Synthesis and antiviral evaluation of α-d-2′,3′- didehydro-2′,3′-dideoxy-3′-C-hydroxymethyl nucleosides

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 20, 2010, Pages 6013-6016

  Yamada, Kohei ^a   Hayakawa, Hiroyuki ^a   Sakata, Shinji ^a   Ashida, Noriyuki ^a   Yoshimura, Yuichi ^b  

^a YAMASA CORPORATION   (Japan)

^b TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Antiviral; Nucleosides; SN2 Reaction

Indexed keywords

2',3' DIDEOXYNUCLEOSIDE DERIVATIVE; ALPHA DEXTRO 2',3' DIDEHYDRO 2',3' DIDEOXY 3' C HYDROXYMETHYL NUCLEOSIDE; ANTIVIRUS AGENT; IODIDE ION; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG DESIGN; DRUG SYNTHESIS; RING OPENING;

ANTIVIRAL AGENTS; CYTOMEGALOVIRUS; HIV; HUMANS; NUCLEOSIDES; SIMPLEXVIRUS; VIRUS DISEASES; VIRUSES;

EID: 77956920954     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.08.071     Document Type: Article

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30. 4). The solvent was removed under reduced pressure, and the residue was purified by column chromatography over silica gel (2.2 × 13 cm, 30-50% AcOEt in n-hexane) to give 15a (174 mg, 69%) and 16a (9 mg, 3%) as an amorphous foam, respectively.
31. 5: C, 51.97; H, 5.55; N, 11.02. Found: C, 51.80; H, 5.61; N, 10.94.
32. 2O: C, 48.04; H, 5.72; N, 16.81. Found: C, 48.03; H, 5.86; N, 17.02.
33. 2O: C, 49.85; H, 5.02; N, 26.42. Found: C, 49.87; H, 4.93; N, 26.54.
34. Antiviral activities, except against HIV, and cytotoxicities were assayed at the Biological Laboratory of Yamasa Corp. Anti-HIV activity was tested at the Rational Drug Design Laboratories, Fukushima, Japan. We greatly appreciate the assistance of the staff there.