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Original Articles

Studies on the Alkylation of Derivatives of Guanines

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Pages 225-256 | Received 24 Sep 1986, Published online: 24 Oct 2006

Keep up to date with the latest research on this topic with citation updates for this article.

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PravinL. Kotian, V. Satish Kumar, Tsu-Hsing Lin, Yahya El-Kattan, Ajit Ghosh, Minwan Wu, Xiaogang Cheng, Shanta Bantia, YarlagaddaS. Babu & Pooran Chand. (2006) An Efficient Synthesis Of Acyclic N7- and N9-Adenine Nucleosides Via Alkylation With Secondary Carbon Electrophiles to Introduce Versatile Functional Groups At the C-1 Position of Acyclic Moiety. Nucleosides, Nucleotides & Nucleic Acids 25:2, pages 121-140.
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J.-C. Meillon, L. Griffe, R. Storer & G. Gosselin. (2005) RAPID ACCESS TO 2′-BRANCHED-CARBOCYCLIC NUCLEOSIDES AND THEIR 4′-EPIMERS FROM 2-ALKYL-CYCLOPENTENE-1-ONES. Nucleosides, Nucleotides & Nucleic Acids 24:5-7, pages 695-699.
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Ruifang Wang, Xinchao Chen, John C. Drach, Earl R. Kern & Jiri Zemlicka. (2003) Synthesis and Biological Activity of 2-Aminopurine Methylenecyclopropane Analogues of Nucleosides. Nucleosides, Nucleotides & Nucleic Acids 22:2, pages 135-144.
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Toyoto Hijiya, Keizo Yamashita, Mitsuhiko Kojima, Yumiko Uchida, Satoshi Katayama, Takayoshi Torii, Hiroshi Shiragami & Kunisuke Izawa. (1999) An Economical Synthesis of Famciclovir. Nucleosides and Nucleotides 18:4-5, pages 653-654.
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BernadetteM. Choudary, GrahamR. Geen, TrevorJ. Grinter, FionaS. MacBeath & MartinJ. Parratt. (1994) Influence of Remote Structure Upon Regioselectivity in the N-Alkylation of 2-Amino-6-Chloropurine: Application to the Synthesis of Penciclovir. Nucleosides and Nucleotides 13:4, pages 979-996.
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SergeyN. Mikhailov, EkaterinaV. Efimtseva, SergeyV. Meshkov & EarlR. Kern. (1994) Nucleoside Analogues on the Basis of 4(R),5(R)-Dihydroxymethyl-2-methyl-1,3-dioxolane. Nucleosides and Nucleotides 13:1-3, pages 615-623.
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Finn Priess Clausen & J⊘rgen Juhl-Christensen. (1993) SYNTHESIS OF 9-SUBSTITUTED GUANINES. A REVIEW. Organic Preparations and Procedures International 25:4, pages 373-401.
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Choung Un Kim, PeterF. Misco & JohnC. Martin. (1990) Synthesis of 9-[(Phosphonomethoxy)methyl]guanine and 9-[2-Hydroxy-1-(phosphonomethoxy)ethyl]guanine. Nucleosides and Nucleotides 9:4, pages 579-585.
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Articles from other publishers (30)

