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Nucleoside Analogues: Synthesis And Biological Properties Of Azanucleoside Derivatives

D. Hernández, A. Boto
Published 2014 · Chemistry

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The azanucleosides are nucleoside analogues where the furanose ring is replaced by a nitrogen-containing ring or chain. Many azanucleosides are potent antiviral, anticancer and antimicrobial agents, or serve as valuable components of oligonucleotides with improved stability, binding or hybridization properties. Therefore, the development of new analogues is a very active area in medicinal and synthetic chemistry. Their synthesis and their interesting biological properties are discussed in this microreview.
This paper references
10.2174/0929867013373471
Sugar-modified nucleosides in past 10 years, a review.
E. Ichikawa (2001)
10.1016/0960-894X(95)00373-2
Incorporation of a pyrene nucleoside analogue into synthetic oligodeoxynucleotides using a nucleoside-like synthon
I. Prokhorenko (1995)
10.1021/JM0203332
8-Aza-immucillins as transition-state analogue inhibitors of purine nucleoside phosphorylase and nucleoside hydrolases.
G. B. Evans (2003)
10.1002/EJOC.200901320
Recent Developments in the Synthesis of Pyrrolidine‐Containing Iminosugars
Bridget L. Stocker (2010)
10.1016/S0040-4039(97)00845-9
Stereoselective synthesis of a terpyrrolidine unit, a potential building block for anion recognition
H. Arndt (1997)
10.1080/07328319708006219
A Novel Class of 4′-Aza Analogues of 2′,3′-Dideoxynucleosides as Potential Anti-HIV Drugs
A. Leggio (1997)
10.1039/B709797M
Recent highlights in modified oligonucleotide chemistry.
A. Cobb (2007)
10.1016/j.bmcl.2009.04.017
Synthesis of analogs of forodesine HCl, a human purine nucleoside phosphorylase inhibitor-Part I.
Vivekanand P. Kamath (2009)
10.1002/EJOC.201100767
Synthesis of 5-Alkynyl Isoxazolidinyl Nucleosides
R. Romeo (2011)
10.1021/JA710733G
L-Enantiomers of transition state analogue inhibitors bound to human purine nucleoside phosphorylase.
A. Rinaldo-Matthis (2008)
10.1021/jo100397a
Synthesis of acyclic nucleosides with a chiral amino side chain by the Mitsunobu coupling reaction.
H. Guo (2010)
10.1016/j.bmcl.2009.12.081
Structural diversity of nucleoside phosphonic acids as a key factor in the discovery of potent inhibitors of rat T-cell lymphoma thymidine phosphorylase.
Petr Kočalka (2010)
10.1016/S0040-4020(99)00837-6
SYNTHESIS AND STRUCTURAL STUDIES OF MONOCYCLIC 4'-AZA-L-NUCLEOSIDES
C. V. Varaprasad (1999)
10.1016/S0040-4039(02)00712-8
Chemo-, regio- and stereoselective Mitsunobu reaction of unprotected pyrimidine bases with hydroxypyrrolidines
B. Richichi (2002)
10.1002/JHET.5570310630
Approaches toward the synthesis of 2,5-disubstituted-1,3-thiazolidines
P. Faury (1994)
10.1021/OL007029S
Synthesis of pyrrolidine C-nucleosides via Heck reaction.
A. Haeberli (2001)
10.1016/J.TETLET.2004.05.042
Facile synthesis of acyclic azanucleosides from N-pivaloyloxymethyl amides and sulfonamides: synthesis of aza-analogues of Ganciclovir
Mariola Koszytkowska-Stawińska (2004)
10.1016/S0040-4020(98)00274-9
Samarium diiodide-induced radical cyclization of oxime ether connected with formyl group: Synthesis of 4-pyrimidinyl- and 4-purinylpyrrolidin-3-ol nucleoside analogues
H. Miyabe (1998)
10.1016/j.jim.2010.12.001
Potential therapeutic applications of antisense morpholino oligonucleotides in modulation of splicing in primary immunodeficiency diseases.
L. Du (2011)
10.1016/j.bmc.2008.05.056
N-Arylmethyl substituted iminoribitol derivatives as inhibitors of a purine specific nucleoside hydrolase.
A. Goeminne (2008)
10.1016/j.bmc.2009.04.054
Synthesis and antiviral activity evaluation of acyclic 2′-azanucleosides bearing a phosphonomethoxy function in the side chain
Mariola Koszytkowska-Stawińska (2009)
10.1016/0960-894X(96)00316-2
Modelisation, synthesis and antiviral evaluation of new 2,3-disubstituted thiazolidinone nucleoside analogues
J. Graciet (1996)
10.1016/S0040-4020(98)00821-7
SYNTHESIS AND BIOLOGICAL PROPERTIES OF A NEW SERIES OF 5-SUBSTITUTED-PYRIMIDINE-L-NUCLEOSIDE ANALOGUES
N. Westwood (1998)
10.1055/S-1993-25935
First synthesis of 4'-acetamido-2'-deoxythymidine
Baoguo Huang (1993)
10.1016/S1567-5769(01)00056-X
Purine nucleoside phosphorylase inhibitor BCX-1777 (Immucillin-H)--a novel potent and orally active immunosuppressive agent.
S. Bantia (2001)
10.1016/j.bmc.2010.08.024
Synthesis and biological evaluation of diastereoisomerically pure N,O-nucleosides.
O. Bortolini (2010)
10.1021/jo901604w
An efficient route to acyclic C-nucleosides and fused-ring analogues of uridine from exo-glycals.
Gérald Enderlin (2009)
10.1080/07328319908044728
Phosphonate Analogues of Peptide Nucleic Acids and Related Compounds: Synthesis and Hybridization Properties
V. Efimov (1999)
10.1021/JM960400Q
Expeditious syntheses of sugar-modified nucleosides and collections thereof exploiting furan-, pyrrole-, and thiophene-based siloxy dienes.
G. Rassu (1997)
10.1039/c2cc18012j
Practical biocatalytic desymmetrization of meso-N-heterocyclic dicarboxamides and their application in the construction of aza-sugar containing nucleoside analogs.
