2'-Deoxy-2'-fluoroadenosine - CAS 64183-27-3
Catalog: |
BB032393 |
Product Name: |
2'-Deoxy-2'-fluoroadenosine |
CAS: |
64183-27-3 |
Synonyms: |
2'-Fluoro-2'-deoxyadenosine; (2R,3R,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol; 9-(2-Fluoro-2-deoxy-beta-D-ribofuranosyl)-purin-6-amine; 9-(2-Deoxy-2-fluoro-beta-D-ribofuranosyl)adenine; 6-Amino-9-(2-deoxy-2-fluoro-beta-D-ribofuranosyl)-9H-purine |
IUPAC Name: | (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol |
Description: | 2'-Deoxy-2'-fluoroadenosine (CAS# 64183-27-3) is a useful compound for the preparation of AB680, which is a potent and selective inhibitor of CD73. |
Molecular Weight: | 269.23 |
Molecular Formula: | C10H12FN5O3 |
Canonical SMILES: | C1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)CO)O)F |
InChI: | InChI=1S/C10H12FN5O3/c11-5-7(18)4(1-17)19-10(5)16-3-15-6-8(12)13-2-14-9(6)16/h2-5,7,10,17-18H,1H2,(H2,12,13,14)/t4-,5-,7-,10-/m1/s1 |
InChI Key: | ZGYYPTJWJBEXBC-QYYRPYCUSA-N |
Boiling Point: | 628.6±65.0 ℃ (Predicted) |
Melting Point: | 228-231 ℃ |
Purity: | ≥ 95 % |
Density: | 2.01±0.1 g/cm3 (Predicted) |
Solubility: | Soluble in Acetonitrile (Slightly), Methanol (Slightly, Heated) |
Appearance: | White to off-white solid |
Storage: | Store at -20 ℃ under inert atmosphere |
MDL: | MFCD09750859 |
LogP: | -0.42160 |
GHS Hazard Statement: | H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
Precautionary Statement: | P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501 |
Signal Word: | Warning |
Publication Number | Title | Priority Date |
WO-2021203043-A2 | Targeted inhibition using engineered oligonucleotides | 20200402 |
CN-111534493-A | Purine nucleoside phosphorylase mutant, gene and application | 20200401 |
WO-2021178209-A1 | Aptamers and use thereof | 20200303 |
WO-2021152146-A1 | Process for the production of closed linear dna | 20200131 |
WO-2021152147-A1 | Closed linear dna with modified nucleotides | 20200131 |
PMID | Publication Date | Title | Journal |
22579483 | 20120615 | S-Adenosylhomocysteine hydrolase of the protozoan parasite Trichomonas vaginalis: potent inhibitory activity of 9-(2-deoxy-2-fluoro-β,D-arabinofuranosyl)adenine | Bioorganic & medicinal chemistry letters |
20532912 | 20100901 | Susceptibility in vitro of clinically metronidazole-resistant Trichomonas vaginalis to nitazoxanide, toyocamycin, and 2-fluoro-2'-deoxyadenosine | Parasitology research |
19388075 | 20090501 | Structure of a mutant human purine nucleoside phosphorylase with the prodrug, 2-fluoro-2'-deoxyadenosine and the cytotoxic drug, 2-fluoroadenine | Protein science : a publication of the Protein Society |
18026095 | 20080101 | Unnatural substrates reveal the importance of 8-oxoguanine for in vivo mismatch repair by MutY | Nature chemical biology |
16245934 | 20051101 | Insight into the roles of tyrosine 82 and glycine 253 in the Escherichia coli adenine glycosylase MutY | Biochemistry |
Complexity: | 338 |
Compound Is Canonicalized: | Yes |
Covalently-Bonded Unit Count: | 1 |
Defined Atom Stereocenter Count: | 4 |
Defined Bond Stereocenter Count: | 0 |
Exact Mass: | 269.09241742 |
Formal Charge: | 0 |
Heavy Atom Count: | 19 |
Hydrogen Bond Acceptor Count: | 8 |
Hydrogen Bond Donor Count: | 3 |
Isotope Atom Count: | 0 |
Monoisotopic Mass: | 269.09241742 |
Rotatable Bond Count: | 2 |
Topological Polar Surface Area: | 119 Å2 |
Undefined Atom Stereocenter Count: | 0 |
Undefined Bond Stereocenter Count: | 0 |
XLogP3: | 0 |
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