-transparent.png){kind=logo}
Synthesis, Anti-HBV, and Anti-HIV Activities of 3'-Halogenated Bis(hydroxymethyl)-cyclopentenyladenines. 2018
Hiroki Kumamoto, and
Shuhei Imoto, and
Masayuki Amano, and
Nobuyo Kuwata-Higashi, and
Masanori Baba, and
Hiroaki Mitsuya, and
Yuki Odanaka, and
Satoko Shimbara Matsubayashi, and
Hiromichi Tanaka, and
Kazuhiro Haraguchi
Nihon Pharmaceutical University, 10281 Komuro, Inamachi, Kita-adachi-gun, Saitama 362-0806, Japan.
Synthesis of 3'-halogeno analogues (5a-d) of 9-[c-4,t-5-bis(hydroxymethyl)-cyclopent-2-en-r-1-yl]-9H-adenine (BCA, 3) was accomplished by means of dual utilization of the vinyl sulfone functional moieties in both 10 and 16 utilizing a SN2' conjugate-addition reaction and a sulfur-extrusive stannylation, respectively. Evaluation of the antiviral activities of 5a-d revealed that introduction of a halogeno-substituent into the 3'-position of (-)-BCA diminished its anti-HIV-1 activity but increased the inhibitory activity for the reverse transcriptase of HBV in that the 3'-fluorinated BCA 5d exhibited the highest activity without significant cytotoxicity.
| UI | MeSH Term | Description | Entries |
|---|
Related Publications
Hiroki Kumamoto, and
Shuhei Imoto, and
Masayuki Amano, and
Nobuyo Kuwata-Higashi, and
Masanori Baba, and
Hiroaki Mitsuya, and
Yuki Odanaka, and
Satoko Shimbara Matsubayashi, and
Hiromichi Tanaka, and
Kazuhiro Haraguchi
April 1999,
Journal of medicinal chemistry,
Hiroki Kumamoto, and
Shuhei Imoto, and
Masayuki Amano, and
Nobuyo Kuwata-Higashi, and
Masanori Baba, and
Hiroaki Mitsuya, and
Yuki Odanaka, and
Satoko Shimbara Matsubayashi, and
Hiromichi Tanaka, and
Kazuhiro Haraguchi
February 2009,
Bioorganic & medicinal chemistry letters,
Hiroki Kumamoto, and
Shuhei Imoto, and
Masayuki Amano, and
Nobuyo Kuwata-Higashi, and
Masanori Baba, and
Hiroaki Mitsuya, and
Yuki Odanaka, and
Satoko Shimbara Matsubayashi, and
Hiromichi Tanaka, and
Kazuhiro Haraguchi
February 2011,
Tetrahedron letters,
Hiroki Kumamoto, and
Shuhei Imoto, and
Masayuki Amano, and
Nobuyo Kuwata-Higashi, and
Masanori Baba, and
Hiroaki Mitsuya, and
Yuki Odanaka, and
Satoko Shimbara Matsubayashi, and
Hiromichi Tanaka, and
Kazuhiro Haraguchi
August 2009,
European journal of medicinal chemistry,
Hiroki Kumamoto, and
Shuhei Imoto, and
Masayuki Amano, and
Nobuyo Kuwata-Higashi, and
Masanori Baba, and
Hiroaki Mitsuya, and
Yuki Odanaka, and
Satoko Shimbara Matsubayashi, and
Hiromichi Tanaka, and
Kazuhiro Haraguchi
March 2001,
Yao xue xue bao = Acta pharmaceutica Sinica,
Hiroki Kumamoto, and
Shuhei Imoto, and
Masayuki Amano, and
Nobuyo Kuwata-Higashi, and
Masanori Baba, and
Hiroaki Mitsuya, and
Yuki Odanaka, and
Satoko Shimbara Matsubayashi, and
Hiromichi Tanaka, and
Kazuhiro Haraguchi
December 1996,
Journal of medicinal chemistry,
Hiroki Kumamoto, and
Shuhei Imoto, and
Masayuki Amano, and
Nobuyo Kuwata-Higashi, and
Masanori Baba, and
Hiroaki Mitsuya, and
Yuki Odanaka, and
Satoko Shimbara Matsubayashi, and
Hiromichi Tanaka, and
Kazuhiro Haraguchi
December 1970,
Il Farmaco; edizione scientifica,
Hiroki Kumamoto, and
Shuhei Imoto, and
Masayuki Amano, and
Nobuyo Kuwata-Higashi, and
Masanori Baba, and
Hiroaki Mitsuya, and
Yuki Odanaka, and
Satoko Shimbara Matsubayashi, and
Hiromichi Tanaka, and
Kazuhiro Haraguchi
January 1980,
Journal of medicinal chemistry,
Hiroki Kumamoto, and
Shuhei Imoto, and
Masayuki Amano, and
Nobuyo Kuwata-Higashi, and
Masanori Baba, and
Hiroaki Mitsuya, and
Yuki Odanaka, and
Satoko Shimbara Matsubayashi, and
Hiromichi Tanaka, and
Kazuhiro Haraguchi
May 1992,
Journal of medicinal chemistry,
Hiroki Kumamoto, and
Shuhei Imoto, and
Masayuki Amano, and
Nobuyo Kuwata-Higashi, and
Masanori Baba, and
Hiroaki Mitsuya, and
Yuki Odanaka, and
Satoko Shimbara Matsubayashi, and
Hiromichi Tanaka, and
Kazuhiro Haraguchi
January 2004,
Journal of medicinal chemistry,
