- High catalytic activity of a new Ag phosphorus ylide complex supported on montmorillonite: synthesis, characterization, and application for room temperature nitro reduction
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In this work, the phosphorus ylide, [PPh3CHC(O)CH2Cl], was reacted with AgNO3 to give the [Ag{C(H)PPh3C(O)CH2Cl}2]+NO3? as the product. Then, it was supported on the modified montmorillonite nanoclay to prepare a new catalyst for the reduction reaction. The structure and morphology of the nanoclay catalyst were characterized by FT-IR, X-ray powder diffraction, scanning electron microscopy, energy-dispersive X-ray analysis and transmission electron microscopy techniques; also, the content of silver was obtained by inductively coupled plasma analyzer. This composition was exploited to study its catalytic activity in the reduction in aromatic nitro compounds; it displayed the high catalytic activity. Factors such as catalyst amount, solvent, temperature and reaction time were all systematically investigated to elucidate their effects on the yield of catalytic reduction in nitroarenes. This catalytic system exhibited high activity toward aromatic nitro compounds under mild conditions. The catalyst was reused five times without any significant loss in its catalytic activity.
- Karami, Kazem,Rahimi, Mahzad,Dinari, Mohammad
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- Preparation and biological evaluation of BACE1 inhibitors: Leveraging trans-cyclopropyl moieties as ligand efficient conformational constraints
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Inhibition of BACE1 has become an important strategy in the quest for disease modifying agents to slow the progression of Alzheimer's disease. We previously reported the fragment-based discovery of LY2811376, the first BACE1 inhibitor reported to demonstrate robust reduction of human CSF Aβ in a Phase I clinical trial. We also reported on the discovery of LY2886721, a potent BACE1 inhibitor that reached phase 2 clinical trials. Herein we describe the preparation and structure activity relationships (SAR) of a series of BACE1 inhibitors utilizing trans-cyclopropyl moieties as conformational constraints. The design, details of the stereochemically complex organic synthesis, and biological activity of these BACE1 inhibitors is described.
- Audia, James E.,Barberis, Mario,Beck, James P.,Boggs, Leonard N.,Borders, Anthony R.,Boyer, Robert D.,Brier, Richard A.,Erickson, Jon A.,Garcia-Losada, Pablo,Green, Steven J.,Hembre, Erik J.,Hendle, J?rg,Lopez, Jose E.,Mathes, Brian M.,May, Patrick C.,Mergott, Dustin J.,Minguez, Jose Miguel,Monk, Scott A.,Porter, Warren J.,Rankovic, Zoran,Shi, Yuan,Stout, Stephanie L.,Timm, David E.,Watson, Brian M.,Winneroski, Leonard L.,Yang, Zhixiang
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Read Online
- FLUORESCENT SYSTEMS FOR BIOLOGICAL IMAGING AND USES THEREOF
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The invention relates to compounds of formula I, in which Y, Ar1, Ar2, X, R1 and R2 are defined herein, and to their use in a variety of biological imaging techniques and therapeutic methods. In aspects, the invention relates to conjugates comprising the compounds of formula I and their associated uses and therapeutic uses.
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- AZEPANE DERIVATIVES AND METHODS OF TREATING HEPATITIS B INFECTIONS
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Provided herein are compounds useful for the treatment of HBV infection in a subject in need thereof, pharmaceutical compositions thereof, and methods of inhibiting, suppressing, or preventing HBV infection in the subject.
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Paragraph 0550
(2015/09/22)
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- AZEPANE DERIVATIVES AND METHODS OF TREATING HEPATITIS B INFECTIONS
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Provided herein are compounds useful for the treatment of HBV infection in a subject in need thereof, pharmaceutical compositions thereof, and methods of inhibiting, suppressing, or preventing HBV infection in the subject.
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- One-pot eschenmoser episulfide contractions in DMSO: Applications to the synthesis of fuligocandins A and B and a number of vinylogous amides
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Practical total syntheses of the natural products fuligocandin A (2a) and fuligocandin B (3) have been achieved through a convergent strategy depending on the Eschenmoser episulfide contraction as a key step. Conducting the reaction in DMSO proved to be an efficient and general method for the synthesis of a variety of vinylogous amides, such as azepan-2- ylidenepropan-2-one. 2011 American Chemical Society.