Guang Huan Shen & Joon Hee Hong. (2020) Chemical Synthesis of Acyclic Nucleoside Phosphonate Analogs Linked with Cyclic Systems between the Phosphonate and the Base Moieties. Current Medicinal Chemistry 27:35, pages 5918-5948.
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Pramod K. Sahu, Tamima Umme, Jinha Yu, Akshata Nayak, Gyudong Kim, Minsoo Noh, Jae-Young Lee, Dae-Duk Kim & Lak Shin Jeong. (2015) Selenoacyclovir and Selenoganciclovir: Discovery of a New Template for Antiviral Agents. Journal of Medicinal Chemistry 58:21, pages 8734-8738.
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Tushar Mahajan, Mari Ytre-Arne, Pernille Strøm-Andersen, Bjørn Dalhus & Lise-Lotte Gundersen. (2015) Synthetic Routes to N-9 Alkylated 8-Oxoguanines; Weak Inhibitors of the Human DNA Glycosylase OGG1. Molecules 20:9, pages 15944-15965.
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Vladimir V. Bakharev, Victor E. Parfenov, Alexander A. Gidaspov, Andrey A. Pimenov, Pavel A. Slepukhin & Kyrill Yu. Suponitsky. (2015) Alkylation of 5-dimethylaminotetrazolo-[1,5-a][1,3,5]triazin-7-one. Chemistry of Heterocyclic Compounds 51:8, pages 745-748.
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Elin Julianti, Hana Oh, Hyi-Seung Lee, Dong-Chan Oh, Ki-Bong Oh & Jongheon Shin. (2012) Acremolin, a new 1H-azirine metabolite from the marine-derived fungus Acremonium strictum. Tetrahedron Letters 53:23, pages 2885-2886.
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Won Jun Choi, Yun Jung Ko, Girish Chandra, Hyuk Woo Lee, Hea Ok Kim, Hyo Jung Koh, Hyung Ryong Moon, Young Hoon Jung & Lak Shin Jeong. (2012) Stereoselective synthesis and anti-HCV activity of conformationally restricted 2′-C-substituted carbanucleosides. Tetrahedron 68:4, pages 1253-1261.
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Ke-Ling Xu, Zhi Guan & Yan-Hong He. (2011) Acidic proteinase from Aspergillus usamii catalyzed Michael addition of ketones to nitroolefins. Journal of Molecular Catalysis B: Enzymatic 71:3-4, pages 108-112.
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Jin-Tao Wang, Qing Xia, Xiao-Hui Zheng, Huo-Yan Chen, Hui Chao, Zong-Wan Mao & Liang-Nian Ji. (2010) An effective approach to artificial nucleases using copper(ii) complexes bearing nucleobases. Dalton Transactions 39:8, pages 2128.
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Roman Keder, Hana Dvořáková & Dalimil Dvořák. (2009) New Approach to the Synthesis of N 7 -Arylguanines and N 7 -Aryladenines . European Journal of Organic Chemistry 2009:10, pages 1522-1531.
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Jun-Liang Wang, Jian-Ming Xu, Qi Wu, De-Shui Lv & Xian-Fu Lin. (2009) Promiscuous enzyme-catalyzed regioselective Michael addition of purine derivatives to α,β-unsaturated carbonyl compounds in organic solvent. Tetrahedron 65:12, pages 2531-2536.
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Tony Bouisset, Gilles Gosselin, Ludovic Griffe, Jean-Christophe Meillon & Richard Storer. (2008) Synthesis of 2′-C-methyl-branched isonucleosides. Tetrahedron 64:28, pages 6657-6661.
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Zhaohua Yan, Shaoman Zhou, Earl R. Kern & Jiri Zemlicka. (2006) Synthesis of methylenecyclopropane analogues of antiviral nucleoside phosphonates. Tetrahedron 62:11, pages 2608-2615.
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Gilles Gosselin, Ludovic Griffe, Jean-Christophe Meillon & Richard Storer. (2006) A short and novel synthesis of carbocyclic nucleosides and 4′-epi-carbocyclic nucleosides from 2-cyclopenten-1-ones. Tetrahedron 62:5, pages 906-914.
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Han Fu & Yulin Lam. (2005) Traceless Solid-Phase Synthesis of N1,N7-Disubstituted Purines. Journal of Combinatorial Chemistry 7:5, pages 734-738.
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Leo A. Paquette & Shuzhi Dong. (2005) Stereoselective Synthesis of β-Anomeric 4‘-Thiaspirocyclic Ribonucleosides Carrying the Full Complement of RNA-Level Hydroxyl Substitution. The Journal of Organic Chemistry 70:14, pages 5655-5664.
