- Cyclometalated iridium complex as well as preparation method and application thereof
-
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a cyclometalated iridium complex, the structural formula of the cyclometalated iridium complex is shown as a formula I, and n is equal to 2 or 3; wherein R is carbazolyl or diphenylamino group, and L^X is an auxiliary ligand containing N and/or O. The invention also provides a preparation method and application of the iridium complex. Six novel cyclometalated iridium complexes with novel structures are obtained by introducing diphenylamine and carbazole units to a 2phenylbenzothiazole cyclometalated ligand, three light-emitting colors are yellow (TM 1-3, [lambda]Em -560 nm), and three light-emitting colors are red (TM 4-6, lambda Em 618-636 nm); therefore, the emission wavelength of the compound is tuned, and the electroluminescent property of the material is improved by improving the hole transport property of the material.
- -
-
Paragraph 0043-0046
(2021/05/01)
-
- Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling
-
Cooperative bimetallic catalysis is a fundamental approach in modern synthetic chemistry. We report bimetallic cooperative catalysis for the direct decarbonylative heteroarylation of ubiquitous carboxylic acids via acyl C-O/C-H coupling. This novel catalytic system exploits the cooperative action of a copper catalyst and a palladium catalyst in decarbonylation, which enables highly chemoselective synthesis of important heterobiaryl motifs through the coupling of carboxylic acids with heteroarenes in the absence of prefunctionalization or directing groups. This cooperative decarbonylative method uses common carboxylic acids and shows a remarkably broad substrate scope (>70 examples), including late-stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to gain insight into the mechanism of the reaction. The key step involves intersection of the two catalytic cycles via transmetallation of the copper–aryl species with the palladium(II) intermediate generated by oxidative addition/decarbonylation.
- Liu, Chengwei,Ji, Chong-Lei,Zhou, Tongliang,Hong, Xin,Szostak, Michal
-
p. 10690 - 10699
(2021/04/09)
-
- Hydrogen-Bond-Donor Solvents Enable Catalyst-Free (Radio)-Halogenation and Deuteration of Organoborons
-
A hydrogen bond donor solvent assisted (radio)halogenation and deuteration of organoborons has been developed. The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Most importantly, compared to literature methods, our conditions are more consistent with the principals of green chemistry (e.g., metal-free, strong oxidant-free, more straightforward conditions).
- Yang, Yi,Gao, Xinyan,Zeng, Xiaojun,Han, Junbin,Xu, Bo
-
supporting information
p. 1297 - 1300
(2020/12/23)
-
- Design, synthesis, and biological evaluations of novel 3-amino-4-ethynyl indazole derivatives as Bcr-Abl kinase inhibitors with potent cellular antileukemic activity
-
Breakpoint cluster region-Abelson (Bcr-Abl) kinase is a key driver in the pathophysiology of chronic myelogenous leukemia (CML). Broadening the chemical diversity of Bcr-Abl kinase inhibitors with novel chemical entities possessing favorable target potency and cellular efficacy is a current medical demand for CML treatment. In this respect, a new series of ethynyl bearing 3-aminoindazole based Bcr-Abl inhibitors has been designed, synthesized, and biologically evaluated. The target compounds were designed based on introducing the key structural features of ponatinib, alkyne spacer and diarylamide, into the previously reported indazole II to improve its Bcr-Abl inhibitory activity and overcome its poor cellular potency. All target compounds elicited potent activity against Bcr-AblWT with sub-micromolar IC50 values ranging 4.6–667 nM. In addition, certain derivatives exhibited promising potency over the clinically imatinib-resistant Bcr-AblT315I. Among the target molecules, compounds 9c, 9h and 10c stood as the most potent derivatives with IC50 values of 15.4 nM, 4.6 nM, and 25.8 nM, respectively, against Bcr-AblWT. Interestingly, 9h showed 2 folds and 3.6 times superior potency to the lead indazole II and 10c, respectively, against Bcr-AblT315I. Molecular docking of 9h pointed out its possibility to be a type II kinase inhibitor. Furthermore, all compounds, except 9b, showed highly potent antiproliferative activity against the Bcr-Abl positive leukemia K562 cell (MTT assay) surpassing the modest activity of lead indazole II. Moreover, the most potent members 9h and 10c exerted potent antileukemic activity against NCI leukemia panel, particularly K562 cell (SRB assay) with GI50 less than 10 nM, being superior to the FDA approved drug imatinib. Further biochemical hERG and cellular toxicity, phosphorylation assay, and NanoBRET target engagement of 9h underscored its merits as a promising candidate for CML therapy.
