A new class of HIV-1-specific 6-substituted acyclouridine derivatives: synthesis and anti-HIV-1 activity of 5- or 6-substituted analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT).
Identifieur interne : 000164 ( Ncbi/Merge ); précédent : 000163; suivant : 000165A new class of HIV-1-specific 6-substituted acyclouridine derivatives: synthesis and anti-HIV-1 activity of 5- or 6-substituted analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT).
Auteurs : H. Tanaka [Japon] ; M. Baba ; H. Hayakawa ; T. Sakamaki ; T. Miyasaka ; M. Ubasawa ; H. Takashima ; K. Sekiya ; I. Nitta ; S. ShigetaSource :
- Journal of medicinal chemistry [ 0022-2623 ] ; 1991.
Descripteurs français
- KwdFr :
- Antiviraux (synthèse chimique), Humains, Indicateurs et réactifs, Lignée cellulaire, Relation structure-activité, Structure moléculaire, Survie cellulaire (), Thymine (), Thymine (analogues et dérivés), Thymine (pharmacologie), Thymine (synthèse chimique), VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ().
- MESH :
- analogues et dérivés : Thymine.
- pharmacologie : Thymine.
- synthèse chimique : Antiviraux, Thymine.
- Humains, Indicateurs et réactifs, Lignée cellulaire, Relation structure-activité, Structure moléculaire, Survie cellulaire, Thymine, VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
English descriptors
- KwdEn :
- MESH :
- chemical , analogs & derivatives : Thymine.
- chemical , chemical synthesis : Antiviral Agents, Thymine.
- chemical , chemistry : Thymine.
- drug effects : Cell Survival, HIV-1.
- chemical , pharmacology : Thymine.
- Cell Line, Humans, Indicators and Reagents, Molecular Structure, Structure-Activity Relationship.
Abstract
A series of novel acyclouridine derivatives substituted at both the C-5 and C-6 positions were synthesized for the purpose of improving the activity of a recently reported HIV-1-specific lead, 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT). Preparation of C-6 substituted derivatives was carried out based on the following three methods: (1) LDA (lithium diisopropylamide) lithiation of a thymine derivative (4) and subsequent reaction with electrophiles, (2) an addition-elimination reaction of HEPT or its 6-(phenylsulfinyl) derivative (10), or (3) palladium-catalyzed cross-coupling between a 6-iodo derivative (16) and terminal alkynes. Following the methods, 21 C-6 substituted analogues were synthesized. Among these, 6-(cyclohexylthio) (8), 6-phenoxy (13), and 6-benzyl (27) derivatives showed anti-HIV-1 (HTLV-IIIB) activity with EC50 values of 8.2, 85, and 23 microM, respectively. Preparation of C-5 substituted derivatives was based on either LTMP (lithium 2,2,6,6-tetramethylpiperidide) lithiation of 6-(phenylthio)uracil derivative 37 or the above mentioned palladium-catalyzed cross-coupling of a 5-iodo-6-(phenylthio)uracil derivative (38). Following these methods, 11 C-5 substituted analogues were synthesized. Some 5-substituted derivatives (5-I, 44; 5-CH = CPh2, 49; 5-CH = CHPh (Z), 54; and 5-CH = CH2, 55) were more active than HEPT, but their selectivity indices (SI = CC50/EC50) were lower than that of HEPT. Compound 8 was also evaluated against another HIV-1 strain (HTLV-IIIRF) and HIV-2 strains (LAV-2ROD and LAV-2EHO). Only HTLV-IIIRF was as sensitive as HTLV-IIIB.
