- Synthesis of 2-alkoxy-8-hydroxyadenylpeptides: Towards synthetic epitope-based vaccines
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The preparation of three different 2-alkoxy-8-hydroxyadenylpeptide conjugates has been accomplished by solid-phase synthesis combined with 'on-resin' Cu(I) catalyzed Huisgen cycloaddition. The immunogenicity of the compounds has been evaluated in IL-12 production and antigen presentation assays.
- Weterings, Jimmy J.,Khan, Selina,van der Heden, Gerbrand J.,Drijfhout, Jan W.,Melief, Cornelis J.M.,Overkleeft, Herman S.,van der Burg, Sjoerd H.,Ossendorp, Ferry,van der Marel, Gijsbert A.,Filippov, Dmitri V.
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Read Online
- Iodine-catalyzed oxidative functionalization of purines with (thio)ethers or methylarenes for the synthesis of purin-8-one analogues
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An efficient oxidative functionalization of purine-like substrates with (thio)ethers or methylarenes under mild conditions is described. Using I2as the catalyst, and TBHP as the oxidant, this protocol provides a valuable synthetic tool for the assembly of a wide range of 9-alkyl(benzyl)purin-8-one derivatives with high atom- and step-economy and exceptional functional group tolerance.
- Zhuge, Juanping,Jiang, Ziyang,Jiang, Wei,Histand, Gary,Lin, Dongen
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supporting information
p. 5121 - 5126
(2021/06/21)
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- Regioselective alkylation reaction of purines under microwave irradiation
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The alkylation of purines which is generally carried out after anion formation by treatment with a base and alkyl halide is complicated and in the best cases, mixtures of N-alkylated compounds are obtained. Purine derivatives can be acquired from alkylati
- Ginard, Jaume,Jahani, Daniel,Mur, Nuria,Pujol, Maria Dolors,Vi?as, Miquel,Vinuesa, Arturo
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- CYSTEINE BINDING COMPOSITIONS AND METHODS OF USE THEREOF
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Purine-derived covalent probes (e.g., halo or di-halo-substituted purine based covalent probes) and related ligands are described. The compounds can be used to identify reactive nucleophilic amino acid residues, such as reactive cysteine residues, in prot
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Page/Page column 87
(2021/01/29)
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- Direct, Regioselective N-Alkylation of 1,3-Azoles
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Regioselective N-alkylation of 1,3-azoles is a valuable transformation. Organomagnesium reagents were discovered to be competent bases to affect regioselective alkylation of various 1,3-azoles. Counterintuitively, substitution selectively occurred at the more sterically hindered nitrogen atom. Numerous examples are provided, on varying 1,3-azole scaffolds, with yields ranging from 25 to 95%.
- Chen, Shuai,Graceffa, Russell F.,Boezio, Alessandro A.
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supporting information
p. 16 - 19
(2016/01/15)
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- Stereocontrolled approach for the syntheses of 3-isopurine nucleosides: 3-(2-deoxy-β-d-ribofuranosyl)xanthine and isoguanine by intramolecular glycosylation
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3-Isopurine nucleosides, namely 3-(ribofuranosyl)purine nucleosides, are interesting owing to their potential biological activity and as components of modified oligonucleotides. A regio- and stereocontrolled method was developed for the synthesis of β-2′-
- Sugimura, Hideyuki,Endo, Sho,Ishizuka, Ken
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p. 6019 - 6021
(2015/10/28)
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- N-Alkylation of 2,6-dichloropurine hydrochloride with a variety of alcohols over alumina catalyst
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2,6-Dichloropurine hydrochloride reacts with various types of alcohols using different alumina catalysts and converts into its N-9-alkyl-2-chloro-6- hydroxy-9H-purine products to an extent of 49-74%. The product selectivity depends on the stability of carbocation generated from the alcohol. More stable carbocation formulates both N-7 and N-9-alkyl-2,6-dichloropurine products, whereas the less stable carbocation results in exclusively N-9-alkyl-2-chloro-6- hydroxy-9H-purine. The catalytic activity of alumina prepared using the sol-gel method has larger Brunauer, Emmett, and Teller (BET) surface area and hence shows significantly greater catalytic activity than the commercially available alumina samples. Copyright
- Tumma, Harikrishna,Nagaraju,Reddy, K. Vijayakumar
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experimental part
p. 1856 - 1866
(2010/07/02)
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- PURINYL DERIVATIVES AND THEIR USE AS POTASSIUM CHANNEL MODULATORS
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This invention relates to novel purinyl derivatives and their use as potassium channel modulating agents. Moreover the invention is directed to pharmaceutical compositions useful for the treatment or alleviation of diseases or disorders associated with the activity of potassium channels.
