2-AMINO-6-CHLOROPURINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H4ClN5
Molecular Weight	169.572
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(Cl)=C2NC=NC2=N1

InChI

InChIKey=RYYIULNRIVUMTQ-UHFFFAOYSA-N

InChI=1S/C5H4ClN5/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H3,7,8,9,10,11)

HIDE SMILES / InChI

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
purine nucleotide biosynthetic process 1 Target ID: GO:0006164 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5638558	Inhibitor 8504

PubMed

Title	Date	PubMed
Phosphonate analogues of cyclopropavir phosphates and their E-isomers. Synthesis and antiviral activity.	2009-06-01	19410465
(Z)- and (E)-2-(1,2-dihydroxyethyl)methylenecyclopropane analogues of 2'-deoxyadenosine and 2'-deoxyguanosine. Synthesis of all stereoisomers, absolute configuration, and antiviral activity.	2009-05-28	19397271
Additive Pummerer reaction of 3,5-O-(di-tert-butyl)silylene-4-thiofuranoid glycal: a high-yield and beta-selective entry to 4'-thioribonucleosides.	2009-03-20	19243156
2-Position base-modified analogues of adenophostin A as high-affinity agonists of the D-myo-inositol trisphosphate receptor: in vitro evaluation and molecular modeling.	2008-03-07	18247493
Synthesis of altritol nucleoside phosphoramidites for oligonucleotide synthesis.	2007-09	18428966
Synthesis of 2,2,3-tris(hydroxymethyl)methylenecyclopropane analogues of nucleosides.	2007	17479434
Fluoroanalogues of anti-cytomegalovirus agent cyclopropavir: synthesis and antiviral activity of (E)- and (Z)-9-{[2,2-bis(hydroxymethyl)-3-fluorocyclopropylidene]methyl}-adenines and guanines.	2007	17454732
Synthesis of "reversed" methylenecyclopropane analogues of antiviral phosphonates.	2007	17162591
Efficient N-arylation and N-alkenylation of the five DNA/RNA nucleobases.	2006-11-24	17109545
9-{[3-fluoro-2-(hydroxymethyl)cyclopropylidene]methyl}adenines and -guanines. Synthesis and antiviral activity of all stereoisomers1.	2006-10-05	17004726
Oxanosine is a substrate of adenosine deaminase. Implications for the quest for a toxicological marker for nitrosation activity.	2005-12	16359173
Synthesis and preliminary biological evaluation of O6-[4-(2-[18F]fluoroethoxymethyl)benzyl]guanine as a novel potential PET probe for the DNA repair protein O6-alkylguanine-DNA alkyltransferase in cancer chemotherapy.	2005-10-15	15993610
Synthesis of 9-alkyl and 9-heteroalkyl substituted 2-amino-6-guanidinopurines and their influence on the NO-production in macrophages.	2005-04-15	15781401
Stereoselective synthesis of 9-beta-d-arabianofuranosyl guanine and 2-amino-9-(beta-d-arabianofuranosyl)purine.	2005-02-01	15664837
Synthesis of 2-amino-6-(4-[11C]methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester as a novel potential PET gene reporter probe for HBV and HSV-tk in cancers.	2005-01-17	15598575
Conformationally constrained purine mimics. Incorporation of adenine and guanine into spirocyclic nucleosides.	2004-08-20	15307723
Syntheses and base-pairing properties of locked nucleic acid nucleotides containing hypoxanthine, 2,6-diaminopurine, and 2-aminopurine nucleobases.	2004-05-28	15153000
Synthesis and antiviral activity of (Z)- and (E)-2,2-[bis(hydroxymethyl)cyclopropylidene]methylpurines and -pyrimidines: second-generation methylenecyclopropane analogues of nucleosides.	2004-01-29	14736238
Synthesis of base substituted 2-hydroxy-3-(purin-9-yl)-propanoic acids and 4-(purin-9-yl)-3-butenoic acids.	2003-12	14714763
Facilitation of addition-elimination reactions in pyrimidines and purines using trifluoroacetic acid in trifluoroethanol.	2003-11-21	14651112
Synthesis and preliminary biological evaluation of radiolabeled O6-benzylguanine derivatives, new potential PET imaging agents for the DNA repair protein O6-alkylguanine-DNA alkyltransferase in breast cancer.	2003-05	12767398
Structure-activity relationships of (S,Z)-2-aminopurine methylenecyclopropane analogues of nucleosides. Variation of purine-6 substituents and activity against herpesviruses and hepatitis B virus.	2003-04-10	12672254
Synthesis of 7-hydroxy(phenyl)ethylguanines by alkylation of 2-amino-6-chloropurine with allyl-protected bromohydrins.	2003-03-06	12605478
Synthesis of (Z)-(2,3-bis-hydroxymethyl)methylenecyclopropane analogues of purine nucleosides.	2003-03	12816385
Efficient syntheses of 2-chloro-2'-deoxyadenosine (cladribine) from 2'-deoxyguanosine(1).	2003-02-07	12558425
Three 2-aminopurine derivatives.	2003-01	12506238
Structure-activity relationships of 2'-fluoro-2',3'-unsaturated D-nucleosides as anti-HIV-1 agents.	2002-03-14	11882000
Synthesis of 2-alkyl-substituted-N6-methyladenine derivatives as potential adenosine receptor ligand.	2001-12	11794524
Methylene-gem-difluorocyclopropane analogues of nucleosides: synthesis, cyclopropene-methylenecyclopropane rearrangement, and biological activity.	2001-11-08	11689090
Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyl-transferase from Toxoplasma gondii.	1995-11-09	7503772

Patents

Name

Type

Language

FAMCICLOVIR RELATED COMPOUND F

Preferred Name

English

2-AMINO-6-CHLOROPURINE

Systematic Name

English

1H-PURIN-2-AMINE, 6-CHLORO-

Systematic Name

English

9H-PURIN-2-AMINE, 6-CHLORO-

Systematic Name

English

6-CHLORO-2-AMINOPURINE

Systematic Name

English

PURINE, 2-AMINO-6-CHLORO-

Systematic Name

English

6-CHLORO-7H-PURIN-2-AMINE

Systematic Name

English

FAMCICLOVIR RELATED COMPOUND F [USP-RS]

Common Name

English

6-CHLORO-2-PURINAMINE

Systematic Name

English

6-CHLORO-1H-PURIN-2-AMINE

Systematic Name

English

NSC-29570

Code

English

6-CHLOROGUANINE

Common Name

English

6-CHLORO-9H-PURIN-2-YL-2-AMINE

Common Name

English

2-AMINO-6-CHLORO-9H-PURINE

Systematic Name

English

Code System Code Type Description

CHEBI

72345