- El-Damasy, Ashraf K.,Jin, Heewon,Seo, Seon Hee,Bang, Eun-Kyoung,Keum, Gyochang
-
-
- NOVEL INDAZOLE DERIVATIVES AND PHARMACEUTICAL COMPOSITION FOR PREVENTING, ALLEVIATING OR TREATING CANCER CONTAINING THE SAME
-
Disclosed are a compound selected from novel indazole derivatives, pharmaceutically acceptable salts thereof, hydrates thereof and stereoisomers thereof, a method for preparing the compound, and a pharmaceutical composition for preventing, alleviating or treating cancer containing the compound as an active ingredient. The novel indazole derivatives exhibit excellent ABL/DDR1 inhibitory efficacy and anti-proliferative efficacy against cancer cells, specifically blood cancer cells, and inhibitory activity against ABL T315I point mutations, thus being useful for the prevention, alleviation or treatment of cancer, specifically blood cancer, especially chronic myelogenous leukemia.
- -
-
Paragraph 0200-0201
(2020/12/25)
-
- BTK Inhibitors and uses thereof
-
The invention discloses a bruton's tyrosine kinase (BTK) inhibitor and use thereof. Specifically, the invention provides heteroaromatic compounds or stereoisomers, geometrical isomers, tautomers, racemates, nitrogen oxides, hydrates, solvates, metabolites and pharmaceutically acceptable salts or prodrugs thereof, and pharmaceutical compositions containing the heteroaromatic compounds; the invention also discloses use of the heteroaromatic compounds or the pharmaceutical compositions containing the heteroaromatic compounds in preparation of medicines; the medicines can be used for treating autoimmune diseases, inflammatory diseases or proliferative diseases.
- -
-
Paragraph 1552-1557
(2020/05/02)
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- Discovery of [1,2,4]triazole derivatives as new metallo-β-lactamase inhibitors
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The emergence and spread of metallo-β-lactamase (MBL)-mediated resistance to β-lactam antibacterials has already threatened the global public health. A clinically useful MBL inhibitor that can reverse β-lactam resistance has not been established yet. We here report a series of [1,2,4]triazole derivatives and analogs, which displayed inhibition to the clinically relevant subclass B1 (Verona integron-encoded MBL-2) VIM-2. 3-(4-Bromophenyl)-6,7-dihydro-5H-[1,2,4]triazolo [3,4-b][1,3]thiazine (5l) manifested the most potent inhibition with an IC50 (half-maximal inhibitory concentration) value of 38.36 μM. Investigations of 5l against other B1 MBLs and the serine β-lactamases (SBLs) revealed the selectivity to VIM-2. Molecular docking analyses suggested that 5l bound to the VIM-2 active site via the triazole involving zinc coordination and made hydrophobic interactions with the residues Phe61 and Tyr67 on the flexible L1 loop. This work provided new triazole-based MBL inhibitors and may aid efforts to develop new types of inhibitors combating MBL-mediated resistance.
- Yuan, Chen,Yan, Jie,Song, Chen,Yang, Fan,Li, Chao,Wang, Cheng,Su, Huiling,Chen, Wei,Wang, Lijiao,Wang, Zhouyu,Qian, Shan,Yang, Lingling
-
-
- Efficient synthesis of esters through oxone-catalyzed dehydrogenation of carboxylic acids and alcohols
-
Since esters are important organic synthesis intermediates, an environmentally friendly oxone catalyzed-esterification of carboxylic acids with alcohols has been developed. A series of carboxylic acid esters are obtained in high yield. This strategy requires mild reaction conditions, providing an attractive alternative for the construction of valuable carbonyl esters. Electron-rich and electron-deficient groups are compatible with the standard conditions and a variety of substrates are demonstrated. Moreover, the reaction could easily be adapted to typical prodrugs, drugs and gram-scale synthesis.
- Hou, Fei,Wang, Xi-Cun,Quan, Zheng-Jun
-
supporting information
p. 9472 - 9476
(2019/01/03)
-
- Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids
-
A convenient, efficient and practical visible-light-induced decarboxylative iodination of aromatic carboxylic acids has been developed, and the corresponding aryl iodides were obtained in good yields. The method shows some advantages including the use of readily available aromatic carboxylic acids as the starting materials, simple and mild conditions, high efficiency, wide substrate scope and tolerance of various functional groups.
- Jiang, Min,Yang, Haijun,Jin, Yunhe,Ou, Lunyu,Fu, Hua
-
supporting information
p. 1572 - 1577
(2018/06/26)
-
- Late stage iodination of biologically active agents using a one-pot process from aryl amines
-
A simple and effective one-pot tandem procedure that generates aryl iodides from readily available aryl amines via stable diazonium salts has been developed. The operationally simple procedure and mild conditions allow late-stage iodination of a wide range of aryl compounds bearing various functional groups and substitution patterns. A novel synthetic strategy involving the preparation of nitroaryl compounds followed by a chemoselective tin(ii) dichloride reduction and the use of the one-pot diazotisation-iodination transformation was also developed. The general applicability of this approach was demonstrated with the preparation of a number of medicinally important compounds including CNS1261, a SPECT imaging agent of the N-methyl-d-aspartate (NMDA) receptor and IBOX, a compound used to detect amyloid plaques in the brain.
