{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T10:38:49Z","timestamp":1760783929912},"reference-count":5,"publisher":"SAGE Publications","issue":"3","license":[{"start":{"date-parts":[[2004,6,1]],"date-time":"2004-06-01T00:00:00Z","timestamp":1086048000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/journals.sagepub.com\/page\/policies\/text-and-data-mining-license"},{"start":{"date-parts":[[2004,6,1]],"date-time":"2004-06-01T00:00:00Z","timestamp":1086048000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/journals.sagepub.com\/page\/policies\/text-and-data-mining-license"}],"content-domain":{"domain":["journals.sagepub.com"],"crossmark-restriction":true},"short-container-title":["Antivir Chem Chemother"],"published-print":{"date-parts":[[2004,6]]},"abstract":"<jats:p> We investigated the potential of 4\u2032- C-substituted nucleosides for the treatment of HIV-1 and HBV. Of the nucleosides we prepared, several 4\u2032- C-ethynyl-2\u2032-deoxypurine nucleosides showed the most potent anti-HIV activity. However, two candidates, 4\u2032-C-ethynyl-2\u2032-deoxyguanosine and 9-(2-deoxy-4-C-ethynyl-\u03b2-D- ribo-pentofuranosyl)-2,6-diaminopurine, were very toxic during in vivo study. On the other hand, lamivudine (3TC) is known to show remarkable activity against HIV and HBV with lower cytotoxicity. Therefore, we attempted to synthesize the L-enantiomer of 4\u2032- C-ethynyl-2\u2032-deoxypurine nucleosides in 20\u201321 steps. These methods consisted of preparing 4-C-ethynyl-L-sugar, starting from D-arabinose and then condensing the L-sugar derivative with 2,6-diaminopurine. 4\u2032- C-Ethynyl-2\u2032-deoxyguanosine was also prepared by enzymatic deamination from the 2,6-diaminopurine derivative. The compounds' antiviral activity against HIV and HBV was then evaluated. Unfortunately, they demonstrated no activity and no cytotoxicity. <\/jats:p>","DOI":"10.1177\/095632020401500306","type":"journal-article","created":{"date-parts":[[2015,3,16]],"date-time":"2015-03-16T17:01:37Z","timestamp":1426525297000},"page":"161-167","update-policy":"http:\/\/dx.doi.org\/10.1177\/sage-journals-update-policy","source":"Crossref","is-referenced-by-count":3,"title":["Attempt to Reduce Cytotoxicity by Synthesizing the L-Enantiomer of 4\u2032-<i>C<\/i>-Ethynyl-2\u2032-Deoxypurine Nucleosides as Antiviral Agents against HIV and HBV"],"prefix":"10.1177","volume":"15","author":[{"given":"Kenji","family":"Kitano","sequence":"first","affiliation":[{"name":"Biochemical Division, Yamasa Corporation, Choshi, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Satoru","family":"Kohgo","sequence":"additional","affiliation":[{"name":"Biochemical Division, Yamasa Corporation, Choshi, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kohei","family":"Yamada","sequence":"additional","affiliation":[{"name":"Biochemical Division, Yamasa Corporation, Choshi, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shinji","family":"Sakata","sequence":"additional","affiliation":[{"name":"Biochemical Division, Yamasa Corporation, Choshi, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Noriyuki","family":"Ashida","sequence":"additional","affiliation":[{"name":"Biochemical Division, Yamasa Corporation, Choshi, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hiroyuki","family":"Hayakawa","sequence":"additional","affiliation":[{"name":"Biochemical Division, Yamasa Corporation, Choshi, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Daisuke","family":"Nameki","sequence":"additional","affiliation":[{"name":"Laboratory of Virus Immunology, Research Center for AIDS, Institute for Virus Research, Kyoto University, Kyoto, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Eiichi","family":"Kodama","sequence":"additional","affiliation":[{"name":"Laboratory of Virus Immunology, Research Center for AIDS, Institute for Virus Research, Kyoto University, Kyoto, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masao","family":"Matsuoka","sequence":"additional","affiliation":[{"name":"Laboratory of Virus Immunology, Research Center for AIDS, Institute for Virus Research, Kyoto University, Kyoto, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hiroaki","family":"Mitsuya","sequence":"additional","affiliation":[{"name":"Department of Internal Medicine II, Kumamoto University, School of Medicine, Kumamoto, Japan"},{"name":"Experimental Retrovirology Section, Medicine Branch, Division of Clinical Sciences, National Cancer Institute, Bethesda, Md., USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hiroshi","family":"Ohrui","sequence":"additional","affiliation":[{"name":"Division of Life Science, Graduate School of Life Sciences, Tohoku University, Sendai, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"179","published-online":{"date-parts":[[2004,6,1]]},"reference":[{"key":"bibr1-095632020401500306","doi-asserted-by":"publisher","DOI":"10.1021\/jo00034a006"},{"key":"bibr2-095632020401500306","doi-asserted-by":"publisher","DOI":"10.1016\/0166-3542(96)06966-5"},{"key":"bibr3-095632020401500306","doi-asserted-by":"publisher","DOI":"10.1271\/bbb.65.1879"},{"key":"bibr4-095632020401500306","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)00345-6"},{"key":"bibr5-095632020401500306","doi-asserted-by":"publisher","DOI":"10.1021\/jm000209n"}],"container-title":["Antiviral Chemistry and Chemotherapy"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/journals.sagepub.com\/doi\/pdf\/10.1177\/095632020401500306","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.sagepub.com\/doi\/pdf\/10.1177\/095632020401500306","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,9,3]],"date-time":"2024-09-03T18:34:44Z","timestamp":1725388484000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.sagepub.com\/doi\/10.1177\/095632020401500306"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2004,6]]},"references-count":5,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2004,6]]}},"alternative-id":["10.1177\/095632020401500306"],"URL":"https:\/\/doi.org\/10.1177\/095632020401500306","relation":{},"ISSN":["0956-3202","2040-2066"],"issn-type":[{"type":"print","value":"0956-3202"},{"type":"electronic","value":"2040-2066"}],"subject":[],"published":{"date-parts":[[2004,6]]}}}