200,000+ products from a single source!

sales@angenechem.com

Home > Bromides > 82768-44-3

82768-44-3

82768-44-3 | Uridine, 5-(2-bromoethenyl)-2'-deoxy-

CAS No: 82768-44-3 Catalog No: AG004TFT MDL No:

Product Description

Catalog Number:
AG004TFT
Chemical Name:
Uridine, 5-(2-bromoethenyl)-2'-deoxy-
CAS Number:
82768-44-3
Molecular Formula:
C11H13BrN2O5
Molecular Weight:
333.1353
IUPAC Name:
5-(2-bromoethenyl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
InChI:
InChI=1S/C11H13BrN2O5/c12-2-1-6-4-14(11(18)13-10(6)17)9-3-7(16)8(5-15)19-9/h1-2,4,7-9,15-16H,3,5H2,(H,13,17,18)/t7-,8+,9+/m0/s1
InChI Key:
ODZBBRURCPAEIQ-DJLDLDEBSA-N
SMILES:
BrC=Cc1cn([C@H]2C[C@@H]([C@H](O2)CO)O)c(=O)[nH]c1=O

Properties

Complexity:
450  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Defined Bond Stereocenter Count:
0
Exact Mass:
332.001g/mol
Formal Charge:
0
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
333.138g/mol
Monoisotopic Mass:
332.001g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
99.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
1  
XLogP3:
-0.4  

