- Vinyl Phosphonic Acid Functionalized Silica Polymer Nanocomposites for the Acylation of Phenol
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Abstract: In order to overcome the corrosive problems of homogeneous vinyl phosphonic acid (VPA), ordered mesoporous silica (SBA-15) is functionalized with VPA via in situ radical polymerization method to achieve SBA/VPA nanocomposites with different amou
- Amit, Dubey,Verma, Savita
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p. 724 - 733
(2022/01/13)
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- BI-FUNCTIONAL COMPOUNDS AND METHODS FOR TARGETED UBIQUITINATION OF ANDROGEN RECEPTOR
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The present invention relates to bi-functional compounds which function to recruit endogenous proteins to an E3 ubiquitin ligase for degradation, and methods for using same. More specifically, the present disclosure provides specific proteolysis targeting chimera (PROTAC) molecules which find utility as modulators of targeted ubiquitination of a variety of polypeptides and other proteins, in particular the androgen receptor of a slice variant of AR which lacks the LBD, labelled as AR-V7, which are then degraded and/or otherwise inhibited by the compounds as described herein.
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Paragraph 00182-00185
(2021/11/26)
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- A unified approach to the salicylaldehyde containing polyketide natural products: Total synthesis of ent-pyriculol, ent-epipyriculol, ent-dihydropyriculol, ent-epidihydropyriculol, sordariol, sordarial, 12-methoxy sordariol, and agropyrenol
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Many fungal metabolites are salicylaldehyde containing polyketide natural products and are often isolated from the fungus culture broth. These metabolites commonly exhibit phytotoxicity, however, some compounds exerted other biological activities including immunosuppressive activity. We have developed a unified synthetic strategy that provides easy access to ent-pyriculol, ent-epipyriculol, ent-dihydropyriculol, ent-epidihydropyriculol, trans-sordariol, trans-sordarial, 12-methoxy sordariol and agropyrenol.
- Mahesh, Gaddam,Raghavaiah, Jakka,Sudhakar, Gangarajula
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- Substrate substitution effects in the Fries rearrangement of aryl esters over zeolite catalysts
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The catalytic transformation of aryl esters to hydroxyacetophenones via Fries rearrangement over solid acids is of interest to avoid the use of corrosive and toxic Lewis and Br?nsted acids traditionally applied. Microporous zeolites are known to catalyze the reaction of simple substrates such as phenyl acetate, but their application to substituted derivatives has received limited attention. To refine structure-activity relationships, here we examine the impact of various parameters including the solvent polarity, water content, acidic properties, and framework type on the reaction scheme in the Fries rearrangement of p-tolyl acetate over common solid acids. The results confirm the importance of providing a high concentration of accessible Br?nsted acid sites, with beta zeolites exhibiting the best performance. Extension of the substrate scope by substituting methyl groups in multiple positions identifies a framework-dependent effect on the rearrangement chemistry and highlights the potential for the transformation of dimethylphenyl acetates. Kinetic studies show that the major competitive path of cleavage of the ester C-O bond usually occurs in parallel to the Fries rearrangement. The possibility of sequentially acylating the resulting phenol depends on the substrate and reaction conditions.
- Bonrath, Werner,Létinois, Ulla,Lin, Ronghe,Medlock, Jonathan,Mitchell, Sharon,Netscher, Thomas,Pérez-Ramírez, Javier,Stemmler, René T.
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p. 4282 - 4292
(2020/07/30)
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- MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)
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The present invention relates to compounds of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof that are useful as modulators of STING (Stimulator of Interferon Genes). The present invention further relates to the compounds of formula (I) for use as a medicament and to a pharmaceutical composition comprising said compounds.
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Page/Page column 54-55
(2020/01/08)
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- Ligand-Promoted Palladium-Catalyzed C?H Acetoxylation of Simple Arenes
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The palladium-catalyzed C?H oxidation of simple arenes is an attractive strategy to obtain phenols, which have many applications in the fine chemicals industry. Although some advances have been made in this research area, low reactivity and selectivity are, in general, observed. This report describes a new catalytic system for the efficient C?H acetoxylation of simple arenes based on Pd(OAc)2 and a pyridinecarboxylic acid ligand.
- Valderas, Carolina,Naksomboon, Kananat,Fernández-Ibá?ez, M. ángeles
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p. 3213 - 3217
(2016/10/24)
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- Magnetically separable γ-Fe2O3 nanoparticles: An efficient catalyst for acylation of alcohols, phenols, and amines using sonication energy under solvent free condition
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This paper reports a facile synthesis of magnetically separable iron oxide (γ-Fe2O3) nanoparticles using thermolysis method. The structural and morphological study of the synthesized γ-Fe2O3 nanoparticles was carried out using X-ray diffraction (XRD), field emission gun-scanning electron microscopy (FEG-SEM), energy dispersive X-ray spectrum (EDS), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), and X-ray photoelectron spectroscopy (XPS) techniques. The electron microscopy reveals that the γ-Fe2O3 nanoparticles have spherical morphology with a particle size in the range of 40-100 nm. The XPS study confirmed the Fe is in +3 oxidation state. The synthesized γ-Fe2O3 nanoparticles have been used as an efficient heterogeneous catalyst for the organic transformation between phenols, alcohols, and amines with acetic anhydride under sonication using mild reaction conditions. Various electrons withdrawing and electrons donating substrates show an excellent yield of desired products with the advantage of magnetic separation and reusability of γ-Fe2O3 nanocatalyst.
