305-85-1Relevant articles and documents
2,6-diiodo-4-nitrophenol, 2,6-diiodo-4-nitrophenyl acetate and 2,6-diiodo-4-nitroanisole: Interplay of hydrogen bonds, iodo-nitro interactions and aromatic π-π-stacking interactions to give supramolecular structures in one, two and three dimensions
Garden, Simon J.,Da Cunha, Fernanda R.,Wardell, James L.,Skakle, Janet M.S.,Low, John N.,Glidewell, Christopher
, p. o463-o466 (2002)
In 2,6-diiodo-4-nitrophenol, C6H3I2NO3, the molecules are linked, by an O-H...O hydrogen bond and two iodo-nitro interactions, into sheets, which are further linked into a three-dimensional framework by aromatic π-π-stacking interactions. The molecules of 2,6-diiodo-4-nitrophenyl acetate, C8H5I2NO4, lie across a mirror plane in space group Pnma, with the acetyl group on the mirror, and they are linked by a single iodo-nitro interaction to form isolated sheets. The molecules of 2,6-diiodo-4-nitroanisole, C7H5I2NO3, are linked into isolated chains by a single two-centre iodo-nitro interaction.
One-Pot Synthesis of N-Iodo Sulfoximines from Sulfides
Zupanc, An?e,Jereb, Marjan
, p. 5991 - 6000 (2021/05/05)
This is the first report on the synthesis and characterization of N-iodo sulfoximines. The synthesis was designed as a room temperature one-pot cascade reaction from readily available sulfides as starting compounds, converted into sulfoximines by reaction with ammonium carbonate and (diacetoxyiodo)benzene, followed by iodination with N-iodosuccinimide or iodine in situ, in up to 90% isolated yields, also at a multigram scale. Iodination of aryls with N-iodo sulfoximines, oxidation, and conversion to N-SCF3 congeners have been demonstrated.
Molecularly Imprinted Synthetic Glucosidase for the Hydrolysis of Cellulose in Aqueous and Nonaqueous Solutions
Li, Xiaowei,Zangiabadi, Milad,Zhao, Yan
supporting information, p. 5172 - 5181 (2021/05/04)
Molecular imprinting is a powerful and yet simple method to create multifunctional binding sites within a cross-linked polymer network. We report a new class of synthetic glucosidase prepared through molecular imprinting and postfunctionalization of cross-linked surfactant micelles. These catalysts are protein-sized water-soluble nanoparticles that can be modified in multiple ways. As their natural counterparts, they bind a glucose-containing oligo- or polysaccharide. They contain acidic groups near the glycosidic bond to be cleaved, with the number and distance of the acid groups tuned systematically. Hydrolysis of cellulose in a key step in biomass conversion but is hampered by the incalcitrance of the highly crystalline cellulose fibers. The synthetic glucosidases are shown to hydrolyze cellobiose and cellulose under a variety of conditions. The best catalyst, with a biomimetic double acid catalytic motif, can hydrolyze cellulose with one-fifth of the activity of commercial cellulases in aqueous buffer. As a highly cross-linked polymeric nanoparticle, the synthetic catalyst is stable at elevated temperatures in both aqueous and nonaqueous solvents. In a polar aprotic solvent/ionic liquid mixture, it hydrolyzes cellulose several times faster than commercial cellulases in aqueous buffer. When deposited on magnetic nanoparticles, it retains 75% of its activity after 10 cycles of usage.
Quinazoline derivative and preparation method and application thereof
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Paragraph 0099-0100, (2020/07/15)
The invention discloses a novel compound 4-(3 '-R substituted-5'-R substituted-4 '-hydroxyanilino) quinazoline derivative and a preparation method and application thereof. The structural formulas of the compound are shown as formulas I and II. The compound has good activity of preventing and treating chicken coccidiosis and can be used as a therapeutic agent for preventing and treating chicken coccidiosis in the field of preparation of medicines for preventing and treating chicken coccidiosis.
Iodination of industrially important aromatic compounds with aqueous potassium triiodide
Sharma,Srivastava,Agarwal,Diwedi
, p. 433 - 436 (2016/06/13)
A new reagent system consisting of aqueous KI3in AcOH and NaIO4as oxidant has been found to be effective in iodinating a variety of commercially important aromatic substrates under ambient conditions. The presence of Na2SO3enhances the yield and the product purity. The procedure ensures high yields (72–98%) at room temperature in a short reaction time. A remarkable feature of this system is that even acidsensitive functionalities like anilines can be iodinated quantitatively.