P. Chen (2012)
10.1016/J.BMC.2005.06.034
Irreversibly inhibitory kinetics of 3,5-dihydroxyphenyl decanoate on mushroom (Agaricus bisporus) tyrosinase.
Ling Qiu (2005)
10.1016/S0040-4020(98)00186-0
Syntheses of isoxazolinyl and isoxazolidinyl nucleoside analogues
Shifeng Pan (1998)
10.1016/J.TETASY.2004.10.030
Asymmetric syntheses of protected (2S,3S,4S)-3-hydroxy-4-methylproline and 4 ‘-tert-butoxyamido-2 ‘-deoxythymidine
Wei-hua Meng (2004)
10.1016/S0960-894X(97)00085-1
New hetero-oligomeric peptide nucleic acids with improved binding properties to complementary DNA
S. Jordan (1997)
10.1002/ANIE.199416541
Synthesis of an Azathymidine and Its Incorporation into Oligonucleotides
K. Altmann (1994)
10.1016/0040-4020(95)00020-9
4′-Methyloxycarbamyl-3′-deoxy-5-methyluridine; synthesis of a novel nucleoside analogue
L. Pickering (1995)
10.1016/S1567-5769(03)00076-6
Mechanism of inhibition of T-acute lymphoblastic leukemia cells by PNP inhibitor--BCX-1777.
S. Bantia (2003)
10.1021/OL060448Q
Hybridization of pyrrolidinyl peptide nucleic acids and DNA: selectivity, base-pairing specificity, and direction of binding.
T. Vilaivan (2006)
10.1073/PNAS.88.24.11540
Application of crystallographic and modeling methods in the design of purine nucleoside phosphorylase inhibitors.
S. Ealick (1991)
10.1021/jo200060f
Stereoselective synthesis of PSI-352938: a β-D-2'-deoxy-2'-α-fluoro-2'-β-C-methyl-3',5'-cyclic phosphate nucleotide prodrug for the treatment of HCV.
P. Reddy (2011)
10.1055/S-1999-3609
Aza-C-nucleosides as a New Class of Nucleosides
M. Sorensen (1999)
10.1021/JO990576A
Homochiral α-d- and β-d-Isoxazolidinylthymidines via 1,3-Dipolar Cycloaddition†
U. Chiacchio (1999)
10.1021/JM0100077
Synthesis and structure-activity relationships of naphthamides as dopamine D3 receptor ligands.
Y. Huang (2001)
10.1039/B413542C
Backbone-extended pyrrolidine peptide nucleic acids (bepPNA): design, synthesis and DNA/RNA binding studies.
T. Govindaraju (2005)
10.1021/jm040158k
New approaches toward anti-HIV chemotherapy.
E. Clercq (2005)
10.1016/S0040-4020(00)00586-X
Synthesis of (−)-Brevioxime
D. A. Clark (2000)
10.1016/J.BMC.2006.01.028
Synthesis and biological evaluation of phosphonated dihydroisoxazole nucleosides.
G. Romeo (2006)
10.1080/07328319808005153
Asymmetric synthesis of oxazolidine nucleosides and related chemistry.
J. Du (1998)
10.1016/S0040-4020(03)00772-5
Stereoselective synthesis of new bicyclic N,O-iso-homonucleoside analogues
B. Richichi (2003)
10.1055/S-2007-984514
Synthesis of Pyrazolinyl Heterocycles via Adenine- or Imidazole-Containing Nitrilimine Cycloaddition
F. Foti (2007)
10.1021/ja7104398
Transition-state interactions revealed in purine nucleoside phosphorylase by binding isotope effects.
A. S. Murkin (2008)
10.1021/JA071087S
Acyclic ribooxacarbenium ion mimics as transition state analogues of human and malarial purine nucleoside phosphorylases.
E. A. Taylor (2007)
10.1002/EJOC.201001610
The Synthesis and Conformation of Dihydroxypiperidinyl Derivates of Nucleobases as Novel Iminosugar Nucleoside Analogs
D. Rejman (2011)
10.1016/j.bmc.2012.08.045
Trimeric purine nucleoside phosphorylase: exploring postulated one-third-of-the-sites binding in the transition state.
B. Wielgus-Kutrowska (2012)
10.1016/j.bmcl.2012.10.128
Sulfonylpiperidines as novel, antibacterial inhibitors of Gram-positive thymidylate kinase (TMK).
G. Martínez-Botella (2013)
10.1021/JM00246A019
Synthesis of some glycoside analogs and related compounds from 9-amino-6-(methylthio)-9H-purine.
C. Temple (1975)
10.1016/J.TETLET.2006.10.117
New compounds via Mannich reaction of cytosine, paraformaldehyde and cyclic secondary amines
D. Prukała (2006)
10.1248/CPB.43.1601
STEREOSPECIFIC SYNTHESIS OF NOVEL 1, 3-THIAZOLIDIN-2-YL ANALOGUES OF PSEUDOURIDINE
A. Inaba (1995)
10.1016/J.TET.2007.08.032
Synthesis and antiviral properties of aza-analogues of ganciclovir derived from 5,5-bis(hydroxymethyl)pyrrolidin-2-one
Mariola Koszytkowska-Stawińska (2007)
10.1016/S0040-4039(00)76729-3
Total syntheses of N-boc-protected 3′-deoxy-4′-azathymidine and 4′-azauridine
G. Rassu (1994)
10.1039/c3cc43273d
Electrochemical synthesis of azanucleoside derivatives using a lithium perchlorate-nitromethane system.
Shokaku Kim (2013)
10.1016/j.tet.2008.08.027
Synthesis of N-methyl-d-ribopyranuronamide nucleosides
Shi-Qiong Yang (2008)
10.1016/j.ejmech.2011.11.021
Design, synthesis, antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a 1,2,3-triazole linker
D. G. Piotrowska (2012)
10.1021/JO050057+
Synthesis of 3'-deoxy-3'-difluoromethyl azanucleosides from trans-4-hydroxy-l-proline.
X. Qiu (2005)
10.1021/JO034048H
N7-guanine as a C+ mimic in hairpin aeg/aepPNA-DNA triplex: probing binding selectivity by UV-Tm and kinetics by fluorescence-based strand-invasion assay.
