Optically Active Antifungal Azoles. XII. Synthesis and Antifungal Activity of the Water-Soluble Prodrugs of 1-[(1R, 2R)-2-(2, 4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone
1-[(1R, 2R)-2-(2, 4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (1: TAK-456) was selected as a candidate for clinical trials, but since its water-solubility was insufficient for an injectable formulation, the quaternary triazo...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2001, Vol.49(9), pp.1102-1109 |
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| creator | ICHIKAWA, Takashi KITAZAKI, Tomoyuki MATSUSHITA, Yoshihiro YAMADA, Masami HAYASHI, Ryogo YAMAGUCHI, Masashi KIYOTA, Yutaka OKONOGI, Kenji ITOH, Katsumi |
| description | 1-[(1R, 2R)-2-(2, 4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (1: TAK-456) was selected as a candidate for clinical trials, but since its water-solubility was insufficient for an injectable formulation, the quaternary triazolium salts 2 were designed as water-soluble prodrugs. Among the prodrugs prepared, 4-acetoxymethyl-1-[(2R, 3R)-2-(2, 4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-1-terazolyl)phenyl]-1-imidazolidinyl]butyl]-1H-1, 2, 4-triazolium chloride (2a: TAK-457) was selected as an injectable candidate for clinical trials based on the results of evaluations on solubility, stability, hemolytic effect and in vivo antifungal activities. |
| doi_str_mv | 10.1248/cpb.49.1102 |
| format | Article |
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XII. Synthesis and Antifungal Activity of the Water-Soluble Prodrugs of 1-[(1R, 2R)-2-(2, 4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone</title><source>J-STAGE Free</source><source>MEDLINE</source><source>EZB-FREE-00999 freely available EZB journals</source><source>Free Full-Text Journals in Chemistry</source><creator>ICHIKAWA, Takashi ; KITAZAKI, Tomoyuki ; MATSUSHITA, Yoshihiro ; YAMADA, Masami ; HAYASHI, Ryogo ; YAMAGUCHI, Masashi ; KIYOTA, Yutaka ; OKONOGI, Kenji ; ITOH, Katsumi</creator><creatorcontrib>ICHIKAWA, Takashi ; KITAZAKI, Tomoyuki ; MATSUSHITA, Yoshihiro ; YAMADA, Masami ; HAYASHI, Ryogo ; YAMAGUCHI, Masashi ; KIYOTA, Yutaka ; OKONOGI, Kenji ; ITOH, Katsumi</creatorcontrib><description>1-[(1R, 2R)-2-(2, 4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (1: TAK-456) was selected as a candidate for clinical trials, but since its water-solubility was insufficient for an injectable formulation, the quaternary triazolium salts 2 were designed as water-soluble prodrugs. Among the prodrugs prepared, 4-acetoxymethyl-1-[(2R, 3R)-2-(2, 4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-1-terazolyl)phenyl]-1-imidazolidinyl]butyl]-1H-1, 2, 4-triazolium chloride (2a: TAK-457) was selected as an injectable candidate for clinical trials based on the results of evaluations on solubility, stability, hemolytic effect and in vivo antifungal activities.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.49.1102</identifier><identifier>PMID: 11558595</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>1,2,3-trisubstituted-2-butanol ; Alkylation ; Animals ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antifungal agents ; Antifungal Agents - chemical synthesis ; Antifungal Agents - pharmacology ; Antifungal Agents - therapeutic use ; antifungal azole ; Aspergillus fumigatus - drug effects ; Azoles - chemical synthesis ; Azoles - pharmacology ; Azoles - therapeutic use ; Biological and medical sciences ; Candida albicans - drug effects ; Candidiasis - drug therapy ; Candidiasis - microbiology ; Half-Life ; Hemolysis - drug effects ; Imidazoles - chemical synthesis ; Imidazoles - pharmacology ; Imidazoles - therapeutic use ; In Vitro Techniques ; Magnetic Resonance Spectroscopy ; Medical sciences ; Mice ; Mice, Inbred ICR ; Microbial Sensitivity Tests ; Pharmacology. Drug treatments ; Prodrugs - chemical synthesis ; Prodrugs - pharmacology ; Prodrugs - therapeutic use ; Rats ; Solubility ; TAK-456 ; TAK-457 ; Tetrazoles - chemical synthesis ; Tetrazoles - pharmacology ; Tetrazoles - therapeutic use ; triazolium salt ; water-soluble prodrug</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2001, Vol.49(9), pp.1102-1109</ispartof><rights>2001 The Pharmaceutical Society of Japan</rights><rights>2002 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 2001</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c538t-2eb436f7d2491658c86b748e92324e3409826278036cc4b870e151be7a8ba4f33</citedby><cites>FETCH-LOGICAL-c538t-2eb436f7d2491658c86b748e92324e3409826278036cc4b870e151be7a8ba4f33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1876,4009,27902,27903,27904</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14070425$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11558595$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>ICHIKAWA, Takashi</creatorcontrib><creatorcontrib>KITAZAKI, Tomoyuki</creatorcontrib><creatorcontrib>MATSUSHITA, Yoshihiro</creatorcontrib><creatorcontrib>YAMADA, Masami</creatorcontrib><creatorcontrib>HAYASHI, Ryogo</creatorcontrib><creatorcontrib>YAMAGUCHI, Masashi</creatorcontrib><creatorcontrib>KIYOTA, Yutaka</creatorcontrib><creatorcontrib>OKONOGI, Kenji</creatorcontrib><creatorcontrib>ITOH, Katsumi</creatorcontrib><title>Optically Active Antifungal Azoles. XII. Synthesis and Antifungal Activity of the Water-Soluble Prodrugs of 1-[(1R, 2R)-2-(2, 4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>1-[(1R, 2R)-2-(2, 4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (1: TAK-456) was selected as a candidate for clinical trials, but since its water-solubility was insufficient for an injectable formulation, the quaternary triazolium salts 2 were designed as water-soluble prodrugs. Among the prodrugs prepared, 4-acetoxymethyl-1-[(2R, 3R)-2-(2, 4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-1-terazolyl)phenyl]-1-imidazolidinyl]butyl]-1H-1, 2, 4-triazolium chloride (2a: TAK-457) was selected as an injectable candidate for clinical trials based on the results of evaluations on solubility, stability, hemolytic effect and in vivo antifungal activities.</description><subject>1,2,3-trisubstituted-2-butanol</subject><subject>Alkylation</subject><subject>Animals</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antifungal agents</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - pharmacology</subject><subject>Antifungal Agents - therapeutic use</subject><subject>antifungal azole</subject><subject>Aspergillus fumigatus - drug effects</subject><subject>Azoles - chemical synthesis</subject><subject>Azoles - pharmacology</subject><subject>Azoles - therapeutic use</subject><subject>Biological and medical sciences</subject><subject>Candida albicans - drug effects</subject><subject>Candidiasis - drug therapy</subject><subject>Candidiasis - microbiology</subject><subject>Half-Life</subject><subject>Hemolysis - drug effects</subject><subject>Imidazoles - chemical synthesis</subject><subject>Imidazoles - pharmacology</subject><subject>Imidazoles - therapeutic use</subject><subject>In Vitro