Literature

Title Journal
Characterization of pyrimidine nucleoside phosphorylase of Mycoplasma hyorhinis: implications for the clinical efficacy of nucleoside analogues. The Biochemical journal 20120701
Antitumor effects of oncolytic adenovirus armed with Drosophila melanogaster deoxyribonucleoside kinase in colorectal cancer. Oncology reports 20120501
Antivirals for management of herpes zoster including ophthalmicus: a systematic review of high-quality randomized controlled trials. Antiviral therapy 20120101
Potent anticancer effects of lentivirus encoding a Drosophila melanogaster deoxyribonucleoside kinase mutant combined with brivudine. Asian Pacific journal of cancer prevention : APJCP 20120101
RP101 (brivudine) binds to heat shock protein HSP27 (HSPB1) and enhances survival in animals and pancreatic cancer patients. Journal of cancer research and clinical oncology 20110901
Phenotypic and genetic characterization of varicella-zoster virus mutants resistant to acyclovir, brivudine and/or foscarnet. Medical microbiology and immunology 20110801
Expression of herpes simplex virus type 1 recombinant thymidine kinase and its application to a rapid antiviral sensitivity assay. Antiviral research 20110801
Emergence of herpes simplex virus-1 syncytial variants with altered virulence for mice after selection with a natural carrageenan. Sexually transmitted diseases 20110601
Cellular pharmacology of multi- and duplex drugs consisting of ethynylcytidine and 5-fluoro-2'-deoxyuridine. Investigational new drugs 20110401
Novel resistance-associated mutations of thymidine kinase and DNA polymerase genes of herpes simplex virus type 1 and type 2. Antiviral therapy 20110101
Non-nucleosidic inhibition of Herpes simplex virus DNA polymerase: mechanistic insights into the anti-herpetic mode of action of herbal drug withaferin A. BMC bioinformatics 20110101
[64-year-old patient with efflorescences on the upper and lower legs]. Deutsche medizinische Wochenschrift (1946) 20100901
New trends in nucleoside biotechnology. Acta naturae 20100701
Epstein-Barr virus encephalitis after kidney transplantation and successful treatment with brivudine. Transplant international : official journal of the European Society for Organ Transplantation 20100601
Phenotypic and genotypic characterization of acyclovir-resistant clinical isolates of herpes simplex virus. Antiviral research 20100601
[Varicella and herpes zoster. Part 2: therapy and prevention]. Medizinische Klinik (Munich, Germany : 1983) 20100601
[Skin involvement in zoster]. Klinische Monatsblatter fur Augenheilkunde 20100501
Interaction between capecitabine and brivudin in a patient with breast cancer. Nature reviews. Clinical oncology 20100101
Disseminated cutaneous herpes zoster complicated by acyclovir nephrotoxicity and successfully treated with brivudin. European journal of dermatology : EJD 20100101
Early detection of Varicella-Zoster virus (VZV)-specific T-cells before seroconversion in primary varicella infection: case report. Virology journal 20100101
Retained sensitivity to cytotoxic pyrimidine nucleoside analogs in thymidine kinase 2 deficient human fibroblasts. Nucleosides, nucleotides & nucleic acids 20100101
Antiviral treatment and other therapeutic interventions for herpes simplex virus epithelial keratitis. The Cochrane database of systematic reviews 20100101
Herpes zoster oticus: A rare clinical entity. Contemporary clinical dentistry 20100101
Acute hepatitis due to brivudin: a case report. Journal of hepatology 20091101
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20091001
All-oral combination of oral vinorelbine and capecitabine as first-line chemotherapy in HER2-negative metastatic breast cancer: an International Phase II Trial. British journal of cancer 20090721
Inhibition of homologous recombination by treatment with BVDU (brivudin) or by RAD51 silencing increases chromosomal damage induced by bleomycin in mismatch repair-deficient tumour cells. Mutation research 20090512
Fatal drug-drug interaction of brivudine and capecitabine. Acta oncologica (Stockholm, Sweden) 20090101
Antimicrobial strategies: inhibition of viral polymerases by 3'-hydroxyl nucleosides. Drugs 20090101
Synthesis and antimicrobial evaluation of 5-iodopyrimidine analogs. Indian journal of pharmaceutical sciences 20090101
Synthesis of nucleoside-based antiviral drugs in ionic liquids. Bioorganic & medicinal chemistry letters 20081015
Substrate specificity of feline and canine herpesvirus thymidine kinase. Antiviral research 20080801