M. D'Costa (2003)
10.1016/J.TET.2006.03.078
Synthesis of racemic and enantiomeric 3-pyrrolidinyl derivatives of nucleobases
Petr Kočalka (2006)
10.1039/c0cc04646a
Synthesis of isoxazoles by hypervalent iodine-induced cycloaddition of nitrile oxides to alkynes.
Anup M. Jawalekar (2011)
10.1021/jm801421q
Third-generation immucillins: syntheses and bioactivities of acyclic immucillin inhibitors of human purine nucleoside phosphorylase.
K. Clinch (2009)
10.1021/AR00060A007
Adventures in Silicon-Organic Chemistry
H. Vorbrueggen (1995)
10.1021/JM000305O
Synthesis, 18F-Labeling, and Biological Evaluation of Piperidyl and Pyrrolidyl Benzilates as in Vivo Ligands for Muscarinic Acetylcholine Receptors
M. Skaddan (2000)
10.1016/J.TET.2005.10.075
Enantioselective synthesis of homocarbocyclic-2′-oxo-3′-azanucleosides
U. Chiacchio (2006)
10.1016/j.chembiol.2012.04.012
Acyclic immucillin phosphonates: second-generation inhibitors of Plasmodium falciparum hypoxanthine-guanine-xanthine phosphoribosyltransferase.
Keith Z. Hazleton (2012)
10.1002/EJOC.201000997
One-Pot Conversion of Proline Derivatives into Iodinated Iminosugar-Based Nucleosides, Useful Precursors of Highly Functionalized Nucleoside Analogues
A. Boto (2010)
10.1016/j.bmc.2009.02.001
RNA interference in mammalian cells by siRNAs modified with morpholino nucleoside analogues.
N. Zhang (2009)
10.1021/JM0308186
Enantioselective syntheses and cytotoxicity of N,O-nucleosides.
U. Chiacchio (2003)
10.1039/c2ob25835h
Small molecule control of bacterial biofilms.
R. J. Worthington (2012)
10.1021/jm3004619
Discovery of (2S)-1-[4-(2-{6-amino-8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9H-purin-9-yl}ethyl)piperidin-1-yl]-2-hydroxypropan-1-one (MPC-3100), a purine-based Hsp90 inhibitor.
Se-Ho Kim (2012)
10.1021/OP9001142
Development of a Practical Synthesis of a Purine Nucleoside Phosphorylase Inhibitor: BCX-4208
V. Kamath (2009)
10.1039/A900689C
Convenient synthesis of C -aza-2,3-dideoxynucleosides
A. Momotake (1999)
10.1016/S0960-894X(02)00182-8
Heterocyclic nucleoside analogues: design and synthesis of antiviral, modified nucleosides containing isoxazole heterocycles.
Y. Lee (2002)
10.1039/B517883E
Syntheses and bio-activities of the L-enantiomers of two potent transition state analogue inhibitors of purine nucleoside phosphorylases.
K. Clinch (2006)
10.1016/J.TETLET.2011.08.167
High-yield synthesis of pyrrolidinyl PNA monomers
P. Merino (2011)
10.1002/EJOC.201000360
One-Pot Synthesis of Azanucleosides from Proline Derivatives -Stereoselectivity in Sequential Processes
A. Boto (2010)
10.2174/092986706779026110
Synthesis and biological activity of phosphonated nucleosides: part 1. Furanose, carbocyclic and heterocyclic analogues.
A. Piperno (2006)
10.1002/med.21296
Medicinal Chemistry of Fluorinated Cyclic and Acyclic Nucleoside Phosphonates
O. Baszczyňski (2013)
10.1016/J.TET.2008.11.035
Prolinol-based nucleoside phosphonic acids: new isosteric conformationally flexible nucleotide analogues
V. Vaněk (2009)
10.1016/S0968-0896(99)00210-2
Transition state analogue inhibitors of protozoan nucleoside hydrolases.
R. Furneaux (1999)
10.1021/JM0400101
Control of hepatitis C: a medicinal chemistry perspective.
C. P. Gordon (2005)
10.1021/jo2004617
Synthesis of 3-guaninyl- and 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone nucleosides.
Abdullah Saleh (2011)
10.1055/S-1995-5263
Design and Synthesis of D-Ribofuranoamidrazones as Inhibitors of Nucleoside Processing Enzymes
M. Boutellier (1995)
10.1039/B502799C
Synthesis and triplex forming properties of pyrrolidino pseudoisocytidine containing oligodeoxynucleotides.
A. Mayer (2005)
10.1126/SCIENCE.1962210
Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide.
P. Nielsen (1991)
10.2174/156802605774370892
Peptide nucleic acid conjugates: synthesis, properties and applications.
Zhanna V. Zhilina (2005)
10.1021/OL026537U
DNA binding properties of oligodeoxynucleotides containing pyrrolidino C-nucleosides.
A. Haeberli (2002)
10.1016/S0040-4020(01)00284-8
9-Vinylguanine: an easy access to aza-analogs of 2’,3’-dideoxyguanosine
R. Dalpozzo (2001)
10.1016/S0960-894X(00)00168-2
Synthesis and structure-activity relationship of novel pyridyl ethers for the nicotinic acetylcholine receptor.
J. Lee (2000)
10.1002/cmdc.201200022
Truncated Reverse Isoxazolidinyl Nucleosides: A New Class of Allosteric HIV‐1 Reverse Transcriptase Inhibitors
R. Romeo (2012)
10.1021/ar2002304
Peptide vectors for the nonviral delivery of nucleic acids.
Jan Hoyer (2012)
10.1039/P19920002259
Synthesis of [3-(phosphonomethoxy)pyrrolidin-1-yl] derivatives of pyrimidines and purines: analogues of 2′,3′-dideoxynucleotides
M. R. Harnden (1992)
10.1016/J.JMB.2006.03.026
Transition-state complex of the purine-specific nucleoside hydrolase of T. vivax: enzyme conformational changes and implications for catalysis.
W. Versées (2006)
10.1016/J.ANTIVIRAL.2005.05.001
Antiviral drug discovery and development: where chemistry meets with biomedicine.
E. Clercq (2005)
10.1016/j.ejmech.2010.08.026
Exploring new inhibitors of Plasmodium falciparum purine nucleoside phosphorylase.
