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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H11N5O2
Molecular Weight 233.2266
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2',3'-DIDEOXY-2',3'-DIDEHYDROADENOSINE

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](CO)C=C3

InChI

InChIKey=JFUOUIPRAAGUGF-NKWVEPMBSA-N
InChI=1S/C10H11N5O2/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(3-16)17-7/h1-2,4-7,16H,3H2,(H2,11,12,13)/t6-,7+/m0/s1

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
1987 Aug
Both 2',3'-dideoxythymidine and its 2',3'-unsaturated derivative (2',3'-dideoxythymidinene) are potent and selective inhibitors of human immunodeficiency virus replication in vitro.
1987 Jan 15
The anti-HTLV-III (anti-HIV) and cytotoxic activity of 2',3'-didehydro-2',3'-dideoxyribonucleosides: a comparison with their parental 2',3'-dideoxyribonucleosides.
1987 Jul
The 2',3'-dideoxyriboside of 2,6-diaminopurine selectively inhibits human immunodeficiency virus (HIV) replication in vitro.
1987 May 29
Synthesis and anti-HIV activity of various 2'- and 3'-substituted 2',3'-dideoxyadenosines: a structure-activity analysis.
1987 Nov
Investigations on the anti-HIV activity of 2',3'-dideoxyadenosine analogues with modifications in either the pentose or purine moiety. Potent and selective anti-HIV activity of 2,6-diaminopurine 2',3'-dideoxyriboside.
1988 Apr 1
Comparative activity of 2',3'-saturated and unsaturated pyrimidine and purine nucleosides against human immunodeficiency virus type 1 in peripheral blood mononuclear cells.
1988 Oct 1
Potential prodrug derivatives of 2',3'-didehydro-2',3'-dideoxynucleosides. Preparations and antiviral activities.
1992 Jul 24
Conversion of 2',3'-dideoxyadenosine (ddA) and 2',3'-didehydro-2',3'-dideoxyadenosine (d4A) to their corresponding aryloxyphosphoramidate derivatives markedly potentiates their activity against human immunodeficiency virus and hepatitis B virus.
1997 Jun 30
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
1999 May 6
Activities of masked 2',3'-dideoxynucleoside monophosphate derivatives against human immunodeficiency virus in resting macrophages.
2000 Jan
Stereoselective synthesis of a novel carbocyclic nucleoside.
2001 Nov 2
Synthesis and studies of 3'-C-trifluoromethyl nucleoside analogues bearing adenine or cytosine as the base.
2002 Oct
Inhibition of hepatitis B virus by a novel L-nucleoside, beta-L-D4A and related analogues.
2003 Aug
[Inhibition of the replication of hepatitis B virus in vitro by a novel nucleoside analogue (beta-L-D4A)].
2003 Jul
[Effect and mechanism of beta-L-D4A (a novel nucleoside analog) against hepatitis B virus].
2003 May
Synthesis, structure-activity relationships, and drug resistance of beta-d-3'-fluoro-2',3'-unsaturated nucleosides as anti-HIV Agents.
2004 Jun 17
[Synthesis of a novel L-nucleoside, beta-L-D4A and its inhibition on the replication of hepatitis B virus in vitro].
2005 Sep
Synthesis and conformational analysis of new cyclobutane-fused nucleosides.
2006 Feb 2
Effect and mechanism of beta-L-D4A on DNA polymerase alpha.
2007 Dec 14
[Isosteric triphosphonate analogues of dNTP: synthesis and substrate properties toward various DNA polymerases].
2007 Sep-Oct
Inhibition of reverse transcriptase activity of hepatitis B virus polymerase by β-l-D4A-TP.
2008
Efficacies of beta-L-D4A against Hepatitis B virus in 2.2.15 cells.
2008 Feb 28
Effects of two novel nucleoside analogues on different hepatitis B virus promoters.
2008 Mar 28
Synthesis and antiviral evaluation of thieno[3,4-d]pyrimidine C-nucleoside analogues of 2',3'-dideoxy- and 2',3'-dideoxy-2',3'-didehydro-adenosine and -inosine.
2009 Mar 15
Name Type Language
2',3'-DIDEOXY-2',3'-DIDEHYDROADENOSINE
Systematic Name English
2',3'-DIDEHYDRO-2',3'-DIDEOXYADENOSINE
Systematic Name English
DIDANOSINE IMPURITY I
EP   WHO-IP  
Common Name English
NSC-108602
Code English
DIDANOSINE IMPURITY I [WHO-IP]
Common Name English
ADENOSINE, 2',3'-DIDEHYDRO-2',3'-DIDEOXY-
Systematic Name English
ADENINE, 9-(2,3-DIDEOXY-.BETA.-D-GLYCERO-PENT-2-ENOFURANOSYL)-
Common Name English
PENT-2-ENOFURANOSIDE, ADENINE-9 2,3-DIDEOXY-
Common Name English
DIDANOSINE IMPURITY I [EP IMPURITY]
Common Name English
Code System Code Type Description
PUBCHEM
64975
Created by admin on Sat Dec 16 02:55:34 GMT 2023 , Edited by admin on Sat Dec 16 02:55:34 GMT 2023
PRIMARY
EPA CompTox
DTXSID70875924
Created by admin on Sat Dec 16 02:55:34 GMT 2023 , Edited by admin on Sat Dec 16 02:55:34 GMT 2023
PRIMARY
CAS
7057-48-9
Created by admin on Sat Dec 16 02:55:34 GMT 2023 , Edited by admin on Sat Dec 16 02:55:34 GMT 2023
PRIMARY
NSC
108602
Created by admin on Sat Dec 16 02:55:34 GMT 2023 , Edited by admin on Sat Dec 16 02:55:34 GMT 2023
PRIMARY
FDA UNII
SK35877HI5
Created by admin on Sat Dec 16 02:55:34 GMT 2023 , Edited by admin on Sat Dec 16 02:55:34 GMT 2023
PRIMARY