Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol

Background Spiropyrrolidine tethered piperidone heterocyclic hybrids were synthesized with complete regio- and stereoselectively in excellent yield via a tandem three-component 1,3-dipolar cycloaddition and subsequent enamine reaction in [bmim]Br. The synthesized compounds were evaluated for their a...

Full description

Saved in:
Bibliographic Details
Published in:BMC chemistry 2018-09, Vol.12 (1), p.95-11, Article 95
Main Authors: Arumugam, Natarajan, Almansour, Abdulrahman I., Kumar, Raju Suresh, Al-thamili, Dhaifallah M., Periyasami, Govindasami, Periasamy, V. S., Athinarayanan, Jegan, Alshatwi, Ali A., Mahalingam, S. M., Menéndez, J. Carlos
Format: Article
Language:English
Subjects:
Anticancer properties
Antiproliferative activity
Apoptosis
Apoptosis induction
Cancer
Cell death
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Chemo divergent multicomponent reactions
Cycloaddition
Domino reactions
Organic and Medicinal Chemistry
Piperidone
Short Report
Spiropyrrolidine
Stereoselectivity
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-c637t-411eb8383c408a53edb05dec430f16855ed7b5ed172a3b800c036cc84636d6103
cites cdi_FETCH-LOGICAL-c637t-411eb8383c408a53edb05dec430f16855ed7b5ed172a3b800c036cc84636d6103
container_end_page 11
container_issue 1
container_start_page 95
container_title BMC chemistry
container_volume 12
creator Arumugam, Natarajan
Almansour, Abdulrahman I.
Kumar, Raju Suresh
Al-thamili, Dhaifallah M.
Periyasami, Govindasami
Periasamy, V. S.
Athinarayanan, Jegan
Alshatwi, Ali A.
Mahalingam, S. M.
Menéndez, J. Carlos
description Background Spiropyrrolidine tethered piperidone heterocyclic hybrids were synthesized with complete regio- and stereoselectively in excellent yield via a tandem three-component 1,3-dipolar cycloaddition and subsequent enamine reaction in [bmim]Br. The synthesized compounds were evaluated for their anticancer activity against FaDu hypopharyngeal tumor cells. Findings Interestingly, most compounds displayed cytotoxicities similar to the standard anticancer agent bleomycin, with two of them ( 5a and 5g ) being slightly more active than the reference drug. Conclusion Synthesized compounds have also been evaluated for their apoptosis-inducing properties in a cancer cell model, finding that treatment with compounds 5a – e led to apoptotic cell death.
doi_str_mv 10.1186/s13065-018-0462-x
format article
fullrecord <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_44da3c947c7f4fe0a84221dd626f84ef</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_44da3c947c7f4fe0a84221dd626f84ef</doaj_id><sourcerecordid>2099043042</sourcerecordid><originalsourceid>FETCH-LOGICAL-c637t-411eb8383c408a53edb05dec430f16855ed7b5ed172a3b800c036cc84636d6103</originalsourceid><addsrcrecordid>eNp1ks2KFDEUhQtRnHH0AdxIwI2b0vxVKr0RZPBnYEAQBXchldzqTpOuWybVTdej-LamrXGcEdwk4d7vnuSEU1XPGX3NmFZvMhNUNTVluqZS8fr4oDpnbcNr1ojvD--cz6onOW8pbTRT7ePqTFDWCqH4efXzC6wDEjt4kidIgBkiuCkcgOR5mDaQQybYF2AKzg4OEsljSIjHMHiMOM4pYQw-DEBg14H34MkYRkjBY6ltoKiim10MjmzmrpQz8aV7KFyfcEcKVY84EWezsx7ImHBCh_Fp9ai3McOzm_2i-vbh_dfLT_X1549Xl--ua6dEO9WSMei00MJJqm0jwHe08eCkoD1TumnAt11ZWMut6DSljgrlnJZKKK8YFRfV1aLr0W7NmMLOptmgDeZ3AdPa2FTMRzBSeivcSrau7WUP1GrJOfNecdVrCX3RertojftuB97BMCUb74ne7wxhY9Z4MIqxVdPIIvDqRiDhjz3kyexCdhCjHQD32XC6WtFiTfKCvvwH3eI-DeWrTpQWrebq5I4tlEuYc4L-9jGMmlOIzBIiU0JkTiEyxzLz4q6L24k_qSkAX4BcWsMa0t-r_6_6C0dm2Bo</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2098378260</pqid></control><display><type>article</type><title>Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol</title><source>Publicly Available Content Database (Proquest) (PQ_SDU_P3)</source><source>Springer Nature - SpringerLink Journals - Fully Open Access</source><source>PubMed Central</source><source>Free Full-Text Journals in Chemistry</source><creator>Arumugam, Natarajan ; Almansour, Abdulrahman I. ; Kumar, Raju Suresh ; Al-thamili, Dhaifallah M. ; Periyasami, Govindasami ; Periasamy, V. S. ; Athinarayanan, Jegan ; Alshatwi, Ali A. ; Mahalingam, S. M. ; Menéndez, J. Carlos</creator><creatorcontrib>Arumugam, Natarajan ; Almansour, Abdulrahman I. ; Kumar, Raju Suresh ; Al-thamili, Dhaifallah M. ; Periyasami, Govindasami ; Periasamy, V. S. ; Athinarayanan, Jegan ; Alshatwi, Ali A. ; Mahalingam, S. M. ; Menéndez, J. Carlos</creatorcontrib><description>Background Spiropyrrolidine tethered piperidone heterocyclic hybrids were synthesized with complete regio- and stereoselectively in excellent yield via a tandem three-component 1,3-dipolar cycloaddition and subsequent enamine reaction in [bmim]Br. The synthesized compounds were evaluated for their anticancer activity against FaDu hypopharyngeal tumor cells. Findings Interestingly, most compounds displayed cytotoxicities similar to the standard anticancer agent bleomycin, with two of them ( 5a and 5g ) being slightly more active than the reference drug. Conclusion Synthesized compounds have also been evaluated for their apoptosis-inducing properties in a cancer cell model, finding that treatment with compounds 5a – e led to apoptotic cell death.</description><identifier>ISSN: 1752-153X</identifier><identifier>EISSN: 1752-153X</identifier><identifier>EISSN: 2661-801X</identifier><identifier>DOI: 10.1186/s13065-018-0462-x</identifier><identifier>PMID: 30173362</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>Anticancer properties ; Antiproliferative activity ; Apoptosis ; Apoptosis induction ; Cancer ; Cell death ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Chemo divergent multicomponent reactions ; Cycloaddition ; Domino reactions ; Organic and Medicinal Chemistry ; Piperidone ; Short Report ; Spiropyrrolidine ; Stereoselectivity</subject><ispartof>BMC chemistry, 2018-09, Vol.12 (1), p.95-11, Article 95</ispartof><rights>The Author(s) 2018</rights><rights>Chemistry Central Journal is a copyright of Springer, (2018). All Rights Reserved. © 2018. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c637t-411eb8383c408a53edb05dec430f16855ed7b5ed172a3b800c036cc84636d6103</citedby><cites>FETCH-LOGICAL-c637t-411eb8383c408a53edb05dec430f16855ed7b5ed172a3b800c036cc84636d6103</cites><orcidid>0000-0001-9073-155X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/2098378260/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2098378260?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30173362$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Arumugam, Natarajan</creatorcontrib><creatorcontrib>Almansour, Abdulrahman I.</creatorcontrib><creatorcontrib>Kumar, Raju Suresh</creatorcontrib><creatorcontrib>Al-thamili, Dhaifallah M.</creatorcontrib><creatorcontrib>Periyasami, Govindasami</creatorcontrib><creatorcontrib>Periasamy, V. S.</creatorcontrib><creatorcontrib>Athinarayanan, Jegan</creatorcontrib><creatorcontrib>Alshatwi, Ali A.</creatorcontrib><creatorcontrib>Mahalingam, S. M.</creatorcontrib><creatorcontrib>Menéndez, J. Carlos</creatorcontrib><title>Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol</title><title>BMC chemistry</title><addtitle>Chemistry Central Journal</addtitle><addtitle>Chem Cent J</addtitle><description>Background Spiropyrrolidine tethered piperidone heterocyclic hybrids were synthesized with complete regio- and stereoselectively in excellent yield via a tandem three-component 1,3-dipolar cycloaddition and subsequent enamine reaction in [bmim]Br. The synthesized compounds were evaluated for their anticancer activity against FaDu hypopharyngeal tumor cells. Findings Interestingly, most compounds displayed cytotoxicities similar to the standard anticancer agent bleomycin, with two of them ( 5a and 5g ) being slightly more active than the reference drug. Conclusion Synthesized compounds have also been evaluated for their apoptosis-inducing properties in a cancer cell model, finding that treatment with compounds 5a – e led to apoptotic cell death.