Home Halogens 1-β-D-Arabinofuranosyl-5-[(1E)-2-bromoethenyl]-2,4(1H,3H)-pyrimidinedione

1-β-D-Arabinofuranosyl-5-[(1E)-2-bromoethenyl]-2,4(1H,3H)-pyrimidinedione

CAS No.:
77181-69-2
Catalog Number:
AG003AJW
Molecular Formula:
C11H13BrN2O6
Molecular Weight:
349.1347
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
Product Description
Catalog Number:
AG003AJW
Chemical Name:
1-β-D-Arabinofuranosyl-5-[(1E)-2-bromoethenyl]-2,4(1H,3H)-pyrimidinedione
CAS Number:
77181-69-2
Molecular Formula:
C11H13BrN2O6
Molecular Weight:
349.1347
MDL Number:
MFCD00866949
IUPAC Name:
5-[(E)-2-bromoethenyl]-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
InChI:
InChI=1S/C11H13BrN2O6/c12-2-1-5-3-14(11(19)13-9(5)18)10-8(17)7(16)6(4-15)20-10/h1-3,6-8,10,15-17H,4H2,(H,13,18,19)/b2-1+/t6-,7-,8+,10-/m1/s1
InChI Key:
GCQYYIHYQMVWLT-HQNLTJAPSA-N
SMILES:
Br/C=C/c1cn(c(=O)[nH]c1=O)[C@@H]1O[C@@H]([C@H]([C@@H]1O)O)CO
UNII:
C7VOZ162LV
Properties
Complexity:
480  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
1  
Exact Mass:
347.996g/mol
Formal Charge:
0
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
349.137g/mol
Monoisotopic Mass:
347.996g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
119A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.9  
Literature
Title Journal
3'-[4-Aryl-(1,2,3-triazol-1-yl)]-3'-deoxythymidine analogues as potent and selective inhibitors of human mitochondrial thymidine kinase. Journal of medicinal chemistry 20100408
5-alkynyl analogs of arabinouridine and 2'-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells. Journal of medicinal chemistry 20070614
Novel selective human mitochondrial kinase inhibitors: design, synthesis and enzymatic activity. Bioorganic & medicinal chemistry 20070415
Susceptibilities of several clinical varicella-zoster virus (VZV) isolates and drug-resistant VZV strains to bicyclic furano pyrimidine nucleosides. Antimicrobial agents and chemotherapy 20050301
Synthesis and antiviral activities of 1'-carbon-substituted 4'-thiothymidines. Bioorganic & medicinal chemistry 20041015
Inactivity of the bicyclic pyrimidine nucleoside analogues against simian varicella virus (SVV) does not correlate with their substrate activity for SVV-encoded thymidine kinase. Biochemical and biophysical research communications 20040319
In vitro selection of drug-resistant varicella-zoster virus (VZV) mutants (OKA strain): differences between acyclovir and penciclovir? Antiviral research 20040301
Drug interaction ontology (DIO) for inferences of possible drug-drug interactions. Studies in health technology and informatics 20040101
In vitro activity of potential anti-poxvirus agents. Antiviral research 20030101
[Molecular toxicological mechanism of the lethal interactions of the new antiviral drug, sorivudine, with 5-fluorouracil prodrugs and genetic deficiency of dihydropyrimidine dehydrogenase]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20020801
Design, synthesis and enzymatic activity of highly selective human mitochondrial thymidine kinase inhibitors. Bioorganic & medicinal chemistry letters 20010521
2'-O-Acyl/alkyl-substituted arabinosyl nucleosides as inhibitors of human mitochondrial thymidine kinase. Biochemical pharmacology 20010315
Recent developments in herpesvirus therapy. Herpes : the journal of the IHMF 20010301
Effects of light intensity, n-alcohols, water-soluble colorants, and solution viscosity on photoisomerization of sorivudine. Pharmaceutical development and technology 20010101
Selective activity of various antiviral compounds against HHV-7 infection. Antiviral research 19990801
Synthesis of novel 4'-C-methyl-pyrimidine nucleosides and their biological activities. Bioorganic & medicinal chemistry letters 19990322
Anti-herpesvirus activity profile of 4'-thioarabinofuranosyl purine and uracil nucleosides and activity of 1-beta-D-2'-fluoro-4'-thioarabinofuranosyl guanine and 2,6-diaminopurine against clinical isolates of human cytomegalovirus. Antiviral research 19980801
