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  4. KUMAMOTO Hiroki, Ph.D. / Associate Professor

KUMAMOTO Hiroki, Ph.D. / Associate Professor

Division of Organic and Medicinal Chemistry

Department of Pharmaceutical Sciences

Research Topics

1. Design and synthesis of the novel carbocyclic nucleoside analogues and evaluation of their biological activities.

2. Synthetic endeavor for the novel fluorine containing nucleosides.

3. Application of the radical-mediated sulfur-extrusive stannylation for the modification of nucleosides.

Nucleosides play an important role not only in a human cell but for replication and multiplication of most of pathogens such as viruses, bacteria and cancer cells. Therefore, chemical modification of naturally occurring nucleosides or preparation of artificial nucleoside analogues have brought the great development for lots of excellent drugs. Based on the context, our group has been continuing to research for the synthesis and development of novel bio-active nucleoside analogues, representatively employing the radical-mediated stannylation and carbon-carbon bond formation.

Representative Publications

1. Kumamoto, H.; Imoto, S.; Amano, M.; Kuwata-Higashi, N.; Baba, M.; Mitsuya, H.; Odanaka, Y.; Shimbara-Matsubayashi,S.; Tanaka, H.; Haraguchi, K. “Synthesis, anti-HBV, and anti-HIV activities of 3´-halogenated bis(hydroxymethyl) cyclopentenyl adenines” ACS Med. Chem. Lett. 9, 1211-1216 (2018).

2. Kumamoto, H.; Fukano, M.;, Nakano, T.; Iwagami, K.; Takeyama, C.; Kohgo, S.; Imoto, S.; Amano, M.; Kuwata-Higashi, N.; Aoki, M.; Abe, H.; Mitsuya, H.; Fukuhara, K.; Haraguchi, K. “Diastereoselective synthesis of 6"-(Z)- and 6" (E)-fluoro analogues of anti-hepatitis B vireus agent entecavir and its evaluation of the activity and toxicity profile of the diastereomers“ Org. Chem. 81, 2827-2836 (2016).

3. Kumamoto, H.; Kawahigashi, S.; Wakabayashi, H.; Nakano, T.; Miyaike, T.; Kitagawa, Y.; Abe, H.; Ito, M.; Haraguchi, K.; Balzarini, J.; Baba, M.; Tanaka, H. “Tuning efficiency of the 4-exo-trig cyclization by the electronic effect: ring closure of 3,3-difluoro-4-pentenylcarbon radicals and synthesis of a gem-difluorocyclobutane nucleoside“ Chem. Commun. 48, 10993-10995 (2012).

4. Kumamoto, H.; Kobayashi, M.; Kato, N.; Balzarini, J.; Tanaka, H.; “Synthesis of 5’-fluoro-2’-b-methyl analogues of Neplanocin“ J. Oeg. Chem. 2685-2691. (2011).