5-Bromovinyl 2'-deoxyuridine phosphorylation by mitochondrial and cytosolic thymidine kinase (TK2 and TK1) and its use in selective measurement of TK2 activity in crude extracts. Nucleosides, nucleotides & nucleic acids 20080601
[Case report: again just an idiopathic facial nerve palsy?]. MMW Fortschritte der Medizin 20080522
Structural studies of nucleoside analog and feedback inhibitor binding to Drosophila melanogaster multisubstrate deoxyribonucleoside kinase. The FEBS journal 20080501
Synthesis and antitumor activity of a heterodinucleotide of BVDU and gemcitabine. Nucleosides, nucleotides & nucleic acids 20080501
6-Azathymidine-4'-thionucleosides: synthesis and antiviral evaluation. Journal of enzyme inhibition and medicinal chemistry 20080201
Perineal muco-cutaneous herpes zoster treated with brivudin. The Journal of dermatological treatment 20080101
Susceptibility of Autographa californica multiple nucleopolyhedrovirus to inhibitors of DNA replication. Journal of virological methods 20071201
Recommendations for the management of herpes zoster. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20070101
Molecular modelling studies on the binding of some protides to the putative human phosphoramidase Hint1. Nucleosides, nucleotides & nucleic acids 20070101
RP101 improves the efficacy of chemotherapy in pancreas carcinoma cell lines and pancreatic cancer patients. Anti-cancer drugs 20061001
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20060901
Bromovinyl-deoxyuridine: A selective substrate for mitochondrial thymidine kinase in cell extracts. Biochemical and biophysical research communications 20060526
Antiviral activity of cyclosaligenyl prodrugs of the nucleoside analogue bromovinyldeoxyuridine against herpes viruses. International journal of antimicrobial agents 20060501
New antiviral agents. Indian journal of pediatrics 20060401
[Update in the treatment of herpes zoster]. Actas dermo-sifiliograficas 20060301
Linear Darier disease with herpes zoster superinfection treated successfully by brivudine. The British journal of dermatology 20060201
Inhibitory efficacy of cyclosal-nucleoside monophosphates of aciclovir and brivudin on DNA synthesis of orthopoxvi ruses. Antiviral chemistry & chemotherapy 20060101
[Varicella-zoster virus infections--2: Zoster pain -- therapy and prevention]. MMW Fortschritte der Medizin 20060101
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20060101
Insecticidal activity of the pyrimidine nucleoside analogue (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU). Pest management science 20050801
Altered deoxyribonucleotide pools in T-lymphoblastoid cells expressing the multisubstrate nucleoside kinase of Drosophila melanogaster. The FEBS journal 20050801
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20050401
Susceptibilities of several clinical varicella-zoster virus (VZV) isolates and drug-resistant VZV strains to bicyclic furano pyrimidine nucleosides. Antimicrobial agents and chemotherapy 20050301
(E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU). Medicinal research reviews 20050101
Brivudin compared with famciclovir in the treatment of herpes zoster: effects in acute disease and chronic pain in immunocompetent patients. A randomized, double-blind, multinational study. Journal of the European Academy of Dermatology and Venereology : JEADV 20050101
[On the mailing list: use of acyclovir in patients on hemodialysis]. Giornale italiano di nefrologia : organo ufficiale della Societa italiana di nefrologia 20050101
Dexamethasone inhibits the HSV-tk/ ganciclovir bystander effect in malignant glioma cells. BMC cancer 20050101
[Antiherpetic therapy]. Oftalmologia (Bucharest, Romania : 1990) 20050101
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20050101
Naphthyl phosphoramidate derivatives of BVdU as potential anticancer agents: design, synthesis and biological evaluation. Nucleosides, nucleotides & nucleic acids 20050101
Current management of herpes zoster: the European view. American journal of clinical dermatology 20050101
Acute retinal necrosis. Seminars in ophthalmology 20050101
Discovery and development of BVDU (brivudin) as a therapeutic for the treatment of herpes zoster. Biochemical pharmacology 20041215
Functional expression of thymidine kinase in human leukaemic and colorectal cells, delivered as EGFP fusion protein by herpesvirus saimiri-based vector. Cancer gene therapy 20040901
First regioselective enzymatic alkoxycarbonylation of primary amines. Synthesis of novel 5'- and 3'-carbamates of pyrimidine 3',5'-diaminonucleoside derivatives including BVDU analogues. The Journal of organic chemistry 20040305
