136834-22-5

Usage

Uses

Used in Pharmaceutical Industry:
N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-2'-fluoroadenosine 3'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite] is used as a key intermediate in the synthesis of modified nucleotides for improving metabolic stability. The enhanced stability allows these modified nucleotides to be more effective in various biological applications, such as gene silencing and regulation of gene expression.
Used in Biotechnology Industry:
In the biotechnology industry, this adenosine derivative is utilized in the preparation of microRNA inhibitors. MicroRNAs are small, non-coding RNA molecules that play a crucial role in the regulation of gene expression. By inhibiting specific microRNAs, researchers can study their functions and potentially develop novel therapeutic strategies for various diseases.
Used in Chemical Synthesis:
N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-2'-fluoroadenosine 3'-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite] is also used as a building block in the synthesis of more complex molecules with potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science. Its unique structure and functional groups make it a valuable component in the development of new compounds with specific properties and functions.

Upstream product

• 136834-21-4 N-(9-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)3-fluoro-4-hydroxytetrahydrofuran-2-yl)9H-purin-6yl)benzamide triethylammonium salt 
• 79896-97-2 N6-benzoyl-9-β-D-arabinofuranosyladenine 
• 136834-20-3 N-(9-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide 
• 136834-18-9 N⁶-benzoyl-9-(3,5-di-O-tetrahydropyran-2-yl-β-D-arabinofuranosyl)adenine 
• 146954-64-5 N⁶-benzoyl-2'-deoxy-2'-fluoro-3',5'-di-O-tetrahydropyran-2-yladenosine 
• 136834-19-0 N⁶-benzoyl-9-<2-O-(trifluoromethylsulfonyl)-3,5-di-O-tetrahydropyran-2-yl-β-D-arabinofuranosyl>adenine 
• 102691-36-1 N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 98-88-4 benzoyl chloride 
• 124482-92-4 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine 
• 20187-82-0 2'-fluorodeoxyadenosine 
• 20187-82-0 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine 
• 97614-43-2 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose 
• 123318-82-1 clofarabine 

Relevant academic research and scientific papers

Cyclic dinucleotide analogues, pharmaceutical composition of analogues and applications of analogues and pharmaceutical composition

The invention discloses cyclic dinucleotide analogues, a pharmaceutical composition of the analogues and applications of the analogues and the pharmaceutical composition. The cyclic dinucleotide analogs (I), an isomer, prodrug, stable isotope derivative or pharmaceutically acceptable salt of the analogs have a structure shown in the specification. The cyclic dinucleotide analogs provided by the invention can be used as regulators of stimulator of interferon genes (STIG) and related signaling pathways, and can effectively treat and/or alleviate multiple types of diseases, including but not limited to malignant tumors, inflammation, autoimmune diseases and infectious diseases; and in addition, the STING regulators can also be used as vaccine adjuvants.

CYCLIC DI-NUCLEOTIDES AS STIMULATOR OF INTERFERON GENES MODULATORS

The present disclosure relates to a compound of formulae (I) or (II), or a pharmaceutically acceptable salt, a solvate, a hydrate thereof, a pharmaceutical composition comprising a compound of formulae (I) or (II), and use thereof, wherein various Markush

Cyclic dinucleotide compound, preparation method and application thereof

The invention discloses a cyclic dinucleotide compound, a preparation method and an application thereof, specifically, the invention relates to a compound of a formula (I), a pharmaceutically acceptable salt thereof, the preparation method thereof, and the application in the preparation of a medicine for treatment and/or prevention of a disease associated with activation of STING protein or as a vaccine adjuvant. The diseases associated with activation of the STING protein include viral infections, bacterial infections, cancers, diseases related to the immune system, and the like.

Antisense modulation of polo-like kinase expression

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.

Antisense modulation of perilipin expression

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.

Antisense modulation of EDG5 expression

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.

ANTISENSE MODULATION OF EDG1 EXPRESSION

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.

Oligonucleotides containing 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-adenine and -guanine: Synthesis, hybridization and antisense properties

Synthesis of 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-adenine (7, ara-A2′F) and -guanine (12, ara-G2′F) was accomplished via the condensation of 2,6-dichloropurine (1) with 2-deoxy-2-fluoro-1,3,5-tri-O-benzoyl-α-D-arabinofuranose (2) as a key chemical step. Condensation of silylated N6-benzoyladenine (6) with 2 gave, after deblocking and chromatographic separation, ara-A2′F (7) (14%), it's α-anomer 8 (14%) and N7-α-isomer 9 (25%). The PSEUROT analysis of N9-β-D-arabinosides 7 and 12 manifested slight preference for the S rotamer (64%) for the former, and an equal population of the N and S rotamers for the latter. The arabinosides 7 and 12 were used for the preparation of the respective phosphoamidite building blocks 13 and 14 for automated oligonucleotide synthesis. Four 15-mer oligonucleotides (ONs) complementary to the initiation codon region of firefly luciferase mRNA were prepared: unmodified 2′-deoxy-ON (AS 1) and containing (i) ara-A2′F instead of the only A (AS2), (ii) ara-G2′F vs. 3-G from the 5′-terminus (AS3), and (iii) both arabinosides at the same positions (AS4). All these ONs display practically the same (i) affinity to both complementary DNA and RNA, and (ii) ability to inhibit a luciferase gene expression in a cell-free transcription-translation system.

Uniformly modified 2'-deoxy-2'-fluoro phosphorothioate oligonucleotides as nuclease-resistant antisense compounds with high affinity and specificity for RNA targets

'Uniformly' modified phosphodiester or phosphorothioate oligonucleotides incorporating 2'-deoxy-2'-fluoroadenosine, -guanosine, -uridine, and - cytidine, reported herein for the first time, when hybridized with RNA afforded consistent additive enhancement of duplex stability without compromising base-pair specificity. CD spectra of the 2'-deoxy-2'-fluoro- modified oligonucleotides hybridized with RNA indicated that the duplex adopts a fully A-form conformation. The 2'-deoxy-2'-fluoro-modified oligonucleotides in phosphodiester form were not resistant to nucleases; however, the modified phosphorothioate oligonucleotides were highly nuclease resistant and retained exceptional binding affinity to the RNA targets. The stabilizing effects of the 2'-deoxy-2'-fluoro modifications on RNA-DNA duplexes were shown to be superior to those of the 2'-O-methylribo substitutions. RNA hybrid duplexes with uniformly 2'-deoxy-2'-fluoro-modified oligonucleotides did not support HeLa RNase H activity; however, incorporation of the modifications into 'chimeric' oligonucleotides has been shown to activate mammalian RNase H. 'Uniformly' modified 2'-deoxy-2'-fluoro phosphorothioate oligonucleotides afforded antisense molecules with (1) high binding affinity and selectivity for the RNA target and (2) stability toward nucleases.