- Pettersson, Birgitta,Hasimbegovic, Vedran,Bergman, Jan
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p. 1554 - 1561
(2011/05/19)
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- Total synthesis of fuligocandines A and B
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A practical synthesis of the biologically active cycloanthranilylproline derivatives fuligocandines A and B is described, starting from l-proline and isatoic anhydride, employing an Eschenmoser episulfide contraction as the key step.
- Pettersson, Birgitta,Hasimbegovic, Vedran,Bergman, Jan
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scheme or table
p. 238 - 239
(2010/03/24)
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- A convergent total synthesis of (+)-febrifugine
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Febrifugine was synthesized in ten steps from N-Boc 4-aminobutan-1-ol by a convergent approach. Georg Thieme Verlag Stuttgart.
- Sieng, Bora,Ventura, Oscar Lozano,Bellosta, Véronique,Cossy, Janine
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scheme or table
p. 1216 - 1218
(2009/04/04)
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- New nitrogenated siloxy butadienes from 1,3-dichloroacetone
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New 1-formamido-2-siloxy-1,3-butadienes have been generated from 1,3-dichloroacetone by means of phosphorane formation, formamido substitution, Wittig olefination and silylation. The procedure demonstrates the utility and versatility of this methodology for the formation of polysubstituted dienes, designed as useful building blocks for the synthesis of polycyclic alkaloids and related analogues.
- Alonso, Dulce,Caballero, Esther,Medarde, Manuel,Tomé, Fernando
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p. 907 - 910
(2008/02/03)
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- Synthesis of 3-oxooxa- and 3-oxoazacycloalk-4-enes by ring-closing metathesis. Application to the synthesis of an inhibitor of cathepsin K
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3-Oxooxa- and 3-oxoazacycloalk-4-enes were obtained with good yield from 1-(ω-alkenyloxy)- and 1-(ω-alkenylamino)-but-3-en-2-ones by using a ring-closing metathesis. This methodology has been used to synthesize an inhibitor of cathepsin K.
- Taillier, Catherine,Hameury, Thomas,Bellosta, Véronique,Cossy, Janine
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p. 4472 - 4490
(2008/02/01)
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- Synthesis of substituted 1-thiocyanatobutadienes and their application in a Diels-Alder/[3,3] sigmatropic rearrangement tandem reaction
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The retrosynthetic analysis of Ibogamine, a natural psychotropic alkaloid with exceptional anti-addictive properties found in both enantiomeric forms, requires an efficient access to a racemic cyclohexene. This cyclohexene can be obtained via the sequence Diels-Alder/[3,3] sigmatropic rearrangement reaction starting from substituted 1-thiocyanatobutadienes. An efficient synthesis of the enone, a stable precursor of 1-thiocyanatobutadienes, is reported. Enolisation of this enone was studied to find the optimal conditions to get the desired 1-thiocyanatobutadienes with good Z-selectivity. Springer-Verlag 2005.
- Lanaspeze, Sebastien,Neier, Reinhard
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p. 597 - 607
(2007/10/03)
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- Design, synthesis and evaluation of trisubstituted thiazoles targeting Plasmodium falciparum cysteine proteases
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The Plasmodium falciparum cysteine proteases, falcipains, have been established as novel targets for antimalarial drug design. Using the de novo design approach, several trisubstituted thiazole analogs were generated as potential inhibitors of these enzymes. A general and convenient synthetic approach for these novel trisubstituted thiazoles is reported here. Substituents at the 4th and 5th positions of the target thiazoles were introduced by a Hantzsch reaction, and the chain at the second position was extended through a Sandmeyer reaction, formylation, and Wittig olefination. In vitro enzyme inhibition studies have identified three inhibitors (14, 16, 23) of the falcipains with one (14) showing dual activity against both falcipain-2 and falcipain-3 and IC50 values of 6.6 and 29.4 μM, respectively. Birkhaeuser Boston 2005.
- Goud, P. Mallikarjun,Sheri, Anjaneyulu,Desai, Prashant V.,Watkins, E. Blake,Tekwani, Babu,Sabnis, Yogesh,Gut, Jiri,Rosenthal, Philip J.,Avery, Mitchell A.
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- Diels-Alder reactivity of 4-aryl-1-phthalimido-2-siloxy-1,3-butadienes
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The reaction of (1Z,3E) and (1E,3E) 4-aryl-1-phthalimido-2-trialkylsiloxy- 1,3-butadienes with maleimides and quinones has been studied. The observed exo-stereospecifity can be attributed to the simultaneous presence of the phthalimido and aryl groups, which produce strong hindrance during the endo approach.