</description><subject>Anticancer properties</subject><subject>Antiproliferative activity</subject><subject>Apoptosis</subject><subject>Apoptosis induction</subject><subject>Cancer</subject><subject>Cell death</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Chemo divergent multicomponent reactions</subject><subject>Cycloaddition</subject><subject>Domino reactions</subject><subject>Organic and Medicinal Chemistry</subject><subject>Piperidone</subject><subject>Short Report</subject><subject>Spiropyrrolidine</subject><subject>Stereoselectivity</subject><issn>1752-153X</issn><issn>1752-153X</issn><issn>2661-801X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNp1ks2KFDEUhQtRnHH0AdxIwI2b0vxVKr0RZPBnYEAQBXchldzqTpOuWybVTdej-LamrXGcEdwk4d7vnuSEU1XPGX3NmFZvMhNUNTVluqZS8fr4oDpnbcNr1ojvD--cz6onOW8pbTRT7ePqTFDWCqH4efXzC6wDEjt4kidIgBkiuCkcgOR5mDaQQybYF2AKzg4OEsljSIjHMHiMOM4pYQw-DEBg14H34MkYRkjBY6ltoKiim10MjmzmrpQz8aV7KFyfcEcKVY84EWezsx7ImHBCh_Fp9ai3McOzm_2i-vbh_dfLT_X1549Xl--ua6dEO9WSMei00MJJqm0jwHe08eCkoD1TumnAt11ZWMut6DSljgrlnJZKKK8YFRfV1aLr0W7NmMLOptmgDeZ3AdPa2FTMRzBSeivcSrau7WUP1GrJOfNecdVrCX3RertojftuB97BMCUb74ne7wxhY9Z4MIqxVdPIIvDqRiDhjz3kyexCdhCjHQD32XC6WtFiTfKCvvwH3eI-DeWrTpQWrebq5I4tlEuYc4L-9jGMmlOIzBIiU0JkTiEyxzLz4q6L24k_qSkAX4BcWsMa0t-r_6_6C0dm2Bo</recordid><startdate>20180901</startdate><enddate>20180901</enddate><creator>Arumugam, Natarajan</creator><creator>Almansour, Abdulrahman I.</creator><creator>Kumar, Raju Suresh</creator><creator>Al-thamili, Dhaifallah M.</creator><creator>Periyasami, Govindasami</creator><creator>Periasamy, V. S.</creator><creator>Athinarayanan, Jegan</creator><creator>Alshatwi, Ali A.</creator><creator>Mahalingam, S. M.</creator><creator>Menéndez, J. Carlos</creator><general>Springer International Publishing</general><general>Springer Nature B.V</general><general>BMC</general><scope>C6C</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7SR</scope><scope>7X7</scope><scope>7XB</scope><scope>8AO</scope><scope>8BQ</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>K9.</scope><scope>KB.</scope><scope>M0S</scope><scope>M2O</scope><scope>MBDVC</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0001-9073-155X</orcidid></search><sort><creationdate>20180901</creationdate><title>Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol</title><author>Arumugam, Natarajan ; Almansour, Abdulrahman I. ; Kumar, Raju Suresh ; Al-thamili, Dhaifallah M. ; Periyasami, Govindasami ; Periasamy, V. S. ; Athinarayanan, Jegan ; Alshatwi, Ali A. ; Mahalingam, S. M. ; Menéndez, J. Carlos</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c637t-411eb8383c408a53edb05dec430f16855ed7b5ed172a3b800c036cc84636d6103</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Anticancer properties</topic><topic>Antiproliferative activity</topic><topic>Apoptosis</topic><topic>Apoptosis induction</topic><topic>Cancer</topic><topic>Cell death</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Chemo divergent multicomponent reactions</topic><topic>Cycloaddition</topic><topic>Domino reactions</topic><topic>Organic and Medicinal Chemistry</topic><topic>Piperidone</topic><topic>Short Report</topic><topic>Spiropyrrolidine</topic><topic>Stereoselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Arumugam, Natarajan</creatorcontrib><creatorcontrib>Almansour, Abdulrahman I.</creatorcontrib><creatorcontrib>Kumar, Raju Suresh</creatorcontrib><creatorcontrib>Al-thamili, Dhaifallah M.</creatorcontrib><creatorcontrib>Periyasami, Govindasami</creatorcontrib><creatorcontrib>Periasamy, V. S.</creatorcontrib><creatorcontrib>Athinarayanan, Jegan</creatorcontrib><creatorcontrib>Alshatwi, Ali A.</creatorcontrib><creatorcontrib>Mahalingam, S. M.