- Synthesis method of 2 ’ -fluoro -2 ’ - deoxyuridine and intermediate thereof
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The synthesis method of 2 ’ -fluoro -2 ’ - deoxyuridine is novel in synthetic route, simple and convenient to operate, high in yield, good in safety, free of column chromatography and suitable for industrial production. Among them R is a hydroxyl protecting group, most preferably a tetrahydropyranyl group (THP group) as a hydroxyl protecting group. R is a conventional protecting group for the hydroxyl group in the art, and R THP
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Paragraph 0093-0095
(2021/11/26)
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- Copper(II)nitrate catalyzed regioselective protection of primary alcohols with 4,4′-dimethoxytrityl and 2,7-dimethyl-9-phenyl xanthen-9-yl groups in nucleosides and carbohydrates
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Regioselective protection of primary hydroxyl group in nucleoside and carbohydrate analogs was accomplished using dimethoxytrityl alcohol (DMTr-OH) or dimethylpixyl alcohol (DMPx-OH) in presence of copper(II)nitrate as a Lewis acid catalyst. Excellent selectivity was observed for the protection of primary hydroxyl group over secondary while glycosidic bond remain unaffected. Utility of this methodology was further exemplified via DMTr- and DMPx-protection of alipahtic acyclic and cyclic diols.
- Penjarla, Srishylam,Prasad, S. Rajendra,Reddy, Dhande Sudhakar,Banerjee, Shyamapada,Penta, Santhosh,Sanghvi, Yogesh S.
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p. 232 - 247
(2018/05/14)
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- DDQ mediated regiospecific protection of primary alcohol and deprotection under neutral conditions: Application of new p-methoxy benzyl-pixyl ether as reagent of choice for nucleoside protection
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A simple and efficient protocol is described for regiosepecific protection of primary hydroxyl group both in nucleosides and other molecules with p-methoxy-benzyl 2,7-dimethyl pixylether (MBDPE) in presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). Furthermore, swift deprotection of 2, 7-dimethylpixyl (DMPx) is accomplished with DDQ in MeOH. Both procedures are successfully implemented on gram-scale synthesis of modified nucleosides. This protocol offers mild and neutral conditions for selective protection and deprotection of DMPx group while compatible in presence of other conventional protecting groups such as benzoyl, benzyl, THP, TBDPS and acetonide.
- Srishylam, Penjarla,Raji Reddy,Banerjee, Shyamapada,Penta, Santhosh,Sanghvi, Yogesh S.
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supporting information
p. 2588 - 2591
(2017/06/13)
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- 3-methyl uridine and 4-methyl cytidine nucleoside compound, synthetic method and its pharmaceutical use
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The invention discloses a 3-methyluridine and 4-methylcytidine nucleosides compound and a synthesis method and pharmaceutical application thereof, belonging to the field of medicinal chemistry. The compound has a structural formula as shown in the specification. The compound has the effects of simultaneously modifying sugar rings and basic groups, increasing the activity of the compound and reducing the toxicity, provides a good application prospect for development of like medicines and can be applied to preparation of anti-HBV (Hepatitis B virus) medicines. The synthesis method is simple and feasible and provides conditions for mass synthesis of the compound.
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- Novel Dideoxynucleoside Derivatives
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The present invention discloses a 5′-amino-2′-fluoro-2′,5′-dideoxynucleoside derivative represented by the following formula [1]: (wherein R1 represents a nucleic acid base which may have a protecting group; R2 represents a hydrogen atom or a protecting group of an amino group; R3 represents a hydrogen atom or a protecting group of a hydroxyl group); a dideoxynucleoside-insoluble carrier bound substance prepared by binding said dideoxynucleoside derivative to an insoluble carrier, and an oligonucleotide analogue into which said dideoxynucleoside derivative is introduced. The oligonucleotide analogue being introduced with a dideoxynucleoside derivative of the present invention has excellent thermal stability and also high binding affinity when duplex is formed. Also, it is anticipated that it has high resistance to nucleases. Further, the dideoxynucleoside derivative of the present invention can be used as an amidite reagent to be used for nucleic acid synthesis, and also as a starting material for solid phase synthesis of nucleic acid by binding the amidite reagent to a solid phase.
