- Synthesis of novel isoindolone-based medium-sized macromolecules and triazole containing heterocyclic compounds
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A series of novel isoindolone-based macromolecules of medium-sized heterocyclic rings, such as 7,8-dihydro-6H-benzo[4,5][1,6,3]dioxazonino[2,3-a]isoindol-14(9aH)-one derivatives (5a-l), were synthesized and its frame work incorporating with a triazole moiety on phenol, ie, 2-(4-((1-(2-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)isoindoline-1,3-dione (9a-f) and also a triazole moiety on carboxylic acid, ie, (1-(2-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methyl 4-(1,3-dioxoisoindolin-2-yl)benzoate derivatives (13a-e) with various substitutions on aryl ring system have synthesized. All the synthesized compounds were characterized and confirmed with IR, 1H NMR, 13C NMR, and ESI mass spectral analysis.
- Boddu, Lingaiah,Potlapati, Varakumar,Subhashini
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p. 3197 - 3205
(2019/11/11)
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- Synthesis and Reactivity of 18F-Labeled α,α-Difluoro-α-(aryloxy)acetic Acids
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In this work, we describe the 18F-labeling of α,α-difluoro-α-(aryloxy)acetic acid derivatives and demonstrate that these building blocks are amenable to post-18F-fluorination functionalization. Protodecarboxylation offers a new entry to 18F-difluoromethoxyarene, and the value of this approach is further demonstrated with coupling processes leading to representative 18F-labeled TRPV1 inhibitors and TRPV1 antagonists.
- Khotavivattana, Tanatorn,Calderwood, Samuel,Verhoog, Stefan,Pfeifer, Lukas,Preshlock, Sean,Vasdev, Neil,Collier, Thomas L.,Gouverneur, Véronique
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supporting information
p. 568 - 571
(2017/02/10)
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- Potential for minimal self-replicating systems in a dynamic combinatorial library of equilibrating imines
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The presence of a self-replicator in a dynamic combinatorial library (DCL) offers function above and beyond libraries under thermodynamic control, moving towards out-of-equilibrium systems which mimic biological networks. In this work, we examine a previously reported DCL based on reversible imine formation to give amphiphilic structures. The amphiphilic imines were readily produced in organic solvents, and were found to aggregate to micelles in water as judged by diffusion-ordered NMR spectroscopy, dynamic light scattering and interferometric scattering microscopy. Unfortunately, the autocatalytic formation of products was not observed in water, and preformed imines slowly hydrolysed to aldehyde and amine components at neutral pD.
- Morrow, Sarah M.,Bissette, Andrew J.,Fletcher, Stephen P.
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supporting information
p. 5005 - 5010
(2017/07/27)
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- A phthalimidation protocol that follows protein defined parameters
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This work outlines the first phthalimidation protocol suitable for protein labeling and performed in aqueous media at room temperature and neutral pH with no catalyst or co-reagent required. The methodology is suitable for a range of amines and its efficiency was determined with chemoselective and site-selective protein labeling. This journal is
- Singudas, Rohith,Adusumalli, Srinivasa Rao,Joshi, Pralhad Namdev,Rai, Vishal
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supporting information
p. 473 - 476
(2015/01/09)
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- Synthesis of high thermal stability polybenzoxazoles via ortho-imide-functional benzoxazine monomers
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We report our work for preparing cross-linked polyimide via a series of imide functional benzoxazine resins as precursors. The structures of synthesized monomers have been confirmed by 1H NMR and FT-IR. Among this class of benzoxazine monomers, the ortho-imide functional benzoxazine resins show useful features both in the synthesis of benzoxazine monomers and the properties of the corresponding thermosets. For the cross-linked polyimides based on ortho-imide functional benzoxazine, an additional route is adopted to form a more thermally stable cross-linked polybenzoxazole with the release of carbon dioxide. The ortho-imide functional benzoxazine resins show the possibility to form high performance and even super high performance thermosets with low cost and easy processability. The thermal properties are evaluated by DSC and TGA.
- Zhang, Kan,Liu, Jia,Ohashi, Seishi,Ishida, Hatsuo,Liu, Xiaoyun,Han, Zhewen
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p. 1330 - 1338
(2015/07/28)
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- Pd-catalyzed chemoselective carbonylation of aminophenols with iodoarenes: Alkoxycarbonylation vs aminocarbonylation
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Palladium-catalyzed chemoselective carbonylation of aminophenols with iodoarenes was realized by changing ligand and base. 3- or 4-Aminophenols afforded esters in high yields and selectivities using 1,3-bis(diphenylphosphino)propane as the ligand and K2CO3 as the base, and gave amides in high yields and selectivities using 1,3-bis(diisobutylphosphino)propane as the ligand and DBU as the base. 2-Aminophenol only gave amides in high yields under both conditions.