</creatorcontrib><creatorcontrib>Menéndez, J. Carlos</creatorcontrib><collection>SpringerOpen</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Engineered Materials Abstracts</collection><collection>Health &amp; Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>ProQuest Pharma Collection</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Research Library (Alumni Edition)</collection><collection>Materials Science &amp; Engineering Collection</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>Research Library Prep</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>ProQuest Health &amp; Medical Complete (Alumni)</collection><collection>Materials Science Database</collection><collection>Health &amp; Medical Collection (Alumni Edition)</collection><collection>ProQuest research library</collection><collection>Research Library (Corporate)</collection><collection>Materials science collection</collection><collection>Publicly Available Content Database (Proquest) (PQ_SDU_P3)</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>BMC chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Arumugam, Natarajan</au><au>Almansour, Abdulrahman I.</au><au>Kumar, Raju Suresh</au><au>Al-thamili, Dhaifallah M.</au><au>Periyasami, Govindasami</au><au>Periasamy, V. S.</au><au>Athinarayanan, Jegan</au><au>Alshatwi, Ali A.</au><au>Mahalingam, S. M.</au><au>Menéndez, J. Carlos</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol</atitle><jtitle>BMC chemistry</jtitle><stitle>Chemistry Central Journal</stitle><addtitle>Chem Cent J</addtitle><date>2018-09-01</date><risdate>2018</risdate><volume>12</volume><issue>1</issue><spage>95</spage><epage>11</epage><pages>95-11</pages><artnum>95</artnum><issn>1752-153X</issn><eissn>1752-153X</eissn><eissn>2661-801X</eissn><abstract>Background Spiropyrrolidine tethered piperidone heterocyclic hybrids were synthesized with complete regio- and stereoselectively in excellent yield via a tandem three-component 1,3-dipolar cycloaddition and subsequent enamine reaction in [bmim]Br. The synthesized compounds were evaluated for their anticancer activity against FaDu hypopharyngeal tumor cells. Findings Interestingly, most compounds displayed cytotoxicities similar to the standard anticancer agent bleomycin, with two of them ( 5a and 5g ) being slightly more active than the reference drug. Conclusion Synthesized compounds have also been evaluated for their apoptosis-inducing properties in a cancer cell model, finding that treatment with compounds 5a – e led to apoptotic cell death.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><pmid>30173362</pmid><doi>10.1186/s13065-018-0462-x</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0001-9073-155X</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1752-153X
ispartof BMC chemistry, 2018-09, Vol.12 (1), p.95-11, Article 95
issn 1752-153X
1752-153X
2661-801X
language eng
recordid cdi_doaj_primary_oai_doaj_org_article_44da3c947c7f4fe0a84221dd626f84ef
source Publicly Available Content Database (Proquest) (PQ_SDU_P3); Springer Nature - SpringerLink Journals - Fully Open Access; PubMed Central; Free Full-Text Journals in Chemistry
subjects Anticancer properties
Antiproliferative activity
Apoptosis
Apoptosis induction
Cancer
Cell death
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Chemo divergent multicomponent reactions
Cycloaddition
Domino reactions
Organic and Medicinal Chemistry
Piperidone
Short Report
Spiropyrrolidine
Stereoselectivity
title Regio and stereoselective synthesis of anticancer spirooxindolopyrrolidine embedded piperidone heterocyclic hybrids derived from one-pot cascade protocol
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T17%3A25%3A11IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Regio%20and%20stereoselective%20synthesis%20of%20anticancer%20spirooxindolopyrrolidine%20embedded%20piperidone%20heterocyclic%20hybrids%20derived%20from%20one-pot%20cascade%20protocol&rft.jtitle=BMC%20chemistry&rft.au=Arumugam,%20Natarajan&rft.date=2018-09-01&rft.volume=12&rft.issue=1&rft.spage=95&rft.epage=11&rft.pages=95-11&rft.artnum=95&rft.issn=1752-153X&rft.eissn=1752-153X&rft_id=info:doi/10.1186/s13065-018-0462-x&rft_dat=%3Cproquest_doaj_%3E2099043042%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c637t-411eb8383c408a53edb05dec430f16855ed7b5ed172a3b800c036cc84636d6103%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2098378260&rft_id=info:pmid/30173362&rfr_iscdi=true