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Page/Page column 22-23
(2008/12/04)
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- 2-AMIDO-6-AMINO-8-OXOPURINE DERIVATIVES AS TOLL-LIKE RECEPTOR MODULATORS FOR THE TREATMENT OF CANCER AND VIRAL INFECTIONS, SUCH AS HEPATITIS C
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This invention relates to purine derivatives, to processes for their preparation, to compositions containing them and to their use. The present invention provides compounds of formula (I) wherein R1, R2, R3, R9, R9a and Y are defined in the description. More particularly, the present invention relates to the use of purine derivatives in the treatment of a variety of viral infections and immune or inflammatory disorders, including those in which the modulation, in particular agonism, of Toll-Like Receptors (TLRs) is implicated. Accordingly, the compounds of the invention are useful in the treatment of infectious disease such as Hepatitis (e.g. HCV, HBV), genetically related viral infections, inflammatory diseases such as asthma and arthritis, and cancer.
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Page/Page column 57
(2010/11/24)
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- 2,6-DIHALOGENO-8-SUBSTITUENT-PURINE COMPOUND AND PROCESS FOR PRODUCING THE SAME
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The present invention relates to a compound represented by the formula (1) : wherein-A- is wherein X1 and X2 are each independently a halogen atom,------ is a single bond or a double bond, andR1, R2 and Z are each as defined in the description, or a salt thereof, a production method thereof and the like. A 2,6-dihalogeno-8-substituted-purine compound or a salt thereof, which is useful as an intermediate for producing medicaments, can be conveniently produced from a 2,6-dihalogenopurine compound or a salt thereof, and a 2,6-dihalogeno-8-substituted-purine compound or a salt thereof can be easily provided.
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Page/Page column 16
(2010/02/14)
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- Tetrabutylammonium fluoride-assisted rapid N9-alkylation on purine ring: Application to combinatorial reactions in microtiter plates for the discovery of potent sulfotransferase inhibitors in situ
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Tremendous efforts have been invested in the synthesis of purine libraries due to their importance in targeting various enzymes involved in different diseases and cellular processes. The synthesis of N9-alkylated purine scaffolds relied mostly
- Brik, Ashraf,Wu, Chung-Yi,Best, Michael D.,Wong, Chi-Huey
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p. 4622 - 4626
(2007/10/03)
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- Regiochemistry in Stille couplings of 2,6-dihalopurines
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The regiochemistry in Stille couplings of 2,6-dihalopurines have been studied. 2,6-Dichloropurines react selectively in the 6-position, and 6-chloro-2-iodopurines and 2-bromo-6-chloropurines in the 2-position.
- Langli, Geir,Gundersen, Lise-Lotte,Rise, Frode
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p. 5625 - 5638
(2007/10/03)
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- Heterocyclic compounds for enhancing antitumor activity
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2,6-Diaminopurines, 3,5-diamino-6,7,8,9-tetrahydrobenzo[b]thiophene[2,3-d]pyrimidines and 2,4-diaminothieno[3,2-d]pyrimidines useful as inhibitors of P-glycoproteins and potentiators of chemotherapeutic agents.
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- SYNTHESIS OF GUANINE FROM 3-METHYLXANTHINE
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A new preparative method of obtaining guanine from 3-methylxanthine has been developed.
- Kochergin, P. M.,Persanova, L. V.,Aleksandrova, E. V.,Gutorov, L. A.,Korsunskii, V. S.
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p. 337 - 339
(2007/10/03)
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- Regioselective Pd-mediated coupling between 2,6-dichloropurines and organometallic reagents
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Selective coupling in the purine 6-position has been achieved, by reacting N-benzylated 2,6-dichloropurines with organotin and organozinc reagents. The positional identity of the products were established from long range HETCOR or nOe NMR experiments.
- Gundersen, Lise-Lotte,Langli, Geir,Rise, Frode
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p. 1945 - 1948
(2007/10/02)
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- Mitsunobu reactions for the synthesis of carbocyclic analogues of nucleosides: Examintion of the regioselectivity
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In order to provide a general synthetic method for carbocyclic nucleosides, regioselectivities in Mitsunobu reaction of purine, pyrimidin-2-one and their substituted derivatives with a variety of alcohols with a variety of alcohols were examined and found to depend upon both substituents of the bases and kind of the alcohols.
- Toyota,Katagiri,Kaneko
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p. 1295 - 1305
(2007/10/02)
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