- INHIBITORS OF PURINE NUCLEOSIDE PHOSPHORYLASE - SYNTHESIS AND USE THEREOF FOR TREATMENT OF T-CELL ACUTE LYMPHOBLASTIC LEUKEMIA AND LYMPHOMA
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The present invention relates to new compounds of general formula I, their synthesis, their pharmaceutically acceptable salts, and their use in treatment of T-cell acute lymphoblastic leukemia and lymphoma.
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Page/Page column 24
(2021/05/07)
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- Rapid Access to Azabicyclo[3.3.1]nonanes by a Tandem Diverted Tsuji–Trost Process
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A three-step synthesis of the 2-azabicyclo[3.3.1]nonane ring system from simple pyrroles, employing a combined photochemical/palladium-catalysed approach is reported. Substrate scope is broad, allowing the incorporation of a wide range of functionality relevant to medicinal chemistry. Mechanistic studies demonstrate that the process occurs by acid-assisted C?N bond cleavage followed by β-hydride elimination to form a reactive diene, demonstrating that efficient control of what might be considered off-cycle reactions can result in productive tandem catalytic processes. This represents a short and versatile route to the biologically important morphan scaffold.
- Steeds, Hannah G.,Knowles, Jonathan P.,Yu, Wai L.,Richardson, Jeffery,Cooper, Katie G.,Booker-Milburn, Kevin I.
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supporting information
p. 14330 - 14334
(2020/10/12)
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- One-pot synthesis of hypervalent diaryl(iodo)bismuthanes from o-carbonyl iodoarenes by zincation
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Diaryl(iodo)bismuthanes possessing a hypervalent C=O???Bi-I bond were conveniently synthesized in a one-pot reaction by using arylzinc reagents generated from o-carbonyl iodobenzenes and zinc powder under ultrasonication. This method is superior to the conventional organolithium and Grignard methods because it has a wide functional group tolerance, requires no protecting group manipulations, and proceeds under mild reaction conditions that do not need low temperature control. Furthermore, no intermediate triarylbismuthane precursor for the hypervalent iodobismuthane is necessary.
- Murafuji, Toshihiro,Hafizur Rahman,Magarifuchi, Daiki,Narita, Masahiro,Miyakawa, Isamu,Ishiguro, Katsuya,Kamijo, Shin
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- Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions
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The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon. The electronic effects are studied in other contexts, including hydroacyloxylation and hydroamination, and similar trends in directionality are predominant although not uniformly observed.
- Costello, Jeff P.,Ferreira, Eric M.
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p. 9934 - 9939
(2019/12/24)
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- Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds
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Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.
- Iida, Keisuke,Ishida, Shunsuke,Watanabe, Takamichi,Arai, Takayoshi
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- Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds
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Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.
- Iida, Keisuke,Ishida, Shunsuke,Watanabe, Takamichi,Arai, Takayoshi
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p. 7411 - 7417
(2019/06/18)
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- Palladium-Catalyzed, Norbornene-Mediated, ortho-Amination ipso-Amidation: Sequential C-N Bond Formation
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A palladium-catalyzed, norbornene-mediated ortho- and ipso-C-N bond-forming Catellani reaction is reported. This reaction proceeds through a sequential intermolecular amination followed by intramolecular cyclization of a tethered amide. The products, ortho-aminated dihydroquinolinones, were generated in moderate to good yields and are present in bioactive molecules. This work highlights the challenge of competing intra- vs intermolecular palladium-catalyzed processes.
- Whyte, Andrew,Olson, Maxwell E.,Lautens, Mark
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supporting information
p. 345 - 348
(2018/01/27)
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- Cu-Catalyzed Enantioselective Ring Opening of Cyclic Diaryliodoniums toward the Synthesis of Chiral Diarylmethanes
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A Cu-catalyzed enantioselective desymmetrizing ring-opening reaction of six-membered cyclic diaryliodonium salts with carboxylic acids or thioacids is reported for the facile access to chiral diarylmethanes. A Cu/[cyclopropyl bis(oxazoline)] catalyst well
- Li, Bin,Chao, Zengyin,Li, Chunyu,Gu, Zhenhua
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supporting information
p. 9400 - 9403
(2018/07/30)
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- Total synthesis of selaginpulvilins A and C
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An efficient formal total synthesis of two compounds from the selaginpulvilin family of natural products, selaginpulvilin A and C, has been successfully achieved. The tetradehydro Diels-Alder (TDDA) reaction between an enyne and alkyne has been utilized for the creation of the necessary fluorene skeleton. Attempts at the conversion of selaginpulvilin A to selaginpulvilin B, F and H were unsuccessful.