- Sloan, Nikki L.,Luthra, Sajinder K.,McRobbie, Graeme,Pimlott, Sally L.,Sutherland, Andrew
-
p. 54881 - 54891
(2017/12/12)
-
- Silver-Mediated 18F-Labeling of Aryl-CF3 and Aryl-CHF2 with 18F-Fluoride
-
We report the synthesis of [18F]arylCF3 and [18F]arylCHF2 derivatives from arylCF2Br and arylCHFCl precursors applying a silver-mediated halogen exchange with [18F]fluoride. In the absence of Ag(I)OTf, no reaction takes place at room temperature for both classes of substrates; this result demonstrates the beneficial role of silver(I) as a means to induce 18F-incorporation under very mild conditions.
- Verhoog, Stefan,Pfeifer, Lukas,Khotavivattana, Tanatorn,Calderwood, Samuel,Collier, Thomas Lee,Wheelhouse, Katherine,Tredwell, Matthew,Gouverneur, Véronique
-
supporting information
p. 25 - 28
(2015/12/26)
-
- Using the same hydroxamic acid derivative and HDAC8 inhibitor (by machine translation)
-
Disclosed are: a compound which is capable of inhibiting the function of HDAC8; and an HDAC8 inhibitor. Specifically disclosed is a hydroxamic acid derivative which is characterized by being composed of a compound represented by general formula (1) (wherein X represents an aromatic substituent or an optionally substituted 3-8 membered ring, and n represents an integer of 0-20), or a pharmaceutically acceptable salt, hydrate, solvate or prodrug thereof.
- -
-
Paragraph 0028; 0029
(2016/10/09)
-
- HIGH GLASS TRANSITION TEMPERATURE "MEDIUM-SIZED" AMBIPOLAR HOST MATERIALS
-
Disclosed herein are am bipolar host compounds represented by formula (I), wherein: a) R4 is an optionally substituted aryl or an optionally substituted heteroaryl group; b) n is at least 2; e) for each (ii) at least one of R1, R2 and R3 is independently an optionally substituted carbazole group, and the remaining of R1, R2 and R3 are independently selected from hydrogen, halogen and a C1-20 organic group: and d ) Y is selected from (III), wherein R5 is an.optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkyl group or an optionally substituted heteroalkyl group, and wherein R6 is hydrogen,, an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkyl -group or an optionally substituted heteroalky! group. The compounds can be used in OLED devices and are ambipolar. The OLED devices can show high efficiency and high luminance.
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-
Page/Page column 29; 30
(2014/02/15)
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- Copper-catalyzed decarboxylative methylation of aromatic carboxylic acids with PhI(OAc)2
-
The copper-catalyzed decarboxylative methylation of aromatic carboxylic acids was developed by using PhI(OAc)2 to provide a new strategy for the methylation of aryl acids through the decarboxylation of alkyl acids. The mechanism and the roles of each reactant in the reaction were investigated extensively. Copyright
- Jiang, Yuyu,Pan, Shulei,Zhang, Yanghui,Yu, Jingxun,Liu, Hongqiang
-
supporting information
p. 2027 - 2031
(2014/04/17)
-
- Cu-catalyzed fluorination of diaryliodonium salts with KF
-
A mild Cu-catalyzed nucleophilic fluorination of unsymmetrical diaryliodonium salts with KF is described. This protocol preferentially fluorinates the smaller aromatic ligand on iodine(III). The reaction exhibits a broad substrate scope and proceeds with high chemoselectivity and functional group tolerance. DFT calculations implicate a CuI/CuIII catalytic cycle.
- Ichiishi, Naoko,Canty, Allan J.,Yates, Brian F.,Sanford, Melanie S.
-
supporting information
p. 5134 - 5137
(2013/10/22)
-
- Selective oxidation of alcohols to esters using heterogeneous Co 3O4-N@C catalysts under mild conditions
-
Novel cobalt-based heterogeneous catalysts have been developed for the direct oxidative esterification of alcohols using molecular oxygen as benign oxidant. Pyrolysis of nitrogen-ligated cobalt(II) acetate supported on commercial carbon transforms typical homogeneous complexes to highly active and selective heterogeneous Co3O4-N@C materials. By applying these catalysts in the presence of oxygen, the cross and self-esterification of alcohols to esters proceeds in good to excellent yields.
- Jagadeesh, Rajenahally V.,Junge, Henrik,Pohl, Marga-Martina,Radnik, Joerg,Brueckner, Angelika,Beller, Matthias
-
supporting information
p. 10776 - 10782
(2013/08/23)
-
- Regioselective bromination and iodination of aromatic substrates promoted by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane
-
Selective and efficient bromination and iodination of aromatic compounds by ammonium bromide and ammonium iodide, respectively, under promotion of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane have been explored. Mild reaction conditions, high selectivity and yield, and high reaction rate are some of the major advantages of this synthetic method.
