Synthesis and structure-activity relationships of 7.BETA.-((Z)-2-(2-aminothiazol-4-yl)-3-(substituted)-2-propenoyl-amino)-3-desacetoxymethylcephalosporins.
Koji IshikuraTadatoshi KubotaKyôji MinamiYoshio HamashimaHIROMU NAKASHIMIZUKIYOSHI MOTOKAWATadashi Yoshida
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3-Hydroxymethyl-7β-phenylacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester(Ⅰ) was prepared in 48% yield by deacetylation of 7-aminocephalosporanic acid,followed by sequential protection of the amino and carboxyl group with phenylacetic chloride and diphenylazomethane,respectively.Selective oxidation of Ⅰ with 2-iodoxybenzoic acid in acetonitrile gave the oxidized product 3-formyl-7β-phenylacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester(Ⅱ) in 94% yield.
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ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis and biological activity of substance P C-terminal hexapeptide analogues: structure-activity studiesConstantine Poulos, John R. Brown, and Christopher C. JordanCite this: J. Med. Chem. 1986, 29, 7, 1281–1284Publication Date (Print):July 1, 1986Publication History Published online1 May 2002Published inissue 1 July 1986https://pubs.acs.org/doi/10.1021/jm00157a028https://doi.org/10.1021/jm00157a028research-articleACS PublicationsRequest reuse permissionsArticle Views59Altmetric-Citations18LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts
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The present report describes a novel and efficient method for enrichment of 7-amino-3-[(Z)-propen-1-yl]-3-cephem-4-carboxylic acid (1) in a mixture of (Z/E) 7-amino-3[(Z/E)-propen-1-yl]-3-cephem-4-carboxylic acid via formation of 7-β-isopropylideneammonium salt in acidic conditions. This method provides high yield and 7-amino-3-[(Z)-propen-1-yl]-3-cephem-4-carboxylic acid (1) having a low E-isomer content from a mixture containing very high proportion of E-isomer. The usage of these isopropylidene ammonium salts provides a method for separation of mixtures of cephalosporins where geometric isomerism about a double bond exists.
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A intermediate of Cefcapene 7-[1-(2-tert.-butoxycarbonylaminothiazol-4-yl)-1(Z)-pentencarboxamido]-3-hydroxymethyl-3-cephem-4-carboxylic acid in overall yield of 90.2% was synthesized by acidylation of 1-(2-tert.-butoxycarbonylaminothiazol-4-yl)-1(Z)-pentencarboxylic acid with methanesulphonyl chloride,then combination with hydroxymethyl-7-amino-cephalosporanic acid.The structure of product were confirmed 1H NMR,MS and IR.
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ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTumor inhibitors. 124. Structural requirements for antileukemic activity among the naturally occurring and semisynthetic maytansinoidsS. Morris Kupchan, Albert T. Sneden, Alan R. Branfman, Gary A. Howie, Lionel I. Rebhun, Wilson E. McIvor, Regina W. Wang, and Terry C. SchnaitmanCite this: J. Med. Chem. 1978, 21, 1, 31–37Publication Date (Print):January 1, 1978Publication History Published online1 May 2002Published inissue 1 January 1978https://pubs.acs.org/doi/10.1021/jm00199a006https://doi.org/10.1021/jm00199a006research-articleACS PublicationsRequest reuse permissionsArticle Views620Altmetric-Citations73LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts
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Resveratrol (3,5,4'-trihydroxy-trans-stilbene) is a well-known natural polyphenol compound. It is reported that resveratrol possesses strong anti-oxidative, anti-inflammatory, cardiovascular protective and cancer chemo-preventive effects. Therefore, there has been a considerable interest in its biological activity, pharmacological activity and also synthetic resveratrol analogues in recent years. Up to now, many new resveratrol derivatives have been synthesized and some new biological activities of these compounds have been found, so in the treatment of Alzheimer's disease and the inhibition of influenza H1N1 neuraminidase. Structure-activity studies revealed that crucial elements of parental components are required for specific effects. This review summarizes the available literatures on the structure-activity relationships and pharmacological properties of resveratrol analogues.
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Very little is known about the structure-activity relationship of quinolone antibacterials at the 2-position. Because of the loss of biological activity with 2-methyl and 2-hydroxyl substitution, modifications at C-2 were generally considered to be unfavourable. Quinolone derivatives having a ring between positions 1 and 2 were recently shown to have biological activity. The sulfur-bridged analogs such as the benzothiazolo[3,2-a]quinolone, KB-5246 and NAD-394 have been reported to be highly active in vitro. The authors have synthesized 2-methylthiociprofloxacin, 2-methylofloxacin, the 5-oxopyrrolo[1,2-a]quinoline and isothiazolonaphthyridine to assess the importance of the sulfur atom on biological activity as well as the effect of C-2 substituent on the spatial arrangements of N-1 or the 3-carboxylic group. It was found that the planarity between the 4-keto and 3-carboxylic acid groups of quinoline molecules is the most important criterion for biological activity. The syntheses of the above four compounds are also described.
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Synthesis of AVNA (7-amino-3-vinylcephem-4-carboxylic acid) from GCLE (7-phenylacetamide-3-chlorormethylcephem-4-carboxylic acid p-m-ethoxybenzyl ester) includes 2 steps:converting GCLE into GVNE (7-phenylacetamide-3-vinyl-3-cephem-4-carboxylic acid p-m-ethoxybenzyl ester) using Wittig Reaction,and then converting GVNE into AVNA using “iminochloride compound.
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Nitrofurazone
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