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J., Barbachyn M. R., Hutchinson D. K., Manninen P. R., <i>J. Med. Chem.<\/i>, 51, 1981\u20131990 (2008) and related references cited therein."},{"key":"2","unstructured":"2) Lawrence L., Danese P., DeVito J., Franceschi F., Sutcliffe J., <i>Antimicrob. Agents Chemother.<\/i>, 52, 1653\u20131662 (2008) and related references cited therein."},{"key":"3","unstructured":"3) Locke J. B., Finn J., Hilgers M., Morales G., Rahawi S., Kedar G. C., Picazo J. J., Im W., Shaw K. J., Stein J. L., <i>Antimicrob. Agents Chemother.<\/i>, 54, 5337\u20135343 (2010) and related references cited therein."},{"key":"4","unstructured":"4) Gibson S. E., Castaldi M. P., <i>Angew. Chem. Int. Ed.<\/i>, 45, 4718\u20134720 (2006)."},{"key":"5","unstructured":"5) Trouche N., Wieckowski S., Sun W., Chaloin O., Hoebeke J., Fournel S., Guichard G., <i>J. Am. Chem. Soc.<\/i>, 129, 13480\u201313492 (2007)."},{"key":"6","unstructured":"6) Balzarini J., <i>Antiviral Res.<\/i>, 71, 237\u2013247 (2006) and related references cited therein."},{"key":"7","unstructured":"7) Camille G. W., \u201cThe Practice of Medicinal Chemistry,\u201d 3nd ed., Academic Press, San Diego, 2008 and related references cited therein."},{"key":"8","unstructured":"8) Humblet V., Misra P., Bhushan K. R., Nasr K., Ko Y., Tsukamoto T., Pannier N., Frangioni J. V., Maison W., <i>J. Med. Chem.<\/i>, 52, 544\u2013550 (2009)."},{"key":"9","unstructured":"9) Oshovsky G. V., Reinhoudt D. N., Verboom W., <i>Angew. Chem. Int. Ed.<\/i>, 46, 2366\u20132393 (2007)."},{"key":"10","unstructured":"10) Fujisaki F., Usami H., Nakashima S., Iwashita S., Kurose Y., Kashige N., Miake F., Sumoto K., <i>HETEROCYCLES<\/i>, 83, 1843\u20131851 (2011)."},{"key":"11","unstructured":"11) Fujisaki F., Usami H., Nakashima S., Nishida S., Fujioka T., Kashige N., Miake F., Sumoto K., <i>HETEROCYCLES<\/i>, 87, 665\u2013675 (2013)."},{"key":"12","unstructured":"12) Fujisaki F., Hiromatsu S., Matsumura Y., Fukami A., Kashige N., Miake F., Sumoto K., <i>J. Heterocyclic Chem.<\/i>, 50, 417\u2013424 (2013)."},{"key":"13","unstructured":"13) Mibu N., Yokomizo K., Saisho M., Oishi M., Aki H., Miyata T., Sumoto K., <i>HETEROCYCLES<\/i>, 83, 385\u2013393 (2011)."},{"key":"14","unstructured":"14) Mibu N., Yokomizo K., Oishi M., Miyata T., Sumoto K., <i>Chem. Pharm. Bull.<\/i>, 56, 1052\u20131058 (2008)."},{"key":"15","unstructured":"15) Mibu N., Yokomizo K., Miyata T., Sumoto K., <i>Chem. Pharm. Bull.<\/i>, 55, 1406\u20131411 (2007)."},{"key":"16","unstructured":"16) Fujisaki F., Shoji K., Sumoto K., <i>HETEROCYCLES<\/i>, 78, 213\u2013220 (2009)."},{"key":"17","unstructured":"17) Fujisaki F., Shoji K., Sumoto K., <i>Chem. Pharm. Bull.<\/i>, 57, 1415\u20131420 (2009)."},{"key":"18","unstructured":"18) Fujisaki F., Shoji K., Shimodouzono M., Kashige N., Miake F., Sumoto K., <i>Chem. Pharm. Bull.<\/i>, 58, 1123\u20131126 (2010)."},{"key":"19","unstructured":"19) Fujisaki F., Egami M., Toyofuku K., Sumoto K., <i>HETEROCYCLES<\/i>, 87, 133\u2013145 (2013)."