- Azarifar, Davood,Khosravi, Kaveh,Najminejad, Zohreh,Soleimani, Khadijeh
-
experimental part
p. 321 - 326
(2012/08/14)
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- Synthesis and incorporation into cyclic peptides of tolan amino acids and their hydrogenated congeners: Construction of an array of A-B-loop mimetics of the Cε3 domain of human IgE
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The disruption of the human immunolobulin E-high affinity receptor I (IgE-FcεRI) protein-protein interaction (PPI) is a validated strategy for the development of anti asthma therapeutics. Here, we describe the synthesis of an array of conformationally constrained cyclic peptides based on an epitope of the A-B loop within the Cε3 domain of IgE. The peptides contain various tolan (i.e., 1,2-biarylethyne) amino acids and their fully and partially hydrogenated congeners as conformational constraints. Modest antagonist activity (IC50 ~660 μM) is displayed by the peptide containing a 2,2′-tolan, which is the one predicted by molecular modeling to best mimic the conformation of the native A-B loop epitope in IgE.
- Offermann, Daniel A.,McKendrick, John E.,Sejberg, Jimmy J. P.,Mo, Bingli,Holdom, Mary D.,Helm, Birgit A.,Leatherbarrow, Robin J.,Beavil, Andrew J.,Sutton, Brian J.,Spivey, Alan C.
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experimental part
p. 3197 - 3214
(2012/05/19)
-
- Rapid discovery of highly potent and selective inhibitors of histone deacetylase 8 using click chemistry to generate candidate libraries
-
To find HDAC8-selective inhibitors, we designed a library of HDAC inhibitor candidates, each containing a zinc-binding group that coordinates with the active-site zinc ion, linked via a triazole moiety to a capping structure that interacts with residues on the rim of the active site. These compounds were synthesized by using click chemistry. Screening identified HDAC8-selective inhibitors including C149 (IC50 = 0.070 μM), which was more potent than PCI-34058 (6) (IC50 = 0.31 μM), a known HDAC8 inhibitor. Molecular modeling suggested that the phenylthiomethyl group of C149 binds to a unique hydrophobic pocket of HDAC8, and the orientation of the phenylthiomethyl and hydroxamate moieties (fixed by the triazole moiety) is important for the potency and selectivity. The inhibitors caused selective acetylation of cohesin in cells and exerted growth-inhibitory effects on T-cell lymphoma and neuroblastoma cells (GI50 = 3-80 μM). These findings suggest that HDAC8-selective inhibitors have potential as anticancer agents.
- Suzuki, Takayoshi,Ota, Yosuke,Ri, Masaki,Bando, Masashige,Gotoh, Aogu,Itoh, Yukihiro,Tsumoto, Hiroki,Tatum, Prima R.,Mizukami, Tamio,Nakagawa, Hidehiko,Iida, Shinsuke,Ueda, Ryuzo,Shirahige, Katsuhiko,Miyata, Naoki
-
p. 9562 - 9575
(2013/01/16)
-
- Superelectrophilic iodination of deactivated arenes with triiodoisocyanuric acid
-
The reaction of triiodoisocyanuric acid (TICA) with deactivated arenes in acidic medium led to the efficient and regioselective formation of the corresponding iodoarenes, in 55-88% isolated yield. The acidity of the medium was found to be the most important factor influencing the electrophilic iodination of weakly nucleophilic substrates by TICA. Georg Thieme Verlag Stuttgart New York.
- Da Ribeiro, Rodrigo S.,Esteves, Pierre M.,De Mattos, Marcio C. S.
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experimental part
p. 739 - 744
(2011/04/24)
-
- On the use of 2-(trimethylsilyl)iodobenzene as a benzyne precursor
-
A mild method for the generation of benzynes from 2-(trimethylsilyl) iodobenzene derivatives is reported. The employment of silver fluoride in conjunction with caesium fluoride is key for promoting useful levels of elimination and providing benzyne derived products in good yields. Moreover, the substrates are accessed by a novel alkynyl iodide cycloaddition.
- Crossley, James A.,Kirkham, James D.,Browne, Duncan L.,Harrity, Joseph P. A.
-
experimental part
p. 6608 - 6610
(2011/01/12)
-
- POLYMERIZABLE AMBIPOLAR HOSTS FOR PHOSPHORESCENT GUEST EMITTERS
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The inventions describe disclosed and described herein relate to polymerizable ambipolar monomers, useful for making polymer or copolymer host materials for guest phosphorescent metal complexes, which together can form emission layers of organic light emitting diodes (OLEDs). Methods of making the ambipolar monomers are also described. Formula (I) wherein at least one of the R1, R2 and R3 groups is an optionally substituted carbazole group.
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Page/Page column 45
(2011/01/12)
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- Synthesis of berberineefflux pump inhibitor hybrid antibacterials
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This article describes the compact synthesis of two isomeric dual-action hybrid antimicrobials where the 13-position of the antibacterial berberine has been linked via 3′-and 4′-methylene bridges to INF55 (5-nitro-2-phenylindole), an inhibitor of the bacterial NorA multidrug-resistance pump. Copyright Taylor & Francis Group, LLC.
- Bremner, John B.,Kelso, Michael J.
