Crossref Cited-by Linking logo

Collect. Czech. Chem. Commun. 2000, 65, 1683-1697
https://doi.org/10.1135/cccc20001683

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

Michal Hoceka,*, Antonín Holýa, Ivan Votrubaa and Hana Dvořákováb

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, CZ-16610 Prague 6, Czech Republic
b Laboratory of NMR Spectroscopy, Institute of Chemical Technology, Prague, CZ-166 28 Prague 6, Czech Republic

Crossref Cited-by Linking

  • Xia Ran, Xie Ming-Sheng, Niu Hong-Ying, Qu Gui-Rong, Guo Hai-Ming: Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO4 in water. Green Chem. 2014, 16, 1077. <https://doi.org/10.1039/C3GC41658E>
  • Qu Gui-Rong, Xin Peng-Yang, Niu Hong-Ying, Jin Xin, Guo Xiao-Ting, Yang Xi-Ning, Guo Hai-Ming: Microwave promoted palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of 6-chloropurines with sodium tetraarylborate in water. Tedrahedron 2011, 67, 9099. <https://doi.org/10.1016/j.tet.2011.09.082>
  • Nauš Petr, Perlíková Pavla, Pohl Radek, Hocek Michal: Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2′-C-methylribonucleosides, arabinonucleosides and 2′-deoxy-2′-fluoroarabinonucleosides. Collect. Czech. Chem. Commun. 2011, 76, 957. <https://doi.org/10.1135/cccc2011082>
  • Nauš Petr, Pohl Radek, Votruba Ivan, Džubák Petr, Hajdúch Marián, Ameral Ria, Birkuš Gabriel, Wang Ting, Ray Adrian S., Mackman Richard, Cihlar Tomas, Hocek Michal: 6-(Het)aryl-7-Deazapurine Ribonucleosides as Novel Potent Cytostatic Agents. J. Med. Chem. 2010, 53, 460. <https://doi.org/10.1021/jm901428k>
  • Kang Fu‐An, Sui Zhihua, Murray William V.: Phosphonium Coupling in the Direct Bond Formations of Tautomerizable Heterocycles via C–OH Bond Activation. Eur. J. Org. Chem. 2009, 2009, 461. <https://doi.org/10.1002/ejoc.200801004>
  • Kang Fu-An, Sui Zhihua, Murray William V.: Pd-Catalyzed Direct Arylation of Tautomerizable Heterocycles with Aryl Boronic Acids via C−OH Bond Activation Using Phosphonium Salts. J. Am. Chem. Soc. 2008, 130, 11300. <https://doi.org/10.1021/ja804804p>
  • Nauš Petr, Kuchař Martin, Hocek Michal: Cytostatic and Antiviral 6-Arylpurine Ribonucleosides IX. Synthesis and Evaluation of 6-Substituted 3-Deazapurine Ribonucleosides. Collect. Czech. Chem. Commun. 2008, 73, 665. <https://doi.org/10.1135/cccc20080665>
  • Kimoto Michiko, Moriyama Kei, Yokoyama Shigeyuki, Hirao Ichiro: Cytostatic evaluations of nucleoside analogs related to unnatural base pairs for a genetic expansion system. Bioorganic & Medicinal Chemistry Letters 2007, 17, 5582. <https://doi.org/10.1016/j.bmcl.2007.07.088>
  • Zhu Ruizhi, Qu Fanqi, Quéléver Gilles, Peng Ling: Direct synthesis of 5-aryltriazole acyclonucleosides via Suzuki coupling in aqueous solution. Tetrahetron Lett 2007, 48, 2389. <https://doi.org/10.1016/j.tetlet.2007.01.154>
  • Tobrman Tomáš, Dvořák Dalimil: Reductive Dimerization of 2- and 6-Iodopurines: Side Reaction in Pd-Catalyzed Cross-Coupling of Iodopurines. Collect. Czech. Chem. Commun. 2007, 72, 1365. <https://doi.org/10.1135/cccc20071365>
  • Hocek Michal, Šilhár Peter, Shih I-hung, Mabery Eric, Mackman Richard: Cytostatic and antiviral 6-arylpurine ribonucleosides. Part 7: Synthesis and evaluation of 6-substituted purine l-ribonucleosides. Biorg Med Chem Lett 2006, 16, 5290. <https://doi.org/10.1016/j.bmcl.2006.07.092>
  • Wan Jinqiao, Zhu Ruizhi, Xia Yi, Qu Fanqi, Wu Qiongyou, Yang Guangfu, Neyts Johan, Peng Ling: Synthesis of 5-aryltriazole ribonucleosides via Suzuki coupling and promoted by microwave irradiation. Tetrahetron Lett 2006, 47, 6727. <https://doi.org/10.1016/j.tetlet.2006.07.103>