- Chinta, Bhavani Shankar,Baire, Beeraiah
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p. 262 - 265
(2018/01/12)
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- F- Nucleophilic-Addition-Induced [3 + 2] Annulation: Direct Access to CF3-Substituted Indenes
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An efficient [3 + 2] annulation of (2,2-difluorovinyl)-2-iodoarenes and internal alkynes was developed for the synthesis of 1-(trifluoromethyl)-1H-indenes. The success of this strategy hinges upon a well-balanced process for the generation of two transient reactive species, specifically trifluoroethylsilver and alkenylpalladium intermediates, in the same molecule, as well as a smooth transmetalation step, which delicately joins together these two different metallic intermediates.
- Tang, Hai-Jun,Zhang, Yu-Feng,Jiang, Yi-Wen,Feng, Chao
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supporting information
p. 5190 - 5193
(2018/09/12)
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- Formal total synthesis of selaginpulvilin D
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An efficient and mild synthetic strategy for the total synthesis of selaginpulvilin D has been reported. A highly chemoselective enyne-alkyne dehydro Diels-Alder reaction has been employed for the construction of the tricyclic fluorene framework present i
- Chinta, Bhavani Shankar,Baire, Beeraiah
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supporting information
p. 5908 - 5911
(2017/07/25)
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- Lewis Acid Catalyzed Formal Intramolecular [3 + 3] Cross-Cycloaddition of Cyclopropane 1,1-Diesters for Construction of Benzobicyclo[2.2.2]octane Skeletons
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A novel Lewis acid catalyzed formal intramolecular [3 + 3] cross-cycloaddition (IMCC) of cyclopropane 1,1-diesters has been successfully developed. This supplies an efficient and conceptually new strategy for construction of bridged bicyclo[2.2.2]octane skeletons. This [3 + 3]IMCC could be run up to gram scale and from easily prepared starting materials. This [3 + 3]IMCC, together with our previously reported [3 + 2]IMCC strategy, can afford either the bicyclo[2.2.2]octane or bicyclo[3.2.1]octane skeletons from the similar starting materials by regulating the substituents on vinyl group.
- Ma, Weiwei,Fang, Jie,Ren, Jun,Wang, Zhongwen
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supporting information
p. 4180 - 4183
(2015/09/15)
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- Enantioselective allylation of selected ortho-substituted benzaldehydes: A comparative study
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We report a systematic study of the allylation of ortho-substituted benzaldehydes under catalysis of a Lewis base (N, Ndioxide), a Lewis acid (Keck allylation), and a Bronsted acid. ortho-Halobenzaldehydes were used as the aldehydic substrates, and specia
- Hessler, Filip,Betk, Robert,Kadlkov, Aneta,Belle, Roman,Kotora, Martin
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supporting information
p. 7245 - 7252
(2015/01/09)
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- Gold(I)-catalyzed iodination of arenes
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A wide variety of electron-rich arenes were efficiently converted into the corresponding iodinated compounds via a gold(I)-catalyzed reaction under mild conditions. Georg Thieme Verlag Stuttgart. New York.
- Leboeuf, David,Ciesielski, Jennifer,Frontier, Alison J.
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supporting information
p. 399 - 402
(2014/03/21)
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- Intriguing substituent effect in modified Hoveyda-Grubbs metathesis catalysts incorporating a chelating iodo-benzylidene ligand
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A series of modified Hoveyda-Grubbs catalysts incorporating a chelating iodo-benzylidene ligand were prepared and characterized. The presence of electron-withdrawing ring substituents in the para position to the iodide was found to decrease the catalytic activity, revealing that dissociation of the Ru...I-Ar bond is not the rate-determining step.
- Barbasiewicz, Michal,Blocki, Krzysztof,Malinska, Maura,Pawlowski, Robert
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supporting information
p. 355 - 358
(2013/02/22)
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- Palladium-catalyzed insertion of N-tosylhydrazones for the synthesis of isoindolines
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Isoindolines are synthesized by palladium-catalyzed coupling reaction of N-(2-iodobenzyl) anilines with α,β-unsaturated N-tosylhydrazones. The reaction has several potential advantages: (1) toleration of a wide range of functional groups, (2) easy to handle and with mild conditions, (3) enriches the isoindoline family, (4) two new bonds form in one step.