Huaqing Cui (2010)
10.1021/JM060547+
Simplified analogues of immucillin-G retain potent human purine nucleoside phosphorylase inhibitory activity.
Teresa Semeraro (2006)
10.1016/S0040-4020(00)00194-0
Synthesis of transition state analogue inhibitors for purine nucleoside phosphorylase and N-riboside hydrolases
G. B. Evans (2000)
10.1002/1522-2675(20000607)83:6<1049::AID-HLCA1049>3.0.CO;2-1
δ‐Peptide Analogues of Pyranosyl‐RNA, Part 1 , Nucleo‐δ‐peptides Derived from Conformationally Constrained Nucleo‐δ‐amino Acids: Preparation of Monomers
G. Karig (2000)
10.1016/S0040-4020(01)81716-6
Polyhydroxylated pyrrolidines from sugar lactomes: Synthesis of 1,4-dideoxy-1,4-imino-d-glucitol from d-galactonolactone and syntheses of 1,4-dideoxy-1,4-imino-d-allitol, 1,4-dideoxy-1,4-imino-d-ribitol, and (2s,3r,4s)-3,4-dihydroxyproline from d-gulonolactone
G. Fleet (1988)
10.1021/BI034003A
Ionic states of substrates and transition state analogues at the catalytic sites of N-ribosyltransferases.
A. Sauve (2003)
10.1016/S0040-4039(00)97169-7
Pyrrolidine and piperidine aminosugars from dicarbonyl sugars in one step. Concise synthesis of 1-deoxynojirimycin
A. Reitz (1990)
10.1021/jm100898v
Design and synthesis of potent "sulfur-free" transition state analogue inhibitors of 5'-methylthioadenosine nucleosidase and 5'-methylthioadenosine phosphorylase.
A. Longshaw (2010)
10.1016/j.bmcl.2009.05.122
The phosphoramidate ProTide approach greatly enhances the activity of beta-2'-C-methylguanosine against hepatitis C virus.
C. Mcguigan (2009)
10.1016/J.TET.2006.11.047
Synthesis of diastereomeric 3-hydroxy-4-pyrrolidinyl derivatives of nucleobases
D. Rejman (2007)
10.1016/S0040-4020(96)01172-6
Synthesis of transition state inhibitors for N-riboside hydrolases and transferases
R. Furneaux (1997)
10.1002/EJOC.201201384
Synthesis of Nucleobase‐Functionalized Morpholino‐Modified Nucleoside Monomers Through Palladium‐Catalyzed Cross‐Coupling Reactions
Bappaditya Nandi (2013)
10.1021/OL0069655
Pyrrolidine nucleic acids: DNA/PNA oligomers with 2-hydroxy/aminomethyl- 4-(thymin-1-yl)pyrrolidine-N-acetic acid.
V. Kumar (2001)
10.1021/JA970828U
Unusually Strong Binding of a Designed Transition-State Analog to a Base-Excision DNA Repair Protein
L. Deng (1997)
10.1021/jm201694y
Fluorophosphonylated nucleoside derivatives as new series of thymidine phosphorylase multisubstrate inhibitors.
S. Diab (2012)
10.1016/J.TET.2008.06.074
Solvent-free, microwave assisted 1,3-cycloaddition of nitrones with vinyl nucleobases for the synthesis of N,O-nucleosides
O. Bortolini (2008)
10.1021/JA00129A039
Specific binding of the DNA repair enzyme AlkA to a pyrrolidine-based inhibitor
O. Schärer (1995)
10.1021/BI980658D
One-third-the-sites transition-state inhibitors for purine nucleoside phosphorylase.
R. W. Miles (1998)
10.1016/J.TET.2008.11.069
Novel oligonucleotide analogues containing a morpholinoamidine unit
S. Pérez-Rentero (2009)
10.1021/cr800464r
Chemical synthesis of heterocyclic-sugar nucleoside analogues.
G. Romeo (2010)
10.1039/P19750001798
Unconventional nucleotide analogues. Part XIV. (2S,4S)-2-Hydroxy-methyl- and 2-carboxy-4-(pyrimidin-1-yl)pyrrolidines
F. Kaspersen (1975)
10.1016/S0040-4039(00)61548-4
Pyrrolidine based analogs of 3′-deoxythymidine
K. Altmann (1993)
10.1021/OL035293Q
Synthesis of a transition state analogue inhibitor of purine nucleoside phosphorylase via the Mannich reaction.
G. B. Evans (2003)
10.1016/S0960-894X(99)00619-8
Synthesis and hybridization properties of oligonucleotides containing 6-membered azasugar nucleotides.
K. Jung (1999)
10.1021/CR00016A004
AIDS-driven nucleoside chemistry.
D. M. Huryn (1992)
10.1081/NCN-100105906
SYNTHESIS AND BINDING AFFINITY OF A CHIRAL PNA ANALOGUE
Y. Li (2001)
10.1016/J.TET.2010.12.029
The synthesis of piperidine nucleoside analogs—a comparison of several methods to access the introduction of nucleobases
Soňa Kovačková (2011)
10.1021/JM9805687
Synthesis and serotonergic activity of 3-[2-(pyrrolidin-1-yl)ethyl]indoles: potent agonists for the h5-HT1D receptor with high selectivity over the h5-HT1B receptor.
F. Sternfeld (1999)
10.1016/j.bmc.2012.09.026
Synthesis, evaluation of anti-HIV-1 and anti-HCV activity of novel 2',3'-dideoxy-2',2'-difluoro-4'-azanucleosides.
Saúl Martínez-Montero (2012)
10.1016/J.BMCL.2006.04.085
Azadideoxyadenosine: synthesis, enzymology, and anti-HIV activity.
A. Nishonov (2006)
10.1021/jo3004452
Design and divergent synthesis of aza nucleosides from a chiral imino sugar.
Saúl Martínez-Montero (2012)
10.1016/j.tet.2009.11.001
Tetrahedron report number 898Recent advances in the synthesis of fluorinated nucleosides
Xiao-Long Qiu (2010)
10.1016/j.bmcl.2008.08.047
Immucillins in custom catalytic-site cavities.
