Singlet oxygen-mediated synthesis of malarial chemotherapeutic agents
Identifieur interne : 001435 ( Istex/Corpus ); précédent : 001434; suivant : 001436Singlet oxygen-mediated synthesis of malarial chemotherapeutic agents
Auteurs : Sachin Malik ; Suroor A. Khan ; Priya Ahuja ; Satish K. Arya ; Shikha Sahu ; Kapendra SahuSource :
- Medicinal Chemistry Research [ 1054-2523 ] ; 2013-12-01.
English descriptors
Abstract
Abstract: Malaria is the leading infectious disease found in humans, affecting third-world countries. Worldwide, more than two billion people are at risk of malaria, with about 500 million clinical cases of malaria each year and one million deaths. In this focused review, an effort has been made to summarize the reactions of singlet oxygen with organic substrates, their stereoselectivity, stereospecificity and utilization in generating dioxetanes and endoperoxides. The study of production and reactivity indications of this exceptional molecule has emerged as a rich and diverse area in the synthesis of antimalarials like artemisinin and its semisynthetic derivatives, structurally simple 1,2,4-trioxanes, sesquiterpene isonitriles, synthetic cyclic, and other acyclic peroxides. Artermisinin, a mainstay in antimalarial drug therapy, meets the dual challenge posed by drug-resistant parasites and rapid advancement of lethal malarial threat. The cardinal mechanism of peroxidation and ring closure in its production are induced by singlet oxygen and acid. Moreover, its complex structure restricts the complete chemical synthesis of artemisinin. Consequently, the limited availability coupled with increasing demand for artemisinin has paved the way for the preparation of synthetic alternatives of artemisinin and its derivatives. Likewise, past evidence of the structure–activity relationship indicate the importance of singlet oxygen in antimalarial drug synthesis. It is anticipated that this compendium on the chemistry of singlet oxygen will be of use to organic/medicinal chemists and pharmacologists working on antimalarial drug development.
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DOI: 10.1007/s00044-013-0578-4
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ISTEX:069165AB54872A31905C2148EA42114DA3D8B530Le document en format XML
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Grant="OpenAccess"></AbstractGrant><BodyPDFGrant Grant="Restricted"></BodyPDFGrant><BodyHTMLGrant Grant="Restricted"></BodyHTMLGrant><BibliographyGrant Grant="Restricted"></BibliographyGrant><ESMGrant Grant="Restricted"></ESMGrant></ArticleGrants></ArticleInfo><ArticleHeader><AuthorGroup><Author AffiliationIDS="Aff1" CorrespondingAffiliationID="Aff1"><AuthorName DisplayOrder="Western"><GivenName>Sachin</GivenName><FamilyName>Malik</FamilyName></AuthorName><Contact><Phone>+91-11-26059681</Phone><Phone>+91-11-26059688</Phone><Fax>+91-11-6988874</Fax><Fax>+91 8860135605</Fax><Email>pr.sachinmalik@gmail.com</Email></Contact></Author><Author AffiliationIDS="Aff1"><AuthorName DisplayOrder="Western"><GivenName>Suroor</GivenName><GivenName>A.</GivenName><FamilyName>Khan</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff1"><AuthorName DisplayOrder="Western"><GivenName>Priya</GivenName><FamilyName>Ahuja</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff1"><AuthorName DisplayOrder="Western"><GivenName>Satish</GivenName><GivenName>K.</GivenName><FamilyName>Arya</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff2"><AuthorName DisplayOrder="Western"><GivenName>Shikha</GivenName><FamilyName>Sahu</FamilyName></AuthorName></Author><Author AffiliationIDS="Aff1"><AuthorName DisplayOrder="Western"><GivenName>Kapendra</GivenName><FamilyName>Sahu</FamilyName></AuthorName></Author><Affiliation ID="Aff1"><OrgDivision>Department of Pharmaceutical Chemistry, Faculty of Pharmacy</OrgDivision><OrgName>Jamia Hamdard</OrgName><OrgAddress><City>New Delhi</City><Postcode>110062</Postcode><Country Code="IN">India</Country></OrgAddress></Affiliation><Affiliation ID="Aff2"><OrgDivision>Department of Chemistry</OrgDivision><OrgName>Govt. (Autonomous) Girls P.G. College of Excellence</OrgName><OrgAddress><City>Sagar</City><Postcode>470002</Postcode><State>Madhya Pradesh</State><Country Code="IN">India</Country></OrgAddress></Affiliation></AuthorGroup><Abstract