SrasV1, Main, Exploration, bibRecord, 006468

Synthesis and antiviral/antitumor evaluation of 2-amino- and 2-carboxamido-3-arylsulfonylthiophenes and related compounds as a new class of diarylsulfones

Identifieur interne : 006468 ( Main/Exploration ); précédent : 006467; suivant : 006469

Synthesis and antiviral/antitumor evaluation of 2-amino- and 2-carboxamido-3-arylsulfonylthiophenes and related compounds as a new class of diarylsulfones

Auteurs : Chad E. Stephens [États-Unis] ; Takita M. Felder [États-Unis] ; J. Walter Sr Sowell [États-Unis] ; Graciela Andrei [Belgique] ; Jan Balzarini [Belgique] ; Robert Snoeck [Belgique] ; Erik De Clercq [Belgique]

Source :

Bioorganic & medicinal chemistry [ 0968-0896 ] ; 2001.

RBID : Pascal:01-0300988

Descripteurs français

English descriptors

KwdEn :
- Anti-HIV Agents (chemical synthesis), Anti-HIV Agents (pharmacology), Anti-HIV Agents (therapeutic use), Antineoplastic Agents (chemical synthesis), Antineoplastic Agents (pharmacology), Antineoplastic Agents (therapeutic use), Antiviral, Antiviral Agents (chemical synthesis), Antiviral Agents (pharmacology), Arylsulfonic Acids (chemical synthesis), Benzene derivatives, Breast Neoplasms (drug therapy), Carboxamide, Cells, Cultured, Chemical synthesis, Colonic Neoplasms (drug therapy), Cytomegalovirus, Cytomegalovirus (drug effects), HIV-1 (drug effects), HIV-1 virus, HIV-2 (drug effects), Humans, In vitro, Inhibitory Concentration 50, Leukemia (drug therapy), Nitrogen heterocycle, Simplexvirus (drug effects), Structure activity relation, Sulfone, Sulfur heterocycle, Thiophene derivatives, Thiophenes (chemical synthesis), Thiophenes (pharmacology), Thiophenes (therapeutic use), Varicella zoster virus.
MESH :
- chemical , chemical synthesis : Anti-HIV Agents, Antineoplastic Agents, Antiviral Agents, Arylsulfonic Acids, Thiophenes.
- chemical , pharmacology : Anti-HIV Agents, Antineoplastic Agents, Antiviral Agents, Thiophenes.
- chemical , therapeutic use : Anti-HIV Agents, Antineoplastic Agents, Thiophenes.
- drug effects : Cytomegalovirus, HIV-1, HIV-2, Simplexvirus.
- drug therapy : Breast Neoplasms, Colonic Neoplasms, Leukemia.
- Cells, Cultured, Humans, Inhibitory Concentration 50.

Abstract

Based on general SARs previously described for anti-HIV-I diarylsulfone derivatives, a series of 2-amino- and 2-carboxamido-3-arylsulfonylthiophenes has been prepared and evaluated as potential antiviral and antitumor agents. In cell culture, some of the 2-aminothiophenes exhibited moderate and selective activity against HIV-1, with 2-amino-3-(2-nitro-phenylsulfonyl)thiophene (7e) being most attractive (EC₅₀ = 3.8 μg/mL, CC₅₀ = > 100 μg/mL). In broad-spectrum antiviral assays, the 3-arylsulfonyl-2-(trifluoroacetamido)thiophenes (8c-g) and 2-acetamido-3-arylsulfonyl-5-nitrothiophenes (9f-g) proved considerably active (IC₅₀ = 0.1-10 μg/mL) against human cytomegalovirus (CMV) and/or varicella zoster virus (VZV). Based on the activity of the trifluoroacetamides, ring-modified furan, N-(substituted)pyrrole, phenyl, and 3,4-thiophene analogues were prepared, and these compounds were also active against CMV and/or VZV, with the notable exception of the 3,4-thiophene derivative. In contrast to other amines, the 2-aminopyrrole precursors (13a-d) also exhibited potent activity against CMV. Unfortunately, most of these compounds displayed significant cytotoxicity against human fibroblasts, the cells supporting CMV and VZV replication, and thus selectivity indices were low. The most notable exception to this was the naphthyl-substituted aminopyrrole 13d, which exhibited both potent (IC₅₀ = 0.3 3 μg/mL) and selective (CC₅₀ = > 50 μg/mL) activity against CMV. Finally, thiophene aryl amides 8i k displayed moderate in vitro activity against certain leukemia, breast, and colon cancer cell lines.

