{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,28]],"date-time":"2026-03-28T06:18:18Z","timestamp":1774678698222,"version":"3.50.1"},"reference-count":47,"publisher":"Pharmaceutical Society of Japan","issue":"3","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chem. Pharm. Bull.","CHEMICAL &amp; PHARMACEUTICAL BULLETIN"],"published-print":{"date-parts":[[2026,3,28]]},"DOI":"10.1248\/cpb.c25-00679","type":"journal-article","created":{"date-parts":[[2026,3,27]],"date-time":"2026-03-27T22:08:50Z","timestamp":1774649330000},"page":"274-288","source":"Crossref","is-referenced-by-count":0,"title":["From 1,4- to 1,5-Disubstituted Triazoles: Enhanced Three-Dimensionality and Aqueous Solubility"],"prefix":"10.1248","volume":"74","author":[{"given":"Fumika","family":"Karaki","sequence":"first","affiliation":[{"name":"Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5\u20139\u20131 Shirokane, Minato-ku, Tokyo 108\u20138641, Japan"},{"name":"Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5\u20139\u20131 Shirokane, Minato-ku, Tokyo 108\u20138641, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kei","family":"Ishii","sequence":"additional","affiliation":[{"name":"Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5\u20139\u20131 Shirokane, Minato-ku, Tokyo 108\u20138641, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kyoko","family":"Hidaka","sequence":"additional","affiliation":[{"name":"Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5\u20139\u20131 Shirokane, Minato-ku, Tokyo 108\u20138641, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kotomi","family":"Sato","sequence":"additional","affiliation":[{"name":"Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5\u20139\u20131 Shirokane, Minato-ku, Tokyo 108\u20138641, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kasumi","family":"Suzuki","sequence":"additional","affiliation":[{"name":"Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5\u20139\u20131 Shirokane, Minato-ku, Tokyo 108\u20138641, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chie","family":"Hagiwara","sequence":"additional","affiliation":[{"name":"Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5\u20139\u20131 Shirokane, Minato-ku, Tokyo 108\u20138641, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hideaki","family":"Fujii","sequence":"additional","affiliation":[{"name":"Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5\u20139\u20131 Shirokane, Minato-ku, Tokyo 108\u20138641, Japan"},{"name":"Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5\u20139\u20131 Shirokane, Minato-ku, Tokyo 108\u20138641, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"163","reference":[{"key":"1","doi-asserted-by":"crossref","unstructured":"1) Brown D. G., Bostr\u00f6m J., <i>J. Med. Chem.