-
body text
p. 3561 - 3568
(2011/03/17)
-
- RADIOIODINATION METHOD
-
The present invention provides a method for the synthesis of radioiodinated compounds which is advantageous over prior art methods. Using a hydrazine or an aminoxy in place of a primary amine for indirect radioiodination facilitates a much quicker reaction thus reducing reaction time and increasing the yield. In addition, where there are primary amines in the molecule to be radioiodinated, such as the N-terminus of a peptide or lysine residues, reaction at the hydrazine or aminoxy is greatly favoured.
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Page/Page column 25
(2010/08/09)
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- Directional hydrogen bonding controlled 2D self-organization of phenyleneethynylenes: From linear assembly to rectangular network
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The effect of the carboxylic acid substituent position of phenyleneethynylene systems on the 2D self-organization is revealed by scanning tunneling microscopy.
- Ramesh,Thomas, K. George
-
supporting information; experimental part
p. 3457 - 3459
(2010/07/16)
-
- Tetraalkylammonium dichloroiodates as iodinating agents: Absence of activity in solid phases and superelectrophilic activity in sulfuric acid
-
In contrast to published results, tetraalkylammonium dichloroiodates (Alk4N+ICl2-) cannot be iodinating reagents for arenes in solvent-free conditions. Nevertheless, tetraalkylammonium dichloroiodates in sulfuric acid solutions or in the presence of Ag 2SO4 in H2SO4 possess superelectrophilic properties and act as very convenient and efficient iodinating agents for deactivated arenes. Georg Thieme Verlag Stuttgart.
- Filimonov, Victor D.,Semenischeva, Nadya I.,Krasnokutskaya, Elena A.,Ho, Yun Hwang,Chi, Ki-Whan
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p. 401 - 404
(2008/09/20)
-
- Alpha-helical mimetics
-
Benzoyl urea derivatives that are alpha helical peptides mimetics that mimic BH3-only proteins, compositions containing them, their conjugation to cell-targeting-moieties, and their use in the regulation of cell death are disclosed. The benzoyl urea derivatives are capable of binding to and neutralizing pro-survival Bcl-2 proteins. Use of benzoyl urea derivatives in the treatment and/or prophylaxis of diseases or conditions associated with deregulation of cell death are also described.
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Page/Page column 105
(2011/05/18)
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- Synthesis and evaluation of synthetic retinoid derivatives as inducers of stem cell differentiation
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All-trans-retinoic acid (ATRA) and its associated analogues are important mediators of cell differentiation and function during the development of the nervous system. It is well known that ATRA can induce the differentiation of neural tissues from human pluripotent stem cells. However, it is not always appreciated that ATRA is highly susceptible to isomerisation when in solution, which can influence the effective concentration of ATRA and subsequently its biological activity. To address this source of variability, synthetic retinoid analogues have been designed and synthesised that retain stability during use and maintain biological function in comparison to ATRA. It is also shown that subtle modifications to the structure of the synthetic retinoid compound impacts significantly on biological activity, as when exposed to cultured human pluripotent stem cells, synthetic retinoid 4-(5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalen-2-ylethynyl)benzoic acid, 4a (para-isomer), induces neural differentiation similarly to ATRA. In contrast, stem cells exposed to synthetic retinoid 3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylethynyl)benzoic acid, 4b (meta-isomer), produce very few neurons and large numbers of epithelial-like cells. This type of structure-activity-relationship information for such synthetic retinoid compounds will further the ability to design more targeted systems capable of mediating robust and reproducible tissue differentiation.
- Christie, Victoria B.,Barnard, Jonathan H.,Batsanov, Andrei S.,Bridgens, Caroline E.,Cartmell, Emily B.,Collings, Jonathan C.,Maltman, Daniel J.,Redfern, Christopher P. F.,Marder, Todd B.,Przyborski, Stefan,Whiting, Andrew
-
experimental part
p. 3497 - 3507
(2009/02/05)
-
- New anti-viral drugs for the treatment of the common cold
-
Human Rhinovirus (HRV) is the most important aetiologic agent of common cold in adults and children. HRV is a single-stranded, positive sense RNA virus and, despite the high level of conservation among different serotypes, sequence alignment of viral protease 3C with mammalian protease reveals no homology. Thus, protease 3C is an optimal target for the development of anti-HRV agents. In the present work we investigated the design, the synthesis and the development of new potential reversible inhibitors against HRV protease 3C. Docking studies on the crystallized structure of HRV2 protease 3C led us to the design and the synthesis of a series of 3,5 disubstituted benzamides able to act as analogues of the substrate. We also developed 1,3,5 trisubstituted benzamides where aromatic substitutions on the aryl ring led us to investigate the importance of π-π interaction on the stabilization of protease 3C-inhibitor complex. All structures were tested for enzymatic inhibition on HRV14 protease 3C. Results highlighted the inhibitory activity of compounds 13, 14, and 20 (91%, 81%, and 85% at 10 μM, respectively), with the latter exhibiting an ID50 (dose that inhibits 50% of the viral cytopathic effect) on HRV-14 = 25 μg/ml.