- Bhosale, Manohar A.,Ummineni, Divya,Sasaki, Takehiko,Nishio-Hamane, Daisuke,Bhanage, Bhalchandra M.
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- The first vinyl acetate mediated organocatalytic transesterification of phenols: A step towards sustainability
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The present report outlines our efforts toward a simple yet elegant protocol for O-acylation of a wide variety of phenols. This highly enabling and solventless method relies on vinyl acetate as an innocuous acyl donor and DABCO as an organocatalyst. Operational simplicity, excellent yields, higher and faster conversion rates without excess reagents, a simple workup and essentially no need of columns are some of the salient features of the reported protocol.
- Kumar, Manoj,Bagchi, Sourav,Sharma, Anuj
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supporting information
p. 8329 - 8336
(2015/11/10)
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- Oxidative dearomatization and unusual intramolecular Diels-Alder reaction of cyclohexa-2,4-dienone: Synthesis and photoreaction of oxa-tricyclo[5.2.2.01,5]undec-10-ene-8-ones
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Abstract An efficient synthesis of annulated bicyclo[2.2.2]octane having β,γ-enone chromophoric system and triplet sensitized 1,2-acyl shift rearrangement leading to the formation of angular oxa-triquinane is described. Oxidative dearomatization, intramolecular Diels-Alder reaction of 6,6-spiroepoxycyclohexa-2,4-dienone and oxa-di-π-methane reaction are the key features of our approach.
- Das, Beauty,Singh, Vishwakarma
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p. 1982 - 1985
(2015/03/30)
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- Acetylation of alcohols and phenols by zinc zirconium phosphate as an efficient heterogeneous catalyst under solvent-free conditions
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An efficient method for the acetylation of a wide range of alcohols as well as phenols with acetic anhydride in good to excellent yields under solvent-free conditions, using zinc zirconium phosphate as the catalyst was investigated. The catalyst was characterized by XRD, inductivity coupled plasma-optical emission spectroscopy, and scanning electron microscope. Products are easily isolated and the protocol is mild and green, compared to the existing methods. Graphical abstract: [Figure not available: see fulltext.]
- Hajipour, Abdol Reza,Karimi, Hirbod,Karimzadeh, Morteza
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p. 1461 - 1472
(2014/09/30)
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- NEW PROCESSES FOR PREPARING 4-SUBSTITUTED IMIDAZOLES
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There is provided a novel process for the preparation of a compound of formula (I), (Formula (I)). There is also provided novel processes to intermediates of the compound of formula (I), as well as novel intermediates themselves.
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Page/Page column 40; 41
(2013/03/26)
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- Broensted acidic ionic liquid as an efficient catalyst for acetylation of alcohols and phenols
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A novel Broensted acidic room temperature ionic liquid (1-H-3-methyl-imidazolium bisulfate) is found to catalyze efficiently the acetylation of a wide rang of alcohols as well as phenols with acetic anhydride in good to excellent yields at 50°C under solvent-free conditions. Products are easily isolated by extraction with ether and the protocol is mild and green, compared to the existing method based on toxic solvents.
- Hajipour, Abdol R.,Khazdooz, Leila,Ruoho, Arnold E.
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experimental part
p. 398 - 403
(2009/12/06)
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- Synthesis and biological evaluation of coumarin-based inhibitors of NAD(P)H: Quinone oxidoreductase-1 (NQO1)
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The synthesis is reported here of two novel series of inhibitors of human NAD(P)H quinone oxidoreductase-1 (NQO1), an enzyme overexpressed in several types of tumor cell. The first series comprises substituted symmetric dicoumarol analogues; the second series contains hybrid compounds where one 4-hydroxycoumarin systemis replaced by a different aromatic moiety. Several compounds show equivalent or improved NQO1 inhibition over dicoumarol, both in the presence and in the absence of added protein. Further, correlation is demonstrated between the ability of these agents to inhibit NQO1 and computed binding affinity. We have solved the crystal structure of NQO1 complexed to a hybrid compound and find good agreement with the in silico model. For both MIA PaCa-2 pancreatic tumor cells and HCT116 colon cancer cells, dicoumarol shows the greatest toxicity of all compounds. Thus, we provide a computational, synthetic, and biological platform to generate competitive NQO1 inhibitors with superior pharmacological properties to dicoumarol. This will allow a more definitive study of NQO1 activity in cells, in particular, its drug activating/detoxifying properties and ability to modulate oncoprotein stability. 2009 American Chemical Society.
- Nolan, Karen A.,Doncaster, Jeremy R.,Dunstan, Mark S.,Scott, Katherine A.,Frenkel, A. David,Siegel, David,Ross, David,Barnes, John,Levy, Colin,Leys, David,Whitehead, Roger C.,Stratford, Ian J.,Bryce, Richard A.
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experimental part
p. 7142 - 7156
(2010/07/20)
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- Synthesis and Absolute Configuration of Pyriculol
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A total synthesis of optically active pyriculol is described.The Wittig reaction between an aldehyde 19 and a triphenylphosphonium ylide 12 gave an intermediate 20.Successive treatment of 20 with p-toluenesulfonic acid, active manganese dioxide, and potassium carbonate gave (3'R,4'S)-pyriculol (23), which was identical with natural pyriculol (1) in all respects.From this synthesis the absolute stereochemistry of pyriculol (1) was determined to be 2--6-hydroxybenzaldehyde.
- Suzuki, Masanobu,Sugiyama, Takeyoshi,Watanabe, Masashi,Murayama, Tetsuya,Yamashita, Kyohei
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p. 1121 - 1128
(2007/10/02)
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