A. S. Murkin (2008)
10.1007/s00253-006-0434-2
Promising nucleic acid analogs and mimics: characteristic features and applications of PNA, LNA, and morpholino
S. Karkare (2006)
10.1016/J.TETLET.2009.06.137
Alternative route towards the convergent synthesis of a human purine nucleoside phosphorylase inhibitor—forodesine HCl
V. Kamath (2009)
10.1080/07328319608002037
MODEL SYNTHESES OF THIAZOLIDINE NUCLEOSIDE ANALOGUES
G. Rassu (1996)
10.1021/OL048649M
Mannich-Type C-Nucleosidations in the 5,8-Diaza-7,9-dicarba-purine Family1
B. Han (2004)
10.1016/J.TET.2009.02.071
Pyrrolidine N-alkylphosphonates and related nucleotide analogues: synthesis and stereochemistry
D. Rejman (2009)
10.1016/j.bmcl.2009.09.040
Synthesis of modified homo-N-nucleosides from the reactions of mesityl nitrile oxide with 9-allylpurines and their influence on lipid peroxidation and thrombin inhibition.
Andreas Thalassitis (2009)
10.1021/JO035744K
Imino-C-nucleoside synthesis: heteroaryl lithium carbanion additions to a carbohydrate cyclic imine and nitrone.
G. B. Evans (2004)
10.1016/S0960-894X(00)00393-0
Use of proline bioisosteres in potential HIV protease inhibitors: phenylalanine-2-thiophenoxy-3-pyrrolidinone: synthesis and anti-HIV evaluation.
J. L. Kraus (2000)
10.1002/EJOC.201201443
Tuning the Stereoselectivity in One‐Pot Scission/Addition Processes: Synthesis of Azanucleotide Analogues from Proline Derivatives
Javier Miguélez‐Ramos (2013)
10.1074/jbc.M505033200
Energetic Mapping of Transition State Analogue Interactions with Human and Plasmodium falciparum Purine Nucleoside Phosphorylases*♦
A. Lewandowicz (2005)
10.1021/JA9600385
Inhibition of ricin by an rna stem-loop containing a ribo-oxycarbonium mimic
Xiangyang Chen (1996)
10.1016/J.TET.2006.05.029
Isoxazoline-carbocyclic aminols for nucleoside synthesis through aza-Diels-Alder reactions
P. Quadrelli (2006)
10.1016/S0040-4039(99)00854-0
Synthesis of new pyrrolidine C-nucleosides via Staudinger-aza-Wittig cyclization of γ-azido ketone
D. C. Kim (1999)
10.1016/j.cbpa.2009.09.030
Non-natural nucleic acids for synthetic biology.
D. Appella (2009)
10.1016/S0960-894X(99)00201-2
N-substituted-3-arylpyrrolidines: potent and selective ligands at serotonin 1A receptor.
K. H. Ahn (1999)
10.1021/cb300316n
In vivo validation of thymidylate kinase (TMK) with a rationally designed, selective antibacterial compound.
T. A. Keating (2012)
10.1021/JM030455+
Synthesis of a potent transition-state inhibitor of 5'-deoxy-5'-methylthioadenosine phosphorylase.
V. Kamath (2004)
10.1039/B006903P
Unusual RNA and DNA binding properties of a novel pyrrolidine–amide oligonucleotide mimic (POM)
D. T. Hickman (2000)
10.1016/J.BMC.2004.09.040
Synthesis of 2',3'-dideoxy-2'-monofluoromethyl azanucleosides.
Xiao-Long Qiup (2005)
10.1016/J.BMC.2004.11.044
Exploring human adenosine A3 receptor complementarity and activity for adenosine analogues modified in the ribose and purine moiety.
Philippe van Rompaey (2005)
10.1021/JM0613370
Application of the phosphoramidate ProTide approach to 4'-azidouridine confers sub-micromolar potency versus hepatitis C virus on an inactive nucleoside.
P. Perrone (2007)
10.1080/15257779408012166
The Synthesis of 4′-t-Butylcarbamyl- and 4′-p-Toluenesulphonamidyl-2′,3′-Dideoxy Pyrimidine Nucleoside Analogues
L. Pickering (1994)
10.1021/jm300662d
Synthesis of novel N-branched acyclic nucleoside phosphonates as potent and selective inhibitors of human, Plasmodium falciparum and Plasmodium vivax 6-oxopurine phosphoribosyltransferases.
D. Hocková (2012)
10.1021/JM00128A015
Replacement of the 3'-CH group by nitrogen in the carbocyclic analogue of thymidine.
K. M. Ng (1989)
10.1135/CCCC2009022
Synthesis and hybridization of oligonucleotides modified at AMP sites with adenine pyrrolidine phosphonate nucleotides
D. Rejman (2009)
10.1016/j.bmc.2012.03.047
Truncated phosphonated C-1'-branched N,O-nucleosides: a new class of antiviral agents.
R. Romeo (2012)
10.1016/S0040-4039(01)90037-1
De novo-synthesis of carbohydrates preparation of 4-amino-4-deoxy-d,l-ribose derivatives
A. K. Forrest (1984)
10.1016/J.TETASY.2008.04.028
Diastereoselective synthesis of a collection of new homonucleoside mimetics containing pyrrolo[1,2-b]isoxazoline and pyrrolidine rings
V. Mannucci (2008)
10.1016/J.TET.2008.01.133
Diastereoselective synthesis of d-xylo-isoxazolidinyl nucleosides
E. Hýrošová (2008)
10.1021/JA061403N
Transition state analogue discrimination by related purine nucleoside phosphorylases.
Erika A Taylor Ringia (2006)
10.1016/J.TET.2011.01.020
1,3-Dipolar cycloaddition approach to pyrrolidine analogues of C-nucleosides related to pseudouridine
E. Coutouli-Argyropoulou (2011)
10.1039/A802247J
Synthesis and properties of C-aza-2-deoxy-L-lyxonucleosides†
M. Yokoyama (1998)
10.1021/jo902485m
Synthesis of C-4'truncated phosphonated carbocyclic 2'-oxa-3'-azanucleosides as antiviral agents.
A. Piperno (2010)
10.1021/jm400779n
Inhibition of the Escherichia coli 6-oxopurine phosphoribosyltransferases by nucleoside phosphonates: potential for new antibacterial agents.
