The synthesis and biological activity of two analogs of the anti‐HIV alkaloid michellamine B
Identifieur interne : 001654 ( Istex/Checkpoint ); précédent : 001653; suivant : 001655The synthesis and biological activity of two analogs of the anti‐HIV alkaloid michellamine B
Auteurs : Velaparthi Upender [États-Unis] ; Daniel J. Pollart [États-Unis] ; Jyanwei Liu [États-Unis] ; Peter D. Hobbs [États-Unis] ; Cris Olsen [États-Unis] ; Wan-Ru Chao [États-Unis] ; Bonnie Bowden [États-Unis] ; Jac L. Crase [États-Unis] ; David W. Thomas [États-Unis] ; Anjali Pandey [États-Unis] ; John A. Lawson [États-Unis] ; Marcia I. Dawson [États-Unis]Source :
- Journal of Heterocyclic Chemistry [ 0022-152X ] ; 1996-07.
Abstract
Two simplified analogs of the dimeric naphthalenyltetrahydroisoquinoline alkaloid michellamine B [4′,4″‐didesmethoxy‐2′,2″‐didesmethylmichellamine B and 6,8‐dihydroxy‐5‐(1′,1″‐dihydroxy‐2′,2″‐binaphthalen‐4′‐yl)‐1R,3R‐dimethyl‐1,2,3,4‐tetrahydroisoquinoline] were synthesized using Suzuki palladiumcatalyzed biaryl cross‐coupling of 4‐(2‐benzyl‐6,8‐dibenzyloxy‐1R,3R‐dimethyl‐1,2,3,4‐tetrahydroisoquinolin‐5‐yl)‐1‐benzyloxy‐2‐bromonaphthalene to its corresponding atropisomeric 2‐naphthaleneboronic acid and 1‐benzyloxy‐2‐naphthaleneboronic acid, respectively. These analogs inhibited recombinant HIV reverse transcriptase with IC5() values of 62 μM and 1000 μM, respectively, whereas the IC5() value for michellamine B was 33 μM. Both michellamine B and the analogs inhibited the phosphorylation of histories by rat brain protein kinase C. The analogs were more active (IC50 values of 36 μM and 30 μM, respectively) than michellamine B (IC50 = 130 μM).
Url:
DOI: 10.1002/jhet.5570330460
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Lawson</name></author><author><name sortKey="Dawson, Marcia I" sort="Dawson, Marcia I" uniqKey="Dawson M" first="Marcia I." last="Dawson">Marcia I. 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Pollart</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Alabama</region></placeName><wicri:cityArea>Virucidal Testing Section, Southern Research Institute, Birmingham</wicri:cityArea></affiliation><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Californie</region></placeName><wicri:cityArea>Current Address: Gene Trace Systems Inc., 333 Ravens‐wood Avenue, Menlo Park</wicri:cityArea></affiliation></author><author><name sortKey="Liu, Jyanwei" sort="Liu, Jyanwei" uniqKey="Liu J" first="Jyanwei" last="Liu">Jyanwei Liu</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Alabama</region></placeName><wicri:cityArea>Virucidal Testing Section, Southern Research Institute, Birmingham</wicri:cityArea></affiliation></author><author><name sortKey="Hobbs, Peter D" sort="Hobbs, Peter D" uniqKey="Hobbs P" first="Peter D." last="Hobbs">Peter D. Hobbs</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Alabama</region></placeName><wicri:cityArea>Virucidal Testing Section, Southern Research Institute, Birmingham</wicri:cityArea></affiliation></author><author><name sortKey="Olsen, Cris" sort="Olsen, Cris" uniqKey="Olsen C" first="Cris" last="Olsen">Cris Olsen</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Alabama</region></placeName><wicri:cityArea>Virucidal Testing Section, Southern Research Institute, Birmingham</wicri:cityArea></affiliation></author><author><name sortKey="Chao, Wan U" sort="Chao, Wan U" uniqKey="Chao W" first="Wan-Ru" last="Chao">Wan-Ru Chao</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Alabama</region></placeName><wicri:cityArea>Virucidal Testing Section, Southern Research Institute, Birmingham</wicri:cityArea></affiliation></author><author><name sortKey="Bowden, Bonnie" sort="Bowden, Bonnie" uniqKey="Bowden B" first="Bonnie" last="Bowden">Bonnie Bowden</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Alabama</region></placeName><wicri:cityArea>Virucidal Testing Section, Southern Research Institute, Birmingham</wicri:cityArea></affiliation></author><author><name sortKey="Crase, Jac L" sort="Crase, Jac L" uniqKey="Crase J" first="Jac L." last="Crase">Jac L. Crase</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Alabama</region></placeName><wicri:cityArea>Virucidal Testing Section, Southern Research Institute, Birmingham</wicri:cityArea></affiliation><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Californie</region></placeName><wicri:cityArea>Current Address: Microcide Pharmaceuticals, Inc., 850 Maude Avenue, Mountain View</wicri:cityArea></affiliation></author><author><name sortKey="Thomas, David W" sort="Thomas, David W" uniqKey="Thomas D" first="David W." last="Thomas">David W. Thomas</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Alabama</region></placeName><wicri:cityArea>Virucidal Testing Section, Southern Research Institute, Birmingham</wicri:cityArea></affiliation></author><author><name sortKey="Pandey, Anjali" sort="Pandey, Anjali" uniqKey="Pandey A" first="Anjali" last="Pandey">Anjali Pandey</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Alabama</region></placeName><wicri:cityArea>Virucidal Testing Section, Southern