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Page/Page column 6; 9
(2008/06/13)
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- PROCESS FOR PRODUCING 2 -DEOXY-2 -FLUOROURIDINE
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1-β-D-Arabinofuranosyluracil in 3',5'-hydroxyl-protected form is reacted with a trifluoromethanesulfonylating agent in the presence of an organic base to convert it into a 2'-triflate form, and then it is reacted with a fluorinating agent containing "a salt or complex formed by an organic base and hydrofluoric acid" to produce 2'-deoxy-2'-fluorouridine in 3',5'-hydroxyl-protected form. A deprotecting agent is further caused to act thereon to obtain 2'-deoxy-2'-fluorouridine. The 2'-deoxy-2'-fluorouridine obtained can efficiently be purified by temporarily converting it into a 3',5'-diacetyl form, recrystallizing the 3',5'-diacetyl form, and then deacetylating it. Thus, high-purity 2'-deoxy-2'-fluorouridine can be produced.
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Page/Page column 18-19
(2008/06/13)
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- Antisense modulation of CD40 ligand expression
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Antisense compounds, compositions and methods are provided for modulating the expression of CD40 ligand. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding CD40 ligand. Methods of using these compounds for modulation of CD40 ligand expression and for treatment of diseases associated with expression of CD40 ligand are provided.
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Page/Page column 18
(2008/06/13)
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- Synthesis and in vitro anti-HCV activity of β-D- and L-2′-deoxy-2′-fluororibonucleosides
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Based on the discovery of β-D-2′-deoxy-2′-fluorocytidine as a potent anti-hepatitis C virus (HCV) agent, a series of β-D- and L-2′-deoxy-2′-fluororibonucleosides with modifications at 5 and/or 4 positions were synthesized and evaluated for their in vitro activity against HCV and bovine viral diarrhea virus (BVDV). The introduction of the 2′-fluoro group was achieved by either fluorination of 2,2′-anhydronucleosides with hydrogen fluoride-pyridine or potassium fluoride, or a fluorination of arabinonucleosides with DAST. Among the 27 analogues synthesized, only the 5-fluoro compounds, namely β-D-2′- deoxy-2′,5-difluorocytidine (5), had anti-HCV activity in the subgenomic HCV replicon cell line, and inhibitory activity against ribosomal RNA. As β-D-N4-hydroxycytidine (NHC) had previously shown potent anti-HCV activity, the two functionalities of the N4-hydroxyl and the 2′-fluoro were combined into one molecule, yielding β-D-2′- deoxy-2′-fluoro-N4-hydroxycytidine (12). However, this nucleoside showed neither anti-HCV activity nor toxicity. All the L-forms of the analogues were devoid of anti-HCV activity. None of the compounds showed anti-BVDV activity, suggesting that the BVDV system cannot reliably predict anti-HCV activity in vitro. Copyright Taylor & Francis, Inc.
- Shi, Junxing,Du, Jinfa,Ma, Tianwei,Pankiewicz, Krzysztof W.,Patterson, Steven E.,Hassan, Abdalla E. A.,Tharnish, Phillip M.,McBrayer, Tamara R.,Lostia, Stefania,Stuyver, Lieven J.,Watanabe, Kyoichi A.,Chu, Chung K.,Schinazi, Raymond F.,Otto, Michael J.
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p. 875 - 879
(2007/10/03)
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- Antisense modulation of polo-like kinase expression
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Antisense compounds, compositions and methods are provided for modulating the expression of polo-like kinase. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding polo-like kinase. Methods of using these compounds for modulation of polo-like kinase expression and for treatment of diseases associated with expression of polo-like kinase are provided.
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Page/Page column 18
(2008/06/13)
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- Modulation of DC-SIGN expression
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Compounds, compositions and methods are provided for modulating the expression of DC-SIGN. The compositions comprise oligonucleotides, targeted to nucleic acid encoding DC-SIGN. Methods of using these compounds for modulation of DC-SIGN expression and for diagnosis and treatment of diseases and conditions associated with expression of DC-SIGN are provided.
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Page/Page column 12
(2008/06/13)
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- Modulation of CEACAM1 expression
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Compounds, compositions and methods are provided for modulating the expression of CEACAM1. The compositions comprise oligonucleotides, targeted to nucleic acid encoding CEACAM1. Methods of using these compounds for modulation of CEACAM1 expression and for diagnosis and treatment of disease associated with expression of CEACAM1 are provided.