<\/i>, <b>59<\/b>, 4443\u20134458 (2016).","DOI":"10.1021\/acs.jmedchem.5b01409"},{"key":"2","doi-asserted-by":"crossref","unstructured":"2) Stevens J. S., Byard S. J., Muryn C. A., Schroeder S. L. M., <i>J. Phys. Chem. B<\/i>, <b>114<\/b>, 13961\u201313969 (2010).","DOI":"10.1021\/jp106465u"},{"key":"3","doi-asserted-by":"crossref","unstructured":"3) Varughese S., Kiran M. S. R. N., Solanko K. A., Bond A. D., Ramamurty U., Desiraju G. R., <i>Chem. Sci.<\/i>, <b>2<\/b>, 2236\u20132242 (2011).","DOI":"10.1039\/c1sc00430a"},{"key":"4","doi-asserted-by":"crossref","unstructured":"4) Kim J., Jung J., Koo J., Cho W., Lee W. S., Kim C., Park W., Park S. B., <i>Nat. Commun.<\/i>, <b>7<\/b>, 13196 (2016).","DOI":"10.1038\/ncomms13196"},{"key":"5","doi-asserted-by":"crossref","unstructured":"5) Iusupov I. R., Lukyanenko E. R., Altieri A., Kurkin A. V., <i>ChemMedChem<\/i>, <b>17<\/b>, e202200394 (2022).","DOI":"10.1002\/cmdc.202200394"},{"key":"6","doi-asserted-by":"crossref","unstructured":"6) Lipinski C. A., Lombardo F., Dominy B. W., Feeney P. J., <i>Adv. Drug Deliv. Rev.<\/i>, <b>23<\/b>, 3\u201325 (1997).","DOI":"10.1016\/S0169-409X(96)00423-1"},{"key":"7","doi-asserted-by":"crossref","unstructured":"7) Lovering F., Bikker J., Humblet C., <i>J. Med. Chem.<\/i>, <b>52<\/b>, 6752\u20136756 (2009).","DOI":"10.1021\/jm901241e"},{"key":"8","doi-asserted-by":"crossref","unstructured":"8) Ritchie T. J., Macdonald S. J. F., Young R. J., Pickett S. D., <i>Drug Discov. Today<\/i>, <b>16<\/b>, 164\u2013171 (2011).","DOI":"10.1016\/j.drudis.2010.11.014"},{"key":"9","doi-asserted-by":"crossref","unstructured":"9) Ishikawa M., Hashimoto Y., <i>J. Med. Chem.<\/i>, <b>54<\/b>, 1539\u20131554 (2011).","DOI":"10.1021\/jm101356p"},{"key":"10","doi-asserted-by":"crossref","unstructured":"10) Ozaki S., Nakagawa Y., Shirai O., Kano K., <i>J. Pharm. Sci.<\/i>, <b>103<\/b>, 3524\u20133531 (2014).","DOI":"10.1002\/jps.24139"},{"key":"11","doi-asserted-by":"crossref","unstructured":"11) Brown D. G., Gagnon M. M., Bostr\u00f6m J., <i>J. Med. Chem.<\/i>, <b>58<\/b>, 2390\u20132405 (2015).","DOI":"10.1021\/jm501894t"},{"key":"12","doi-asserted-by":"crossref","unstructured":"12) Topliss J. G., <i>J. Med. Chem.<\/i>, <b>20<\/b>, 463\u2013469 (1977).","DOI":"10.1021\/jm00214a001"},{"key":"13","doi-asserted-by":"crossref","unstructured":"13) Hiramatsu M., Ichikawa Y., Tomoshige S., Makishima M., Muranaka A., Uchiyama M., Yamaguchi T., Hashimoto Y., Ishikawa M., <i>Chem. Asian J.<\/i>, <b>11<\/b>, 2210\u20132217 (2016).","DOI":"10.1002\/asia.201600744"},{"key":"14","doi-asserted-by":"crossref","unstructured":"14) Rostovtsev V. V., Green L. G., Fokin V. V., Sharpless K. B., <i>Angew. Chem. Int. Ed.<\/i>, <b>41<\/b>, 2596\u20132599 (2002).","DOI":"10.1002\/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4"},{"key":"15","doi-asserted-by":"crossref","unstructured":"15) Torn\u00f8e C. W., Christensen C., Meldal M., <i>J. Org. Chem.