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Design, synthesis and biological evaluation of chalconyl blended triazole allied organosilatranes as giardicidal and trichomonacidal agents
A series of chalconyl blended triazole allied silatranes (7a–g/8a–g/9a–g) were synthesized in good yields using a simple, economical and biocompatible synthetic route. The blend of three different pharmacologically active moieties into a single scaffold resulted into synergistic effect in their bio-...
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Published in: | European journal of medicinal chemistry 2016-01, Vol.108, p.287-300 |
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creator | Singh, Gurjaspreet Arora, Aanchal Mangat, Satinderpal Singh Rani, Sunita Kaur, Hargobinder Goyal, Kapil Sehgal, Rakesh Maurya, Indresh Kumar Tewari, Rupinder Choquesillo-Lazarte, Duane Sahoo, Subash Kaur, Navneet |
description | A series of chalconyl blended triazole allied silatranes (7a–g/8a–g/9a–g) were synthesized in good yields using a simple, economical and biocompatible synthetic route. The blend of three different pharmacologically active moieties into a single scaffold resulted into synergistic effect in their bio-activity. Various substitutions were tried to study the structure activity relationship (SAR) of the synthesized compounds on the basis of biological results. All the newly synthesized compounds were well characterized by IR, 1H and 13C NMR, low resolution mass spectroscopy and elemental analysis. The structures of 7a and 7c were authenticated by single crystal X-ray crystallography. These compounds were screened by using Molinspiration software for their physicochemical properties and all the compounds showed good oral bioavailability. The antiparasitic activity of the newly synthesized compounds was evaluated against unicellular parasites (Giardia lamblia and Trichomonas vaginalis) in comparison to standard drug (metronidazole) by 3-(4,5-dimethylthiazol-yl)-diphenyl tetrazolium bromide (MTT) assay. All the compounds displayed significant activity against G. lamblia and T. vaginalis with IC50 values ranging from 19.58–131.2 μM to 18.24–101.26 μM respectively. The entire library of compounds was found to be more active than metronidazole except 9a, 9f and 9g. Notably, 9e and 7e were found to be most significant against G. lamblia and T. vaginalis respectively.
A series of 1,2,3-triazole and chalcone allied organosilatranes (7a–g, 8a–g, 9a–g) are synthesized and well characterized by various spectroscopic techniques. The synthesized compounds are passed through the computer based screening for their physicochemical properties and then tested for their antigiardial and antitrichomonal activities. The compounds showing good activities are then tested for their cytotoxicity against Hek-293 and HeLa cells. [Display omitted]
•A series of chalconyl blended triazole allied organosilatranes was synthesized.•The hybrid molecules are passed through the computer based screening of their physicochemical properties.•All the organosilatranes are investigated for their antigiardial and antitrichomonal activities.•9e and 7e were found to be most significant against Giardia lamblia and Trichomonas vaginalis respectively.•Evaluated for their in vitro cytotoxicity against Hek-293 and HeLa cells. |
doi_str_mv | 10.1016/j.ejmech.2015.11.029 |
format | article |
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A series of 1,2,3-triazole and chalcone allied organosilatranes (7a–g, 8a–g, 9a–g) are synthesized and well characterized by various spectroscopic techniques. The synthesized compounds are passed through the computer based screening for their physicochemical properties and then tested for their antigiardial and antitrichomonal activities. The compounds showing good activities are then tested for their cytotoxicity against Hek-293 and HeLa cells. [Display omitted]
