A 3D-QSAR CoMSIA study on 3-azolylmethylindoles as anti-leishmanial agents

A three-dimensional quantitative structure-activity relationship (3D-QSAR) study using Comparative Molecular Similarity Indices Analysis (CoMSIA) was conducted on a series of 3-azolylmethylindoles as anti-leishmanial agents. Evaluation of 24 compounds synthesized in our laboratory served to establis...

Full description

Saved in:
Bibliographic Details
Published in:SAR and QSAR in environmental research 2006-06, Vol.17 (3), p.299-309
Main Authors: Giraud, F., Loge, C., Le Borgne, M., Pagniez, F., Na, Y. M., Le Pape, P.
Format: Article
Language:English
Subjects:
3D-QSAR
Chemical Sciences
Cheminformatics
CoMSIA
CYP51
Indoles
L. mexicana
Leishmania
Life Sciences
Medicinal Chemistry
Microbiology and Parasitology
Parasitology
Pharmaceutical sciences
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c357t-3872dc86f378b133b697cb8f9d2f3a04e608d69361eb3f10894d6eefd624ee0a3
cites cdi_FETCH-LOGICAL-c357t-3872dc86f378b133b697cb8f9d2f3a04e608d69361eb3f10894d6eefd624ee0a3
container_end_page 309
container_issue 3
container_start_page 299
container_title SAR and QSAR in environmental research
container_volume 17
creator Giraud, F.
Loge, C.
Le Borgne, M.
Pagniez, F.
Na, Y. M.
Le Pape, P.
description A three-dimensional quantitative structure-activity relationship (3D-QSAR) study using Comparative Molecular Similarity Indices Analysis (CoMSIA) was conducted on a series of 3-azolylmethylindoles as anti-leishmanial agents. Evaluation of 24 compounds synthesized in our laboratory served to establish the model. A random search was performed on the library of compounds, and molecules of the training set were aligned on common elements of template molecule 13, one of the most active compounds. The best predictions were obtained from multifit procedure with a CoMSIA model combining steric, electrostatic, hydrophobic and hydrogen bond acceptor fields (q 2  = 0.594, r 2  = 0.897). The model was validated using an external test set of 7 compounds giving a satisfactory predictive r 2 value of 0.649. Information obtained from CoMSIA contour maps could be used for further design of more promising inhibitors.
doi_str_mv 10.1080/10659360600787494
format article
fullrecord <record><control><sourceid>proquest_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_01689291v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>19853390</sourcerecordid><originalsourceid>FETCH-LOGICAL-c357t-3872dc86f378b133b697cb8f9d2f3a04e608d69361eb3f10894d6eefd624ee0a3</originalsourceid><addsrcrecordid>eNqFkN9rFDEQgINUbHv6B_i2T4U-bJ3s7OUH-LJctT05Ea3CvYXcbuJFsps2yVW3f333OPGlUGFghuH7hpkh5C2FCwoC3lFgc4kMGAAXvJb1C3JCoZIl1Gx9tK9ZVU7A-picpvQLAAQCf0WOkUPFpMAT8qkp8LL8etN8Kxbh882yKVLedWMRhgJL_RD86HuTt6N3Qxe8SYWeYsiu9Malba8Hp32hf5ohp9fkpdU-mTd_84z8-Pjh--K6XH25Wi6aVdninOcSBa-6VjCLXGwo4oZJ3m6ElV1lUUNtGIiOTVtTs0E73SnrjhljO1bVxoDGGTk_zN1qr26j63UcVdBOXTcrte8BZUJWkt7TiT07sLcx3O1Myqp3qTXe68GEXVJUijmihAmkB7CNIaVo7L_JFNT-2erJsyfn_cFxgw2x179D9J3KevQh2qiH1iWFz-n8v_oTS-U_GR8BQpeTAQ</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>19853390</pqid></control><display><type>article</type><title>A 3D-QSAR CoMSIA study on 3-azolylmethylindoles as anti-leishmanial agents</title><source>Taylor and Francis Science and Technology Collection</source><creator>Giraud, F. ; Loge, C. ; Le Borgne, M. ; Pagniez, F. ; Na, Y. M. ; Le Pape, P.</creator><creatorcontrib>Giraud, F. ; Loge, C. ; Le Borgne, M. ; Pagniez, F. ; Na, Y. M. ; Le Pape, P.</creatorcontrib><description>A three-dimensional quantitative structure-activity relationship (3D-QSAR) study using Comparative Molecular Similarity Indices Analysis (CoMSIA) was conducted on a series of 3-azolylmethylindoles as anti-leishmanial agents. Evaluation of 24 compounds synthesized in our laboratory served to establish the model. A random search was performed on the library of compounds, and molecules of the training set were aligned on common elements of template molecule 13, one of the most active compounds. The best predictions were obtained from multifit procedure with a CoMSIA model combining steric, electrostatic, hydrophobic and hydrogen bond acceptor fields (q 2  = 0.594, r 2  = 0.897). The model was validated using an external test set of 7 compounds giving a satisfactory predictive r 2 value of 0.649. Information obtained from CoMSIA contour maps could be used for further design of more promising inhibitors.