Microwave assisted synthesis and structure–activity relationship of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides as anti-microbial agents
A series of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl, 1,2-benzothiazine-3-carbohydrazide 1,1-dioxides was synthesized from commercially available sodium saccharin. Base catalyzed ring expansion of methyl (1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)acetate followed by ultrasound mediated hydr...
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| Veröffentlicht in: | European journal of medicinal chemistry 2011-06, Vol.46 (6), p.2368-2377 |
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| creator | Ahmad, Naveed Zia-ur-Rehman, Muhammad Siddiqui, Hamid Latif Ullah, Muhammad Fasih Parvez, Masood |
| description | A series of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl, 1,2-benzothiazine-3-carbohydrazide 1,1-dioxides was synthesized from commercially available sodium saccharin. Base catalyzed ring expansion of methyl (1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)acetate followed by ultrasound mediated hydrazinolysis and subsequent reaction with 1-phenylethanones under the influence of microwaves yielded the title compounds. Besides, microwave assisted synthesis of 1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide and 4-methyl-1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide is also discussed. Most of the synthesized compounds were found to possess moderate to significant anti-microbial (anti-bacterial and anti-fungal) activities. It is found that compounds with greater lipophilicity (N-methyl analogues) possessed higher anti-bacterial activities.
Microwave assisted synthesis of a series of biologically active 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl, 1,2-benzothiazine-3-carbohydrazide 1,1-dioxides along with the synthesis of 1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol-5,5-dioxide and 4-methyl-1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol-5,5-dioxide from commercially available sodium saccharin is reported. [Display omitted]
► 4-Hydroxy-N′-[1-phenylethylidene]-2H/2-methyl, 1,2-benzothiazine-3-carbohydrazide 1,1-dioxides. ► 1,4-Dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide. ► 4-Methyl-1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide. ► Anti-fungal and anti-bacterial assay. ► Microwave assisted synthesis. |
| doi_str_mv | 10.1016/j.ejmech.2011.03.020 |
| format | Article |
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Microwave assisted synthesis of a series of biologically active 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl, 1,2-benzothiazine-3-carbohydrazide 1,1-dioxides along with the synthesis of 1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol-5,5-dioxide and 4-methyl-1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol-5,5-dioxide from commercially available sodium saccharin is reported. [Display omitted]
► 4-Hydroxy-N′-[1-phenylethylidene]-2H/2-methyl, 1,2-benzothiazine-3-carbohydrazide 1,1-dioxides. ► 1,4-Dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide. ► 4-Methyl-1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide. ► Anti-fungal and anti-bacterial assay. ► Microwave assisted synthesis.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2011.03.020</identifier><identifier>PMID: 21470723</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Kidlington: Elsevier Masson SAS</publisher><subject>1,2-Benzothiazine 1,1-dioxide ; 1,4-Dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antifungal agents ; Antifungal Agents - chemical synthesis ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacology ; Bacteria - drug effects ; Benzothiazine carbohydrazides ; Biological and medical sciences ; Crystallography, X-Ray ; Dose-Response Relationship, Drug ; Fungi - drug effects ; General aspects ; Hydrazines - chemical synthesis ; Hydrazines - chemistry ; Hydrazines - pharmacology ; Medical sciences ; Microbial Sensitivity Tests ; Microwaves ; Microwaves assisted synthesis ; Models, Molecular ; Molecular Structure ; Pharmacology. Drug treatments ; Sodium saccharin ; Stereoisomerism ; Structure-Activity Relationship ; Thiazines - chemical synthesis ; Thiazines - chemistry ; Thiazines - pharmacology</subject><ispartof>European journal of medicinal chemistry, 2011-06, Vol.46 (6), p.2368-2377</ispartof><rights>2011 Elsevier Masson SAS</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c457t-d83fc6ef0723becb6753e4d7f3af3dfdd4fa0585ffa06c0e348b7b782162d7af3</citedby><cites>FETCH-LOGICAL-c457t-d83fc6ef0723becb6753e4d7f3af3dfdd4fa0585ffa06c0e348b7b782162d7af3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2011.03.020$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24170617$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21470723$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ahmad, Naveed</creatorcontrib><creatorcontrib>Zia-ur-Rehman, Muhammad</creatorcontrib><creatorcontrib>Siddiqui, Hamid Latif</creatorcontrib><creatorcontrib>Ullah, Muhammad Fasih</creatorcontrib><creatorcontrib>Parvez, Masood</creatorcontrib><title>Microwave assisted synthesis and structure–activity relationship of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides as anti-microbial agents</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>A series of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl, 1,2-benzothiazine-3-carbohydrazide 1,1-dioxides was synthesized from commercially available sodium saccharin. Base catalyzed ring expansion of methyl (1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)acetate followed by ultrasound mediated hydrazinolysis and subsequent reaction with 1-phenylethanones under the influence of microwaves yielded the title compounds. Besides, microwave assisted synthesis of 1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide and 4-methyl-1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide is also discussed. Most of the synthesized compounds were found to possess moderate to significant anti-microbial (anti-bacterial and anti-fungal) activities. It is found that compounds with greater lipophilicity (N-methyl analogues) possessed higher anti-bacterial activities.
