall yield). Finally, the advanced phyllanthocin intermediate (+)-49 is converted in five steps (42% overall yield) to (+)-phyllanthocindiol (5b), the aglycon of phyllanthostatin 3.
- Smith III, Amos B.,Fukui, Mineo,Vaccaro, Henry A.,Empfield, James R.
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p. 2071 - 2092
(2007/10/02)
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