- Maugeri, Caterina,Alisi, Maria A.,Apicella, Claudia,Cellai, Luciano,Dragone, Patrizia,Fioravanzo, Elena,Florio, Saverio,Furlotti, Guido,Mangano, Giorgina,Ombrato, Rosella,Luisi, Renzo,Pompei, Raffaello,Rincicotti, Vito,Russo, Vincenzo,Vitiello, Marco,Cazzolla, Nicola
-
p. 3091 - 3107
(2008/09/20)
-
- Oxidative iodination of deactivated arenes in concentrated sulfuric acid with I2/NaIO4 and KI/NaIO4 iodinating systems
-
Deactivated arenes were mono- or diiodinated with strong electrophilic I+ reagents, which were prepared from NaIO4 and either I2 or KI in concentrated H2SO4 (minimum 95% by weight). In general a small excess of the dark brown iodinating solution was used (1.1/1.5 equivalents, for nitrobenzene two equivalents was required). The iodinations were conducted at 25-30 °C with a reaction time of 1-2 hours using either a 'direct' or an 'inverse' method of aromatic iodination to give mono- or diiodinated pure products in 31-91% optimized yields. Georg Thieme Verlag Stuttgart.
- Kraszkiewicz, Lukasz,Sosnowski, Maciej,Skulski, Lech
-
p. 1195 - 1199
(2007/10/03)
-
- A Novel Aromatic Iodination Method, with Sodium Periodate Used as the Only Iodinating Reagent
-
Benzene, halobenzenes and some deactivated arenes readily reacted in anhydrous NaIO4/AcOH/Ac2O/concd. H2SO4 mixtures to afford, after quenching with excess aqueous Na2SO3 solution (a reducing agent), purified iodinated products in 27-88 percent yields. This novel method of aromatic iodination is simple, fairly effective and environmentally safe.
- Lulinski, Piotr,Sosnowski, Maciej,Skulski, Lech
-
p. 671 - 675
(2007/10/03)
-
- Eco-friendly oxidative iodination of various arenes with sodium percarbonate as the oxidant http://www.mdpi.org
-
Six easy laboratory procedures are presented for the oxidative iodination of various aromatics, mostly arenes, with either molecular iodine or potassium iodide (used as the sources of iodinating species, I+ or I 3+), in the presence of sodium percarbonate (SPC), a stable, cheap, easy to handle, and eco-friendly commercial oxidant.
- Zielinska, Agnieszka,Skulski, Lech
-
p. 1307 - 1317
(2007/10/03)
-
- An aromatic iodination method, with iodic acid used as the only iodinating reagent
-
Benzene, halobenzenes, and a number of more or less deactivated arenes, including nitrobenzene, readily reacted in anhydrous HIO3/AcOH/ Ac2O/conc. H2SO4 mixtures to probably give ArIO2 intermediates or other hypervalent species (not isolated). The final reaction mixtures were poured into excess aq. Na2SO3 solution (a reductant) to give the purified iodinated products in 39-83% yields.
- Krassowska-Swiebocka, Barbara,Prokopienko, Grazyna,Skulski, Lech
-
p. 394 - 400
(2007/10/03)
-
- Carboxylation and esterification of functionalized arylcopper reagents
-
Functionalized arylcopper reagents have been produced in good yields at 25 °C from activated copper and the corresponding functionalized aryl iodides without the need of traditional organolithium or Grignard precursors. These organocopper compounds will undergo carboxylation with CO2 to form the corresponding copper benzoates. In turn, these salts can be acidified to produce the functionalized aryl acids or treated with appropriate alkyl halides in the presence of a dipolar aprotic solvent to generate the corresponding aryl esters. This methodology permits the formation of functionalized organic acids and esters that could not be generated by the carboxylation of organomagnesium compounds.
- Ebert, Greg W.,Juda, Wayne L.,Kosakowski, Robert H.,Ma, Bing,Dong, Liming,Cummings, Keith E.,Phelps, Mwita V. B.,Mostafa, Adel E.,Luo, Jianyuan
-
p. 4314 - 4317
(2007/10/03)
-
- The conversion of phenols to the corresponding aryl halides under mild conditions
-
Mild, novel procedures have been developed for the syntheses of aryl halides from the corresponding phenols in modest to good yields via boronate ester intermediates.
- Thompson, Alicia L. S.,Kabalka, George W.,Akula, Murthy R.,Huffman, John W.
-
p. 547 - 550
(2007/10/03)
-
- Eco-friendly Oxidative Iodination of Various Arenes with a Urea-Hydrogen Peroxide Adduct (UHP) as the Oxidant
-
Three easy eco-friendly laboratory procedures are presented for the oxidative iodination of various activated and deactivated arenes with molecular iodine, in the presence of UHP (percarbamide), a stable, strongly H-bonded, solid urea-hydrogen peroxide adduct as the oxidant.
