Parallel synthesis, molecular modelling and further structure-activity relationship studies of new acylthiocarbamates as potent non-nucleoside HIV-1 reverse transcriptase inhibitors.
Identifieur interne : 001822 ( PubMed/Checkpoint ); précédent : 001821; suivant : 001823Parallel synthesis, molecular modelling and further structure-activity relationship studies of new acylthiocarbamates as potent non-nucleoside HIV-1 reverse transcriptase inhibitors.
Auteurs : Andrea Spallarossa [Italie] ; Sara Cesarini ; Angelo Ranise ; Silvia Schenone ; Olga Bruno ; Alberto Borassi ; Paolo La Colla ; Margherita Pezzullo ; Giuseppina Sanna ; Gabriella Collu ; Barbara Secci ; Roberta LoddoSource :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2009.
Descripteurs français
- KwdFr :
- Inhibiteurs de la transcriptase inverse (pharmacologie), Inhibiteurs de la transcriptase inverse (synthèse chimique), Liaison aux protéines, Modèles moléculaires, Mutation faux-sens, Relation structure-activité, Simulation numérique, Thiocarbamates (pharmacologie), Thiocarbamates (synthèse chimique), Transcriptase inverse du VIH (antagonistes et inhibiteurs), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) (génétique).
- MESH :
- antagonistes et inhibiteurs : Transcriptase inverse du VIH.
- génétique : VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
- pharmacologie : Inhibiteurs de la transcriptase inverse, Thiocarbamates.
- synthèse chimique : Inhibiteurs de la transcriptase inverse, Thiocarbamates.
- Liaison aux protéines, Modèles moléculaires, Mutation faux-sens, Relation structure-activité, Simulation numérique, VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
English descriptors
- KwdEn :
- Computer Simulation, HIV Reverse Transcriptase (antagonists & inhibitors), HIV-1 (drug effects), HIV-1 (genetics), Models, Molecular, Mutation, Missense, Protein Binding, Reverse Transcriptase Inhibitors (chemical synthesis), Reverse Transcriptase Inhibitors (pharmacology), Structure-Activity Relationship, Thiocarbamates (chemical synthesis), Thiocarbamates (pharmacology).
- MESH :
- chemical , antagonists & inhibitors : HIV Reverse Transcriptase.
- chemical , chemical synthesis : Reverse Transcriptase Inhibitors, Thiocarbamates.
- drug effects : HIV-1.
- genetics : HIV-1.
- chemical , pharmacology : Reverse Transcriptase Inhibitors, Thiocarbamates.
- Computer Simulation, Models, Molecular, Mutation, Missense, Protein Binding, Structure-Activity Relationship.
Abstract
The structure-activity relationships (SARs) of acylthiocarbamates (ATCs), a new class of non-nucleoside HIV-1 reverse transcriptase inhibitors, have been expanded. Sixty-six new analogues were prepared by parallel solution-phase synthesis. In general, the potency of new ATCs was better than that of the first series and O-[2-phthalimidoethyl] 4-chlorophenyl(3-nitrobenzoyl) thiocarbamate turned out to be the most potent ATC so far synthesized (EC(50)=1.5nM). Several ATCs were active at micromolar concentrations against HIV-1 strains carrying the RT Y181C mutation and one of them was also moderately active against the K103R variant. Docking simulations were carried out to rationalize the most relevant SARs.