In vitro selection of drug-resistant varicella-zoster virus (VZV) mutants (OKA strain): differences between acyclovir and penciclovir? Antiviral research 20040301
Brivudin (bromovinyl deoxyuridine). Drugs 20040101
Lipid-mediated protein delivery of suicide nucleoside kinases. Cancer research 20031015
Comparison of HSV-1 thymidine kinase-dependent and -independent inhibition of replication-competent adenoviral vectors by a panel of drugs. Cancer gene therapy 20031001
[Brivudine as an alternative systemic therapy to aciclovir and ganciclovir in acute retinal necrosis syndrome due to varicella-zoster virus]. Klinische Monatsblatter fur Augenheilkunde 20031001
Synthesis, protonation behavior, conformational analysis, and regioselective enzymatic acylation of the novel diamino analogue of (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU). Nucleosides, nucleotides & nucleic acids 20031001
Inhibition of induced chemoresistance by cotreatment with (E)-5-(2-bromovinyl)-2'-deoxyuridine (RP101). Cancer research 20030915
Herpes zoster guidelines of the German Dermatological Society. Journal of clinical virology : the official publication of the Pan American Society for Clinical Virology 20030801
Cytosolic and mitochondrial deoxyribonucleotidases: activity with substrate analogs, inhibitors and implications for therapy. Biochemical pharmacology 20030801
Crystal structure of varicella zoster virus thymidine kinase. The Journal of biological chemistry 20030704
NB1011 induces Ser15 phosphorylation of p53 and activates the G2/M checkpoint. Anti-cancer drugs 20030701
Oral brivudin in comparison with acyclovir for improved therapy of herpes zoster in immunocompetent patients: results of a randomized, double-blind, multicentered study. Antiviral research 20030601
Oral brivudin in comparison with acyclovir for herpes zoster: a survey study on postherpetic neuralgia. Antiviral research 20030601
Brivudine: a herpes virostatic with rapid antiviral activity and once-daily dosing. Drugs of today (Barcelona, Spain : 1998) 20030501
Herpes zoster guideline of the German Dermatology Society (DDG). Journal of clinical virology : the official publication of the Pan American Society for Clinical Virology 20030401
Homology modelling and docking studies on Varicella Zoster Virus Thymidine kinase. European journal of medicinal chemistry 20030401
Apoptosis induced by (E)-5-(2-bromovinyl)-2'-deoxyuridine in varicella zoster virus thymidine kinase-expressing cells is driven by activation of c-Jun/activator protein-1 and Fas ligand/caspase-8. Molecular pharmacology 20030201
The role of antivirals in the management of neuropathic pain in the older patient with herpes zoster. Drugs & aging 20030101
CycloSal-BVDUMP pronucleotides: how to convert an antiviral-inactive nucleoside analogue into a bioactive compound against EBV. Journal of medicinal chemistry 20021107
Bicyclic pyrimidine nucleoside analogues (BCNAs) as highly selective and potent inhibitors of varicella-zoster virus replication. The Journal of antimicrobial chemotherapy 20020701
Establishment and use of a cell line expressing HSV-1 thymidine kinase to characterize viral thymidine kinase-dependent drug-resistance. Antiviral research 20020601
Lack of susceptibility of bicyclic nucleoside analogs, highly potent inhibitors of varicella-zoster virus, to the catabolic action of thymidine phosphorylase and dihydropyrimidine dehydrogenase. Molecular pharmacology 20020501
Inhibition of cell growth by NB1011 requires high thymidylate synthase levels and correlates with p53, p21, bax, and GADD45 induction. Molecular cancer therapeutics 20020401
Nucleoside analog cytotoxicity and bystander cell killing of cancer cells expressing Drosophila melanogaster deoxyribonucleoside kinase in the nucleus or cytosol. Biochemical and biophysical research communications 20011123
Hamao Umezawa Memorial Award Lecture: 'An Odyssey in the Viral Chemotherapy Field'. International journal of antimicrobial agents 20011001
Synthesis and antiviral evaluation of phosphoramidate derivatives of (E)-5-(2-bromovinyl)-2'-deoxyuridine. Antiviral chemistry & chemotherapy 20010901
Bystander effects of cancer cell lines transduced with the multisubstrate deoxyribonucleoside kinase of Drosophila melanogaster and synergistic enhancement by hydroxyurea. Molecular pharmacology 20010801
[Controlling herpes zoster. End end to bullae]. MMW Fortschritte der Medizin 20010531