D. Keough (2013)
10.1081/NCN-120015721
A NEW CLASS OF ACYCLIC NUCLEOSIDE PHOSPHONATES: SYNTHESIS AND BIOLOGICAL ACTIVITY OF 9-{[(PHOSPHONOMETHYL)AZIRIDIN-1-YL]METHYL}GUANINE (PMAMG) AND ANALOGUES
G. A. Sheikha (2002)
10.1021/jo00348a020
Synthetic electroorganic chemistry. 14. Synthesis of 5-fluorouracil derivatives having N-acylazacycloalkanes and lactams
T. Nishitani (1982)
10.1135/CCCC20021267
Synthesis of 2',3'-Dideoxy-2'-trifluoromethyl- N -azanucleosides
F. Qing (2002)
10.1016/J.TETLET.2012.09.126
Lithium bromide–DBU mediated synthesis of chlorophosphoramidate-activated morpholino nucleoside subunits
Sankha Pattanayak (2012)
10.1016/0040-4039(94)88498-6
Synthesis of N-substituted hydroxyprolinol phosphoramidites for the preparation of combinatorial libraries
N. Hébert (1994)
10.1021/JM030145R
Exploring structure-activity relationships of transition state analogues of human purine nucleoside phosphorylase.
G. B. Evans (2003)
10.1039/b913546d
Effect of chirality of L/D-proline and prochiral glycine as the linker amino acid in five-atom linked thymidinyl-(alpha-amino acid)-thymidine dimers.
S. Bagmare (2009)
10.1135/CCCC20060015
Synthesis of Aminopropyl Phosphonate Nucleosides with Purine and Pyrimidine Bases
D. Zhou (2006)
10.3998/ARK.5550190.0003.B15
Enantioselective synthesis of isoxazolidinyl nucleosides containing uracil, 5-fluorouracil, thymine and cytosine as new potential anti-HIV drugs
U. Chiacchio (2002)
10.1021/JO01350A033
Pyrrolidine Sugars. Synthesis of 4'-Acetamidoadenosine and Other Derivatives of 4-Amino-4-deoxy-D-ribose1
E. J. Reist (1966)
10.1016/J.BMC.2005.09.024
Synthesis and biological evaluation of phosphonated carbocyclic 2'-oxa-3'-aza-nucleosides.
U. Chiacchio (2006)
10.1021/JM070285R
Phosphonated carbocyclic 2'-oxa-3'-azanucleosides as new antiretroviral agents.
U. Chiacchio (2007)
10.1016/J.TETASY.2009.02.026
Preparation of isoxazolidinyl nucleoside enantiomers by lipase-catalysed kinetic resolution
C. Carnovale (2009)
10.1021/jo3010364
O-Nucleoside, S-nucleoside, and N-nucleoside probes of lumazine synthase and riboflavin synthase.
A. Talukdar (2012)
10.1128/AAC.00470-07
Effect of Phosphonated Carbocyclic 2′-Oxa-3′-Aza-Nucleoside on Human T-Cell Leukemia Virus Type 1 Infection In Vitro
E. Balestrieri (2007)
10.1002/JHET.5570430212
Synthesis of some monocyclic-N-acetyl 4′-aza-D-nucleosides
C. V. Varaprasad (2006)
10.1021/jm800792b
A beta-fluoroamine inhibitor of purine nucleoside phosphorylase.
Jennifer M. Mason (2008)
10.1016/S0957-4166(00)00160-9
Diastereoselective and enantioselective synthesis of 4′-aza analogues of 2′,3′-dideoxynucleosides
U. Chiacchio (2000)
10.1016/j.bmc.2013.02.016
Acyclic phosph(on)ate inhibitors of Plasmodium falciparum hypoxanthine-guanine-xanthine phosphoribosyltransferase.
K. Clinch (2013)
10.1016/S0960-894X(00)80428-X
Synthesis of 9-[2-(phosphonomethoxy)ethylamino]adenine and 9-[(phosphonomethoxy)acetamido]adenine, analogues of a potent anti-HIV acyclonucleotide
Micheal R. Harnden (1992)
10.1016/j.bmcl.2009.03.138
The application of the phosphoramidate ProTide approach confers micromolar potency against hepatitis C virus on inactive agent 4'-azidoinosine: kinase bypass on a dual base/sugar modified nucleoside.
C. Mcguigan (2009)
10.1021/BI990829U
Iminoribitol transition state analogue inhibitors of protozoan nucleoside hydrolases.
R. W. Miles (1999)
10.1016/j.bmc.2013.01.007
Design, synthesis, antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a carbamoyl linker
K. Kokosza (2013)
10.1021/JM030305Z
Synthesis of second-generation transition state analogues of human purine nucleoside phosphorylase.
G. B. Evans (2003)
10.1021/JO001000K
Synthesis of pyrrolidinone PNA: a novel conformationally restricted PNA analogue.
A. Püschl (2001)
10.1021/JO980492M
Synthesis and Properties of C-Azalyxonucleosides.
A. Momotake (1998)
10.1016/j.bmc.2012.07.006
Transition state analogue inhibitors of human methylthioadenosine phosphorylase and bacterial methylthioadenosine/S-adenosylhomocysteine nucleosidase incorporating acyclic ribooxacarbenium ion mimics.
K. Clinch (2012)
10.1081/NCN-200060287
SYNTHESIS OF RACEMIC AND ENANTIOMERIC 3-PYRROLIDINYL DERIVATIVES OF PURINE AND PYRIMIDINE NUCLEOBASES
Petr Kočalka (2005)
10.1080/15257770.2012.724491
Improved Protocol for the Synthesis of Flexibly Protected Morpholino Monomers from Unprotected Ribonucleosides
Sankha Pattanayak (2012)
10.1016/S0968-0896(02)00268-7
New dsDNA binding unnatural oligopeptides with pyrimidine selectivity.
Z. Zhang (2002)
10.1016/S0040-4020(01)00813-4
Simple and efficient routes for the preparation of isoxazolidinyl nucleosides containing cytosine and 5-methyl-cytosine as new potential anti-HIV drugs
E. Colacino (2001)
10.1039/b913066g
1,3-Dipolar cycloadditions: applications to the synthesis of antiviral agents.