PubMed: 1992136
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Shigeta</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="1991">1991</date><idno type="RBID">pubmed:1992136</idno><idno type="pmid">1992136</idno><idno type="wicri:Area/PubMed/Corpus">000264</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000264</idno><idno type="wicri:Area/PubMed/Curation">000264</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">000264</idno><idno type="wicri:Area/PubMed/Checkpoint">000264</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">000264</idno><idno type="wicri:Area/Ncbi/Merge">000164</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">A new class of HIV-1-specific 6-substituted acyclouridine derivatives: synthesis and anti-HIV-1 activity of 5- or 6-substituted analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT).</title><author><name sortKey="Tanaka, H" sort="Tanaka, H" uniqKey="Tanaka H" first="H" last="Tanaka">H. Tanaka</name><affiliation wicri:level="3"><nlm:affiliation>School of Pharmaceutical Science, Showa University, Tokyo, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>School of Pharmaceutical Science, Showa University, Tokyo</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName></affiliation></author><author><name sortKey="Baba, M" sort="Baba, M" uniqKey="Baba M" first="M" last="Baba">M. Baba</name></author><author><name sortKey="Hayakawa, H" sort="Hayakawa, H" uniqKey="Hayakawa H" first="H" last="Hayakawa">H. Hayakawa</name></author><author><name sortKey="Sakamaki, T" sort="Sakamaki, T" uniqKey="Sakamaki T" first="T" last="Sakamaki">T. Sakamaki</name></author><author><name sortKey="Miyasaka, T" sort="Miyasaka, T" uniqKey="Miyasaka T" first="T" last="Miyasaka">T. Miyasaka</name></author><author><name sortKey="Ubasawa, M" sort="Ubasawa, M" uniqKey="Ubasawa M" first="M" last="Ubasawa">M. Ubasawa</name></author><author><name sortKey="Takashima, H" sort="Takashima, H" uniqKey="Takashima H" first="H" last="Takashima">H. Takashima</name></author><author><name sortKey="Sekiya, K" sort="Sekiya, K" uniqKey="Sekiya K" first="K" last="Sekiya">K. Sekiya</name></author><author><name sortKey="Nitta, I" sort="Nitta, I" uniqKey="Nitta I" first="I" last="Nitta">I. Nitta</name></author><author><name sortKey="Shigeta, S" sort="Shigeta, S" uniqKey="Shigeta S" first="S" last="Shigeta">S. Shigeta</name></author></analytic><series><title level="j">Journal of medicinal chemistry</title><idno type="ISSN">0022-2623</idno><imprint><date when="1991" type="published">1991</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral Agents (chemical synthesis)</term><term>Cell Line</term><term>Cell Survival (drug effects)</term><term>HIV-1 (drug effects)</term><term>Humans</term><term>Indicators and Reagents</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term><term>Thymine (analogs & derivatives)</term><term>Thymine (chemical synthesis)</term><term>Thymine (chemistry)</term><term>Thymine (pharmacology)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Antiviraux (synthèse chimique)</term><term>Humains</term><term>Indicateurs et réactifs</term><term>Lignée cellulaire</term><term>Relation structure-activité</term><term>Structure moléculaire</term><term>Survie cellulaire ()</term><term>Thymine ()</term><term>Thymine (analogues et dérivés)</term><term>Thymine (pharmacologie)</term><term>Thymine (synthèse chimique)</term><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Thymine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term><term>Thymine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Thymine</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Thymine</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Cell Survival</term><term>HIV-1</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Thymine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Thymine</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term><term>Thymine</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Cell Line</term><term>Humans</term><term>Indicators and Reagents</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Humains</term><term>Indicateurs et réactifs</term><term>Lignée cellulaire</term><term>Relation structure-activité</term><term>Structure moléculaire</term><term>Survie cellulaire</term><term>Thymine</term><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A series of novel acyclouridine derivatives substituted at