- Zhou, Ping-Xin,Luo, Jian-Yi,Zhao, Lian-Biao,Ye, Yu-Ying,Liang, Yong-Min
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supporting information
p. 3254 - 3256
(2013/05/08)
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- Mild and selective organocatalytic iodination of activated aromatic compounds
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We describe an organocatalytic iodination of activated aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) as the iodine source with thiourea catalysts in acetonitrile. The protocol is applicable to a number of aromatic substrates with significantly different steric and electronic properties. The iodination is generally highly regioselective and provides high yields of isolated products. NMR kinetic investigations conducted in THF-d 8indicate the role of sulfur in the thiourea motif as a nucleophile that is assisted by H-bonding in the key steps of the reaction. Georg Thieme Verlag Stuttgart . New York.
- Jakab, Gergely,Hosseini, Abolfazl,Hausmann, Heike,Schreiner, Peter R.
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supporting information
p. 1635 - 1640
(2013/07/27)
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- New method of synthesis and biological evaluation of some combretastatin A-4 analogues
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A series of novel combretastatin A-4 analogues was synthesized in 36-64% yields by Negishi cross-coupling reaction under mild conditions. The prepared compounds exhibit good cytotoxicity against HBL100 epithelial cell lines (IC50=0.022-10.31 ). Georg Thieme Verlag Stuttgart · New York.
- Malysheva, Yulia B.,Combes, Sebastien,Fedorov, Alexey Yu.,Knochel, Paul,Gavryushin, Andrei E.
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supporting information; experimental part
p. 1205 - 1208
(2012/06/29)
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- Comparison of iodination of methoxylated benzaldehydes and related compounds using iodine/silver nitrate and iodine/periodic acid
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Iodination of the three methoxybenzaldehydes, four dimethoxybenzaldehydes, vanillin, and piperonal by two methods were compared. Iodine and periodic acid gave better yields for iodination for the methoxybenzaldehydes, whereas iodine and silver nitrate generally gave better yields for the rest of the compounds. Copyright Taylor & Francis Group, LLC.
- Hathaway, Bruce A.,White, Kristen L.,McGill, Mark E.
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p. 3855 - 3860
(2008/02/10)
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- Steric Effects on Atropisomerism in Tetraarylporphyrins
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The rate of aryl ring rotation in a series of 5,10,15,20-tetrakis(2-X-5-methoxyphenyl)porphyrins, where X = H, F, Cl, Br, and I, was studied by NMR spectroscopy and chromatography.Where X = Cl, Br, and I, the four atropisomers αβαβ, ααββ, αααβ, and αααα w
- Crossley, Maxwell J.,Field, Leslie D.,Forster, Adrienne J.,Harding, Margaret M.,Sternhell, Sever
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p. 341 - 348
(2007/10/02)
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- Arylation with 1,3-Dinitroarenes and Copper(I) t-Butoxide. Scope and Limitations
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The reaction of 1,3-dinitrobenzene with copper(I) t-butoxide and an iodoarene, which produces a 2,6-dinitrobiphenyl, has been stidied in detail with a variety of substrates.Iodoarenes containing ester, aldehyde, or other halogen functions were effective, but replacement of the iodoarene with a bromoarene, iodoalkyne, or iodoalkene resulted in less efficient coupling, promoting side-reactions.On replacing the second nitro group on the dinitrobenezene with nitrile, ester, amide, or trifluoromethyl groups, little or no coupling was observed.Limiting side-reactions usually involved the decomposition of substrates by t-butoxide via nucleophilic substitution, elimination, or deprotonation.A mechanism based on reversible cupration of the dinitroarene is proposed.
- Carter, Stephen D.,Wallace, Timothy W.
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p. 1601 - 1633
(2007/10/02)
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- Metalation of o-Halostyrene Oxides. Preparation of Benzocyclobutenols
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o-Bromo- and o-iodostyrene oxides are converted in fair to good yield to benzocyclobutenols upon treatment with n-BuLi and MgBr2 in THF or ether at -78 deg C, followed by warming to room temperature.The reaction involves initial halogen-lithium exchange followed either by MgBr2-initiated opening of the epoxide function to a haloalkoxide or rearrangement of the epoxide function to a ketone or aldehyde followed by cyclization.Benzocyclobutenol formation was not successful in the case of o-halostilbene oxides.
- Akguen, Eyup,Glinski, Margaret B.,Dhawan, Kasturi L.,Durst, Tony
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p. 2730 - 2734
(2007/10/02)
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