ID="Abs1" Language="En" OutputMedium="All"><Heading>Abstract</Heading><Para>Malaria is the leading infectious disease found in humans, affecting third-world countries. Worldwide, more than two billion people are at risk of malaria, with about 500 million clinical cases of malaria each year and one million deaths. In this focused review, an effort has been made to summarize the reactions of singlet oxygen with organic substrates, their stereoselectivity, stereospecificity and utilization in generating dioxetanes and endoperoxides. The study of production and reactivity indications of this exceptional molecule has emerged as a rich and diverse area in the synthesis of antimalarials like artemisinin and its semisynthetic derivatives, structurally simple 1,2,4-trioxanes, sesquiterpene isonitriles, synthetic cyclic, and other acyclic peroxides. Artermisinin, a mainstay in antimalarial drug therapy, meets the dual challenge posed by drug-resistant parasites and rapid advancement of lethal malarial threat. The cardinal mechanism of peroxidation and ring closure in its production are induced by singlet oxygen and acid. Moreover, its complex structure restricts the complete chemical synthesis of artemisinin. Consequently, the limited availability coupled with increasing demand for artemisinin has paved the way for the preparation of synthetic alternatives of artemisinin and its derivatives. Likewise, past evidence of the structure–activity relationship indicate the importance of singlet oxygen in antimalarial drug synthesis. It is anticipated that this compendium on the chemistry of singlet oxygen will be of use to organic/medicinal chemists and pharmacologists working on antimalarial drug development.</Para></Abstract><KeywordGroup Language="En" OutputMedium="All"><Heading>Keywords</Heading><Keyword>Artemisinin</Keyword><Keyword>Singlet oxygen</Keyword><Keyword>1,2,4-Trioxanes</Keyword><Keyword>Cyclic diperoxides</Keyword><Keyword>Isonitriles</Keyword></KeywordGroup></ArticleHeader><NoBody></NoBody></Article></Issue></Volume></Journal></Publisher></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Singlet oxygen-mediated synthesis of malarial chemotherapeutic agents</title></titleInfo><titleInfo type="alternative" contentType="CDATA"><title>Singlet oxygen-mediated synthesis of malarial chemotherapeutic agents</title></titleInfo><name type="personal" displayLabel="corresp"><namePart type="given">Sachin</namePart><namePart type="family">Malik</namePart><affiliation>Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, 110062, New Delhi, India</affiliation><affiliation>E-mail: pr.sachinmalik@gmail.com</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Suroor</namePart><namePart type="given">A.</namePart><namePart type="family">Khan</namePart><affiliation>Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, 110062, New Delhi, India</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Priya</namePart><namePart type="family">Ahuja</namePart><affiliation>Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, 110062, New Delhi, India</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Satish</namePart><namePart type="given">K.</namePart><namePart type="family">Arya</namePart><affiliation>Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, 110062, New Delhi, India</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Shikha</namePart><namePart type="family">Sahu</namePart><affiliation>Department of Chemistry, Govt. (Autonomous) Girls P.G. College of Excellence, 470002, Sagar, Madhya Pradesh, India</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Kapendra</namePart><namePart type="family">Sahu</namePart><affiliation>Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, 110062, New Delhi, India</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="review-article" displayLabel="ReviewPaper" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-L5L7X3NF-P">review-article</genre><originInfo><publisher>Springer US; http://www.springer-ny.com</publisher><place><placeTerm type="text">New York</placeTerm></place><dateCreated encoding="w3cdtf">2012-09-05</dateCreated><dateIssued encoding="w3cdtf">2013-12-01</dateIssued><copyrightDate encoding="w3cdtf">2013</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><abstract lang="en">Abstract: Malaria is the leading infectious disease found in humans, affecting