Microwave assisted synthesis of a series of biologically active 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl, 1,2-benzothiazine-3-carbohydrazide 1,1-dioxides along with the synthesis of 1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol-5,5-dioxide and 4-methyl-1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol-5,5-dioxide from commercially available sodium saccharin is reported. [Display omitted]
► 4-Hydroxy-N′-[1-phenylethylidene]-2H/2-methyl, 1,2-benzothiazine-3-carbohydrazide 1,1-dioxides. ► 1,4-Dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide. ► 4-Methyl-1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide. ► Anti-fungal and anti-bacterial assay. ► Microwave assisted synthesis.</description><subject>1,2-Benzothiazine 1,1-dioxide</subject><subject>1,4-Dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antifungal agents</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Bacteria - drug effects</subject><subject>Benzothiazine carbohydrazides</subject><subject>Biological and medical sciences</subject><subject>Crystallography, X-Ray</subject><subject>Dose-Response Relationship, Drug</subject><subject>Fungi - drug effects</subject><subject>General aspects</subject><subject>Hydrazines - chemical synthesis</subject><subject>Hydrazines - chemistry</subject><subject>Hydrazines - pharmacology</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Microwaves</subject><subject>Microwaves assisted synthesis</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Sodium saccharin</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><subject>Thiazines - chemical synthesis</subject><subject>Thiazines - chemistry</subject><subject>Thiazines - pharmacology</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kU1u1DAUxyMEokPhBghlg9jUU38lTjdIqAKKVGADK4Qsx34mHiXOYDtD01XvwE04AIfpSXCYAXas3od-7_nv9y-KxwSvCSb16WYNmwF0t6aYkDVma0zxnWJFRN0gRit-t1hhShmqKONHxYMYNxjjqsb4fnFECRdYULYqfr51Oozf1A5KFaOLCUwZZ586yEWpfK5SmHSaAtzefFc6uZ1LcxmgV8mNPnZuW4625KibTRivZvTu9uYH-kTQtgM_95C6uXcGPHxG9OKUouF3B5ETilrw12PqnLp2HhBDWoV2XNbkhoGSnBBk3HiV8yxk0ZIcGha1rVN9qb6AT_Fhcc-qPsKjQzwuPr56-eH8Al2-f_3m_MUl0rwSCZmGWV2DXf7cgm5rUTHgRlimLDPWGG4VrprK5lBrDIw3rWhFQ0lNjcjMcfFsv3cbxq8TxCQHFzX0vfIwTlE2NRfiTJzVmeR7MguNMYCV2-AGFWZJsFyMkxu5N04uxknMZDYujz05PDC1A5i_Q3-cysDTA6CiVr0NymsX_3GcCFwTkbnnew7yOXYOgozagddgXACdpBnd_5X8Ag2FvzM</recordid><startdate>20110601</startdate><enddate>20110601</enddate><creator>Ahmad, Naveed</creator><creator>Zia-ur-Rehman, Muhammad</creator><creator>Siddiqui, Hamid Latif</creator><creator>Ullah, Muhammad Fasih</creator><creator>Parvez, Masood</creator><general>Elsevier Masson SAS</general><general>Elsevier</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>7X8</scope></search><sort><creationdate>20110601</creationdate><title>Microwave assisted synthesis and structure–activity relationship of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides as anti-microbial agents</title><author>Ahmad, Naveed ; Zia-ur-Rehman, Muhammad ; Siddiqui, Hamid Latif ; Ullah, Muhammad Fasih ; Parvez, Masood</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c457t-d83fc6ef0723becb6753e4d7f3af3dfdd4fa0585ffa06c0e348b7b782162d7af3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>1,2-Benzothiazine 1,1-dioxide</topic><topic>1,4-Dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antifungal agents</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>Bacteria - drug effects</topic><topic>Benzothiazine carbohydrazides</topic><topic>Biological and medical sciences</topic><topic>Crystallography, X-Ray</topic><topic>Dose-Response Relationship, Drug</topic><topic>Fungi - drug effects</topic><topic>General aspects</topic><topic>Hydrazines - chemical synthesis</topic><topic>Hydrazines - chemistry</topic><topic>Hydrazines - pharmacology</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Microwaves</topic><topic>Microwaves assisted synthesis</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Sodium saccharin</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><topic>Thiazines - chemical synthesis</topic><topic>Thiazines - chemistry</topic><topic>Thiazines - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ahmad, Naveed</creatorcontrib><creatorcontrib>Zia-ur-Rehman, Muhammad</creatorcontrib><creatorcontrib>Siddiqui, Hamid Latif</creatorcontrib><creatorcontrib>Ullah, Muhammad Fasih</creatorcontrib><creatorcontrib>Parvez, Masood</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>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ahmad, Naveed</au><au>Zia-ur-Rehman, Muhammad</au><au>Siddiqui, Hamid Latif</au><au>Ullah, Muhammad Fasih</au><au>Parvez, Masood</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave assisted synthesis and structure–activity relationship of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides as anti-microbial agents</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2011-06-01</date><risdate>2011</risdate><volume>46</volume><issue>6</issue><spage>2368</spage><epage>2377</epage><pages>2368-2377</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>A series of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl, 1,2-benzothiazine-3-carbohydrazide 1,1-dioxides was synthesized from commercially available sodium saccharin. Base catalyzed ring expansion of methyl (1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)acetate followed by ultrasound mediated hydrazinolysis and subsequent reaction with 1-phenylethanones under the influence of microwaves yielded the title compounds. Besides, microwave assisted synthesis of 1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide and 4-methyl-1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide is also discussed. Most of the synthesized compounds were found to possess moderate to significant anti-microbial (anti-bacterial and anti-fungal) activities. It is found that compounds with greater lipophilicity (N-methyl analogues) possessed higher anti-bacterial activities.
Microwave assisted synthesis of a series of biologically active 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl, 1,2-benzothiazine-3-carbohydrazide 1,1-dioxides along with the synthesis of 1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol-5,5-dioxide and 4-methyl-1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol-5,5-dioxide from commercially available sodium saccharin is reported. [Display omitted]
► 4-Hydroxy-N′-[1-phenylethylidene]-2H/2-methyl, 1,2-benzothiazine-3-carbohydrazide 1,1-dioxides. ► 1,4-Dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide. ► 4-Methyl-1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide. ► Anti-fungal and anti-bacterial assay. ► Microwave assisted synthesis.</abstract><cop>Kidlington</cop><pub>Elsevier Masson SAS</pub><pmid>21470723</pmid><doi>10.1016/j.ejmech.2011.03.020</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0223-5234 |
| ispartof | European journal of medicinal chemistry, 2011-06, Vol.46 (6), p.2368-2377 |
| issn | 0223-5234 1768-3254 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | 1,2-Benzothiazine 1,1-dioxide 1,4-Dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Antifungal agents Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Antifungal Agents - pharmacology Bacteria - drug effects Benzothiazine carbohydrazides Biological and medical sciences Crystallography, X-Ray Dose-Response Relationship, Drug Fungi - drug effects General aspects Hydrazines - chemical synthesis Hydrazines - chemistry Hydrazines - pharmacology Medical sciences Microbial Sensitivity Tests Microwaves Microwaves assisted synthesis Models, Molecular Molecular Structure Pharmacology. Drug treatments Sodium saccharin Stereoisomerism Structure-Activity Relationship Thiazines - chemical synthesis Thiazines - chemistry Thiazines - pharmacology |
| title | Microwave assisted synthesis and structure–activity relationship of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides as anti-microbial agents |
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