•A series of chalconyl blended triazole allied organosilatranes was synthesized.•The hybrid molecules are passed through the computer based screening of their physicochemical properties.•All the organosilatranes are investigated for their antigiardial and antitrichomonal activities.•9e and 7e were found to be most significant against Giardia lamblia and Trichomonas vaginalis respectively.•Evaluated for their in vitro cytotoxicity against Hek-293 and HeLa cells.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2015.11.029</identifier><identifier>PMID: 26695730</identifier><language>eng</language><publisher>France: Elsevier Masson SAS</publisher><subject>1,2,3-Triazole ; 3-(4,5-Dimethylthiazol-yl)-diphenyl tetrazolium bromide (MTT) ; Antiparasitic Agents - chemical synthesis ; Antiparasitic Agents - chemistry ; Antiparasitic Agents - pharmacology ; Chalcone ; Dose-Response Relationship, Drug ; Drug Design ; Giardia lamblia - drug effects ; Giardicidal activity ; Metronidazole ; Models, Molecular ; Molecular Structure ; Organosilicon Compounds - chemical synthesis ; Organosilicon Compounds - chemistry ; Organosilicon Compounds - pharmacology ; Parasitic Sensitivity Tests ; Silatrane ; Structure-Activity Relationship ; Triazoles - chemical synthesis ; Triazoles - chemistry ; Triazoles - pharmacology ; Trichomonacidal activity ; Trichomonas vaginalis - drug effects</subject><ispartof>European journal of medicinal chemistry, 2016-01, Vol.108, p.287-300</ispartof><rights>2015 Elsevier Masson SAS</rights><rights>Copyright © 2015 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-f88d9bf4dbe11e51bff691cc1048ea219590990fe74712619021451e4051511a3</citedby><cites>FETCH-LOGICAL-c362t-f88d9bf4dbe11e51bff691cc1048ea219590990fe74712619021451e4051511a3</cites><orcidid>0000-0002-8627-420X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26695730$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Singh, Gurjaspreet</creatorcontrib><creatorcontrib>Arora, Aanchal</creatorcontrib><creatorcontrib>Mangat, Satinderpal Singh</creatorcontrib><creatorcontrib>Rani, Sunita</creatorcontrib><creatorcontrib>Kaur, Hargobinder</creatorcontrib><creatorcontrib>Goyal, Kapil</creatorcontrib><creatorcontrib>Sehgal, Rakesh</creatorcontrib><creatorcontrib>Maurya, Indresh Kumar</creatorcontrib><creatorcontrib>Tewari, Rupinder</creatorcontrib><creatorcontrib>Choquesillo-Lazarte, Duane</creatorcontrib><creatorcontrib>Sahoo, Subash</creatorcontrib><creatorcontrib>Kaur, Navneet</creatorcontrib><title>Design, synthesis and biological evaluation of chalconyl blended triazole allied organosilatranes as giardicidal and trichomonacidal agents</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>A series of chalconyl blended triazole allied silatranes (7a–g/8a–g/9a–g) were synthesized in good yields using a simple, economical and biocompatible synthetic route. The blend of three different pharmacologically active moieties into a single scaffold resulted into synergistic effect in their bio-activity. Various substitutions were tried to study the structure activity relationship (SAR) of the synthesized compounds on the basis of biological results. All the newly synthesized compounds were well characterized by IR, 1H and 13C NMR, low resolution mass spectroscopy and elemental analysis. The structures of 7a and 7c were authenticated by single crystal X-ray crystallography. These compounds were screened by using Molinspiration software for their physicochemical properties and all the compounds showed good oral bioavailability. The antiparasitic activity of the newly synthesized compounds was evaluated against unicellular parasites (Giardia lamblia and Trichomonas vaginalis) in comparison to standard drug (metronidazole) by 3-(4,5-dimethylthiazol-yl)-diphenyl tetrazolium bromide (MTT) assay. All the compounds displayed significant activity against G. lamblia and T. vaginalis with IC50 values ranging from 19.58–131.2 μM to 18.24–101.26 μM respectively. The entire library of compounds was found to be more active than metronidazole except 9a, 9f and 9g. Notably, 9e and 7e were found to be most significant against G. lamblia and T. vaginalis respectively.
