Synthesis and evaluation of antiviral activities of branched oxetanosine A.
Project/Area Number |
24590144
|
Research Category |
Grant-in-Aid for Scientific Research (C)
|
Allocation Type | Multi-year Fund |
Section | 一般 |
Research Field |
Drug development chemistry
|
Research Institution | Nihon Pharmaceutical University (2013-2014) Showa University (2012) |
Principal Investigator |
|
Project Period (FY) |
2012-04-01 – 2015-03-31
|
Project Status |
Completed (Fiscal Year 2014)
|
Budget Amount *help |
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
|
Keywords | オキセタノシン / グリカール / オキセタン / 求電子付加 / グリコシル化 / ラジカル反応 / 抗ウイルス活性 / ヌクレオシド |
Outline of Final Research Achievements |
When oxetanoid glycal was reacted silylated N6-benzoyladenine in the presence of N-iodosuccinimide, the desired glycoside was obtained in 25% yield. Reaction of the glycoside with allyltributylstannanen was carried out in the presence of AIBN to furnish 3'-C-allyl derivative in 78% yield as diastereomeric mixture. The allylated nucleoside wa sublected hydride reduction of the ester moety followed by NaOMe-mediated removal of the benzoyl group of the adenine moiety provied the target 3'-C-allyl-oxetanosine A.
|
Report
(4 results)
Research Products
(18 results)
-
-
[Journal Article] Design, Synthesis and Evaluation of Anti-HBV Activity of Hybrid Molecules of Entecavir and Adefovir2015
Author(s)
Imoto, S.; Kohgo, S.; Tokuda, R; Kumamoto, H.; Aoki, M.; Amano, M.; Kuwata-Higashi, N.; mitsuya, H.; Haraguchi, K.
-
Journal Title
Nucleosides, nucleotides & Nucleic Acids
Volume: 43
Related Report
Peer Reviewed
-
-
-
[Journal Article] Synthesis of 3’,4’-difluoro-3’-deoxyribonucleosides and its evaluation of the biological activities: Discovery of a novel type of anti-HCV agent 3’,4’-difluorocordycepin2014
Author(s)
Shimada, H.; Haraguchi, K.; Hotta, K.; Miyaike. T.; Kitagawa, Y.; Tanaka, H.; Kaneda, R.; Abe, H.; Shuto, S.; Mori, K.; Ueda, Y.; Kato, N.; Snoeck, R.; Andrei, G.; Balzarini, Y.
-
Journal Title
Bioorg. Med. Chem.
Volume: 22
Pages: 6174-6182
Related Report
Peer Reviewed / Acknowledgement Compliant
-
-
-
[Journal Article] Tuning efficiency of the 4-exo-trig cyclization by the electronic effect : ring closure of 3, 3-difluoro-4-pentenyl carbon radicals and synthesis of a gem-difluorocyclobutane nucleoside2012
Author(s)
Hiroki Kumamoto, Sachiko Kawahigashi, Hiromi Wakabayashi, Tomohiko Nakano, Tomoko Miyaike, Yasuyuki Kitagawa, Hiroshi Abe, Mika Ito. Kazuhiro Haraguchi, Jan Balzarini, Masanori Baba and Hiromichi Tanaka
-
Journal Title
Chemical Communication
Volume: 48
Issue: 89
Pages: 10993-10995
DOI
Related Report
Peer Reviewed
-
-
-
[Presentation] 4’-Ethynyl-2-fluoro-2’-deoxyadenosine (EFdA) has an extremely high genetic barrier, persistently exerting highly potent activity against a variety of HIV-1 isolates including EFdA-selected HIV-1 variants2015
Author(s)
Maeda, K.; Takamatsu, Y.; Kohgo, S.; Haraguchi, K.; Delino, N. S.; Chang, S. B.; Das, D.; Li, Z.; Kirby, K. A.; Sarafianos, S. G.; Mitsuya, H.
Organizer
Conference on Retroviruses and Opportunistic Infections
Place of Presentation
Seattle, Washington
Year and Date
2015-02-23 – 2015-02-26
Related Report
-
[Presentation] 4’-MODIFIED NUCLEOSIDE ANALOGS: Potent Inhibitors Active against Entecavir-resistant Hepatitis B Virus (HBVETV-RL180M/S202G/M204V)2014
Author(s)
Takamatsu, Y.; Tanaka, Y.; Kohgo, S.; Murakami, S.; Singh, K.; Das, D.; Venzon, D. J.; Amano, M.; Kuwata, N.; Aoki, M.; Delino, N. S.; Hayashi, S.; Takahashi, S.; Haraguchi, K.; Sarafianos, S. G.; Maeda, K.; Mitsuya, H.
Organizer
4th International Conference on Antiviral Microbial Agents and Chemotherapy
Place of Presentation
Washington, DC
Year and Date
2014-09-05 – 2014-09-09
Related Report
-
-
-
-
[Presentation] Synthesis of 4’-ethynyl-2’-deoxy-4’-thioribonucleosides and discovery of a highly potent and less toxic NRTI2012
Author(s)
K. Haraguchi, H. Shimada, G. Akutsu, K. Kimura, H. Tanaka, T. Mamasaki, M. Baba, E. A. Gullen, G. E. Dutschman, Y.-C. Cheng, J. Balzarini
Organizer
International Conference on Antiviral Research 2012
Place of Presentation
Sapporo
Related Report
-
-
[Book] Frontiers in Clininal Drug Reseach2015
Author(s)
Haraguchi, K.; Takeda, S.; Kubota, Y.; Kumamoto, H.; Tanaka, H.; Hamasaki, T.; E; Baba, M.; Paintsil, E.; Cheng, Y.-C.; Urata, Y.,
Total Pages
61
Publisher
Bentham Science Publishing
Related Report