DOI: 10.1016/j.ejmech.2008.10.032
PubMed: 19058881
Affiliations:
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Sixty-six new analogues were prepared by parallel solution-phase synthesis. In general, the potency of new ATCs was better than that of the first series and O-[2-phthalimidoethyl] 4-chlorophenyl(3-nitrobenzoyl) thiocarbamate turned out to be the most potent ATC so far synthesized (EC(50)=1.5nM). Several ATCs were active at micromolar concentrations against HIV-1 strains carrying the RT Y181C mutation and one of them was also moderately active against the K103R variant. Docking simulations were carried out to rationalize the most relevant SARs.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">19058881</PMID><DateCompleted><Year>2009</Year><Month>06</Month><Day>12</Day></DateCompleted><DateRevised><Year>2009</Year><Month>03</Month><Day>27</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1768-3254</ISSN><JournalIssue CitedMedium="Internet"><Volume>44</Volume><Issue>5</Issue><PubDate><Year>2009</Year><Month>May</Month></PubDate></JournalIssue><Title>European journal of medicinal chemistry</Title><ISOAbbreviation>Eur J Med Chem</ISOAbbreviation></Journal><ArticleTitle>Parallel synthesis, molecular modelling and further structure-activity relationship studies of new acylthiocarbamates as potent non-nucleoside HIV-1 reverse transcriptase inhibitors.</ArticleTitle><Pagination><MedlinePgn>2190-201</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.ejmech.2008.10.032</ELocationID><Abstract><AbstractText>The structure-activity relationships (SARs) of acylthiocarbamates (ATCs), a new class of non-nucleoside HIV-1 reverse transcriptase inhibitors, have been expanded. Sixty-six new analogues were prepared by parallel solution-phase synthesis. In general, the potency of new ATCs was better than that of the first series and O-[2-phthalimidoethyl] 4-chlorophenyl(3-nitrobenzoyl) thiocarbamate turned out to be the most potent ATC so far synthesized (EC(50)=1.5nM). Several ATCs were active at micromolar concentrations against HIV-1 strains carrying the RT Y181C mutation and one of them was also moderately active against the K103R variant. Docking simulations were carried out to rationalize the most relevant SARs.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Spallarossa</LastName><ForeName>Andrea</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>Dipartimento di Scienze Farmaceutiche, Università di Genova, Viale Benedetto XV 3, I-16132 Genova, Italy.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Cesarini</LastName><ForeName>Sara</ForeName><Initials>S</Initials></Author><Author ValidYN="Y"><LastName>Ranise</LastName><ForeName>Angelo</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Schenone</LastName><ForeName>Silvia</ForeName><Initials>S</Initials></Author><Author ValidYN="Y"><LastName>Bruno</LastName><ForeName>Olga</ForeName><Initials>O</Initials></Author><Author ValidYN="Y"><LastName>Borassi</LastName><ForeName>Alberto</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>La Colla</LastName><ForeName>Paolo</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Pezzullo</LastName><ForeName>Margherita</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Sanna</LastName><ForeName>Giuseppina</ForeName><Initials>G</Initials></Author><Author ValidYN="Y"><LastName>Collu</LastName><ForeName>Gabriella</ForeName><Initials>G</Initials></Author><Author ValidYN="Y"><LastName>Secci</LastName><ForeName>Barbara</ForeName><Initials>B</Initials></Author><Author ValidYN="Y"><LastName>Loddo</LastName><ForeName>Roberta</ForeName><Initials>R</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2008</Year><Month>11</Month><Day>05</Day></ArticleDate></Article><MedlineJournalInfo><Country>France</Country><MedlineTA>Eur J Med Chem</MedlineTA><NlmUniqueID>0420510</NlmUniqueID><ISSNLinking>0223-5234</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D018894">Reverse Transcriptase Inhibitors</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D013859">Thiocarbamates</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 2.7.7.-</RegistryNumber><NameOfSubstance UI="C514824">reverse transcriptase, Human immunodeficiency virus 1</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 2.7.7.49</RegistryNumber><NameOfSubstance UI="D054303">HIV Reverse Transcriptase</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D003198" MajorTopicYN="N">Computer Simulation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D054303" MajorTopicYN="N">HIV Reverse Transcriptase</DescriptorName><QualifierName UI="Q000037" MajorTopicYN="Y">antagonists & inhibitors</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015497" MajorTopicYN="N">HIV-1</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008958" MajorTopicYN="N">Models, Molecular</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D020125" MajorTopicYN="N">Mutation, Missense</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011485" MajorTopicYN="N">Protein Binding</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D018894" MajorTopicYN="N">Reverse Transcriptase Inhibitors</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity 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Colla, Paolo" uniqKey="La Colla P" first="Paolo" last="La Colla">Paolo La Colla</name><name sortKey="Loddo, Roberta" sort="Loddo, Roberta" uniqKey="Loddo R" first="Roberta" last="Loddo">Roberta Loddo</name><name sortKey="Pezzullo, Margherita" sort="Pezzullo, Margherita" uniqKey="Pezzullo M" first="Margherita" last="Pezzullo">Margherita Pezzullo</name><name sortKey="Ranise, Angelo" sort="Ranise, Angelo" uniqKey="Ranise A" first="Angelo" last="Ranise">Angelo Ranise</name><name sortKey="Sanna, Giuseppina" sort="Sanna, Giuseppina" uniqKey="Sanna G" first="Giuseppina" last="Sanna">Giuseppina Sanna</name><name sortKey="Schenone, Silvia" sort="Schenone, Silvia" uniqKey="Schenone S" first="Silvia" last="Schenone">Silvia Schenone</name><name sortKey="Secci, Barbara" sort="Secci, Barbara" uniqKey="Secci B" first="Barbara" last="Secci">Barbara Secci</name></noCountry><country name="Italie"><noRegion><name sortKey="Spallarossa, Andrea" sort="Spallarossa, Andrea" uniqKey="Spallarossa A" 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