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Page/Page column 26
(2010/02/11)
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- Antisense modulation of CD36 expression
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Antisense compounds, compositions and methods are provided for modulating the expression of CD36. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding CD36. Methods of using these compounds for modulation of CD36 expression and for treatment of diseases associated with expression of CD36 are provided.
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Page/Page column 16
(2010/02/06)
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- Antisense modulation of perilipin expression
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Antisense compounds, compositions and methods are provided for modulating the expression of perilipin. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding perilipin. Methods of using these compounds for modulation of perilipin expression and for treatment of diseases associated with expression of perilipin are provided.
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Page/Page column 18
(2008/06/13)
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- Antisense modulation of EDG5 expression
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Antisense compounds, compositions and methods are provided for modulating the expression of EDG5. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding EDG5. Methods of using these compounds for modulation of EDG5 expression and for treatment of diseases associated with expression of EDG5 are provided.
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Page/Page column 18
(2008/06/13)
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- ANTISENSE MODULATION OF EDG1 EXPRESSION
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Antisense compounds, compositions and methods are provided for modulating the expression of EDG1. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding EDG1. Methods of using these compounds for modulation of EDG1 expression and for treatment of diseases associated with expression of EDG1 are provided.
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Page/Page column 18
(2008/06/13)
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- Antisense modulation of resistin expression
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Antisense compounds, compositions and methods are provided for modulating the expression of resistin. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding resistin. Methods of using these compounds for modulation of resistin expression and for treatment of diseases associated with expression of resistin are provided.
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Page/Page column 18
(2010/02/05)
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- ANTISENSE MODULATION OF ENDOTHELIAL LIPASE EXPRESSION
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Antisense compounds, compositions and methods are provided for modulating the expression of Endothelial Lipase (EL). The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding EL. Methods of using these compounds for modulation of EL expression and for treatment of diseases associated with expression of EL are provided.
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- Antisense modulation of PPP3CB expression
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Antisense compounds, compositions and methods are provided for modulating the expression of PPP3CB. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding PPP3CB. Methods of using these compounds for modulation of PPP3CB expression and for treatment of diseases associated with expression of PPP3CB are provided.
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Page/Page column 18
(2008/06/13)
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- Modulation of diacylglycerol acyltransferase 1 expression
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Compounds, compositions and methods are provided for modulating the expression of diacylglycerol acyltransferase 1. The compositions comprise oligonucleotides, targeted to nucleic acid encoding diacylglycerol acyltransferase 1. Methods of using these compounds for modulation of diacylglycerol acyltransferase 1 expression and for diagnosis and treatment of disease associated with expression of diacylglycerol acyltransferase 1 are provided.
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Page/Page column 12
(2008/06/13)
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- Antisense modulation of G protein-coupled receptor 12 expression
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Antisense compounds, compositions and methods are provided for modulating the expression of G protein-coupled receptor 12. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding G protein-coupled receptor 12. Methods of using these compounds for modulation of G protein-coupled receptor 12 expression and for treatment of diseases associated with expression of G protein-coupled receptor 12 are provided.
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Page/Page column 19
(2010/11/30)
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- OLIGONUCLEOTIDES HAVING MODIFIED NUCLEOSIDE UNITS
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Disclosed are oligonucleotides and oligonucleosides that include one or more modified nucleoside units. The oligonucleotides and oligonucleosides are particularly useful as antisense agents, ribozymes, aptamer, siRNA agents, probes and primers or, when hybridized to an RNA, as a substrate for RNA cleaving enzymes including RNase H and dsRNase.
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- Antisense modulation of phosphoinositide-3-kinase, regulatory subunit 4, p150 expression
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Antisense compounds, compositions and methods are provided for modulating the expression of phosphoinositide-3-kinase, regulatory subunit 4, p150. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding phosphoinositide-3-kinase, regulatory subunit 4, p150. Methods of using these compounds for modulation of phosphoinositide-3-kinase, regulatory subunit 4, p150 expression and for treatment of diseases associated with expression of phosphoinositide-3-kinase, regulatory subunit 4, p150 are provided.
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- Antisense modulation of Rb2/p130 expression
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Antisense compounds, compositions and methods are provided for modulating the expression of Rb2/p130. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding Rb2/p130. Methods of using these compounds for modulation of Rb2/p130 expression and for treatment of diseases associated with expression of Rb2/p130 are provided.