  • Hocek Michal, Šilhár Peter, Pohl Radek: Cytostatic and Antiviral 6-Arylpurine Ribonucleosides VIII. Synthesis and Evaluation of 6-Substituted Purine 3'-Deoxyribonucleosides. Collect. Czech. Chem. Commun. 2006, 71, 1484. <https://doi.org/10.1135/cccc20061484>
  • Hocek Michal, Nauš Petr, Pohl Radek, Votruba Ivan, Furman Phillip A., Tharnish Phillip M., Otto Michael J.: Cytostatic 6-Arylpurine Nucleosides. 6. SAR in Anti-HCV and Cytostatic Activity of Extended Series of 6-Hetarylpurine Ribonucleosides. J. Med. Chem. 2005, 48, 5869. <https://doi.org/10.1021/jm050335x>
  • Čapek Petr, Pohl Radek, Hocek Michal: Synthesis of Enantiomerically Pure (Purin-6-yl)phenylalanines and Their Nucleosides, a Novel Type of Purine-Amino Acid Conjugates. J. Org. Chem. 2005, 70, 8001. <https://doi.org/10.1021/jo051110x>
  • Lakshman Mahesh K., Gunda Padmaja, Pradhan Padmanava: Mild and Room Temperature C−C Bond Forming Reactions of Nucleoside C-6 Arylsulfonates. J. Org. Chem. 2005, 70, 10329. <https://doi.org/10.1021/jo0513764>
  • Liu Jiangqiong, Robins Morris J.: Fluoro, Alkylsulfanyl, and Alkylsulfonyl Leaving Groups in Suzuki Cross-Coupling Reactions of Purine 2‘-Deoxynucleosides and Nucleosides. Org. Lett. 2005, 7, 1149. <https://doi.org/10.1021/ol050063s>
  • Itoh Takahiro, Sato Kimihiko, Mase Toshiaki: A Novel Practical Synthesis of C -2-Arylpurines. Adv. Synth. Catal. 2004, 346, 1859. <https://doi.org/10.1002/adsc.200404159>
  • Gunda Padmaja, Russon Larry M., Lakshman Mahesh K.: Pd-Catalyzed Amination of Nucleoside Arylsulfonates to yieldN6-Aryl-2,6-Diaminopurine Nucleosides. Angew. Chem. 2004, 116, 6532. <https://doi.org/10.1002/ange.200460782>
  • Gunda Padmaja, Russon Larry M., Lakshman Mahesh K.: Pd-Catalyzed Amination of Nucleoside Arylsulfonates to yieldN6-Aryl-2,6-Diaminopurine Nucleosides. Angew. Chem. Int. Ed. 2004, 43, 6372. <https://doi.org/10.1002/anie.200460782>
  • Turek Pavel, Kotora Martin, Tišlerová Iva, Hocek Michal, Votruba Ivan, Císařová Ivana: Cocyclotrimerization of 6-Alkynylpurines with α,ω-Diynes as a Novel Approach to Biologically Active 6-Arylpurines. J. Org. Chem. 2004, 69, 9224. <https://doi.org/10.1021/jo0486342>
  • Liu Jiangqiong, Robins Morris J.: Azoles as Suzuki Cross-Coupling Leaving Groups:  Syntheses of 6-Arylpurine 2‘-Deoxynucleosides and Nucleosides from 6-(Imidazol-1-yl)- and 6-(1,2,4-Triazol-4-yl)purine Derivatives1. Org. Lett. 2004, 6, 3421. <https://doi.org/10.1021/ol048490d>
  • Nauš Petr, Votruba Ivan, Hocek Michal: Covalent Analogues of DNA Base-Pairs and Triplets VII. Synthesis and Cytostatic Activity of Bis(purin-6-yl)acetylene and -diacetylene Nucleosides. Collect. Czech. Chem. Commun. 2004, 69, 1955. <https://doi.org/10.1135/cccc20041955>
  • Hocek Michal: Syntheses of Purines Bearing Carbon Substituents in Positions 2, 6 or 8 by Metal‐ or Organometal‐Mediated C−C Bond‐Forming Reactions. Eur. J. Org. Chem. 2003, 2003, 245. <https://doi.org/10.1002/ejoc.200390025>
  • Turek Pavel, Kotora Martin, Hocek Michal, Cı́sařová Ivana: [2+2+2]-Co-cyclotrimerization 6-alkynylpurines with diynes: a method for preparation of 6-arylpurines. Tetrahetron Lett 2003, 44, 785. <https://doi.org/10.1016/S0040-4039(02)02643-6>
  • Bråthe Anders, Gundersen Lise-Lotte, Nissen-Meyer Jon, Rise Frode, Spilsberg Bjørn: Cytotoxic activity of 6-alkynyl- and 6-alkenylpurines. Biorg Med Chem Lett 2003, 13, 877. <https://doi.org/10.1016/S0960-894X(03)00011-8>
