- Synthesis of some substituted 6-phenyl purine analogues and their biological evaluation as cytotoxic agents
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A series of 6-(4-substituted phenyl)-9-(tetrahydropyran-2-yl)purines 3–9, 6-(4-substituted phenyl)purines 10–16, 9-((4-substituted phenyl)sulfonyl)-6-(4-substituted phenyl)purines 17–32 were prepared and screened initially for their in vitro anticancer activity against selected human cancer cells (liver Huh7, colon HCT116, breast MCF7). 6-(4-Phenoxy-phenyl)purine analogues 9, 16, 30–32, had potent cytotoxic activities. The most active purine derivatives 5–9, 14, 16, 18, 28–32 were further screened for their cytotoxic activity in hepatocellular cancer cells. 6-(4-Phenoxyphenyl)-9-(tetrahydropyran-2-yl)-9H-purine (9) had better cytotoxic activity (IC50 5.4 μM) than the well-known nucleobase analogue 5-FU and known nucleoside drug fludarabine on Huh7 cells. The structure–activity relationship studies reported that the substitution at C-6 positions in purine nucleus with the 4-phenoxyphenyl group is responsible for the anti-cancer activity.
- Kucukdumlu, Asligul,Tuncbilek, Meral,Guven, Ebru Bilget,Atalay, Rengul Cetin
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p. 621 - 632
(2017/09/08)
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- Aqueous-phase Suzuki-Miyaura cross-coupling reactions of free halopurine bases
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The Suzuki-Miyaura reaction of 9-unsubstituted 2-, 6-, and 8-halopurine bases with diverse aryl- and alkenylboronic acids in water-acetonitrile mixtures under microwave irradiation was used for the single-step synthesis of arylpurines. In most cases the p
- Capek, Petr,Vrabel, Milan,Hasnik, Zbynek,Pohl, Radek,Hocek, Michal
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p. 3515 - 3526
(2008/02/10)
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- Synthesis and cytostatic activity of substituted 6-phenylpurine bases and nucleosides: Application of the Suzuki-Miyaura cross-coupling reactions of 6-chloropurine derivatives with phenylboronic acids
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The Suzuki-Miyaura reaction of protected 6-chloropurine and 2-amino-6- chloropurine bases and nucleosides with substituted phenylboronic acids led to the corresponding protected 6-(substituted phenyl)purine derivatives 6-9. Their deprotection yielded a se
- Hocek, Michal,Holy, Antonín,Votruba, Ivan,Dvo?áková, Hana
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p. 1817 - 1825
(2007/10/03)
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- Cytostatic 6-arylpurine nucleosides II. Synthesis of sugar-modified derivatives: 9-(2-deoxy-β-D-erythro-pentofuranosyl)-, 9-(5-deoxy-β-D-ribofuranosyl)- and 9-(2,3-dihydroxypropyl)-6-phenylpurines
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9-(2-Deoxy-β-D-erythro-pentofuranosyl)-6-(4-substituted phenyl)purines, 9-(5-deoxy-β-D-ribofuranosyl)-6-(4-substituted phenyl)purines and 9-(2,3-dihydroxypropyl)-6-(4-substituted phenyl)purines were prepared by the Suzuki-Miyaura cross-coupling reactions of the corresponding protected 9-substituted 6-chloropurines with substituted phenylboronic acids followed by MeONa mediated deprotection. In contrast to the highly active 6-phenylpurine ribonucleosides, the title compounds did not show any considerable cytostatic activity.
- Hocek, Michal,Holy, Antonin,Votruba, Ivan,Dvorakova, Hana
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p. 1683 - 1697
(2007/10/03)
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- The Suzuki-Miyaura cross-coupling reactions of 6-halopurines with boronic acids leading to 6-aryl- and 6-alkenylpurines
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The Suzuki-Miyaura cross-coupling reactions of 9-benzyl-6-chloropurine with boronic acids gave 6-alkylated purines in moderate to excellent yields. The best results with electron rich arylboronic acids were obtained in toluene in the presence of anhydrous
- Havelková, Martina,Hocek, Michal,?esnek, Michal,Dvo?ák, Dalimil
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p. 1145 - 1147
(2007/10/03)
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- Synthesis and structure-activity relationships of 6-heterocyclic- substituted purines as inactivation modifiers of cardiac sodium channels
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Purine-based analogs of SDZ 211-500 (5) were prepared and evaluated as inactivation modifiers of guinea pig or human cardiac sodium (Na) channels expressed in Xenopus oocytes. Substances which remove or slow the Na channel inactivation process in cardiac tissue are anticipated to prolong the effective refractory period and increase inotropy and thus have potential utility as antiarrhythmic agents. Heterocyclic substitution at the 6-position of the purine ring resulted in compounds with increased Na activity and potency, with 5-membered heterocycles being optimal. Only minor modifications to the benzhydrylpiperazine side chain were tolerated. Selected compounds which delayed the inactivation of Na channels were found to increase refractoriness and contractility in a rabbit Langendorff heart model, consistent with the cellular mechanism. Activity in both the oocyte and rabbit heart assays was specific to the S enantiomers. Preliminary in vivo activity has been demonstrated following intravenous infusion. The most promising compound on the basis of in vitro data is the formylpyrrole (S)74, which is 25-fold more potent than DPI 201-106 (1) in the human heart Na channel assay.
- Estep,Josef,Bacon,Carabateas,Rumney IV,Pilling,Krafte,Volberg,Dillon,Dugrenier,Briggs,Canniff,Gorczyca,Stankus,Ezrin
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p. 2582 - 2595
(2007/10/02)
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- 6-Chloropurines and organostannanes in palladium catalyzed cross coupling reactions
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Carbon-carbon bond formation in the purine 6-position can easily be accomplished by palladium catalyzed cross coupling between 6-chloropurines and organostannanes without protection of the purine ring NH function. This technique provides a convenient route to cytokinines.
- Gundersen, Lise-Lotte
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p. 3155 - 3158
(2007/10/02)
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- Synthesis of 6-Alkylpurine Derivatives by Nickel-comlex-catalyzed Coupling Reaction of 6-(Methylthio)purine Derivatives with Grignard Reagents
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6-(Methylthio)purine reacted with RMgX (R=C6H5, CH3(CH2)nCH2 (n=2 to 6), C6H5CH2CH2, (CH3)2C=CHCH2CH2) in the presence of 5 molpercent in refluxing THF for 8h to afford 6-aryl or 6-alkylpurines in 62-74percent yields.By applying
- Sugimura, Hideyuki,Takei, Hisashi
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p. 664 - 666
(2007/10/02)
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