- Caballero, Esther,Alonso, Dulce,Peláez, Rafael,álvarez, Concepción,Puebla, Pilar,Sanz, Francisca,Medarde, Manuel,Tomé, Fernando
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p. 6871 - 6878
(2007/10/03)
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- FURAZANOBENZIMIDAZOLES
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The invention relates to compounds of formula (I) wherein R represents aryl or heteroaryl, X is oxygen, a carbonyl group, an oxime derivative of a carbonyl group or an α,?-unsaturated carbonyl group, and the substituents R1 to R6 have the meanings given in the specification, for use as medicaments, to novel compounds of formula (I), to methods of synthesis of such compounds, to pharmaceutical compositions containing compounds of formula (I), to the use of a compounds of formula (I) for the preparation of a pharmaceutical composition for the treatment of neoplastic and autoimmune diseases, and to methods of treatment of neoplastic and autoimmune diseases using such compounds of formula (I) or of pharmaceutical compositions containing same.
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- 1-Phthalimido-4-(3-indolyl)-2-siloxy-1,3-butadienes: Synthesis and Diels-Alder reactivity
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New 1-phthalimido-4-(3-indolyl)-2-trialkylsiloxy-1,3-butadienes were easily prepared from 1,3-dichloropropanone and their configurations were established from NMR data. Their Diels-Alder reactivity with different maleimides and quinones was studied, high yields of the exo cycloadducts being obtained, as confirmed by X-ray diffraction studies.
- Caballero, Esther,Alonso, Dulce,Peláez, Rafael,Alvarez, Concepción,Puebla, Pilar,Sanz, Francisca,Medarde, Manuel,Tomé, Fernando
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p. 1631 - 1634
(2007/10/03)
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- Antitumour polycyclic acridines. Part 13. Synthesis of 2-substituted 7H-pyrido[4,3,2-kl]acridines by thermolysis of 9-(5-alkyltriazol-1-yl)acridines
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Interaction of phosphoranylidene ketones with 9-azidoacridine in refluxing benzene affords 9-(5-substituted triazol-1-yl)acridines, which, on thermolysis in boiling diphenyl ether at 259 °C, yield 2-substituted 7H-pyrido[4,3,2-kl] acridines in high yields. These tetracyclic acridines are less potent inhibitors of human tumour cells in vitro than their pentacyclic analogues.
- Ellis, Michael J.,Stevens, Malcolm F. G.
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- Synthetic and Mechanistic Studies of the Retro-Claisen Rearrangement 4. An Application to the Total Synthesis of (+)-Laurenyne
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(Matrix Presented) A novel asymmetric total synthesis of marine natural product (+)-Laurenyne has been achieved. The key elements of the strategy are the sequential metal ion-templated SN2′ cyclization affording a highly functionalized chiral vinyl cyclobutane and a retro-Claisen rearrangement for the construction of an eight-membered ring ether.
- Boeckman Jr., Robert K.,Zhang, Jing,Reeder, Michael R.
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p. 3891 - 3894
(2007/10/03)
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- Synthesis and Diels-Alder reactivity of simple 1-phenoxy-1,3-dienes
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An easy and useful method for the preparation of simple 1-phenoxy-2-trialkylsiloxy-1,3-dienes in high yields, has been established and their reactivity in the Diels-Alder reaction at room temperature has been studied. By this procedure, phenoxy substituted cyclohexenes and cyclohexanones of known relative stereochemistry can be obtained.
- Caballero, Esther,Guilhot, Fabien,Lopez, Jose Luis,Medarde, Manuel,Sahagun, Heidi,Tome, Fernando
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p. 6951 - 6954
(2007/10/03)
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- CHLOROACETONYLTRIPHENYLPHOSPHONIUM ET PHOSPHORANNE CORRESPONDANT, ETUDE PHYSICOCHIMIQUE ET CONFORMATION
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The structures of chloroacetonyltriphenylphosphonium and the corresponding phosphorane have been studied by IR, NMR (1H, 13C, 31P) and X-ray crystallography.The compounds have analogous conformations, especially when an enolic form of the phosphonium salt is considered.The molecules are nearly planar with phosphorus, oxygen and chlorine atoms being cis-cis with each other.This arrangement explains the ability of the phosphorane to undergo reactions in which these reactive centers are involved.
- Henichart, J. P.,Houssin, R.,Vaccher, C.,Foulon, M.,Baert, F.
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p. 283 - 294
(2007/10/02)
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