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Christoph Rosenbohm, Daniel Sejer Pedersen, Miriam Frieden, Flemming R. Jensen, Susan Arent, Sine Larsen & Troels Koch. (2004) LNA guanine and 2,6-diaminopurine. Synthesis, characterization and hybridization properties of LNA 2,6-diaminopurine containing oligonucleotides. Bioorganic & Medicinal Chemistry 12:9, pages 2385-2396.
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Anne Kristin Bakkestuen & Lise-Lotte Gundersen. (2003) Regioselective N-9 arylation of purines employing arylboronic acids in the presence of Cu(II). Tetrahedron Letters 44:16, pages 3359-3362.
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Gholam Hossein Hakimelahi, Tai Wei Ly, Ali A. Moosavi-Movahedi, Moti L. Jain, Maryam Zakerinia, Hady Davari, Hui-Ching Mei, Thota Sambaiah, Ali A. Moshfegh & Shahram Hakimelahi. (2001) Design, Synthesis, and Biological Evaluation of Novel Nucleoside and Nucleotide Analogues as Agents against DNA Viruses and/or Retroviruses. Journal of Medicinal Chemistry 44:22, pages 3710-3720.
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Graham R Geen, Peter M Kincey & P.Grant Spoors. (2001) Regioselective alkylation of guanines using 2-acetoxytetrahydrofurans. Tetrahedron Letters 42:9, pages 1781-1784.
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Richard Freer, Graham R Geen, Thomas W Ramsay, Andrew C Share, Graham R Slater & Neil M Smith. (2000) A New Route to Famciclovir via Palladium Catalysed Allylation. Tetrahedron 56:26, pages 4589-4595.
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Warren McComas, Li Chen & Kyungjin Kim. (2000) Convenient synthesis of 2,9-disubstituted guanines mediated by solid-supported reagents. Tetrahedron Letters 41:19, pages 3573-3576.
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Dharmendra Singh, Mukesh J. Wani & Ashok Kumar. (1999) A Simple Solution to the Age Old Problem of Regioselective Functionalization of Guanine:  First Practical Synthesis of Acyclic N 9 - and/or N 7 -Guanine Nucleosides Starting from N 2 , N 9 -Diacetylguanine . The Journal of Organic Chemistry 64:13, pages 4665-4668.
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Briony Brand, Colin B Reese, Quanlai Song & Cristina Visintin. (1999) Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl)butyl]guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-9H-purine (famciclovir). Tetrahedron 55:16, pages 5239-5252.
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Patricia Imbach, Hans-Georg Capraro, Pascal Furet, Helmut Mett, Thomas Meyer & Jürg Zimmermann. (1999) 2,6,9-trisubstituted purines : Optimization towards highly potent and selective CDK1 inhibitors. Bioorganic & Medicinal Chemistry Letters 9:1, pages 91-96.
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R.M. Martín-Aranda, M.A. Vicente-Rodríguez, J.M. López-Pestaña, A.J. López-Peinado, A. Jerez, J. de D. López-González & M.A. Bañares-Muñoz. (1997) Application of basic clays in microwave activated Michael additions: Preparation of N-substituted imidazoles. Journal of Molecular Catalysis A: Chemical 124:2-3, pages 115-121.
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Frank Seela & Peter Leonard. (2004) Studies on the Base‐Pairing Properties of N 7 ‐(2‐Deoxy‐β‐ D ‐ erythro ‐pentofuranosyl)guanine ( N 7 G d ) . Helvetica Chimica Acta 80:4, pages 1301-1318.
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Ildiko M. Buck, Alessandra Eleuteri & Colin B. Reese. (1994) Conversion of guanosine into acyclovir and its 6-deoxy derivative. Tetrahedron 50:30, pages 9195-9206.
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Graham R. Geen, Peter M. Kincey & Bernadette M. Choudary. (1992) Regiospecific Michael additions with 2-aminopurines. Tetrahedron Letters 33:32, pages 4609-4612.
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Rebecca M. Osterman, Brian A. McKittrick & Tze-Ming Chan. (1992) Regiochemical assignment of methylated purines and pyrimidines by selective INEPT. Tetrahedron Letters 33:34, pages 4867-4870.
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Graham R. Geen, Trevor J. Grinter, Peter M. Kincey & Richard L. Jarvest. (1990) The effect of the c-6 substituent on the regioselectivity of n-alkylation of 2-aminopurines. Tetrahedron 46:19, pages 6903-6914.
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