A series of 1,2,3-triazole and chalcone allied organosilatranes (7a–g, 8a–g, 9a–g) are synthesized and well characterized by various spectroscopic techniques. The synthesized compounds are passed through the computer based screening for their physicochemical properties and then tested for their antigiardial and antitrichomonal activities. The compounds showing good activities are then tested for their cytotoxicity against Hek-293 and HeLa cells. [Display omitted]
•A series of chalconyl blended triazole allied organosilatranes was synthesized.•The hybrid molecules are passed through the computer based screening of their physicochemical properties.•All the organosilatranes are investigated for their antigiardial and antitrichomonal activities.•9e and 7e were found to be most significant against Giardia lamblia and Trichomonas vaginalis respectively.•Evaluated for their in vitro cytotoxicity against Hek-293 and HeLa cells.</description><subject>1,2,3-Triazole</subject><subject>3-(4,5-Dimethylthiazol-yl)-diphenyl tetrazolium bromide (MTT)</subject><subject>Antiparasitic Agents - chemical synthesis</subject><subject>Antiparasitic Agents - chemistry</subject><subject>Antiparasitic Agents - pharmacology</subject><subject>Chalcone</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Design</subject><subject>Giardia lamblia - drug effects</subject><subject>Giardicidal activity</subject><subject>Metronidazole</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Organosilicon Compounds - chemical synthesis</subject><subject>Organosilicon Compounds - chemistry</subject><subject>Organosilicon Compounds - pharmacology</subject><subject>Parasitic Sensitivity Tests</subject><subject>Silatrane</subject><subject>Structure-Activity Relationship</subject><subject>Triazoles - chemical synthesis</subject><subject>Triazoles - chemistry</subject><subject>Triazoles - pharmacology</subject><subject>Trichomonacidal activity</subject><subject>Trichomonas vaginalis - drug effects</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp9UcuO0zAUtRCI6Qz8AUJesiDB14mdeIOEBhiQRmIDa8uxb1pXjj3Y6UjlF_hpXLWwZHUfOufcxyHkFbAWGMh3-xb3C9pdyxmIFqBlXD0hGxjk2HRc9E_JhnHeNYJ3_RW5LmXPGBOSsefkikupxNCxDfn9EYvfxre0HOO6q3mhJjo6-RTS1lsTKD6acDCrT5GmmdqdCTbFY6BTwOjQ0TV78ysFpCYEX-uUtyam4oNZs4lY9QrdepOdt95VvZN85dhdWlI0l94W41pekGezCQVfXuIN-fH50_fbL839t7uvtx_uG9tJvjbzODo1zb2bEAAFTPMsFVgLrB_RcFBCMaXYjEM_AJegGIdeAPZMgAAw3Q15c9Z9yOnnAcuqF18shlDXTYei6wvZqOQwygrtz1CbUykZZ_2Q_WLyUQPTJxv0Xp9t0CcbNICuNlTa68uEw7Sg-0f6-_cKeH8GYL3z0WPWxXqMFp3PaFftkv__hD_PD505</recordid><startdate>20160127</startdate><enddate>20160127</enddate><creator>Singh, Gurjaspreet</creator><creator>Arora, Aanchal</creator><creator>Mangat, Satinderpal Singh</creator><creator>Rani, Sunita</creator><creator>Kaur, Hargobinder</creator><creator>Goyal, Kapil</creator><creator>Sehgal, Rakesh</creator><creator>Maurya, Indresh Kumar</creator><creator>Tewari, Rupinder</creator><creator>Choquesillo-Lazarte, Duane</creator><creator>Sahoo, Subash</creator><creator>Kaur, Navneet</creator><general>Elsevier Masson SAS</general><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><orcidid>https://orcid.org/0000-0002-8627-420X</orcidid></search><sort><creationdate>20160127</creationdate><title>Design, synthesis and biological evaluation of chalconyl blended triazole allied organosilatranes as giardicidal and trichomonacidal agents</title><author>Singh, Gurjaspreet ; Arora, Aanchal ; Mangat, Satinderpal Singh ; Rani, Sunita ; Kaur, Hargobinder ; Goyal, Kapil ; Sehgal, Rakesh ; Maurya, Indresh Kumar ; Tewari, Rupinder ; Choquesillo-Lazarte, Duane ; Sahoo, Subash ; Kaur, Navneet</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c362t-f88d9bf4dbe11e51bff691cc1048ea219590990fe74712619021451e4051511a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>1,2,3-Triazole</topic><topic>3-(4,5-Dimethylthiazol-yl)-diphenyl tetrazolium bromide (MTT)</topic><topic>Antiparasitic Agents - chemical synthesis</topic><topic>Antiparasitic Agents - chemistry</topic><topic>Antiparasitic Agents - pharmacology</topic><topic>Chalcone</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Design</topic><topic>Giardia lamblia - drug effects</topic><topic>Giardicidal activity</topic><topic>Metronidazole</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Organosilicon Compounds - chemical synthesis</topic><topic>Organosilicon Compounds - chemistry</topic><topic>Organosilicon Compounds - pharmacology</topic><topic>Parasitic Sensitivity Tests</topic><topic>Silatrane</topic><topic>Structure-Activity Relationship</topic><topic>Triazoles - chemical synthesis</topic><topic>Triazoles - chemistry</topic><topic>Triazoles - pharmacology</topic><topic>Trichomonacidal activity</topic><topic>Trichomonas vaginalis - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Singh, Gurjaspreet</creatorcontrib><creatorcontrib>Arora, Aanchal</creatorcontrib><creatorcontrib>Mangat, Satinderpal