Structure-activity relationship of the affinity of 5-substituted uracil nucleoside analogues for varicella-zoster virus thymidine kinase and their activity against varicella-zoster virus. Antiviral research 19970801
A facile, alternative synthesis of 4'-thioarabinonucleosides and their biological activities. Journal of medicinal chemistry 19970704
Analysis of phosphorylation pathways of antiherpesvirus nucleosides by varicella-zoster virus-specific enzymes. Antimicrobial agents and chemotherapy 19960401
Antiviral activity of selected acyclic nucleoside analogues against human herpesvirus 6. Antiviral research 19951201
Comparative activity of selected antiviral compounds against clinical isolates of varicella-zoster virus. European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology 19950401
Synthesis and antiviral activity of 1-cyclobutyl-5-(2-bromovinyl)uracil nucleoside analogues and related compounds. Journal of medicinal chemistry 19920515
Inhibition of human herpesvirus 6 replication by 9-[4-hydroxy-2-(hydroxymethyl)butyl]guanine (2HM-HBG) and other antiviral compounds. Antimicrobial agents and chemotherapy 19901201
Effect of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil against herpes simplex virus type 1 infection in immunosuppressed mice. Antimicrobial agents and chemotherapy 19901201
Comparative activities of several nucleoside analogs against duck hepatitis B virus in vitro. Antimicrobial agents and chemotherapy 19900701
Effect of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil (brovavir) on experimental infections in mice with herpes simplex virus type 1 strains of different degrees of virulence. Antimicrobial agents and chemotherapy 19900501
(E)-5-(2-bromovinyl)uridine requires phosphorylation by the herpes simplex virus (type 1)-induced thymidine kinase to express its antiviral activity. Biochemical pharmacology 19890615
Effects of various nucleosides on antiviral activity and metabolism of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil against herpes simplex virus types 1 and 2. Antimicrobial agents and chemotherapy 19881001
Efficacies of antiherpesvirus nucleosides against two strains of herpes simplex virus type 1 in Vero and human embryo lung fibroblast cells. Antimicrobial agents and chemotherapy 19880701
Comparison of two bromovinyl nucleoside analogs, 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil and E-5-(2-bromovinyl)-2'-deoxyuridine, with acyclovir in inhibition of Epstein-Barr virus replication. Antimicrobial agents and chemotherapy 19880701
Comparison of susceptibilities of varicella-zoster virus and herpes simplex viruses to nucleoside analogs. Antimicrobial agents and chemotherapy 19860301
In vitro and in vivo antiviral activity of 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil (BV-araU) and related compounds. Antiviral research 19840601
Strains of varicella-zoster virus resistant to 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil. Antimicrobial agents and chemotherapy 19840601
Antiherpes activity of (E)-5-(2-bromovinyl)- and 5-vinyl-1-beta-D-arabinofuranosyluracil and some other 5-substituted uracil arabinosyl nucleosides in two different cell lines. Antiviral research 19830901
Inhibitory effect of E-5-(2-bromovinyl)-1-beta-D-arabinofuranosyluracil on herpes simplex virus replication and DNA synthesis. Journal of virology 19820701
Inhibitory effects of antiherpesviral thymidine analogs against varicella-zoster virus. Antimicrobial agents and chemotherapy 19820201
Antiherpes activity of [E]-5-(1-propenyl)-2'-deoxyuridine and 5-(1-propenyl)-1-beta-D-arabinofuranosyluracil. Antiviral research 19811101
Differential activity of potential antiviral nucleoside analogs on herpes simplex virus-induced and human cellular thymidine kinases. Antimicrobial agents and chemotherapy 19810901
Antiherpesviral and anticellular effects of 1-beta-D-arabinofuranosyl-E-5-(2-halogenovinyl) uracils. Antimicrobial agents and chemotherapy 19810701
Properties