C. Nájera (2009)
10.1021/BI0343830
Over-the-barrier transition state analogues and crystal structure with Mycobacterium tuberculosis purine nucleoside phosphorylase.
A. Lewandowicz (2003)
10.1038/nrd1877
Acyclic nucleoside phosphonates: a key class of antiviral drugs
E. Clercq (2005)
10.1517/13543784.15.12.1601
Novel purine nucleoside analogues for T-cell-lineage acute lymphoblastic leukaemia and lymphoma
F. Ravandi (2006)
10.1016/J.TET.2011.11.035
Synthesis of novel azanorbornylpurine derivatives
H. Hřebabecký (2012)
10.1080/07328319908044742
Synthesis and Properties of Some Morpholino Oligonucleotide Analogues
O. Chakhmakhcheva (1999)
10.1016/0040-4039(95)01769-E
Synthesis and inhibition analysis of five-membered homoazasugars from D-arabinofuranose via an SN2 reaction of the chloromethylsulfonate
S. Hiranuma (1995)
10.1074/jbc.273.15.8592
Specific Binding of a Designed Pyrrolidine Abasic Site Analog to Multiple DNA Glycosylases*
O. Schärer (1998)
10.1016/J.TET.2009.06.067
Highly stereoselective synthesis of novel cyclobutane-fused azanucleosides
R. Flores (2009)
10.1021/jm701265n
Azetidine based transition state analogue inhibitors of N-ribosyl hydrolases and phosphorylases.
G. B. Evans (2008)
10.1021/AR030277E
Conformationally constrained PNA analogues: structural evolution toward DNA/RNA binding selectivity.
V. Kumar (2005)
10.1039/B002063J
Stereoselective synthesis of C-4′-aminouridines (uracil C-4-amino-D-ribonucleosides)
M. Yokoyama (2000)
10.1021/JM050912H
Synthesis and anti-HIV activity of D- and L-thietanose nucleosides.
H. Choo (2006)
10.1002/HLCA.200390093
Bisubstrate Inhibitors for the Enzyme Catechol O-Methyltransferase (COMT): Dramatic Effects of Ribose Modifications on Binding Affinity and Binding Mode
C. Lerner (2003)
10.1021/BI00004A008
Pre-steady-state transition-state analysis of the hydrolytic reaction catalyzed by purine nucleoside phosphorylase.
P. Kline (1995)
10.1074/JBC.C300259200
Achieving the Ultimate Physiological Goal in Transition State Analogue Inhibitors for Purine Nucleoside Phosphorylase*
A. Lewandowicz (2003)
10.1039/A700800G
Synthesis of (difluoromethyl)phosphonate azasugars designed as inhibitors for glycosyl transferases
Jean-Bernard Behr (1997)
10.1016/j.bmc.2008.08.041
Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure
Rafał Gawin (2008)
10.1016/S0040-4039(00)02343-1
Stereoselective synthesis of azanucleosides aza-stavudine (aza-D4T), aza-2′,3′-didehydro-3′-deoxyuridine (aza-D4U), and its hydrogenated analogues from an endocyclic enecarbamate
E. R. Costenaro (2001)
10.1081/NCN-120022737
Isosteric Phosphonate Pyrrolidine-Based Dinucleoside Monophosphate Analogues
V. Vaněk (2003)
10.1002/med.21271
Structure–Activity Relationships in the Development of Allosteric Hepatitis C Virus RNA‐Dependent RNA Polymerase Inhibitors: Ten Years of Research
R. Haudecoeur (2013)
10.1055/S-1999-3559
Synthesis and Biological Activity of Azanucleosides
M. Yokoyama (1999)
10.1016/S0960-894X(00)00121-9
Synthesis and hybridization properties of polyamide based nucleic acid analogues incorporating pyrrolidine-derived nucleoamino acids.
K. Altmann (2000)
10.1021/JM900932G
Highlights in the discovery of antiviral drugs: a personal retrospective.
E. Clercq (2010)
10.1021/JM049399I
Synthesis of phosphonated carbocyclic 2'-oxa-3'-aza-nucleosides: novel inhibitors of reverse transcriptase.
U. Chiacchio (2005)
10.1016/j.bmc.2013.07.031
Synthesis and biological evaluation of furopyrimidine N,O-nucleosides.
R. Romeo (2013)
10.1016/S0040-4039(00)79398-1
Synthesis of pyrrolidin-1-yl analogues of pyrimidine dideoxynucleosides
M. R. Harnden (1991)
10.1081/NCN-100002512
KINETICALLY SELECTIVE BINDING OF SINGLE STRANDED RNA OVER DNA BY A PYRROLIDINE-AMIDE OLIGONUCLEOTIDE MIMIC (POM)
D. T. Hickman (2001)
10.1016/J.JFLUCHEM.2008.02.008
Synthesis of 2′,3′-dideoxy-6′,6′-difluoro-3′-azanucleosides
Xuyi Yue (2008)
10.1039/B716835G
Chimeric (α-amino acid + nucleoside-β-amino acid)npeptide oligomers show sequence specific DNA/RNA recognition
K. Gogoi (2008)
10.1002/EJOC.200700217
Pyrrolidino DNA with Bases Corresponding to the 2-Oxo Deletion Mutants of Thymine and Cytosine: Synthesis and Triplex-Forming Properties
A. Mayer (2007)
10.1021/jm900197j
Stereoselective synthesis and biological evaluations of novel 3'-deoxy-4'-azaribonucleosides as inhibitors of hepatitis C virus RNA replication.
U. Chiacchio (2009)
10.1021/JM00113A017
Synthesis and biological evaluation of 4-purinylpyrrolidine nucleosides.
M. Peterson (1991)
10.1021/JO00090A040
Expeditious Synthesis of Aza sugars by the Double Reductive Amination of Dicarbonyl Sugars
E. W. Baxter (1994)
10.1016/J.BMCL.2004.02.034
Design and synthesis of conformationally frozen peptide nucleic acid backbone: chiral piperidine PNA as a hexitol nucleic acid surrogate.