Research Institute, Birmingham</wicri:cityArea></affiliation><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Californie</region></placeName><wicri:cityArea>Current Address: COR Therapeutics, 256 E. Grand Avenue, South San Francisco</wicri:cityArea></affiliation></author><author><name sortKey="Lawson, John A" sort="Lawson, John A" uniqKey="Lawson J" first="John A." last="Lawson">John A. Lawson</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Alabama</region></placeName><wicri:cityArea>Virucidal Testing Section, Southern Research Institute, Birmingham</wicri:cityArea></affiliation></author><author><name sortKey="Dawson, Marcia I" sort="Dawson, Marcia I" uniqKey="Dawson M" first="Marcia I." last="Dawson">Marcia I. Dawson</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Californie</region></placeName><wicri:cityArea>Bio‐Organic Chemistry Laboratory, SRI International, Menlo Park</wicri:cityArea></affiliation><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Californie</region></placeName><wicri:cityArea>Correspondence address: Bio‐Organic Chemistry Laboratory, SRI International, Menlo Park</wicri:cityArea></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Journal of Heterocyclic Chemistry</title><title level="j" type="alt">JOURNAL OF HETEROCYCLIC CHEMISTRY</title><idno type="ISSN">0022-152X</idno><idno type="eISSN">1943-5193</idno><imprint><biblScope unit="vol">33</biblScope><biblScope unit="issue">4</biblScope><biblScope unit="page" from="1371">1371</biblScope><biblScope unit="page" to="1384">1384</biblScope><biblScope unit="page-count">14</biblScope><publisher>Wiley‐Blackwell</publisher><pubPlace>Hoboken</pubPlace><date type="published" when="1996-07">1996-07</date></imprint><idno type="ISSN">0022-152X</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0022-152X</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Two simplified analogs of the dimeric naphthalenyltetrahydroisoquinoline alkaloid michellamine B [4′,4″‐didesmethoxy‐2′,2″‐didesmethylmichellamine B and 6,8‐dihydroxy‐5‐(1′,1″‐dihydroxy‐2′,2″‐binaphthalen‐4′‐yl)‐1R,3R‐dimethyl‐1,2,3,4‐tetrahydroisoquinoline] were synthesized using Suzuki palladiumcatalyzed biaryl cross‐coupling of 4‐(2‐benzyl‐6,8‐dibenzyloxy‐1R,3R‐dimethyl‐1,2,3,4‐tetrahydroisoquinolin‐5‐yl)‐1‐benzyloxy‐2‐bromonaphthalene to its corresponding atropisomeric 2‐naphthaleneboronic acid and 1‐benzyloxy‐2‐naphthaleneboronic acid, respectively. These analogs inhibited recombinant HIV reverse transcriptase with IC5() values of 62 μM and 1000 μM, respectively, whereas the IC5() value for michellamine B was 33 μM. Both michellamine B and the analogs inhibited the phosphorylation of histories by rat brain protein kinase C. The analogs were more active (IC50 values of 36 μM and 30 μM, respectively) than michellamine B (IC50 = 130 μM).</div></front></TEI><affiliations><list><country><li>États-Unis</li></country><region><li>Alabama</li><li>Californie</li></region></list><tree><country name="États-Unis"><region name="Alabama"><name sortKey="Upender, Velaparthi" sort="Upender, Velaparthi" uniqKey="Upender V" first="Velaparthi" last="Upender">Velaparthi Upender</name></region><name sortKey="Bowden, Bonnie" sort="Bowden, Bonnie" uniqKey="Bowden B" first="Bonnie" last="Bowden">Bonnie Bowden</name><name sortKey="Chao, Wan U" sort="Chao, Wan U" uniqKey="Chao W" first="Wan-Ru" last="Chao">Wan-Ru Chao</name><name sortKey="Crase, Jac L" sort="Crase, Jac L" uniqKey="Crase J" first="Jac L." last="Crase">Jac L. Crase</name><name sortKey="Crase, Jac L" sort="Crase, Jac L" uniqKey="Crase J" first="Jac L." last="Crase">Jac L. Crase</name><name sortKey="Dawson, Marcia I" sort="Dawson, Marcia I" uniqKey="Dawson M" first="Marcia I." last="Dawson">Marcia I. Dawson</name><name sortKey="Dawson, Marcia I" sort="Dawson, Marcia I" uniqKey="Dawson M" first="Marcia I." last="Dawson">Marcia I. Dawson</name><name sortKey="Hobbs, Peter D" sort="Hobbs, Peter D" uniqKey="Hobbs P" first="Peter D." last="Hobbs">Peter D. Hobbs</name><name sortKey="Lawson, John A" sort="Lawson, John A" uniqKey="Lawson J" first="John A." last="Lawson">John A. Lawson</name><name sortKey="Liu, Jyanwei" sort="Liu, Jyanwei" uniqKey="Liu J" first="Jyanwei" last="Liu">Jyanwei Liu</name><name sortKey="Olsen, Cris" sort="Olsen, Cris" uniqKey="Olsen C" first="Cris" last="Olsen">Cris Olsen</name><name sortKey="Pandey, Anjali" sort="Pandey, Anjali" uniqKey="Pandey A" first="Anjali" last="Pandey">Anjali Pandey</name><name sortKey="Pandey, Anjali" sort="Pandey, Anjali" uniqKey="Pandey A" first="Anjali" last="Pandey">Anjali Pandey</name><name sortKey="Pollart, Daniel J" sort="Pollart, Daniel J" uniqKey="Pollart D" first="Daniel J." last="Pollart">Daniel J. Pollart</name><name sortKey="Pollart, Daniel J" sort="Pollart, Daniel J" uniqKey="Pollart D" first="Daniel J." last="Pollart">Daniel J. Pollart</name><name sortKey="Thomas, David W" sort="Thomas, David W" uniqKey="Thomas D" first="David W." last="Thomas">David W. Thomas</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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