(E)-5-(2-bromovinyl)-2'-deoxyuridine potentiates ganciclovir-mediated cytotoxicity on herpes simplex virus-thymidine kinase--expressing cells. Cancer gene therapy 20010501
cycloSaligenyl-5-[(E)-2-bromovinyl]-2'-deoxyuridine monophosphate (cycloSal-BVDUMP) pronucleotides active against Epstein-Barr virus. Chembiochem : a European journal of chemical biology 20010402
A novel approach to thymidylate synthase as a target for cancer chemotherapy. Molecular pharmacology 20010301
Recent developments in herpesvirus therapy. Herpes : the journal of the IHMF 20010301
Mutation of Gln125 to Asn selectively abolishes the thymidylate kinase activity of herpes simplex virus type 1 thymidine kinase. Molecular pharmacology 20010201
Genetic risks of antiviral nucleoside analogues--a survey. Antiviral research 20010201
Enzyme-catalyzed therapeutic agent (ECTA) design: activation of the antitumor ECTA compound NB1011 by thymidylate synthase. Biochemical pharmacology 20010115
Human glioma cells expressing herpes simplex virus thymidine kinase gene treated with acyclovir, ganciclovir and bromovinyldeoxyuridine. Evaluation of their activity in vitro and in nude mice. Neoplasma 20010101
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses. Antiviral research 20000301
Antiviral efficacies of famciclovir, valaciclovir, and brivudin in disseminated herpes simplex virus type 1 infection in mice. Intervirology 19970101
Stereoelectronic properties of five anti-HSV-1 2'-deoxynucleosides analogues with heterocyclic substituents in the 5-position: a comparison with BVDU. Antiviral research 19940801
5-(5-Bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothien-2-yl)-2'-deoxyuridine are equipotent to (E)-5-(2-bromovinyl)-2'-deoxyuridine in the inhibition of herpes simplex virus type I replication. Journal of medicinal chemistry 19910801
Antiherpes virus activity and effect on deoxyribonucleoside triphosphate pools of (E)-5-(2-bromovinyl)-2'-deoxycytidine in combination with deaminase inhibitors. Antiviral research 19900301
(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
Phosphonoformate and phosphonoacetate derivatives of 5-substituted 2'-deoxyuridines: synthesis and antiviral activity. Journal of medicinal chemistry 19880901
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
2'-Fluorinated arabinonucleosides of 5-(2-haloalkyl)uracil: synthesis and antiviral activity. Journal of medicinal chemistry 19870701
Effect of antiviral agents on replication of herpes simplex virus type 1 in brain cultures. Antimicrobial agents and chemotherapy 19861201
Synthesis and antiviral activity of (E)-5-(2-bromovinyl)uracil and (E)-5-(2-bromovinyl)uridine. Journal of medicinal chemistry 19860201
5-(Haloalkyl)-2'-deoxyuridines: a novel type of potent antiviral nucleoside analogue. Journal of medicinal chemistry 19851101
Nucleosides. 133. Synthesis of 5-alkenyl-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosines and related pyrimidine nucleosides as potential antiviral agents. Journal of medicinal chemistry 19850601
Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridines and (E)-5-(2-halovinyl)-2'-deoxycytidines. Journal of medicinal chemistry 19850501
Inhibition of human and woodchuck hepatitis virus DNA polymerase by the triphosphates of acyclovir, 1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)-5-iodocytosine and E-5-(2-bromovinyl)-2'-deoxyuridine. Antiviral research 19840801
Oral antiviral drugs in experimental herpes simplex keratitis. Antimicrobial agents and chemotherapy 19831201
Synergistic antiviral activity of acyclovir and interferon on human cytomegalovirus. Antimicrobial agents and chemotherapy 19830901
Efficacy of (E)-5-(2-bromovinyl)-2'-deoxyuridine against different herpes simplex virus strains in cell culture and against experimental herpes encephalitis in mice. Antiviral research 19821001
Inhibitory effect of E-5-(2-bromovinyl)-1-beta-D-arabinofuranosyluracil on herpes simplex virus replication and DNA synthesis. Journal of virology 19820701
Efficiency and selectivity of (E)-5-(2-bromovinyl)-2'-deoxyuridine and some other 5-substituted 2'-deoxypyrimidine nucleosides as anti-herpes agents. Antiviral research 19820501
In vitro susceptibility of varicella-zoster virus to E-5-(2-bromovinyl)-2'-deoxyuridine and related compounds. Antimicrobial agents and chemotherapy 19820101
Selective inhibition of herpesvirus deoxyribonucleic acid synthesis by acycloguanosine, 2'-fluoro-5-iodo-aracytosine, and (E)-5-(2-bromovinyl)-2'-deoxyuridine. Antimicrobial agents and chemotherapy 19810501

Related Products

© 2019 Angene International Limited. All rights Reserved.