<\/i>, <b>67<\/b>, 3057\u20133064 (2002).","DOI":"10.1021\/jo011148j"},{"key":"16","doi-asserted-by":"crossref","unstructured":"16) May J. H., Fehr J. M., Lorenz J. C., Zakharov L. N., Jasti R., <i>Angew. Chem. Int. Ed.<\/i>, <b>63<\/b>, e202401823 (2024).","DOI":"10.1002\/anie.202401823"},{"key":"17","doi-asserted-by":"crossref","unstructured":"17) Wang Y., Xu S., Shi L., Teh C., Qi G., Liu B., <i>Angew. Chem. Int. Ed.<\/i>, <b>60<\/b>, 14945\u201314953 (2021).","DOI":"10.1002\/anie.202017350"},{"key":"18","doi-asserted-by":"crossref","unstructured":"18) Olivelli A. G., Olelewe C., Wolff L., Parkin S., Webster C. E., Awuah S. G., Huckaba A., <i>Chem. Eur. J.<\/i>, <b>30<\/b>, e202402887 (2024).","DOI":"10.1002\/chem.202402887"},{"key":"19","doi-asserted-by":"crossref","unstructured":"19) Zhang X., Zhang S., Zhao S., Wang X., Liu B., Xu H., <i>Front Chem.<\/i>, <b>9<\/b>, 774977 (2021).","DOI":"10.3389\/fchem.2021.774977"},{"key":"20","doi-asserted-by":"crossref","unstructured":"20) Pasieka A., Diamanti E., Uliassi E., Bolognesi M. L., <i>ChemMedChem<\/i>, <b>18<\/b>, e202300422 (2023).","DOI":"10.1002\/cmdc.202300422"},{"key":"21","doi-asserted-by":"crossref","unstructured":"21) Nemati F., Bischoff-Kont I., Salehi P., Nejad-Ebrahimi S., Mohebbi M., Bararjanian M., Hadian N., Hassanpour Z., Jung Y., Schaerlaekens S., Lucena-Agell D., Oliva M. A., F\u00fcrst R., Nasiri H. R., <i>Bioorg. Chem.<\/i>, <b>115<\/b>, 105135 (2021).","DOI":"10.1016\/j.bioorg.2021.105135"},{"key":"22","doi-asserted-by":"crossref","unstructured":"22) Srinivasan R., Li J., Ng S. L., Kalesh K. A., Yao S. Q., <i>Nat. Protoc.<\/i>, <b>2<\/b>, 2655\u20132664 (2007).","DOI":"10.1038\/nprot.2007.323"},{"key":"23","doi-asserted-by":"crossref","unstructured":"23) Pingitore V., Mart\u00ednez-Bail\u00e9n M., Carmona A. T., M\u00e9sz\u00e1ros Z., Kulik N., Sl\u00e1mov\u00e1 K., K\u0159en V., Bojarov\u00e1 P., Robina I., Moreno-Vargas A. J., <i>Bioorg. Chem.<\/i>, <b>120<\/b>, 105650 (2022).","DOI":"10.1016\/j.bioorg.2022.105650"},{"key":"24","doi-asserted-by":"crossref","unstructured":"24) Lewis W. G., Green L. G., Grynszpan F., Radi\u0107 Z., Carlier P. R., Taylor P., Finn M. G., Sharpless K. B., <i>Angew. Chem. Int. Ed.<\/i>, <b>41<\/b>, 1053\u20131057 (2002).","DOI":"10.1002\/1521-3773(20020315)41:6<1053::AID-ANIE1053>3.0.CO;2-4"},{"key":"25","doi-asserted-by":"crossref","unstructured":"25) Jin X., Daher S. S., Lee M., Buttaro B., Andrade R. B., <i>ACS Med. Chem. Lett.<\/i>, <b>9<\/b>, 907\u2013911 (2018).","DOI":"10.1021\/acsmedchemlett.8b00248"},{"key":"26","doi-asserted-by":"crossref","unstructured":"26) Nozal V., Garc\u00eda-Rubia A., Cuevas E. P., P\u00e9rez C., Tosat-Bitri\u00e1n C., Bartolom\u00e9 F., Carro E., Ram\u00edrez D., Palomo V., Mart\u00ednez A., <i>Angew. Chem. Int. Ed.<\/i>, <b>60<\/b>, 19344\u201319354 (2021).","DOI":"10.1002\/anie.202106295"},{"key":"27","doi-asserted-by":"crossref","unstructured":"27) Zhao R., Zhu J., Jiang X., Bai R., <i>Eur. J. Med. Chem.