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- Notch1 inhibitors for inducing apoptosis
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Compounds, compositions and methods are provided for modulating the expression of Notch1. The compositions comprise oligonucleotides, targeted to nucleic acid encoding Notch1. Methods of using these compounds for modulation of Notch1 expression and for diagnosis and treatment of disease associated with expression Notch1 are provided.
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- Antisense modulation of PLML expression
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Antisense compounds, compositions and methods are provided for modulating the expression of PLML. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding PLML. Methods of using these compounds for modulation of PLML expression and for treatment of diseases associated with expression of PLML are provided.
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- Antisense modulation of MARK3 expression
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Antisense compounds, compositions and methods are provided for modulating the expression of MARK3. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding MARK3. Methods of using these compounds for modulation of MARK3 expression and for treatment of diseases associated with expression of MARK3 are provided.
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- Antisense modulation of histone deacetylase 2 expression
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Antisense compounds, compositions and methods are provided for modulating the expression of histone deacetylase 2. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding histone deacetylase 2. Methods of using these compounds for modulation of histone deacetylase 2 expression and for treatment of diseases associated with expression of histone deacetylase 2 are provided.
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- Antisense modulation of G protein-coupled receptor kinase 6 expression
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Antisense compounds, compositions and methods are provided for modulating the expression of G protein-coupled receptor kinase 6. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding G protein-coupled receptor kinase 6. Methods of using these compounds for modulation of G protein-coupled receptor kinase 6 expression and for treatment of diseases associated with expression of G protein-coupled receptor kinase 6 are provided.
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- Antisense modulation of prox-1 expression
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Antisense compounds, compositions and methods are provided for modulating the expression of prox-1. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding prox-1. Methods of using these compounds for modulation of prox-1 expression and for treatment of diseases associated with expression of prox-1 are provided.
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- Antisense modulation of PPP3R1 expression
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Antisense compounds, compositions and methods are provided for modulating the expression of PPP3R1. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding PPP3R1. Methods of using these compounds for modulation of PPP3R1 expression and for treatment of diseases associated with expression of PPP3R1 are provided.
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- Method for the treatment of protoza infections with 21 -deoxy-21 -fluoropurine nucleosides
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A method for treating two specific protozoal infections, Trichomonas vaginalis and Giardia lamblia, comprising the administration to a mammal in need thereof one of the following purine nucleosides: 2,6-diamino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine 2-amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine 2-amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-6-methoxy-9H-purine.
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- Synthesis and hypnotic and anti-human immunodeficiency virus-1 activities of N3-substituted 2'-deoxy-2'-fluorouridines
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Reaction of 9-[3,5-di-O-(tetrahydropyran-2-yl)-β-D- arabinofuranosyl]uracil (2) with diethylaminosulfur trifluoride in the presence of pyridine afforded 2'-deoxy-2'-flouroriboside 3a, from which 2'- deoxy-2'-fluorocytidine (14b) has been synthesized in good yield. Compound 3a was deprotected and subsequently treated with various benzyl halides or 2- chloro-4-fluoroacetophenone to give corresponding N3-substituted 2'-deoxy- 2'-fluorouridines 5a-c and 6. Compounds 5a-c, as well as 6, showed weak hypnotic activity in mice. Compound 4b showed moderate antiviral activity against human immunodeficiency virus-1 but 3b, 5a-c, and 6 were virtually inactive.
- Sato,Utsumi,Maruyama,Kimura,Yamamoto,Richman
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p. 595 - 598
(2007/10/02)
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- Antiviral compounds
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The present invention relates to 2?-fluoro substituted purine nucleosides and their use in medical therapy, particularly for the treatment of infectious diseases including influenza virus and respiratory syncytial virus infections, to methods for their preparation and to compositions containing them.
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- 2,3'-DIFLUORO- AND 3'-AZIDO-2'-FLUORO SUBSTITUTED DIDEOXYPYRIMIDINES AS POTENTIAL ANTI-HIV AGENTS
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2'-Deoxy-2'-fluorouridine (2) was obtained by reaction of the arabinofuranosyl nucleoside 1 with diethylaminosulfur trifluoride followed by detritylation.After inversion of the configuration at the 3'-position, 4 was used as starting material for the preparation of the 2',3'-disubstituted derivatives 6, 7, 8 and 10.
- Aerschot, A. Van,Herdewijn, P.
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p. 937 - 942
(2007/10/02)
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