- Lulinski, Piotr,Kryska, Anna,Sosnowski, Maciej,Skulski, Lech
-
p. 441 - 445
(2007/10/03)
-
- Easy, inexpensive and effective oxidative iodination of deactivated arenes in sulfuric acid
-
Two 'model' deactivated arenes, benzoic acid and nitrobenzene, were effectively monoiodinated within 1 h at 25-30 °C, with strongly electrophilic I+ reagents, prior prepared from diiodine and various oxidants (CrO3, KMnO4, active MnO2, HIO 3, NaIO3, or NaIO4) in 90% (v/v) concd sulfuric acid (ca. 75 mol% H2SO4). Next, an I2/ NaIO3/90% (v/v) concd H2SO4 exemplary system was used to effectively mono- or diiodinate a number of deactivated arenes. All former papers dealing with the direct iodination of deactivated arenes are briefly reviewed.
- Kraszkiewicz, Lukasz,Sosnowski, MacIej,Skulski, Lech
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p. 9113 - 9119
(2007/10/03)
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- Vitamin d analogues
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Compounds of the formula I wherein X represents hydrogen or hydroxy; R1 and R2, which may be the same or different, represent hydrogen, (C1-C4)alkyl optionally substituted with one hydroxyl group or one or more fluorine atoms, or, together with the carbon atom to which they are attached, R1 and R2 form a (C3-C5)carbocyclic ring; R3 represents (C1-C4)alkyl, (C1-C4)alkoxy or a halogen atom, such as fluorine, chlorine, bromine, or iodine, and in-vivo hydrolyzable esters thereof with pharmaceutically acceptable acids, may be used in the prophylaxis and/or treatment of dieases characterized by abnormal cell differentiation and/or cell proliferation.
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- Chemoselective one-pot reductive deamination of aryl amines
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A one-pot deamination of a wide variety of substituted anilines is described. The process involves a diazotization-dediazotization utilizing acetic acid, sodium nitrite, and sodium bisulfite- inexpensive, 'green' reagents. The process occurs quickly under mild conditions, tolerates sensitive functionality, and gives products in modest-to-good yields (16-88%).
- Geoffroy, Otto J.,Morinelli, Thomas A.,Meier, G. Patrick
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p. 5367 - 5369
(2007/10/03)
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- Iodination of both deactivated and activated arenes with sodium periodate or sodium iodate as the oxidants
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Five easy, relatively inexpensive, and environmentally-safe aromatic oxidative iodination procedures are presented; three of them are particularly suitable for deactivated arenes. Nine deactivated arenes, four halobenzenes, benzene, toluene, and N,N-dimethylaniline were reacted upon with the following anhydrous systems: diiodine/NaIO4 or (in four cases) NaIO3/acetic anhydride/glacial acetic acid, acidified with varying amounts of concd (98%) sulfuric acid; the following workups are explained. The aromatic oxidative iodination reactions proceeded mostly at room temperature and within 1-8 h to give fifteen mono- and two diiodinated purified products (sometimes obtained in 2-3 different ways) in 51-95% yields.
- Lulinski, Piotr,Skulski, Lech
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p. 951 - 956
(2007/10/03)
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- 2,4,6,8-Tetraiodoglycoluril in sulfuric acid as a new powerful reagent for iodination of deactivated arenes
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Deactivated arenes are iodinated readily at 0°C by the action of 2,4,6,8-tetraiodoglycoluril in sulfuric acid to give the iodoarenes in generally good yields. (C) 2000 Elsevier Science Ltd.
- Chaikovski,Filimonov,Yagovkin,Kharlova
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p. 9101 - 9104
(2007/10/03)
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- Substituted-pent-4-ynoic acids
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PCT No. PCT/US96/11613 Sec. 371 Date Sep. 14, 1998 Sec. 102(e) Date Sep. 14, 1998 PCT Filed Jul. 12, 1996 PCT Pub. No. WO97/03945 PCT Pub. Date Feb. 6, 1997Compounds of formula (I) wherein: R1 is -(CR4R5)nC(O)O(CR4R5)mR6, -(CR4R5)nC(O)NR4(CR4R5)mR6, (CR4R5)nO(CR4R5)mR6, or -(CR4R5)rR6: W is alkynyl or 2 carbon atoms; R3 is H or R7; Z is C(O)R13, (CH2)0-1C(O)OR13, (CH2)0-1C(O)NR10R13, (CH2)0-1C(R8R8)OR8, -NHC(O)R7, (CH2)0-1NR10R13, NH[C(O)C(O)OR8], CH2NH[C(O)CNR10R13], CH2S(O)qR7, CH[S(O)qR7]2, dithiolane, (tetrazol-5-yl), thiazol-2-yl, [1,2,4]thiadiazol-5-yl, [1,3,4]oxadiazol-2-yl, imidazol-2-yl, oxazol-2-yl, or (3- or 5-oxadiazolyl[1,2,4]; R7 is -(CR4R5)qR11 or C1-6 alkyl wherein the R11 or C1-6 alkyl group is unsubstituted or substituted one or more times by methyl or ethyl unsubstituted or substituted by 1-3 fluorines, -NR8R10, -CO2R8, -O(CH2qR8, -NR8C(O)R8 or R12; or the pharmaceutically acceptable salts thereof.