both the C-5 and C-6 positions were synthesized for the purpose of improving the activity of a recently reported HIV-1-specific lead, 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT). Preparation of C-6 substituted derivatives was carried out based on the following three methods: (1) LDA (lithium diisopropylamide) lithiation of a thymine derivative (4) and subsequent reaction with electrophiles, (2) an addition-elimination reaction of HEPT or its 6-(phenylsulfinyl) derivative (10), or (3) palladium-catalyzed cross-coupling between a 6-iodo derivative (16) and terminal alkynes. Following the methods, 21 C-6 substituted analogues were synthesized. Among these, 6-(cyclohexylthio) (8), 6-phenoxy (13), and 6-benzyl (27) derivatives showed anti-HIV-1 (HTLV-IIIB) activity with EC50 values of 8.2, 85, and 23 microM, respectively. Preparation of C-5 substituted derivatives was based on either LTMP (lithium 2,2,6,6-tetramethylpiperidide) lithiation of 6-(phenylthio)uracil derivative 37 or the above mentioned palladium-catalyzed cross-coupling of a 5-iodo-6-(phenylthio)uracil derivative (38). Following these methods, 11 C-5 substituted analogues were synthesized. Some 5-substituted derivatives (5-I, 44; 5-CH = CPh2, 49; 5-CH = CHPh (Z), 54; and 5-CH = CH2, 55) were more active than HEPT, but their selectivity indices (SI = CC50/EC50) were lower than that of HEPT. Compound 8 was also evaluated against another HIV-1 strain (HTLV-IIIRF) and HIV-2 strains (LAV-2ROD and LAV-2EHO). Only HTLV-IIIRF was as sensitive as HTLV-IIIB.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="MEDLINE"><PMID Version="1">1992136</PMID><DateCreated><Year>1991</Year><Month>03</Month><Day>12</Day></DateCreated><DateCompleted><Year>1991</Year><Month>03</Month><Day>12</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0022-2623</ISSN><JournalIssue CitedMedium="Print"><Volume>34</Volume><Issue>1</Issue><PubDate><Year>1991</Year><Month>Jan</Month></PubDate></JournalIssue><Title>Journal of medicinal chemistry</Title><ISOAbbreviation>J. Med. Chem.</ISOAbbreviation></Journal><ArticleTitle>A new class of HIV-1-specific 6-substituted acyclouridine derivatives: synthesis and anti-HIV-1 activity of 5- or 6-substituted analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT).</ArticleTitle><Pagination><MedlinePgn>349-57</MedlinePgn></Pagination><Abstract><AbstractText>A series of novel acyclouridine derivatives substituted at both the C-5 and C-6 positions were synthesized for the purpose of improving the activity of a recently reported HIV-1-specific lead, 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT). Preparation of C-6 substituted derivatives was carried out based on the following three methods: (1) LDA (lithium diisopropylamide) lithiation of a thymine derivative (4) and subsequent reaction with electrophiles, (2) an addition-elimination reaction of HEPT or its 6-(phenylsulfinyl) derivative (10), or (3) palladium-catalyzed cross-coupling between a 6-iodo derivative (16) and terminal alkynes. Following the methods, 21 C-6 substituted analogues were synthesized. Among these, 6-(cyclohexylthio) (8), 6-phenoxy (13), and 6-benzyl (27) derivatives showed anti-HIV-1 (HTLV-IIIB) activity with EC50 values of 8.2, 85, and 23 microM, respectively. Preparation of C-5 substituted derivatives was based on either LTMP (lithium 2,2,6,6-tetramethylpiperidide) lithiation of 6-(phenylthio)uracil derivative 37 or the above mentioned palladium-catalyzed cross-coupling of a 5-iodo-6-(phenylthio)uracil derivative (38). Following these methods, 11 C-5 substituted analogues were synthesized. Some 5-substituted derivatives (5-I, 44; 5-CH = CPh2, 49; 5-CH = CHPh (Z), 54; and 5-CH = CH2, 55) were more active than HEPT, but their selectivity indices (SI = CC50/EC50) were lower than that of HEPT. Compound 8 was also evaluated against another HIV-1 strain (HTLV-IIIRF) and HIV-2 strains (LAV-2ROD and LAV-2EHO). Only HTLV-IIIRF was as sensitive as HTLV-IIIB.