P. Lonkar (2004)
10.1016/0040-4039(95)02373-9
Synthesis of 4′-aza analogues of 2′,3′-dideoxythymidine by 1,3-dipolar cycloadditions of nitrones to 1-N-vinyl-thymine
A. Leggio (1996)
10.1021/jm201409u
N-phosphonocarbonylpyrrolidine derivatives of guanine: a new class of bi-substrate inhibitors of human purine nucleoside phosphorylase.
D. Rejman (2012)
10.1073/PNAS.0602590103
The plasma membrane permease PfNT1 is essential for purine salvage in the human malaria parasite Plasmodium falciparum.
Kamal El Bissati (2006)
10.1073/pnas.071050798
Immucillin H, a powerful transition-state analog inhibitor of purine nucleoside phosphorylase, selectively inhibits human T lymphocytes
G. Kicska (2001)
10.1039/c0ob00532k
Amino acids attached to 2'-amino-LNA: synthesis and excellent duplex stability.
Marie W Johannsen (2011)
10.1021/JO00373A017
Synthesis of 2-(4-amino-4-deoxy-.beta.-D-ribofuranosyl)thiazole-4-carboxamide, a carbon-linked nucleoside with a free pyrrolidine sugar
G. Kini (1986)



This paper is referenced by
10.1515/ncrs-2020-0313
Crystal structure of 2-tert-butyl 1-methyl 5-{4-[(methoxycarbonyl)amino]phenyl}-2,5-dihydro-1H-pyrrole-1,2-dicarboxylate, C19H24N2O6
I. Caracelli (2020)
10.1007/s10593-020-02697-2
One-Pot Synthesis of N-(Phosphorylmethyl)Pyrrolidines via Acid-Catalyzed Cascade Elimination/Cyclization/Friedel–Crafts Reaction
L. Vagapova (2020)
10.21608/APRH.2018.5829
Antiviral Nucleoside and Nucleotide Analogs: A Review
S. Mahmoud (2018)
10.1016/j.carres.2019.107855
A practical approach to Dideoxy-1,4- and 1,5-iminopentitols from protected sugar hemiacetals.
Justyna Jaszczyk (2019)
10.3390/molecules23071612
Glycoside Mimics from Glycosylamines: Recent Progress
Cyril Nicolas (2018)
10.1002/anie.201700547
Synthesis of Azanucleosides by Anodic Oxidation in a Lithium Perchlorate-Nitroalkane Medium and Diversification at the 4'-Nitrogen Position.
T. Shoji (2017)
Computational insight into the broad substrate specificity of enzymes that process nucleic acids
S. Lenz (2018)
10.1016/j.ejmech.2015.05.029
Synthesis by microwave-assisted 1,3-dipolar cycloaddition of 1,2,3-triazole 1'-homo-3'-isoazanucleosides and evaluation of their anticancer activity.
Joana Ferreira da Costa (2015)
10.1021/acs.joc.6b03071
Tunable Approach for the Stereoselective Synthesis of 1-C-Diethylphosphono(difluoromethyl) Iminosugars as Glycosyl Phosphate Mimics.
Chloé Cocaud (2017)
10.1134/S1070428020010285
First Analog of Pyrimidine Nucleosides with Two D-Ribofuranose Residues
R. R. Sharipova (2020)
10.1007/s00706-016-1831-6
Synthesis of 1,4-diarylpyrrolotriazepine derivatives by two diverse strategies
Tamas Foeldesi (2016)
10.1002/EJOC.201601034
Microwave versus Conventional Light Activation of O‐Radical Scission Processes
C. Carro (2017)
10.1002/CHIN.201445244
Nucleoside Analogues: Synthesis and Biological Properties of Azanucleoside Derivatives
Dácil Hernández (2014)
10.3390/molecules25092050
Recent Advances in the Chemical Synthesis and Evaluation of Anticancer Nucleoside Analogues
Mieke Guinan (2020)
10.1002/chem.201804285
Synthesis of Ribo-Azanucleosides by Anodic Oxidation: Reactivity Control of Intermediate for Efficient Access to Pharmacophores.
K. Okamoto (2018)
10.1016/j.tet.2017.05.083
Efficient diastereoselective synthesis of a new class of azanucleosides: 2′-homoazanucleosides
Jakob Bouton (2017)
10.1016/j.bmc.2020.115507
An aza-nucleoside, fragment-like inhibitor of the DNA repair enzyme alkyladenine glycosylase (AAG).
Eduard Mas Claret (2020)
10.1039/c4ob01372g
Metal-free, one-pot conversion of proline derivatives into 2-aryl-3-iodo pyrrolidines by a sequential scission-iodination-arylation process.
Venkateswara Rao Batchu (2014)
10.1021/ACS.CHEMREV.6B00466
Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications.
Johan R Johansson (2016)
10.1002/cmdc.201600620
Trachycladines and Analogues: Synthesis and Evaluation of Anticancer Activity
Zisis V. Peitsinis (2017)
10.1039/c7cs00619e
Electrochemical strategies for C-H functionalization and C-N bond formation.
M. Kärkäs (2018)
10.1002/EJOC.201701283
Triazole‐Linked Iminosugars and Aromatic Systems as Simplified UDP‐Galf Mimics: Synthesis and Preliminary Evaluation as Galf‐Transferase Inhibitors
Chloé Cocaud (2017)
10.1002/EJOC.201403485
Perfluoroalkylation of Nitrones for the Synthesis of a Series of Fucosidase Inhibitors
Jadwiga Paszkowska (2015)
10.1039/c7ob02296d
Tricyclanos: conformationally constrained nucleoside analogues with a new heterotricycle obtained from a d-ribofuranose unit.
Máté Kicsák (2018)
10.1039/c5ob00781j
Reusable ionic liquid-catalyzed oxidative coupling of azoles and benzylic compounds via sp(3) C-N bond formation under metal-free conditions.
Wenbo Liu (2015)
10.1039/d0ob01046d
Synthesis of novel homoazanucleosides and their peptidyl analogs.
R. Salunke (2020)
10.3390/molecules24050873
Design, Synthesis and Biological Evaluation of Isoxazole-Based CK1 Inhibitors Modified with Chiral Pyrrolidine Scaffolds
A. Luxenburger (2019)
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