40110-98-3

Usage

InChI:InChI=1/C10H11N5O3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7-6(18-7)4(1-16)17-10/h2-4,6-7,10,16H,1H2,(H2,11,12,13)/t4-,6+,7+,10-/m1/s1

Upstream product

• 58-61-7 adenosine 
• 5536-17-4 arabinosyl adenine 

Downstream Products

• 102997-84-2 6-N-5'-O-Bis<4-methoxytriphenylmethyl>-2',3'-lyxo-anhydroadenosine 
• 29411-70-9 9-(3′-azido-3′-deoxy-β-D-arabinofuranosyl)purine 
• 6998-75-0 3'-deoxydenosine 
• 13276-53-4 9-(2'-deoxy-β-D-threo-ribofuranosyl)-adenine 
• 73-03-0 cordycepin 
• 133776-32-6 Benzoic acid (2R,3S,4S,5R)-4-azido-5-(6-benzoylamino-purin-9-yl)-3-fluoro-tetrahydro-furan-2-ylmethyl ester 

Relevant academic research and scientific papers

S-ANTIGEN TRANSPORT INHIBITING OLIGONUCLEOTIDE POLYMERS AND METHODS

Various embodiments provide STOPS? polymers that are S-antigen transport inhibiting oligonucleotide polymers, processes for making them and methods of using them to treat diseases and conditions. In some embodiments the STOPS? modified oligonucleotides include an at least partially phosphorothioated sequence of alternating A and C units having modifications as described herein. The sequence independent antiviral activity against hepatitis B of embodiments of STOPS? modified oligonucleotides, as determined by HBsAg Secretion Assay, is an EC50 that is less than 100 nM.

MODIFIED OLIGONUCLEOTIDES AND METHODS OF USE IN TAUOPATHIES

Oligonucleotides comprising modifications at the 2' and/or 3' positions(s) along with methods of 5 making and use against Alzheimer disease and other tauopathies are disclosed.

MODIFIED OLIGONUCLEOTIDES AND METHODS OF USE

Modified oligonucleotides comprising modifications at the 2' and/or 3' positions(s) along with methods of making and use, e.g., against HBV are disclosed.

NEW 2' AND/OR 5' AMINO-ACID ESTER PHOSPHORAMIDATE 3'-DEOXY ADENOSINE DERIVATIVES AS ANTI-CANCER COMPOUNDS

The present invention relates to chemical compounds, the compounds for use in a method of treatment, particularly in a method of prophylaxis or treatment for cancer, a process for preparation of the compounds and pharmaceutical compositions comprising the compounds. The compounds may, in particular, be useful in the treatment of leukaemia, lymphoma and/or solid tumours inhomo sapiens. The compounds are derivatives of cordycepin (3'-deoxyadenosine) having a 2' and/or 5'- amino-acid ester phosphoramidate moeity.

Convenient preparation of carbonyl compounds from 1,2-diols utilizing Mitsunobu conditions

1,1-Disubstituted 1,2-diols are efficiently converted into carbonyl compounds by reaction with triphenylphosphine and diethyl azodicarboxylate. (C) 2000 Elsevier Science Ltd.

A facile and efficient route to 3',5'-diamino-3',5'-dideoxynucleosides

An efficient synthesis of 9-(3',5'-diamino-3'-5'-dideoxy-β-D-ribofuranosyl)adenine is described (40% overall yield); the synthetic route is applicable to all the nucleoside bases and can serve as a general procedure for the synthesis of 3',5'-diaminonucle

Nucleic acid related compounds. 81. Syntheses of 9-(3-deoxy-β-D-threo- pentofuranosyl)adenine, the core nucleoside of the extraordinarily selective antibiotic agrocin 84, and simplified structural component analogues

Alternative syntheses of 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine (4), the core nucleoside of agrocin 84 [and its 2'-deoxy threo isomer 5] were devised: (1) direct conversion of 9-(β-D-arabinofuranosyl)adenine into 9- (2,3-anhydro-β-D-lyxofuranosyl)adenine and regioselective opening of its oxirane ring with sodium borohydride to give 4 and 5 (~7.5:1); (2) treatment of adenosine with sodium hydride and 2,4,6-triisopropylbenzenesulfonyl chloride, and subjection of the resulting 2'(3')-sulfonates to the reductive [1,2]-hydride shift rearrangement with lithium triethylborohydride to give 4 and 5 (~2:1); and (3) subjection of the phenoxythiocarbonyl esters of 9- [2(3),5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]adenine to Barton deoxygenation, and deprotection to give 4 and 2'-deoxyadenosine (~5:1). Methods (2) and (3) gave lower yields. Syntheses of simplified 6-N- and 5'-O-adenosine phosphoramidate model compounds were explored to examine potential access to such features in the structure proposed for agrocin 84.

REACTION OF ADENINE NUCLEOSIDES, TOSYLATED IN THE CARBOHYDRATE MOIETY, WITH LITHIUM TRIETHYLBOROHYDRIDE

The reaction of lithium triethylborohydride with the 2',3'-di-O-p-tolylsulphonyl derivatives of 9-β-D-ribofuranosyladenine, 9-β-D-arabinofuranosyladenine, 9-β-D-xylofuranosyladenine and 9-β-D-lyxofuranosyladenine was studied.The reaction of 2',3'-di-O-p-tolylsulphonyladenosine with LiEt3BH gave 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine.This rearrangement reaction was used for the synthesis of 9-(3,5-dideoxy-β-D-threo-pentofuranosyl)adenine in one step from 2',3',5'-tri-O-p-tolylsulphonyladenosine in 58percent yield.The p-tolylsulphonyl group in the 2'-"up" configuration of unprotected adenine nucleosides was preferentially attacked by LiEt3BH giving S-O-bond scission.This was shown by the formation of 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine from 2',3'-di-O-p-tolylsulphonyl-9-β-D-arabinofuranosyladenine and by the formation of 9-β-D-lyxofuranosyladenine from 2'-O-p-tolylsulphonyl-9-β-D-lyxofuranosyladenine with LiEt3BH. 9-β-D-Lyxofuranosyladenine was synthesized from 3',5'-di-O-benzoyl-9-β-D-xylofuranosyladenosine in 88percent yield using a triflate displacement reaction.