</description><identifier>ISSN: 1062-936X</identifier><identifier>EISSN: 1029-046X</identifier><identifier>DOI: 10.1080/10659360600787494</identifier><identifier>PMID: 37026983</identifier><language>eng</language><publisher>Taylor &amp; Francis Group</publisher><subject>3D-QSAR ; Chemical Sciences ; Cheminformatics ; CoMSIA ; CYP51 ; Indoles ; L. mexicana ; Leishmania ; Life Sciences ; Medicinal Chemistry ; Microbiology and Parasitology ; Parasitology ; Pharmaceutical sciences</subject><ispartof>SAR and QSAR in environmental research, 2006-06, Vol.17 (3), p.299-309</ispartof><rights>Copyright Taylor &amp; Francis Group, LLC 2006</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c357t-3872dc86f378b133b697cb8f9d2f3a04e608d69361eb3f10894d6eefd624ee0a3</citedby><cites>FETCH-LOGICAL-c357t-3872dc86f378b133b697cb8f9d2f3a04e608d69361eb3f10894d6eefd624ee0a3</cites><orcidid>0000-0003-1398-075X ; 0000-0002-1759-5106 ; 0000-0001-5059-6402 ; 0000-0001-5113-6547</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,776,780,881,27903,27904</link.rule.ids><backlink>$$Uhttps://hal.science/hal-01689291$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Giraud, F.</creatorcontrib><creatorcontrib>Loge, C.</creatorcontrib><creatorcontrib>Le Borgne, M.</creatorcontrib><creatorcontrib>Pagniez, F.</creatorcontrib><creatorcontrib>Na, Y. M.</creatorcontrib><creatorcontrib>Le Pape, P.</creatorcontrib><title>A 3D-QSAR CoMSIA study on 3-azolylmethylindoles as anti-leishmanial agents</title><title>SAR and QSAR in environmental research</title><description>A three-dimensional quantitative structure-activity relationship (3D-QSAR) study using Comparative Molecular Similarity Indices Analysis (CoMSIA) was conducted on a series of 3-azolylmethylindoles as anti-leishmanial agents. Evaluation of 24 compounds synthesized in our laboratory served to establish the model. A random search was performed on the library of compounds, and molecules of the training set were aligned on common elements of template molecule 13, one of the most active compounds. The best predictions were obtained from multifit procedure with a CoMSIA model combining steric, electrostatic, hydrophobic and hydrogen bond acceptor fields (q 2  = 0.594, r 2  = 0.897). The model was validated using an external test set of 7 compounds giving a satisfactory predictive r 2 value of 0.649. Information obtained from CoMSIA contour maps could be used for further design of more promising inhibitors.</description><subject>3D-QSAR</subject><subject>Chemical Sciences</subject><subject>Cheminformatics</subject><subject>CoMSIA</subject><subject>CYP51</subject><subject>Indoles</subject><subject>L. mexicana</subject><subject>Leishmania</subject><subject>Life Sciences</subject><subject>Medicinal Chemistry</subject><subject>Microbiology and Parasitology</subject><subject>Parasitology</subject><subject>Pharmaceutical sciences</subject><issn>1062-936X</issn><issn>1029-046X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNqFkN9rFDEQgINUbHv6B_i2T4U-bJ3s7OUH-LJctT05Ea3CvYXcbuJFsps2yVW3f333OPGlUGFghuH7hpkh5C2FCwoC3lFgc4kMGAAXvJb1C3JCoZIl1Gx9tK9ZVU7A-picpvQLAAQCf0WOkUPFpMAT8qkp8LL8etN8Kxbh882yKVLedWMRhgJL_RD86HuTt6N3Qxe8SYWeYsiu9Malba8Hp32hf5ohp9fkpdU-mTd_84z8-Pjh--K6XH25Wi6aVdninOcSBa-6VjCLXGwo4oZJ3m6ElV1lUUNtGIiOTVtTs0E73SnrjhljO1bVxoDGGTk_zN1qr26j63UcVdBOXTcrte8BZUJWkt7TiT07sLcx3O1Myqp3qTXe68GEXVJUijmihAmkB7CNIaVo7L_JFNT-2erJsyfn_cFxgw2x179D9J3KevQh2qiH1iWFz-n8v_oTS-U_GR8BQpeTAQ</recordid><startdate>20060601</startdate><enddate>20060601</enddate><creator>Giraud, F.</creator><creator>Loge, C.</creator><creator>Le Borgne, M.</creator><creator>Pagniez, F.</creator><creator>Na, Y. M.</creator><creator>Le Pape, P.