Singh</creatorcontrib><creatorcontrib>Rani, Sunita</creatorcontrib><creatorcontrib>Kaur, Hargobinder</creatorcontrib><creatorcontrib>Goyal, Kapil</creatorcontrib><creatorcontrib>Sehgal, Rakesh</creatorcontrib><creatorcontrib>Maurya, Indresh Kumar</creatorcontrib><creatorcontrib>Tewari, Rupinder</creatorcontrib><creatorcontrib>Choquesillo-Lazarte, Duane</creatorcontrib><creatorcontrib>Sahoo, Subash</creatorcontrib><creatorcontrib>Kaur, Navneet</creatorcontrib><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>Singh, Gurjaspreet</au><au>Arora, Aanchal</au><au>Mangat, Satinderpal Singh</au><au>Rani, Sunita</au><au>Kaur, Hargobinder</au><au>Goyal, Kapil</au><au>Sehgal, Rakesh</au><au>Maurya, Indresh Kumar</au><au>Tewari, Rupinder</au><au>Choquesillo-Lazarte, Duane</au><au>Sahoo, Subash</au><au>Kaur, Navneet</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, synthesis and biological evaluation of chalconyl blended triazole allied organosilatranes as giardicidal and trichomonacidal agents</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2016-01-27</date><risdate>2016</risdate><volume>108</volume><spage>287</spage><epage>300</epage><pages>287-300</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><abstract>A series of chalconyl blended triazole allied silatranes (7a–g/8a–g/9a–g) were synthesized in good yields using a simple, economical and biocompatible synthetic route. The blend of three different pharmacologically active moieties into a single scaffold resulted into synergistic effect in their bio-activity. Various substitutions were tried to study the structure activity relationship (SAR) of the synthesized compounds on the basis of biological results. All the newly synthesized compounds were well characterized by IR, 1H and 13C NMR, low resolution mass spectroscopy and elemental analysis. The structures of 7a and 7c were authenticated by single crystal X-ray crystallography. These compounds were screened by using Molinspiration software for their physicochemical properties and all the compounds showed good oral bioavailability. The antiparasitic activity of the newly synthesized compounds was evaluated against unicellular parasites (Giardia lamblia and Trichomonas vaginalis) in comparison to standard drug (metronidazole) by 3-(4,5-dimethylthiazol-yl)-diphenyl tetrazolium bromide (MTT) assay. All the compounds displayed significant activity against G. lamblia and T. vaginalis with IC50 values ranging from 19.58–131.2 μM to 18.24–101.26 μM respectively. The entire library of compounds was found to be more active than metronidazole except 9a, 9f and 9g. Notably, 9e and 7e were found to be most significant against G. lamblia and T. vaginalis respectively.
A series of 1,2,3-triazole and chalcone allied organosilatranes (7a–g, 8a–g, 9a–g) are synthesized and well characterized by various spectroscopic techniques. The synthesized compounds are passed through the computer based screening for their physicochemical properties and then tested for their antigiardial and antitrichomonal activities. The compounds showing good activities are then tested for their cytotoxicity against Hek-293 and HeLa cells. [Display omitted]
•A series of chalconyl blended triazole allied organosilatranes was synthesized.•The hybrid molecules are passed through the computer based screening of their physicochemical properties.•All the organosilatranes are investigated for their antigiardial and antitrichomonal activities.•9e and 7e were found to be most significant against Giardia lamblia and Trichomonas vaginalis respectively.•Evaluated for their in vitro cytotoxicity against Hek-293 and HeLa cells.</abstract><cop>France</cop><pub>Elsevier Masson SAS</pub><pmid>26695730</pmid><doi>10.1016/j.ejmech.2015.11.029</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0002-8627-420X</orcidid></addata></record> |
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subjects | 1,2,3-Triazole 3-(4,5-Dimethylthiazol-yl)-diphenyl tetrazolium bromide (MTT) Antiparasitic Agents - chemical synthesis Antiparasitic Agents - chemistry Antiparasitic Agents - pharmacology Chalcone Dose-Response Relationship, Drug Drug Design Giardia lamblia - drug effects Giardicidal activity Metronidazole Models, Molecular Molecular Structure Organosilicon Compounds - chemical synthesis Organosilicon Compounds - chemistry Organosilicon Compounds - pharmacology Parasitic Sensitivity Tests Silatrane Structure-Activity Relationship Triazoles - chemical synthesis Triazoles - chemistry Triazoles - pharmacology Trichomonacidal activity Trichomonas vaginalis - drug effects |
title | Design, synthesis and biological evaluation of chalconyl blended triazole allied organosilatranes as giardicidal and trichomonacidal agents |
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