{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T21:18:02Z","timestamp":1791148682095,"version":"4.1.0"},"reference-count":13,"publisher":"Pharmaceutical Society of Japan","issue":"10","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chem. Pharm. Bull.","CHEMICAL &amp; PHARMACEUTICAL BULLETIN"],"published-print":{"date-parts":[[2013]]},"DOI":"10.1248\/cpb.c13-00461","type":"journal-article","created":{"date-parts":[[2013,10,1]],"date-time":"2013-10-01T04:58:51Z","timestamp":1380603531000},"page":"1090-1093","source":"Crossref","is-referenced-by-count":19,"title":["Antibacterial Activity of Some 5-Dialkylaminomethylhydantoins and Related Derivatives"],"prefix":"10.1248","volume":"61","author":[{"given":"Fumiko","family":"Fujisaki","sequence":"first","affiliation":[{"name":"Faculty of Pharmaceutical Science, Fukuoka University"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Keiko","family":"Toyofuku","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Science, Fukuoka University"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mayu","family":"Egami","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Science, Fukuoka University"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shiori","family":"Ishida","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Science, Fukuoka University"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Naho","family":"Nakamoto","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Science, Fukuoka University"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nobuhiro","family":"Kashige","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Science, Fukuoka University"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fumio","family":"Miake","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Science, Fukuoka University"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kunihiro","family":"Sumoto","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Science, Fukuoka University"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"163","reference":[{"key":"1","unstructured":"1) Fujisaki F., Abe N., Sumoto K., <i>Chem. Pharm. Bull.<\/i>, 52, 1238\u20131241 (2004)."},{"key":"2","unstructured":"2) Fujisaki F., Abe N., Sumoto K., <i>HETEROCYCLES<\/i>, 75, 1681\u20131694 (2008)."},{"key":"3","unstructured":"3) Fujisaki F., Hiromatsu S., Matsumura Y., Fukami A., Kashige N., Miake F., Sumoto K., <i>J. Heterocyclic Chem.<\/i>, 50, 417\u2013424 (2013) and related references cited therein."},{"key":"4","unstructured":"4) Fujisaki F., Usami H., Nakashima S., Iwashita S., Kurose Y., Kashige N., Miake F., Sumoto K., <i>HETEROCYCLES<\/i>, 83, 1843\u20131851 (2011)."},{"key":"5","unstructured":"5) Fujisaki F., Usami H., Nakashima S., Nishida S., Fujioka T., Kashige N., Miake F., Sumoto K., <i>HETEROCYCLES<\/i>, 87, 665\u2013675 (2013)."},{"key":"6","unstructured":"6) Fujisaki F., Shoji K., Shimodouzono M., Kashige N., Miake F., Sumoto K., <i>Chem. Pharm. Bull.<\/i>, 58, 1123\u20131126 (2010) and related references cited therein."},{"key":"7","unstructured":"7) Brickner S. J., Hutchinson D. K., Barbachyn M. R., Manninen P. R., Ulanowicz D. A., Garmon S. A., Grega K. C., Hendges S. K., Toops D. S., Ford C. W., Zurenko G. E., <i>J. Med. Chem.<\/i>, 39, 673\u2013679 (1996)."},{"key":"8","unstructured":"8) Fujisaki F., Egami M., Toyofuku K., Sumoto K., <i>HETEROCYCLES<\/i>, 87, 133\u2013145 (2013)."},{"key":"9","unstructured":"9) Camille G. W., \u201cThe Practice of Medicinal Chemistry,\u201d 3rd ed., Academic Press, San Diego, 2008 and related references cited therein."},{"key":"10","doi-asserted-by":"crossref","unstructured":"10) Krishnamurthy V. M., Estroff L. A., Whitesides G. M., \u201cMethods and Principles in Medicinal Chemistry: Fragment-based Approaches in Drug Discovery,\u201d Vol 34, ed. by Mannhold R., Kubinyi H., Folkers G., Wiley-VCH, Weinheim, 2006, pp. 11\u201353 and related references cited therein.","DOI":"10.1002\/3527608761.ch2"},{"key":"11","unstructured":"11) The obtained compound <b>7<\/b> exhibited very simple symmetrical <sup>13<\/sup>C-NMR in DMSO-<i>d<\/i><sub>6<\/sub>, indicating little difference with respect to the signal assignable to substituted hydantoin rings and a linker diphenylmethane moiety. From a stereochemical viewpoint, however, product <b>7<\/b> can be considered to be a mixture of three twin-drug type molecules, <i>i.e.<\/i>, two C<sub>2<\/sub>-symmetrical molecules that have the same absolute configuration (<i>R<\/i>,<i>R<\/i> or <i>S<\/i>,<i>S<\/i>) regarding two chiral hydantoin rings in the molecules and a Cs-symmetrical <i>meso<\/i> compound having different absolute configurations (<i>R<\/i>,<i>S<\/i>). We distinguished the presence of three predominant stereoisomers in the free base of product <b>7<\/b> by an HPLC method (CHIRALPAK IA\u00ae) with a mobile phase consisting of <i>n<\/i>-hexane\u20132-propanol\u2013diethylamine=150\u2009:\u2009150\u2009:\u20090.2 (v\/v). The ratio of the three peaks (<i>ca.<\/i> 1\u2009:\u20092\u2009:\u20091) was estimated by comparison of these elution peak areas."},{"key":"12","unstructured":"12) The Japanese Society of Chemotherapy (1989), <i>Chemotherapy<\/i>, 38, 102\u2013105 (1990)."},{"key":"13","unstructured":"13) The Japanese Society of Chemotherapy (1992), <i>Chemotherapy<\/i>, 41, 184\u2013189 (1993)."}],"container-title":["Chemical and Pharmaceutical Bulletin"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.jstage.jst.go.jp\/article\/cpb\/61\/10\/61_c13-00461\/_pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,3,18]],"date-time":"2021-03-18T03:27:04Z","timestamp":1616038024000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.jstage.jst.go.jp\/article\/cpb\/61\/10\/61_c13-00461\/_article"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013]]},"references-count":13,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2013]]}},"URL":"https:\/\/doi.org\/10.1248\/cpb.c13-00461","relation":{},"ISSN":["0009-2363","1347-5223"],"issn-type":[{"value":"0009-2363","type":"print"},{"value":"1347-5223","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013]]}}}