</AbstractText></Abstract><AuthorList CompleteYN="N"><Author ValidYN="Y"><LastName>Tanaka</LastName><ForeName>H</ForeName><Initials>H</Initials><AffiliationInfo><Affiliation>School of Pharmaceutical Science, Showa University, Tokyo, Japan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Baba</LastName><ForeName>M</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Hayakawa</LastName><ForeName>H</ForeName><Initials>H</Initials></Author><Author ValidYN="Y"><LastName>Sakamaki</LastName><ForeName>T</ForeName><Initials>T</Initials></Author><Author ValidYN="Y"><LastName>Miyasaka</LastName><ForeName>T</ForeName><Initials>T</Initials></Author><Author ValidYN="Y"><LastName>Ubasawa</LastName><ForeName>M</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Takashima</LastName><ForeName>H</ForeName><Initials>H</Initials></Author><Author ValidYN="Y"><LastName>Sekiya</LastName><ForeName>K</ForeName><Initials>K</Initials></Author><Author ValidYN="Y"><LastName>Nitta</LastName><ForeName>I</ForeName><Initials>I</Initials></Author><Author ValidYN="Y"><LastName>Shigeta</LastName><ForeName>S</ForeName><Initials>S</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D003160">Comparative Study</PublicationType><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>UNITED STATES</Country><MedlineTA>J Med Chem</MedlineTA><NlmUniqueID>9716531</NlmUniqueID><ISSNLinking>0022-2623</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000998">Antiviral Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D007202">Indicators and Reagents</NameOfSubstance></Chemical><Chemical><RegistryNumber>123027-56-5</RegistryNumber><NameOfSubstance UI="C061818">1-((2-hydroxyethoxy)methyl)-6-(phenylthio)thymine</NameOfSubstance></Chemical><Chemical><RegistryNumber>QR26YLT7LT</RegistryNumber><NameOfSubstance UI="D013941">Thymine</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><CitationSubset>X</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName MajorTopicYN="N" UI="D000998">Antiviral Agents</DescriptorName><QualifierName MajorTopicYN="Y" UI="Q000138">chemical synthesis</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D002460">Cell Line</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D002470">Cell Survival</DescriptorName><QualifierName MajorTopicYN="N" UI="Q000187">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D015497">HIV-1</DescriptorName><QualifierName MajorTopicYN="Y" UI="Q000187">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D006801">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D007202">Indicators and Reagents</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D015394">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D013329">Structure-Activity Relationship</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D013941">Thymine</DescriptorName><QualifierName MajorTopicYN="Y" UI="Q000031">analogs & derivatives</QualifierName><QualifierName MajorTopicYN="Y" UI="Q000138">chemical synthesis</QualifierName><QualifierName MajorTopicYN="N" UI="Q000737">chemistry</QualifierName><QualifierName MajorTopicYN="N" UI="Q000494">pharmacology</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>1991</Year><Month>1</Month><Day>1</Day></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>1991</Year><Month>1</Month><Day>1</Day><Hour>0</Hour><Minute>1</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>1991</Year><Month>1</Month><Day>1</Day><Hour>0</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">1992136</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Japon</li></country><region><li>Région de Kantō</li></region><settlement><li>Tokyo</li></settlement></list><tree><noCountry><name sortKey="Baba, M" sort="Baba, M" uniqKey="Baba M" first="M" last="Baba">M. Baba</name><name sortKey="Hayakawa, H" sort="Hayakawa, H" uniqKey="Hayakawa H" first="H" last="Hayakawa">H. Hayakawa</name><name sortKey="Miyasaka, T" sort="Miyasaka, T" uniqKey="Miyasaka T" first="T" last="Miyasaka">T. Miyasaka</name><name sortKey="Nitta, I" sort="Nitta, I" uniqKey="Nitta I" first="I" last="Nitta">I. Nitta</name><name sortKey="Sakamaki, T" sort="Sakamaki, T" uniqKey="Sakamaki T" first="T" last="Sakamaki">T. Sakamaki</name><name sortKey="Sekiya, K" sort="Sekiya, K" uniqKey="Sekiya K" first="K" last="Sekiya">K. Sekiya</name><name sortKey="Shigeta, S" sort="Shigeta, S" uniqKey="Shigeta S" first="S" last="Shigeta">S. Shigeta</name><name sortKey="Takashima, H" sort="Takashima, H" uniqKey="Takashima H" first="H" last="Takashima">H. Takashima</name><name sortKey="Ubasawa, M" sort="Ubasawa, M" uniqKey="Ubasawa M" first="M" last="Ubasawa">M. Ubasawa</name></noCountry><country name="Japon"><region name="Région de Kantō"><name sortKey="Tanaka, H" sort="Tanaka, H" uniqKey="Tanaka H" first="H" last="Tanaka">H. Tanaka</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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