<\/i>, <b>264<\/b>, 116037 (2024).","DOI":"10.1016\/j.ejmech.2023.116037"},{"key":"28","doi-asserted-by":"crossref","unstructured":"28) Bonandi E., Christodoulou M. S., Fumagalli G., Perdicchia D., Rastelli G., Passarella D.,<i>Drug Discov. Today<\/i>, <b>22<\/b>, 1572\u20131581 (2017).","DOI":"10.1016\/j.drudis.2017.05.014"},{"key":"29","doi-asserted-by":"crossref","unstructured":"29) Karaki F., Umemoto S., Ashizawa K., Oki T., Sato N., Ogino T., Ishibashi N., Someya R., Miyano K., Hirayama S., Uezono Y., Fujii H., <i>ChemMedChem<\/i>, <b>14<\/b>, 1840\u20131848 (2019).","DOI":"10.1002\/cmdc.201900398"},{"key":"30","doi-asserted-by":"crossref","unstructured":"30) Johansson J. R., Beke-Somfai T., St\u00e5lsmeden A. S., Kann N., <i>Chem. Rev.<\/i>, <b>116<\/b>, 14726\u201314768 (2016).","DOI":"10.1021\/acs.chemrev.6b00466"},{"key":"31","doi-asserted-by":"crossref","unstructured":"31) Zhang L., Chen X., Xue P., Sun H. H. Y., Williams I. D., Sharpless K. B., Fokin V. V., Jia G., <i>J. Am. Chem. Soc.<\/i>, <b>127<\/b>, 15998\u201315999 (2005).","DOI":"10.1021\/ja054114s"},{"key":"32","doi-asserted-by":"crossref","unstructured":"32) Mahadari M. K., Tague A. J., Keller P. A., Pyne S. G., <i>Tetrahedron<\/i>, <b>81<\/b>, 131916 (2021).","DOI":"10.1016\/j.tet.2020.131916"},{"key":"33","doi-asserted-by":"crossref","unstructured":"33) Cafici L., Pirali T., Condorelli F., Del Grosso E., Massarotti A., Sorba G., Canonico P. L., Tron G. C., Genazzani A. A., <i>J. Comb. Chem.<\/i>, <b>10<\/b>, 732\u2013740 (2008).","DOI":"10.1021\/cc800090d"},{"key":"34","doi-asserted-by":"crossref","unstructured":"34) Ahsanullah M. P., Schmieder P., K\u00fchne R., Rademann J., <i>Angew. Chem. Int. Ed.<\/i>, <b>48<\/b>, 5042\u20135045 (2009).","DOI":"10.1002\/anie.200806390"},{"key":"35","doi-asserted-by":"crossref","unstructured":"35) Gonz\u00e1lez-Calder\u00f3n D., Fuentes-Ben\u00edtes A., D\u00edaz-Torres E., Gonz\u00e1lez-Gonz\u00e1lez C. A., Gonz\u00e1lez-Romero C., <i>Eur. J. Org. Chem.<\/i>, <b>2016<\/b>, 668\u2013672 (2016).","DOI":"10.1002\/ejoc.201501465"},{"key":"36","doi-asserted-by":"crossref","unstructured":"36) Otani Y., Futaki S., Kiwada T., Sugiura Y., Muranaka A., Kobayashi N., Uchiyama M., Yamaguchi K., Ohwada T., <i>Tetrahedron<\/i>, <b>62<\/b>, 11635\u201311644 (2006).","DOI":"10.1016\/j.tet.2006.09.062"},{"key":"37","doi-asserted-by":"crossref","unstructured":"37) Hansch C., Leo A., Taft R. W., <i>Chem. Rev.<\/i>, <b>91<\/b>, 165\u2013195 (1991).","DOI":"10.1021\/cr00002a004"},{"key":"38","doi-asserted-by":"crossref","unstructured":"38) Krasi\u0144ski A., Fokin V. V., Sharpless K. B., <i>Org. Lett.<\/i>, <b>6<\/b>, 1237\u20131240 (2004).","DOI":"10.1021\/ol0499203"},{"key":"39","doi-asserted-by":"crossref","unstructured":"39) Smith C. D., Greaney M. F., <i>Org. Lett.