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QSAR study and conformational analysis of 4-arylthiazolylhydrazones derived from 1-indanones with anti-Trypanosoma cruzi activity
[Display omitted] A set of 4-arylthiazolylhydrazones derived from 1-indanones (TZHs) previously synthesized and assayed against Trypanosoma cruzi, the causative agent of Chagas disease, were explored in terms of conformational analysis. We found that TZHs can adopt four minimum energy conformations:...
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| Published in: | European journal of pharmaceutical sciences 2015-10, Vol.78, p.190-197 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c400t-cbdae40b942d1a77c16d366424a93912d028e3b7bddab5150afe0dfded26c36c3 |
| container_end_page | 197 |
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| container_start_page | 190 |
| container_title | European journal of pharmaceutical sciences |
| container_volume | 78 |
| creator | Noguera, Guido J. Fabian, Lucas E. Lombardo, Elisa Finkielsztein, Liliana |
| description | [Display omitted]
A set of 4-arylthiazolylhydrazones derived from 1-indanones (TZHs) previously synthesized and assayed against Trypanosoma cruzi, the causative agent of Chagas disease, were explored in terms of conformational analysis. We found that TZHs can adopt four minimum energy conformations: cis (A, B and C) and trans. The possible bioactive conformation was selected by a 3D-QSAR model. Different molecular parameters were calculated to produce QSAR second-generation models. These QSAR results are discussed in conjunction with conformational analysis from molecular modeling studies. The main factor to determine the activity of the compounds was the partial charge at the N(3) atom (qN3). The predictive ability of the QSAR equations proposed was experimentally validated. The QSAR models developed in this study will be helpful to design novel potent TZHs. |
| doi_str_mv | 10.1016/j.ejps.2015.07.014 |
| format | article |
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A set of 4-arylthiazolylhydrazones derived from 1-indanones (TZHs) previously synthesized and assayed against Trypanosoma cruzi, the causative agent of Chagas disease, were explored in terms of conformational analysis. We found that TZHs can adopt four minimum energy conformations: cis (A, B and C) and trans. The possible bioactive conformation was selected by a 3D-QSAR model. Different molecular parameters were calculated to produce QSAR second-generation models. These QSAR results are discussed in conjunction with conformational analysis from molecular modeling studies. The main factor to determine the activity of the compounds was the partial charge at the N(3) atom (qN3). The predictive ability of the QSAR equations proposed was experimentally validated. The QSAR models developed in this study will be helpful to design novel potent TZHs.</description><identifier>ISSN: 0928-0987</identifier><identifier>EISSN: 1879-0720</identifier><identifier>DOI: 10.1016/j.ejps.2015.07.014</identifier><identifier>PMID: 26209879</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>Anti-trypanosomal activity ; Antiprotozoal Agents - chemistry ; Antiprotozoal Agents - pharmacology ; Chagas disease ; Conformational analysis ; Hydrazones - chemistry ; Hydrazones - pharmacology ; Indans - chemistry ; Molecular Conformation ; QSAR ; Quantitative Structure-Activity Relationship ; Thiazolylhydrazones ; Trypanosoma cruzi - drug effects ; Trypanosoma cruzi - growth & development</subject><ispartof>European journal of pharmaceutical sciences, 2015-10, Vol.78, p.190-197</ispartof><rights>2015 Elsevier B.V.</rights><rights>Copyright © 2015 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c400t-cbdae40b942d1a77c16d366424a93912d028e3b7bddab5150afe0dfded26c36c3</citedby><cites>FETCH-LOGICAL-c400t-cbdae40b942d1a77c16d366424a93912d028e3b7bddab5150afe0dfded26c36c3</cites></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/26209879$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Noguera, Guido J.</creatorcontrib><creatorcontrib>Fabian, Lucas E.</creatorcontrib><creatorcontrib>Lombardo, Elisa</creatorcontrib><creatorcontrib>Finkielsztein, Liliana</creatorcontrib><title>QSAR study and conformational analysis of 4-arylthiazolylhydrazones derived from 1-indanones with anti-Trypanosoma cruzi activity</title><title>European journal of pharmaceutical sciences</title><addtitle>Eur J Pharm Sci</addtitle><description>[Display omitted]
A set of 4-arylthiazolylhydrazones derived from 1-indanones (TZHs) previously synthesized and assayed against Trypanosoma cruzi, the causative agent of Chagas disease, were explored in terms of conformational analysis. We found that TZHs can adopt four minimum energy conformations: cis (A, B and C) and trans. The possible bioactive conformation was selected by a 3D-QSAR model. Different molecular parameters were calculated to produce QSAR second-generation models. These QSAR results are discussed in conjunction with conformational analysis from molecular modeling studies. The main factor to determine the activity of the compounds was the partial charge at the N(3) atom (qN3). The predictive ability of the QSAR equations proposed was experimentally validated. The QSAR models developed in this study will be helpful to design novel potent TZHs.