third-world countries. Worldwide, more than two billion people are at risk of malaria, with about 500 million clinical cases of malaria each year and one million deaths. In this focused review, an effort has been made to summarize the reactions of singlet oxygen with organic substrates, their stereoselectivity, stereospecificity and utilization in generating dioxetanes and endoperoxides. The study of production and reactivity indications of this exceptional molecule has emerged as a rich and diverse area in the synthesis of antimalarials like artemisinin and its semisynthetic derivatives, structurally simple 1,2,4-trioxanes, sesquiterpene isonitriles, synthetic cyclic, and other acyclic peroxides. Artermisinin, a mainstay in antimalarial drug therapy, meets the dual challenge posed by drug-resistant parasites and rapid advancement of lethal malarial threat. The cardinal mechanism of peroxidation and ring closure in its production are induced by singlet oxygen and acid. Moreover, its complex structure restricts the complete chemical synthesis of artemisinin. Consequently, the limited availability coupled with increasing demand for artemisinin has paved the way for the preparation of synthetic alternatives of artemisinin and its derivatives. Likewise, past evidence of the structure–activity relationship indicate the importance of singlet oxygen in antimalarial drug synthesis. It is anticipated that this compendium on the chemistry of singlet oxygen will be of use to organic/medicinal chemists and pharmacologists working on antimalarial drug development.</abstract><note>Review Article</note><subject lang="en"><genre>Keywords</genre><topic>Artemisinin</topic><topic>Singlet oxygen</topic><topic>1,2,4-Trioxanes</topic><topic>Cyclic diperoxides</topic><topic>Isonitriles</topic></subject><relatedItem type="host"><titleInfo><title>Medicinal Chemistry Research</title></titleInfo><titleInfo type="abbreviated"><title>Med Chem Res</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><originInfo><publisher>Springer</publisher><dateIssued encoding="w3cdtf">2013-10-18</dateIssued><copyrightDate encoding="w3cdtf">2013</copyrightDate></originInfo><subject><genre>Journal-Subject-Collection</genre><topic authority="SpringerSubjectCodes" authorityURI="SC3">Biomedical and Life Sciences</topic></subject><subject><genre>Journal-Subject-Group</genre><topic authority="SpringerSubjectCodes" authorityURI="SCB">Biomedicine</topic><topic authority="SpringerSubjectCodes" authorityURI="SCB21007">Pharmacology/Toxicology</topic><topic authority="SpringerSubjectCodes" authorityURI="SCL14005">Biochemistry, general</topic><topic authority="SpringerSubjectCodes" authorityURI="SCL16008">Cell Biology</topic></subject><identifier type="ISSN">1054-2523</identifier><identifier type="eISSN">1554-8120</identifier><identifier type="JournalID">44</identifier><identifier type="IssueArticleCount">51</identifier><identifier type="VolumeIssueCount">12</identifier><part><date>2013</date><detail type="volume"><number>22</number><caption>vol.</caption></detail><detail type="issue"><number>12</number><caption>no.</caption></detail><extent unit="pages"><start>5633</start><end>5653</end></extent></part><recordInfo><recordOrigin>Springer Science+Business Media New York, 2013</recordOrigin></recordInfo></relatedItem><identifier type="istex">069165AB54872A31905C2148EA42114DA3D8B530</identifier><identifier type="ark">ark:/67375/VQC-P2X7TC5M-M</identifier><identifier type="DOI">10.1007/s00044-013-0578-4</identifier><identifier type="ArticleID">578</identifier><identifier type="ArticleID">s00044-013-0578-4</identifier><accessCondition type="use and reproduction" contentType="copyright">Springer Science+Business Media New York, 2013</accessCondition><recordInfo><recordContentSource authority="ISTEX" authorityURI="https://loaded-corpus.data.istex.fr" valueURI="https://loaded-corpus.data.istex.fr/ark:/67375/XBH-3XSW68JL-F">springer</recordContentSource><recordOrigin>Springer Science+Business Media New York, 2013</recordOrigin></recordInfo></mods><json:item><extension>json</extension><original>false</original><mimetype>application/json</mimetype><uri>https://api.istex.fr/ark:/67375/VQC-P2X7TC5M-M/record.json</uri></json:item></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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