</creator><general>Taylor &amp; Francis Group</general><general>Taylor &amp; Francis</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0003-1398-075X</orcidid><orcidid>https://orcid.org/0000-0002-1759-5106</orcidid><orcidid>https://orcid.org/0000-0001-5059-6402</orcidid><orcidid>https://orcid.org/0000-0001-5113-6547</orcidid></search><sort><creationdate>20060601</creationdate><title>A 3D-QSAR CoMSIA study on 3-azolylmethylindoles as anti-leishmanial agents</title><author>Giraud, F. ; Loge, C. ; Le Borgne, M. ; Pagniez, F. ; Na, Y. M. ; Le Pape, P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c357t-3872dc86f378b133b697cb8f9d2f3a04e608d69361eb3f10894d6eefd624ee0a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>3D-QSAR</topic><topic>Chemical Sciences</topic><topic>Cheminformatics</topic><topic>CoMSIA</topic><topic>CYP51</topic><topic>Indoles</topic><topic>L. mexicana</topic><topic>Leishmania</topic><topic>Life Sciences</topic><topic>Medicinal Chemistry</topic><topic>Microbiology and Parasitology</topic><topic>Parasitology</topic><topic>Pharmaceutical sciences</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Giraud, F.</creatorcontrib><creatorcontrib>Loge, C.</creatorcontrib><creatorcontrib>Le Borgne, M.</creatorcontrib><creatorcontrib>Pagniez, F.</creatorcontrib><creatorcontrib>Na, Y. M.</creatorcontrib><creatorcontrib>Le Pape, P.</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>SAR and QSAR in environmental research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Giraud, F.</au><au>Loge, C.</au><au>Le Borgne, M.</au><au>Pagniez, F.</au><au>Na, Y. M.</au><au>Le Pape, P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A 3D-QSAR CoMSIA study on 3-azolylmethylindoles as anti-leishmanial agents</atitle><jtitle>SAR and QSAR in environmental research</jtitle><date>2006-06-01</date><risdate>2006</risdate><volume>17</volume><issue>3</issue><spage>299</spage><epage>309</epage><pages>299-309</pages><issn>1062-936X</issn><eissn>1029-046X</eissn><abstract>A three-dimensional quantitative structure-activity relationship (3D-QSAR) study using Comparative Molecular Similarity Indices Analysis (CoMSIA) was conducted on a series of 3-azolylmethylindoles as anti-leishmanial agents. Evaluation of 24 compounds synthesized in our laboratory served to establish the model. A random search was performed on the library of compounds, and molecules of the training set were aligned on common elements of template molecule 13, one of the most active compounds. The best predictions were obtained from multifit procedure with a CoMSIA model combining steric, electrostatic, hydrophobic and hydrogen bond acceptor fields (q 2  = 0.594, r 2  = 0.897). The model was validated using an external test set of 7 compounds giving a satisfactory predictive r 2 value of 0.649. Information obtained from CoMSIA contour maps could be used for further design of more promising inhibitors.</abstract><pub>Taylor &amp; Francis Group</pub><pmid>37026983</pmid><doi>10.1080/10659360600787494</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0003-1398-075X</orcidid><orcidid>https://orcid.org/0000-0002-1759-5106</orcidid><orcidid>https://orcid.org/0000-0001-5059-6402</orcidid><orcidid>https://orcid.org/0000-0001-5113-6547</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1062-936X
ispartof SAR and QSAR in environmental research, 2006-06, Vol.17 (3), p.299-309
issn 1062-936X
1029-046X
language eng
recordid cdi_hal_primary_oai_HAL_hal_01689291v1
source Taylor and Francis Science and Technology Collection
subjects 3D-QSAR
Chemical Sciences
Cheminformatics
CoMSIA
CYP51
Indoles
L. mexicana
Leishmania
Life Sciences
Medicinal Chemistry
Microbiology and Parasitology
Parasitology
Pharmaceutical sciences
title A 3D-QSAR CoMSIA study on 3-azolylmethylindoles as anti-leishmanial agents
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-23T21%3A21%3A41IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%203D-QSAR%20CoMSIA%20study%20on%203-azolylmethylindoles%20as%20anti-leishmanial%20agents&rft.jtitle=SAR%20and%20QSAR%20in%20environmental%20research&rft.au=Giraud,%20F.&rft.date=2006-06-01&rft.volume=17&rft.issue=3&rft.spage=299&rft.epage=309&rft.pages=299-309&rft.issn=1062-936X&rft.eissn=1029-046X&rft_id=info:doi/10.1080/10659360600787494&rft_dat=%3Cproquest_hal_p%3E19853390%3C/proquest_hal_p%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c357t-3872dc86f378b133b697cb8f9d2f3a04e608d69361eb3f10894d6eefd624ee0a3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=19853390&rft_id=info:pmid/37026983&rfr_iscdi=true