<\/i>, <b>15<\/b>, 4826\u20134829 (2013).","DOI":"10.1021\/ol402225d"},{"key":"40","doi-asserted-by":"crossref","unstructured":"40) Sauer W. H. B., Schwarz M. K., <i>J. Chem. Inf. Comput. Sci.<\/i>, <b>43<\/b>, 987\u20131003 (2003).","DOI":"10.1021\/ci025599w"},{"key":"41","doi-asserted-by":"crossref","unstructured":"41) Irwin J. J., Tang K. G., Young J., Dandarchuluun C., Wong B. R., Khurelbaatar M., Moroz Y. S., Mayfield J., Sayle R. A., <i>J. Chem. Inf. Model.<\/i>, <b>60<\/b>, 6065\u20136073 (2020).","DOI":"10.1021\/acs.jcim.0c00675"},{"key":"42","doi-asserted-by":"crossref","unstructured":"42) Vigneron S. F., Ohno S., Braz J., Kim J. Y., Kweon O. S., Webb C., Billesb\u00f8lle C. B., Srinivasan K., Bhardwaj K., Irwin J. J., Manglik A., Basbaum A. I., Ellman J. A., Shoichet B. K., <i>ACS Cent. Sci.<\/i>, <b>11<\/b>, 770\u2013790 (2025).","DOI":"10.1021\/acscentsci.5c00052"},{"key":"43","doi-asserted-by":"crossref","unstructured":"43) Massarotti A., Aprile S., Mercalli V., Del Grosso E., Grosa G., Sorba G., Tron G. C., <i>ChemMedChem<\/i>, <b>9<\/b>, 2497\u20132508 (2014).","DOI":"10.1002\/cmdc.201402233"},{"key":"44","doi-asserted-by":"crossref","unstructured":"44) Karaki F., Oki T., Sakao Y., Sato N., Hirayama S., Miyano K., Uezono Y., Fujii H., <i>ChemMedChem<\/i>, <b>16<\/b>, 3463\u20133476 (2021).","DOI":"10.1002\/cmdc.202100322"},{"key":"45","doi-asserted-by":"crossref","unstructured":"45) Karaki F., Takamori T., Kawakami K., Sakurai S., Hidaka K., Ishii K., Oki T., Sato N., Atsumi N., Ashizawa K., Taguchi A., Ura A., Naruse T., Hirayama S., Nonaka M., Miyano K., Uezono Y., Fujii H., <i>Molecules<\/i>, <b>28<\/b>, 6925 (2023).","DOI":"10.3390\/molecules28196925"},{"key":"46","doi-asserted-by":"crossref","unstructured":"46) Maddani M. R., Moorthy S. K., Prabhu K. R., <i>Tetrahedron<\/i>, <b>66<\/b>, 329\u2013333 (2010).","DOI":"10.1016\/j.tet.2009.10.093"},{"key":"47","doi-asserted-by":"crossref","unstructured":"47) Yamada T., Teranishi W., Park K., Jiang J., Tachikawa T., Furusato S., Sajiki H., <i>ChemCatChem<\/i>, <b>12<\/b>, 4052\u20134058 (2020).","DOI":"10.1002\/cctc.202000805"}],"container-title":["Chemical and Pharmaceutical Bulletin"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.jstage.jst.go.jp\/article\/cpb\/74\/3\/74_c25-00679\/_pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,3,28]],"date-time":"2026-03-28T03:25:04Z","timestamp":1774668304000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.jstage.jst.go.jp\/article\/cpb\/74\/3\/74_c25-00679\/_article"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,3,28]]},"references-count":47,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2026]]}},"URL":"https:\/\/doi.org\/10.1248\/cpb.c25-00679","relation":{},"ISSN":["0009-2363","1347-5223"],"issn-type":[{"value":"0009-2363","type":"print"},{"value":"1347-5223","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,3,28]]},"article-number":"c25-00679"}}