U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C5H3ClN4
Molecular Weight 154.557
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 6-CHLOROPURINE

SMILES

ClC1=NC=NC2=C1N=CN2

InChI

InChIKey=ZKBQDFAWXLTYKS-UHFFFAOYSA-N
InChI=1S/C5H3ClN4/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H,7,8,9,10)

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
Purine analogs as potential anticytomegalovirus agents.
1969 Sep
Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyl-transferase from Toxoplasma gondii.
1995 Nov 9
Synthesis and characterization of nucleosides and oligonucleotides bearing adducts of butadiene epoxides on adenine n(6) and guanine n(2).
2001 Apr
Molecular design of a new class of spin-labeled ribonucleosides with N-tert-butylaminoxyl radicals.
2001 May 18
A new method for the synthesis of 2'-O-benzyladenosine using Mitsunobu reaction.
2003 Feb
Introduction of a benzyl group onto the 2'-OH of 6-chloropurine 3'-O-benzoylriboside.
2003 May-Aug
Synthesis and Ca2+-mobilizing activity of purine-modified mimics of adenophostin A: a model for the adenophostin-Ins(1,4,5)P3 receptor interaction.
2003 Nov 6
[Synthesis and biological activity of pseudonucleotides based on the evolution hypothesis of the glycocomponent of nucleic acid].
2003 Sep 1
Molecular design of novel spin-labeled nucleosides directly attached base moiety.
2004
SNAr iodination of 6-chloropurine nucleosides: aromatic Finkelstein reactions at temperatures below -40 degrees C.
2004 Aug 19
Microwave-assisted amination of a chloropurine derivative in the synthesis of acyclic nucleoside analogues.
2005 Feb 28
Evidence for Watson-Crick and not Hoogsteen or wobble base pairing in the selection of nucleotides for insertion opposite pyrimidines and a thymine dimer by yeast DNA pol eta.
2005 Mar 29
Preparation of a fully substituted purine library.
2005 May-Jun
Cytostatic 6-arylpurine nucleosides. 6. SAR in anti-HCV and cytostatic activity of extended series of 6-hetarylpurine ribonucleosides.
2005 Sep 8
Traceless solid-phase synthesis of N1,N7-disubstituted purines.
2005 Sep-Oct
Synthesis of novel 4'-carbon-substituted BCA derivatives based on radical cyclization.
2006
Anti-SARS-CoV activity of nucleoside analogs having 6-chloropurine as a nucleobase.
2006
Preparation and biological activity of 6-benzylaminopurine derivatives in plants and human cancer cells.
2006 Feb 1
De novo asymmetric synthesis of homoadenosine via a palladium-catalyzed N-glycosylation.
2006 Jan 19
Synthesis of fluorinated nucleosides.
2006 Jul
A synthetic route to 9-(polyhydroxyalkyl)purines.
2006 Sep 25
Synthesis and anti-HCV activity Of 2''-beta-hydroxymethylated nucleosides.
2007
Suppression of subgenomic hepatitis C virus replication by 5'-O-masked analogues of 6-chloropurine-2'-deoxyriboside.
2007
Facile synthesis of 1',2'-cis-beta-pyranosyladenine nucleosides.
2007 Dec 10
Palladium-catalyzed cross-coupling reactions in c6 modifications of purine nucleosides.
2007 Mar
A novel noninvasive method for assessing glutathione-conjugate efflux systems in the brain.
2007 May 1
Synthesis and biological evaluation of nucleoside analogues having 6-chloropurine as anti-SARS-CoV agents.
2007 May 1
Bicyclic nucleoside synthesis: a photochemical approach.
2008 May
Synthesis of 6,8,9-tri- and 2,6,8,9-tetrasubstituted purines by a combination of the Suzuki cross-coupling, N-arylation, and direct C-H arylation reactions.
2008 Nov 21
Additive Pummerer reaction of 3,5-O-(di-tert-butyl)silylene-4-thiofuranoid glycal: a high-yield and beta-selective entry to 4'-thioribonucleosides.
2009 Mar 20
Microwave-assisted syntheses of nucleosides and their precursors.
2010 Feb
Photochemical synthesis of nucleoside analogues from cyclobutanones: bicyclic and isonucleosides.
2010 May 26
Semisynthesis of 6-chloropurine-2'-deoxyriboside 5'-dimethoxytrityl 3'-(2-cyanoethyl-N,N-diisopropylamino)phosphoramidite and its use in the synthesis of fluorescently labeled oligonucleotides.
2010 Nov
DNA oligomers containing site-specific and stereospecific exocyclic deoxyadenosine adducts of 1,2,3,4-diepoxybutane: synthesis, characterization, and effects on DNA structure.
2010 Oct 18
Direct synthesis of 6-arylpurines by reaction of 6-chloropurines with activated aromatics.
2010 Sep 3
Patents
Name Type Language
6-CHLOROPURINE
MI  
Systematic Name English
6-CHLOROPURINE [MI]
Common Name English
6-CHLORO-9H-PURINE
Systematic Name English
NSC-744
Code English
Code System Code Type Description
CAS
87-42-3
Created by admin on Fri Dec 15 15:04:01 GMT 2023 , Edited by admin on Fri Dec 15 15:04:01 GMT 2023
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NSC
744
Created by admin on Fri Dec 15 15:04:01 GMT 2023 , Edited by admin on Fri Dec 15 15:04:01 GMT 2023
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PUBCHEM
5359277
Created by admin on Fri Dec 15 15:04:01 GMT 2023 , Edited by admin on Fri Dec 15 15:04:01 GMT 2023
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SMS_ID
300000000020
Created by admin on Fri Dec 15 15:04:01 GMT 2023 , Edited by admin on Fri Dec 15 15:04:01 GMT 2023
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ECHA (EC/EINECS)
201-745-6
Created by admin on Fri Dec 15 15:04:01 GMT 2023 , Edited by admin on Fri Dec 15 15:04:01 GMT 2023
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MERCK INDEX
m3433
Created by admin on Fri Dec 15 15:04:01 GMT 2023 , Edited by admin on Fri Dec 15 15:04:01 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID00861673
Created by admin on Fri Dec 15 15:04:01 GMT 2023 , Edited by admin on Fri Dec 15 15:04:01 GMT 2023
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FDA UNII
OH8700156W
Created by admin on Fri Dec 15 15:04:01 GMT 2023 , Edited by admin on Fri Dec 15 15:04:01 GMT 2023
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