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- Oxidative iodination of arenes with manganese(IV) oxide or potassium permanganate as the oxidants
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Novel and easy laboratory methods (novel Procedures 1-4) are presented for the oxidative mono- and diiodination of both activated and deactivated arenes, which gave the pure iodinated products in 62-89% yields. The reactions were carried out in the anhydrous, strongly acidic system, I2/activated MnO2/AcOH/Ac2O/concd H2SO4, firstly at r.t. for 2 h, then at 45-55 °C for 2-9 h. The resulting mixtures were poured into excess aq Na2SO3 solution buffered with (NH4)2CO3 to neutralize H2SO4. The following workups are given. Similarly, on carrying out the iodination reactions (at 35 °C, for one hour) in the anhydrous, strongly acidic system, I2/KMnO4/AcOH/Ac2O/concd H2SO4, it was possible to mono- or diiodinate several deactivated arenes in 73-87% yields (improved Procedures 5 and 6).
- Lulinski, Piotr,Skulski, Lech
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p. 115 - 120
(2007/10/03)
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- 4,4-(disubstituted)cyclohexan-1-ols monomers and related compounds
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The present invention relates to 4,4(disubstituted)cyclohexan-1-ol monomers and related compounds, pharmaceutical compositions containing these compounds, and their use in treating allergic and inflammatory diseases and for inhibiting the production of Tumor Necrosis Factor (TNF).
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- 3,3-(disubstituted)cyclohexan-1-one monomers and related compounds
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This invention relates to derivatives of 3,3-(disubstituted)cyclohexan-1-one monomers and related compounds which are useful for treating allergic and inflammatory diseases.
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- 4,4-(disubstituted)cyclohexan-1-ols monomers and related compounds
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The present invention relates to novel 4,4-(disubstituted)cyclohexan-1-ols monomers and related compounds, pharmaceutical compositions containing these compounds, and their use in treating allergic and inflammatory diseases and for inhibiting the production to Tumor necrosis Factor (TNF).
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- The direct iodination of arenes with chromium(VI) oxide as the oxidant
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An easy and cheap laboratory method is presented for the direct mono- and diiodination of a number of activated and deactivated arenes. The main iodination reactions occurred at the temperatures not exceeding 65°C for 0.5-12 h in the anhydrous, strongly acidic liquid system, I2/AcOH/Ac2O/H2SO4, in the presence of prior dissolved CrO3 used as the oxidant. The yields of the pure iodinated products varied from 31% (for 3,5- diiodobenzoic acid) up to 90% (for 4-iodoanisole). So far, benzonitrile and some oxidizable aromatics, e.g. naphthalene, fluorene, xanthene, and thiophene, have been found to be unsuitable for the effective iodination. Nevertheless, this novel, simple method of direct iodination is worthy to be extended to other appropriate aromatics.
- Lulinski, Piotr,Skulski, Lech
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p. 1665 - 1669
(2007/10/03)
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- Acid-Mediated Reaction of Bis(pyridine)iodonium(I) Tetrafluoroborate with Aromatic Compounds. A Selective and General Iodination Method
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Reaction of aromatic compounds with bis(pyridine)iodonium(I) tetrafluoroborate (IPy2BF4) in the presence of HBF4 or CF3SO3H in CH2Cl2 at room temperature furnishes monoiodo derivatives with excellent regioselectivity and yields.Use of either acid gives comparable results with activated aromatics, whereas CF3SO3H is much more effective in the iodination of deactivated aromatics.
- Barluenga, Jose,Gonzalez, Jose M.,Garcia-Martin, Miguel A.,Campos, Pedro J.,Asensio, Gregorio
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p. 2058 - 2060
(2007/10/02)
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- An Expeditious and General Aromatic Iodination Procedure
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The reaction of IPy2BF4 with an arene and an acid (HBF4 or CF3SO3H), in CH2Cl2 at room temperature, provides a mild and efficient entry to the preparation of iodinated arenes.
- Barluenga, Jose,Gonzalez, Jose M.,Garcia-Martin, Miguel A.,Campos, Pedro J.,Asensio, Gregorio
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p. 1016 - 1017
(2007/10/02)
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- Correlation of Carbon-13 Substituent-Induced Chemical Shifts: meta- and para-Substituted Methyl Benzoates
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Carbon-13 NMR spectra are reported for 69 substituted methyl benzoates in deuteriochloroform or in its mixture with dimethyl sulphoxide-d6.The substituent-induced chemical shifts (SCS) of the CO carbon correlate poorly with dual substituent parameters (DSP) in all possible modifications, and for meta derivatives in particular this correlation is both overparameterized and imprecise.A much better correlation was obtained with parameters (designated Bm, Bp and Cp) derived previously by principal component analysis (PCA) from a larger set.The SCS of the CH3 carbon correlate very well with the original simple Hammett equation, and no DSP treatment is needed.The clustering of substituents is not consequential in such a large set.KEY WORDS Methyl benzoates 13C NMR Substituent effects
- Budesinsky, Milos,Exner, Otto
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p. 585 - 591
(2007/10/02)
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