},{"key":"20","unstructured":"20) Fujisaki F., Toyofuku K., Egami M., Ishida S., Nakamoto N., Kashige N., Miake F., Sumoto K., <i>Chem. Pharm. Bull.<\/i>, 61, 1090\u20131093 (2013)."},{"key":"21","unstructured":"21) In our previous paper (refs. 19, 20), we showed the preparation of this symmetrical bivalent compound <b>24b<\/b> and its antibacterial activity (MIC) values against <i>S. aureus<\/i> and <i>E. coli<\/i> strains (MIC=0.024 and 0.095\u2009mM, respectively)."},{"key":"22","doi-asserted-by":"crossref","unstructured":"22) 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 Verlag GmbH &amp; Co., KGaA, Weinheim, 2006, pp. 11\u201353 and related references cited therein.","DOI":"10.1002\/3527608761.ch2"},{"key":"23","unstructured":"23) From a stereochemical viewpoint, these products <b>19<\/b>\u2013<b>24<\/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>24b<\/b> by an HPLC method (CHIRALPAK IA\u00ae).<sup>20)<\/sup> We used stereoisomeric mixtures for calorimetric experiments and for the biological evaluation (antibacterial activity)."},{"key":"24","unstructured":"24) Varki A., Cummings R. D., Esko J. D., Freeze H. H., Stanley P., Bertozzi C. R., Hart G. W., Etzler M. E., \u201cEssentials of Glycobiology,\u201d 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N. Y., 2009, p. 719."},{"key":"25","unstructured":"25) Mibu N., Aki H., Ikeda H., Saito A., Uchida W., Yokomizo K., Zhou J., Miyata T., Sumoto K., <i>J. Therm. Anal. Calorim.<\/i>, 113, 1015\u20131018 (2013)."},{"key":"26","unstructured":"26) Mibu N., Yokomizo K., Kashige N., Miake F., Miyata T., Uyeda M., Sumoto K., <i>Chem. Pharm. Bull.<\/i>, 55, 111\u2013114 (2007)."},{"key":"27","doi-asserted-by":"crossref","unstructured":"27) Regarding small molecule antagonists of glycosaminoglycan sulfates, it has been demonstrated that the identification of small molecule antagonists against such glycosaminoglycans may lead to the development of new pharmacological agents to treat infectious diseases that involve a glycosaminoglycan sulfate binding stage (for example, see following reference). Schuksz M., Fuster M. M., Brown J. R., Crawford B. E., Ditto D. P., Lawrence R., Glass C. A., Wang L., Tor Y., Esko J. D., <i>Proc. Natl. Acad. Sci. U.S.A.<\/i>, 105, 13075\u201313080 (2008).","DOI":"10.1073\/pnas.0805862105"},{"key":"28","unstructured":"28) The Japanese Society of Chemotherapy, <i>Chemotherapy<\/i>, 38, 102\u2013105 (1990)."},{"key":"29","unstructured":"29) The Japanese Society of Chemotherapy, <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\/62\/5\/62_c14-00017\/_pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,4,2]],"date-time":"2022-04-02T16:45:36Z","timestamp":1648917936000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.jstage.jst.go.jp\/article\/cpb\/62\/5\/62_c14-00017\/_article"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014]]},"references-count":29,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2014]]}},"URL":"https:\/\/doi.org\/10.1248\/cpb.c14-00017","relation":{},"ISSN":["0009-2363","1347-5223"],"issn-type":[{"value":"0009-2363","type":"print"},{"value":"1347-5223","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014]]}}}