</description><subject>Anti-trypanosomal activity</subject><subject>Antiprotozoal Agents - chemistry</subject><subject>Antiprotozoal Agents - pharmacology</subject><subject>Chagas disease</subject><subject>Conformational analysis</subject><subject>Hydrazones - chemistry</subject><subject>Hydrazones - pharmacology</subject><subject>Indans - chemistry</subject><subject>Molecular Conformation</subject><subject>QSAR</subject><subject>Quantitative Structure-Activity Relationship</subject><subject>Thiazolylhydrazones</subject><subject>Trypanosoma cruzi - drug effects</subject><subject>Trypanosoma cruzi - growth & development</subject><issn>0928-0987</issn><issn>1879-0720</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp9kE9v1DAQxS0EokvhC3BAPnJJGDvZOJG4VBV_KlVCQDlbjmei9SqJF9tZlN745njZliPSSDN68-ZJ82PstYBSgGje7UvaH2IpQWxLUCWI-gnbiFZ1BSgJT9kGOtkW0LXqgr2IcQ8ATavgObuQjTzJ3Yb9_vr96huPacGVmxm59fPgw2SS87MZs2TGNbrI_cDrwoR1TDtn7v24jrsVQ55mihwpuCMhH4KfuCjcjGb-u_jl0i5nJFfchfWQxegnw21Y7h03NrmjS-tL9mwwY6RXD_2S_fj44e76c3H75dPN9dVtYWuAVNgeDdXQd7VEYZSyosGqaWpZm67qhESQLVW96hFNvxVbMAMBDkgoG1vlumRvz7mH4H8uFJOeXLQ0jmYmv0QtFLSikduqzlZ5ttrgYww06ENwU_5eC9An9HqvT-j1Cb0GpTP6fPTmIX_pJ8J_J4-ss-H92UD5y6OjoKN1NFtCF8gmjd79L_8PPrGY_w</recordid><startdate>20151012</startdate><enddate>20151012</enddate><creator>Noguera, Guido J.</creator><creator>Fabian, Lucas E.</creator><creator>Lombardo, Elisa</creator><creator>Finkielsztein, Liliana</creator><general>Elsevier B.V</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></search><sort><creationdate>20151012</creationdate><title>QSAR study and conformational analysis of 4-arylthiazolylhydrazones derived from 1-indanones with anti-Trypanosoma cruzi activity</title><author>Noguera, Guido J. ; Fabian, Lucas E. ; Lombardo, Elisa ; Finkielsztein, Liliana</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c400t-cbdae40b942d1a77c16d366424a93912d028e3b7bddab5150afe0dfded26c36c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Anti-trypanosomal activity</topic><topic>Antiprotozoal Agents - chemistry</topic><topic>Antiprotozoal Agents - pharmacology</topic><topic>Chagas disease</topic><topic>Conformational analysis</topic><topic>Hydrazones - chemistry</topic><topic>Hydrazones - pharmacology</topic><topic>Indans - chemistry</topic><topic>Molecular Conformation</topic><topic>QSAR</topic><topic>Quantitative Structure-Activity Relationship</topic><topic>Thiazolylhydrazones</topic><topic>Trypanosoma cruzi - drug effects</topic><topic>Trypanosoma cruzi - growth & development</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Noguera, Guido J.</creatorcontrib><creatorcontrib>Fabian, Lucas E.</creatorcontrib><creatorcontrib>Lombardo, Elisa</creatorcontrib><creatorcontrib>Finkielsztein, Liliana</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 pharmaceutical sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Noguera, Guido J.</au><au>Fabian, Lucas E.</au><au>Lombardo, Elisa</au><au>Finkielsztein, Liliana</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>QSAR study and conformational analysis of 4-arylthiazolylhydrazones derived from 1-indanones with anti-Trypanosoma cruzi activity</atitle><jtitle>European journal of pharmaceutical sciences</jtitle><addtitle>Eur J Pharm Sci</addtitle><date>2015-10-12</date><risdate>2015</risdate><volume>78</volume><spage>190</spage><epage>197</epage><pages>190-197</pages><issn>0928-0987</issn><eissn>1879-0720</eissn><abstract>[Display omitted]
A set of 4-arylthiazolylhydrazones derived from 1-indanones (TZHs) previously synthesized and assayed against Trypanosoma cruzi, the causative agent of Chagas disease, were explored in terms of conformational analysis. We found that TZHs can adopt four minimum energy conformations: cis (A, B and C) and trans. The possible bioactive conformation was selected by a 3D-QSAR model. Different molecular parameters were calculated to produce QSAR second-generation models. These QSAR results are discussed in conjunction with conformational analysis from molecular modeling studies. The main factor to determine the activity of the compounds was the partial charge at the N(3) atom (qN3). The predictive ability of the QSAR equations proposed was experimentally validated. The QSAR models developed in this study will be helpful to design novel potent TZHs.</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>26209879</pmid><doi>10.1016/j.ejps.2015.07.014</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0928-0987 |
| ispartof | European journal of pharmaceutical sciences, 2015-10, Vol.78, p.190-197 |
| issn | 0928-0987 1879-0720 |
| language | eng |
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| source | ScienceDirect Freedom Collection 2022-2024 |
| subjects | Anti-trypanosomal activity Antiprotozoal Agents - chemistry Antiprotozoal Agents - pharmacology Chagas disease Conformational analysis Hydrazones - chemistry Hydrazones - pharmacology Indans - chemistry Molecular Conformation QSAR Quantitative Structure-Activity Relationship Thiazolylhydrazones Trypanosoma cruzi - drug effects Trypanosoma cruzi - growth & development |
| title | QSAR study and conformational analysis of 4-arylthiazolylhydrazones derived from 1-indanones with anti-Trypanosoma cruzi activity |
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