Ultrasound-promoted rapid and efficient iodination of aromatic and heteroaromatic compounds in the presence of iodine and hydrogen peroxide in water
Ferreira, Irlon M.,Casagrande, Gleison A.,Pizzuti, Lucas,Raminelli, Cristiano
supporting information, p. 2094 - 2102 (2014/07/07)
A rapid and efficient ultrasound-promoted protocol for iodination of aromatic and heteroaromatic compounds, using molecular iodine in the presence of aqueous hydrogen peroxide in water without any cosolvent, has produced versatile iodinated organic molecules with potential application in organic synthesis and medicine in short reaction times and good to excellent yields. Copyright
Iodine(I) reagents in hydrochloric acid-catalyzed oxidative iodination of aromatic compounds by hydrogen peroxide and iodine
Bedrac, Leon,Iskra, Jernej
supporting information, p. 1243 - 1248 (2013/06/27)
Hydrochloric acid activates the oxidative iodination of aromatic compounds with the iodine- hydrogen peroxide system through the formation of an iodine(I) compound as the iodinating reagent. Activation with hydrochloric acid is more powerful than that with sulfuric acid. The formation of dichloroiodic(I) acid (HICl2) with various forms of hydrogen peroxide was followed using UV spectroscopy. The HICl2 was used as the iodinating reagent. In the preparative oxidative iodinaton of various aromatic compounds, hydrochloric acid was used in a catalytic amount and the iodine(I) reagent was formed in situ with 0.5 equiv. hydrogen peroxide and 0.5 equiv. molecular iodine. Two types of reactivity were observed in oxidative iodination with iodine(I) species catalyzed by hydrochloric acid: in the iodination of anisole 1a better yields of iodination were observed with a smaller amount of hydrochloric acid, while on the contrary 4-tert-butyltoluene 1b gave better yields of iodination upon increasing the amount of hydrochloric acid. Reactivity was further manipulated by the choice of the solvent (MeCN, trifluoroethanol, hexafluoro-2-propanol). Copyright
Increased endothelial cell selectivity of triazole-bridged dihalogenated A-ring analogues of combretastatin A-1
Beale, Thomas M.,Bond, Peter J.,Brenton, James D.,Charnock-Jones, D. Stephen,Ley, Steven V.,Myers, Rebecca M.
scheme or table, p. 1749 - 1759 (2012/04/10)
The antiproliferative activity on ovarian cancer (SK-OV-3) cells of a series of triazole-bridged combretastatin analogues (37, 38, 40-43) containing dihalogenation of the A-ring is reported, and compared with their trimethoxy analogues (5, 15, 39). It was found that dihalogenation with either bromine or iodine was a tolerated modification when compared to the parent compound combretastatin (CA-4, 1) and had less effect than B-ring modification on potency. These compounds exhibited G2/M arrest, and maintained antitubulin activity. Further assays on human umbilical vein endothelial cells (HUVECs) demonstrated the potential antivascular effects of these triazoles. Of particular note was a 3,5-diiodo-4-methoxyaryl triazole (43) which had promising 7-fold selectivity for HUVECs over ovarian cancer cells.
A-ring dihalogenation increases the cellular activity of combretastatin-templated tetrazoles
Beale, Thomas M.,Allwood, Daniel M.,Bender, Andreas,Bond, Peter J.,Brenton, James D.,Charnock-Jones, D. Stephen,Ley, Steven V.,Myers, Rebecca M.,Shearman, James W.,Temple, Jill,Unger, Jessica,Watts, Ciorsdaidh A.,Xian, Jian
supporting information; experimental part, p. 177 - 181 (2012/05/05)
The combretastatins have been investigated for their antimitotic and antivascular properties, and it is widely postulated that a 3,4,5-trimethoxyaryl A-ring is essential to maintain potent activity. We have synthesized new tetrazole analogues (32a€"34), demonstrating that 3,5-dihalogenation can consistently increase potency by up to 5-fold when compared to the equivalent trimethoxy compound on human umbilical vein endothelial cells (HUVECs) and a range of cancer cells. Moreover, this increased potency offsets that lost by installing the tetrazole bridge into combretastatin A-4 (1), giving crystalline, soluble compounds that have low nanomolar activity, arrest cells in G2/M phase, and retain microtubule inhibitory activity. Molecular modeling has shown that optimized packing within the binding site resulting in increased Coulombic interaction may be responsible for this improved activity.
Synthesis, characterization, X-ray structural analysis, and iodination ability of benzyl(triphenyl)phosphonium dichloroiodate
Imanieh, Hossein,Ghammamy, Shahriar,Nikje, Mir Mohammad Alavi,Hosseini, Farhang,Aghbolagh, Zahra Shokri,Fun, Hoong-Kun,Khavasi, Hamid Reza,Kia, Reza
experimental part, p. 2248 - 2255 (2012/01/12)
Benzyl(triphenyl)phosphonium dichloroiodate (BTPPICl2), BnPh3P+(ICl2)-, is easily synthesized in a nearly quantitative yield by the addition of BnPh 3P+Cl- to a CH2Cl2 solution of iodine monochloride (ICl). BnPh3P+Cl - can be prepared by the reaction of Ph3P and BnCl. The compound was characterized by physicochemical and spectroscopic methods (elemental analysis, FT-IR, and 1H-NMR). The use of phosphonium counterion improves the quality of the BTPPICl2 crystals. BTPPICl2 crystallizes in the monoclinic system, and its crystal and molecular structure has been determined at 100(1) K by X-ray diffraction. The structure was solved by the direct method and had refined R value of 0.0637 for 699 reflections (I>2σ(I)), space group P21/n with a=12.4700(3), b=13.2196(3), c=14.4580(3) A, β=102.6340(10)°, V=2325.67(9) A3, and Z=4. The I-atom is coordinated by two Cl-atoms as ligands in a linear geometry. This compound is a versatile reagent for the efficient and selective iodination of organic substrates, in particular of aromatic phenols to the corresponding iodo compounds, under mild conditions. To assess the generality of method, a wide variety of phenols with electron-donating and electron-withdrawing substituents were studied. BTPPICl2 is a mild iodination reagent, which offers a new avenue for an expeditious iodination of phenols. The inexpensive, relatively non-toxic reagent, and mild conditions are the positive features of the procedure and reagent. Copyright