  • Agrofoglio Luigi A., Gillaizeau Isabelle, Saito Yoshio: Palladium-Assisted Routes to Nucleosides. Chem. Rev. 2003, 103, 1875. <https://doi.org/10.1021/cr010374q>
  • Hocek Michal, Hocková Dana, Štambaský Jan: Cytostatic 6-Arylpurine Nucleosides V. Synthesis of 8-Substituted 6-Phenylpurine Ribonucleosides. Collect. Czech. Chem. Commun. 2003, 68, 837. <https://doi.org/10.1135/cccc20030837>
  • Lakshman Mahesh K: Palladium-catalyzed C–N and C–C cross-couplings as versatile, new avenues for modifications of purine 2′-deoxynucleosides. J Organomet Chem 2002, 653, 234. <https://doi.org/10.1016/S0022-328X(02)01267-6>
  • Havelková Martina, Dvořák Dalimil, Hocek Michal: Covalent analogues of DNA base-pairs and triplets. Part 3: Synthesis of 1,4- and 1,3-bis(purin-6-yl)benzenes and 1-(1,3-dimethyluracil-5-yl)-3 or 4-(purin-9-yl)benzenes. Tetrahedron 2002, 58, 7431. <https://doi.org/10.1016/S0040-4020(02)00833-5>
  • Hocek Michal, Votruba Ivan: Covalent analogues of DNA base-Pairs and triplets. Part 2: † †For Part I, see ref 1. Synthesis and cytostatic activity of bis(purin-6-yl)acetylenes,-diacetylenes and related compounds. Bioorganic & Medicinal Chemistry Letters 2002, 12, 1055. <https://doi.org/10.1016/S0960-894X(02)00077-X>
  • Lakshman Mahesh K., Thomson Paul F., Nuqui Mark A., Hilmer John H., Sevova Nonka, Boggess Bill: Facile Pd-Catalyzed Cross-Coupling of 2‘-Deoxyguanosine O6-Arylsulfonates with Arylboronic Acids. Org. Lett. 2002, 4, 1479. <https://doi.org/10.1021/ol025673w>
  • Hocek Michal, Holý Antonín, Dvořáková Hana: Cytostatic 6-Arylpurine Nucleosides IV. Synthesis of 2-Substituted 6-Phenylpurine Ribonucleosides. Collect. Czech. Chem. Commun. 2002, 67, 325. <https://doi.org/10.1135/cccc20020325>
  • Hocek Michal, Stará Irena G., Starý Ivo, Dvořáková Hana: Covalent Analogues of DNA Base-Pairs and Triplets IV. Synthesis of Trisubstituted Benzenes Bearing Purine and/or Pyrimidine Rings by Cyclotrimerization of 6-Ethynylpurines and/or 5-Ethynyl-1,3-dimethyluracil. Collect. Czech. Chem. Commun. 2002, 67, 1223. <https://doi.org/10.1135/cccc20021223>
  • Hocek Michal, Dvořáková Hana, Císařová Ivana: Covalent Analogues of DNA Base-Pairs and Triplets V. Synthesis of Purine-Purine and Purine-Pyrimidine Conjugates Connected by Diverse Types of Acyclic Carbon Linkages. Collect. Czech. Chem. Commun. 2002, 67, 1560. <https://doi.org/10.1135/cccc20021560>
  • Hocek Michal, Holy Antonin, Votruba Ivan, Dvorakova Hana: ChemInform Abstract: Cytostatic 6-Arylpurine Nucleosides. Part 2. 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. ChemInform 2001, 32, no. <https://doi.org/10.1002/chin.200120194>
  • Lakshman Mahesh K., Hilmer John H., Martin Jocelyn Q., Keeler John C., Dinh Yen Q. V., Ngassa Felix N., Russon Larry M.: Palladium Catalysis for the Synthesis of Hydrophobic C-6 and C-2 Aryl 2‘-Deoxynucleosides. Comparison of C−C versus C−N Bond Formation as well as C-6 versus C-2 Reactivity. J. Am. Chem. Soc. 2001, 123, 7779. <https://doi.org/10.1021/ja0107172>
  • Véliz Eduardo A., Beal Peter A.: 6-Bromopurine Nucleosides as Reagents for Nucleoside Analogue Synthesis. J. Org. Chem. 2001, 66, 8592. <https://doi.org/10.1021/jo016078v>
  • Hocek Michal, Holý Antonín, Votruba Ivan, Dvořáková Hana: Cytostatic 6-Arylpurine Nucleosides III. Synthesis and Structure-Activity Relationship Study in Cytostatic Activity of 6-Aryl-, 6-Hetaryl- and 6-Benzylpurine Ribonucleosides. Collect. Czech. Chem. Commun. 2001, 66, 483. <https://doi.org/10.1135/cccc20010483>