- Xu, Tongyu,Alper, Howard
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p. 16970 - 16973
(2015/02/02)
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- CARBOHYDRATE FUNCTIONALISED SURFACES
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Carbohydrates are biomolecules that are involved in a range of biological processes and play key roles in, for instance, host immune response and cellular adhesion. Accordingly, functionalisation of medical devices such as stents, valves, catheters, prostheses and other devices for in vivoimplantation with carbohydrates is an area in which considerable interest is developing. Disclosed herein are surfaces having carbohydrates immobilised thereon. The carbohydrate has a linker moiety covalently bound thereto and the linker moiety has a carbon atom that forms a covalent bond with an atom on the target surface. The carbon based bond is a strong, non-hydrolysable covalent bond. Diazonium salts are utilised to produce the functionalised surfaces and they are particularly advantageous as they result in non-toxic readily escapable by-products
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Paragraph 0200; 0204-0206
(2014/09/29)
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- Catalyst-free, eco-friendly, one-pot syntheses of 2-(3H-imidazo [4,5-b] pyridine-2-yl)-N-arylbenzamides in water
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Eco-friendly, one-pot three-component syntheses of 2-(3H-imidazo [4,5-b]pyridine-2-yl)-N-arylbenzamides have been developed by combining phthalic anhydride with anilines and pyridine-2,3-diamine in water without any catalyst. These reactions involves easy workup, provide good yields and use of water as solvent which were the merits of this preparation.
- Reddy, Y. Dathu,Kumar, P. Praveen,Devi, B. Rama,Reddy, Ch. Venkata Ramana,Dubey
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p. 768 - 773
(2015/04/14)
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- New selective O-debenzylation of phenol with Mg/MeOH
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Carboxylate-benzyl and nitro-benzyl groups used in phenols protection were selectively debenzylated with 3-25 equiv of Mg in methanol at room temperature. Good yields of the desired phenols were obtained within 3-10 h from a wide variety of O-(carboxylate-benzyl)- or O-(nitro-benzyl)-phenols. Selective O-debenzylation was possible in the presence of O-(carboxylate-benzyl)- or O-(nitro-benzyl)-phenols with Mg/MeOH.
- Huang, Wei,Zhang, Xu,Liu, Hong,Shen, Jianhua,Jiang, Hualiang
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p. 5965 - 5967
(2007/10/03)
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- Synthesis of 4-(1-oxo-isoindoline) and 4-(5,6-dimethoxy-1-oxo-isoindoline)- substituted phenoxypropanolamines and their β1-, β2-adrenergic receptor binding studies
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Phenoxypropanolamines with 1-oxo-isoindoline (12-16) and 5,6-dimethoxy-1-oxo-isoindoline groups (17-20) at the para position were synthesized. β1, β2-Adrenergic receptor binding affinities for the synthesized compounds were tested and compared with propranolol and atenolol. It was found that the incorporation of para-amidic functionality within the 1-oxo-isoindoline ring and 5,6-dimethoxy-1-oxo- isoindoline ring system led to a high degree of cardioselectivity in the phenoxypropanolamines. Two of the compounds 12 and 20 possessed β1-adrenergic receptor affinity comparable with that of atenolol and both showed a better cardioselectivity than atenolol. Both 12 and 20 are undergoing further pharmacological evaluation.
- Jindal, Dharam P.,Singh, Babita,Coumar, Mohane S.,Bruni, Giancarlo,Massarelli, Paola
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p. 310 - 324
(2007/10/03)
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- Protection of amino group as N-phthalyl derivative using microwave irradiation
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The amino groups for various substrates are protected as N-phthalyl derivatives using solvent free neat condition under microwave exposure.
- Khadilkar, Bhushan M.,Madyar, Virendra R.
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p. 1083 - 1085
(2007/10/03)
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- A facile preparation of phthalimides and a new approach to the synthesis of indoprofen via carbonylation
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This report describes an improved synthesis of a heterocyclic propionic acid, 2-4(1-oxo-2-isoindolinyl) phenyl propionic acid, Indoprofen (I) via carbonylation, a potent anti-inflammatory agent1 and an analgesic. The synthesis highlights the preparation of Indoprofen starting from readily available o-toluic acid and p-amino acetophenone by a sequence of reactions that included oxidative addition of carbonylation.
- Prasad, Chalasani S.N.,Varala, Ravi,Adapa, Srinivas R.
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p. 281 - 286
(2007/10/03)
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- The cyclisation of substituted phthalanilic acids in acetic acid solution. A kinetic study of substituted N-phenylphthalimide formation
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One novel and ten known substituted 3′- and 4′-phthalanilic acids have been prepared. These have been cyclised to two novel and nine known substituted N-phenylphthalimides by heating with glacial acetic acid. Both phthalanilic acids and imides have been characterised in detail and spectroscopic data are given. The kinetics of cyclisation for phthalanilic acids has been examined in detail, and it has emerged that a complex mechanism is operating. This initially involves a reversible, solvent assisted intramolecular nucleophilic attack by amide nitrogen on the carboxylic acid carbonyl. Clear evidence is seen for a long-lived intermediate as a precursor to imide formation. The observed kinetics are rationalised using a model of rapid pre-equilibration, followed by the slow breakdown of the intermediate to imide. Observed rate constants for pre-equilibration show a well behaved, linear Hammett plot (ρ = -1.1), whereas those for formation of imide do not.
- Perry, Christopher J.,Parveen, Zahida
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p. 512 - 521
(2007/10/03)
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