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27646-59-9 | 5'-Thymidylic acid, 2',3'-didehydro-3'-deoxy-
CAS No: 27646-59-9 Catalog No: AG002UBS MDL No:
Product Description
Catalog Number:
AG002UBS
Chemical Name:
5'-Thymidylic acid, 2',3'-didehydro-3'-deoxy-
CAS Number:
27646-59-9
Molecular Formula:
C10H13N2O7P
Molecular Weight:
304.1932
IUPAC Name:
[(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methyl dihydrogen phosphate
InChI:
InChI=1S/C10H13N2O7P/c1-6-4-12(10(14)11-9(6)13)8-3-2-7(19-8)5-18-20(15,16)17/h2-4,7-8H,5H2,1H3,(H,11,13,14)(H2,15,16,17)/t7-,8+/m0/s1
InChI Key:
XLPGURCDSRIXFL-JGVFFNPUSA-N
SMILES:
O=c1[nH]c(=O)n(cc1C)[C@H]1C=C[C@H](O1)COP(=O)(O)O
Properties
Complexity:
538
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
2
Defined Bond Stereocenter Count:
0
Exact Mass:
304.046g/mol
Formal Charge:
0
Heavy Atom Count:
20
Hydrogen Bond Acceptor Count:
7
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
304.195g/mol
Monoisotopic Mass:
304.046g/mol
Rotatable Bond Count:
4
Topological Polar Surface Area:
125A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.9
Literature
| Title | Journal |
|---|---|
| Synthesis, and in vitro enzymatic and antiviral evaluation of d4T polyphosphate derivatives as chain terminators. | Chemistry & biodiversity 20121001 |
| Stereoselective synthesis and antiviral activity of methyl-substituted cycloSal-pronucleotides. | Journal of medicinal chemistry 20120823 |
| Synthesis and in vitro enzymatic and antiviral evaluation of phosphoramidate d4T derivatives as chain terminators. | Organic & biomolecular chemistry 20120107 |
| Diastereoselective synthesis of aryloxy phosphoramidate prodrugs of 3'-deoxy-2',3'-didehydrothymidine monophosphate. | Journal of medicinal chemistry 20101111 |
| 5-(1-Acetoxyvinyl)-cycloSaligenyl-2',3'-dideoxy-2',3'- didehydrothymidine monophosphates, a second type of new, enzymatically activated cycloSaligenyl pronucleotides. | Journal of medicinal chemistry 20081225 |
| Studies on enzyme-cleavable dialkoxymethyl-cyclosaligenyl-2',3'-dideoxy-2',3'-didehydrothymidine monophosphates. | Journal of medicinal chemistry 20081113 |
| Intracellular trapping of cycloSal-pronucleotides: modification of prodrugs with amino acid esters. | Journal of medicinal chemistry 20081023 |
| Comparison of the phosphorylation of 4'-ethynyl 2',3'-dihydro-3'-deoxythymidine with that of other anti-human immunodeficiency virus thymidine analogs. | Antimicrobial agents and chemotherapy 20070501 |
| Enzymatically activated cycloSal-d4T-monophosphates: The third generation of cycloSal-pronucleotides. | Journal of medicinal chemistry 20070405 |
| Bis-cycloSal-d4T-monophosphates: drugs that deliver two molecules of bioactive nucleotides. | Journal of medicinal chemistry 20070322 |
| [Isosteric triphosphonate analogues of dNTP: synthesis and substrate properties toward various DNA polymerases]. | Bioorganicheskaia khimiia 20070101 |
| Defining a molecular mechanism of synergy between nucleoside and nonnucleoside AIDS drugs. | The Journal of biological chemistry 20040220 |
| Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase. | Bioorganic & medicinal chemistry letters 20030915 |
| Structures of human thymidylate kinase in complex with prodrugs: implications for the structure-based design of novel compounds. | Biochemistry 20030311 |
| Assessment of the effect of phosphorylated metabolites of anti-human immunodeficiency virus and anti-hepatitis B virus pyrimidine analogs on the behavior of human deoxycytidylate deaminase. | Molecular pharmacology 20030101 |
| Novel inhibitors of HIV integrase: the discovery of potential anti-HIV therapeutic agents. | Current pharmaceutical design 20030101 |
| Study of different substituted cyclic and acyclic benzylpronucleotides of d4T relative to their hydrolytic stability and antiviral activity. | Nucleosides, nucleotides & nucleic acids 20030101 |
| d4TMP delivery from 7-substituted cycloSal-d4TMPs. | Nucleosides, nucleotides & nucleic acids 20030101 |
| Multidrug-resistant HIV-1 reverse transcriptase: involvement of ribonucleotide-dependent phosphorolysis in cross-resistance to nucleoside analogue inhibitors. | Journal of molecular biology 20021018 |
| Synthesis and evaluation of thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase. | Bioorganic & medicinal chemistry letters 20021007 |
| Comparative study of bis(benzyl)phosphate triesters of 2',3'-dideoxy-2',3'-didehydrothymidine (d4T) and cyclosal-d4TMP--hydrolysis, mechanistic insights and anti-HIV activity. | Antiviral chemistry & chemotherapy 20020301 |
| Benzyl-functionalized cycloSal-d4T monophosphates. | Nucleosides, nucleotides & nucleic acids 20010101 |
| Design and synthesis of lipophilic phosphoramidate d4T-MP prodrugs expressing high potency against HIV in cell culture: structural determinants for in vitro activity and QSAR. | Journal of medicinal chemistry 19991007 |
| Characterization of the activation pathway of phosphoramidate triester prodrugs of stavudine and zidovudine. | Molecular pharmacology 19991001 |
| Synthesis and anti-HIV activity of some novel arylphosphate and H-phosphonate derivatives of 3'-azido-2',3'-dideoxythymidine and 2',3'-didehydro-2',3'-dideoxythymidine. | Antiviral research 19990701 |
| Metabolism and anti-HIV activity of phosphoramidate derivatives of D4T-MP with variations in the amino acid moiety. | Advances in experimental medicine and biology 19980101 |
| Antiretrovirus specificity and intracellular metabolism of 2',3' -didehydro-2',3'-dideoxythymidine (stavudine) and its 5'-monophosphate triester prodrug So324. | Molecular pharmacology 19961101 |
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