Techniques</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Mice, Inbred ICR</subject><subject>Microbial Sensitivity Tests</subject><subject>Pharmacology. Drug treatments</subject><subject>Prodrugs - chemical synthesis</subject><subject>Prodrugs - pharmacology</subject><subject>Prodrugs - therapeutic use</subject><subject>Rats</subject><subject>Solubility</subject><subject>TAK-456</subject><subject>TAK-457</subject><subject>Tetrazoles - chemical synthesis</subject><subject>Tetrazoles - pharmacology</subject><subject>Tetrazoles - therapeutic use</subject><subject>triazolium salt</subject><subject>water-soluble prodrug</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0l2L1DAUBuAiiju7euW9BEQZcTPmq01757B-7MDCyq6isCwlbU9nMmTSMUkX6__23tQZHfSmhZznnBzImyRPKJlRJvLX9baaiWJGKWH3kgnlQuKUMX4_mRBCCsx4xo-SY-_XhLCUSP4wOaI0TfO0SCfJz8tt0LUyZkDzOug7QHMbdNvbpTJo_qMz4Gfo62IxQ9eDDSvw2iNlm3_U2KfDgLoWRYG-qAAOX3emrwygj65rXL_0Y5Ximym9OkXs6iVmeMpOkcBvdWv6znXbFdjBjOeroXHd9wFTvIGwGgzmeErPMY19Y0NwWsW9YjnybWwczG0kN2KncIDgRjBWf8-8jTP1RjfjoW607Sw8Sh60ynh4vP-fJJ_fv_t0do4vLj8szuYXuE55HjCDSvCslQ0TBc3SvM6zSoocCsaZAC5IkbOMyZzwrK5FlUsCNKUVSJVXSrScnyQvdnPjnt968KHcaF-DMcpC1_tSUioJFTLCZ__Bddc7G3crqcgI55KRIqpXO1W7znsHbbl1eqPcUFJSjlkoYxZKUZRjFqJ-up_ZVxtoDnb_-BE83wPlYwRap2yt_cEJIolgo3uzc2sf1BL-AuVidAz8ubTYfca7D6WVciVY_gtAEs_e</recordid><startdate>2001</startdate><enddate>2001</enddate><creator>ICHIKAWA, Takashi</creator><creator>KITAZAKI, Tomoyuki</creator><creator>MATSUSHITA, Yoshihiro</creator><creator>YAMADA, Masami</creator><creator>HAYASHI, Ryogo</creator><creator>YAMAGUCHI, Masashi</creator><creator>KIYOTA, Yutaka</creator><creator>OKONOGI, Kenji</creator><creator>ITOH, Katsumi</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>2001</creationdate><title>Optically Active Antifungal Azoles. XII. Synthesis and Antifungal Activity of the Water-Soluble Prodrugs of 1-[(1R, 2R)-2-(2, 4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone</title><author>ICHIKAWA, Takashi ; KITAZAKI, Tomoyuki ; MATSUSHITA, Yoshihiro ; YAMADA, Masami ; HAYASHI, Ryogo ; YAMAGUCHI, Masashi ; KIYOTA, Yutaka ; OKONOGI, Kenji ; ITOH, Katsumi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c538t-2eb436f7d2491658c86b748e92324e3409826278036cc4b870e151be7a8ba4f33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>1,2,3-trisubstituted-2-butanol</topic><topic>Alkylation</topic><topic>Animals</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antifungal agents</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - pharmacology</topic><topic>Antifungal Agents - therapeutic use</topic><topic>antifungal azole</topic><topic>Aspergillus fumigatus - drug effects</topic><topic>Azoles - chemical synthesis</topic><topic>Azoles - pharmacology</topic><topic>Azoles - therapeutic use</topic><topic>Biological and medical sciences</topic><topic>Candida albicans - drug effects</topic><topic>Candidiasis - drug therapy</topic><topic>Candidiasis - microbiology</topic><topic>Half-Life</topic><topic>Hemolysis - drug effects</topic><topic>Imidazoles - chemical synthesis</topic><topic>Imidazoles - pharmacology</topic><topic>Imidazoles - therapeutic use</topic><topic>In Vitro Techniques</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Mice, Inbred ICR</topic><topic>Microbial Sensitivity Tests</topic><topic>Pharmacology. Drug treatments</topic><topic>Prodrugs - chemical synthesis</topic><topic>Prodrugs - pharmacology</topic><topic>Prodrugs - therapeutic use</topic><topic>Rats</topic><topic>Solubility</topic><topic>TAK-456</topic><topic>TAK-457</topic><topic>Tetrazoles - chemical synthesis</topic><topic>Tetrazoles - pharmacology</topic><topic>Tetrazoles - therapeutic use</topic><topic>triazolium salt</topic><topic>water-soluble prodrug</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>ICHIKAWA, Takashi</creatorcontrib><creatorcontrib>KITAZAKI, Tomoyuki</creatorcontrib><creatorcontrib>MATSUSHITA, Yoshihiro</creatorcontrib><creatorcontrib>YAMADA, Masami</creatorcontrib><creatorcontrib>HAYASHI, Ryogo</creatorcontrib><creatorcontrib>YAMAGUCHI, Masashi</creatorcontrib><creatorcontrib>KIYOTA, Yutaka</creatorcontrib><creatorcontrib>OKONOGI, Kenji</creatorcontrib><creatorcontrib>ITOH, Katsumi</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>ICHIKAWA, Takashi</au><au>KITAZAKI, Tomoyuki</au><au>MATSUSHITA, Yoshihiro</au><au>YAMADA, Masami</au><au>HAYASHI, Ryogo</au><au>YAMAGUCHI, Masashi</au><au>KIYOTA, Yutaka</au><au>OKONOGI, Kenji</au><au>ITOH, Katsumi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Optically Active Antifungal Azoles. XII. Synthesis and Antifungal Activity of the Water-Soluble Prodrugs of 1-[(1R, 2R)-2-(2, 4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2001</date><risdate>2001</risdate><volume>49</volume><issue>9</issue><spage>1102</spage><epage>1109</epage><pages>1102-1109</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>1-[(1R, 2R)-2-(2, 4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (1: TAK-456) was selected as a candidate for clinical trials, but since its water-solubility was insufficient for an injectable formulation, the quaternary triazolium salts 2 were designed as water-soluble prodrugs. Among the prodrugs prepared, 4-acetoxymethyl-1-[(2R, 3R)-2-(2, 4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-1-terazolyl)phenyl]-1-imidazolidinyl]butyl]-1H-1, 2, 4-triazolium chloride (2a: TAK-457) was selected as an injectable candidate for clinical trials based on the results of evaluations on solubility, stability, hemolytic effect and in vivo antifungal activities.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>11558595</pmid><doi>10.1248/cpb.49.1102</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 2001, Vol.49(9), pp.1102-1109 |
| issn | 0009-2363 1347-5223 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_71170147 |
| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | 1,2,3-trisubstituted-2-butanol Alkylation Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antifungal agents Antifungal Agents - chemical synthesis Antifungal Agents - pharmacology Antifungal Agents - therapeutic use antifungal azole Aspergillus fumigatus - drug effects Azoles - chemical synthesis Azoles - pharmacology Azoles - therapeutic use Biological and medical sciences Candida albicans - drug effects Candidiasis - drug therapy Candidiasis - microbiology Half-Life Hemolysis - drug effects Imidazoles - chemical synthesis Imidazoles - pharmacology Imidazoles - therapeutic use In Vitro Techniques Magnetic Resonance Spectroscopy Medical sciences Mice Mice, Inbred ICR Microbial Sensitivity Tests Pharmacology. Drug treatments Prodrugs - chemical synthesis Prodrugs - pharmacology Prodrugs - therapeutic use Rats Solubility TAK-456 TAK-457 Tetrazoles - chemical synthesis Tetrazoles - pharmacology Tetrazoles - therapeutic use triazolium salt water-soluble prodrug |
| title | Optically Active Antifungal Azoles. XII. Synthesis and Antifungal Activity of the Water-Soluble Prodrugs of 1-[(1R, 2R)-2-(2, 4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone |
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