Affiliations:

Le document en format XML

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</placeName>
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</affiliation>
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<author><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name>
<affiliation wicri:level="4"><inist:fA14 i1="02"><s1>Rega Institute of Medical Research, Katholieke Universiteit Leuven</s1>
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<term>Anti-HIV Agents (pharmacology)</term>
<term>Anti-HIV Agents (therapeutic use)</term>
<term>Antineoplastic Agents (chemical synthesis)</term>
<term>Antineoplastic Agents (pharmacology)</term>
<term>Antineoplastic Agents (therapeutic use)</term>
<term>Antiviral</term>
<term>Antiviral Agents (chemical synthesis)</term>
<term>Antiviral Agents (pharmacology)</term>
<term>Arylsulfonic Acids (chemical synthesis)</term>
<term>Benzene derivatives</term>
<term>Breast Neoplasms (drug therapy)</term>
<term>Carboxamide</term>
<term>Cells, Cultured</term>
<term>Chemical synthesis</term>
<term>Colonic Neoplasms (drug therapy)</term>
<term>Cytomegalovirus</term>
<term>Cytomegalovirus (drug effects)</term>
<term>HIV-1 (drug effects)</term>
<term>HIV-1 virus</term>
<term>HIV-2 (drug effects)</term>
<term>Humans</term>
<term>In vitro</term>
<term>Inhibitory Concentration 50</term>
<term>Leukemia (drug therapy)</term>
<term>Nitrogen heterocycle</term>
<term>Simplexvirus (drug effects)</term>
<term>Structure activity relation</term>
<term>Sulfone</term>
<term>Sulfur heterocycle</term>
<term>Thiophene derivatives</term>
<term>Thiophenes (chemical synthesis)</term>
<term>Thiophenes (pharmacology)</term>
<term>Thiophenes (therapeutic use)</term>
<term>Varicella zoster virus</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Acides arènesulfoniques (synthèse chimique)</term>
<term>Agents antiVIH (pharmacologie)</term>
<term>Agents antiVIH (synthèse chimique)</term>
<term>Agents antiVIH (usage thérapeutique)</term>
<term>Antinéoplasiques (pharmacologie)</term>
<term>Antinéoplasiques (synthèse chimique)</term>
<term>Antinéoplasiques (usage thérapeutique)</term>
<term>Antiviraux (pharmacologie)</term>
<term>Antiviraux (synthèse chimique)</term>
<term>Cellules cultivées</term>
<term>Concentration inhibitrice 50</term>
<term>Cytomegalovirus ()</term>
<term>Humains</term>
<term>Leucémies (traitement médicamenteux)</term>
<term>Simplexvirus ()</term>
<term>Thiophènes (pharmacologie)</term>
<term>Thiophènes (synthèse chimique)</term>
<term>Thiophènes (usage thérapeutique)</term>
<term>Tumeurs du côlon (traitement médicamenteux)</term>
<term>Tumeurs du sein (traitement médicamenteux)</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term>
<term>VIH-2 (Virus de l'Immunodéficience Humaine de type 2) ()</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Anti-HIV Agents</term>
<term>Antineoplastic Agents</term>
<term>Antiviral Agents</term>
<term>Arylsulfonic Acids</term>
<term>Thiophenes</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Anti-HIV Agents</term>
<term>Antineoplastic Agents</term>
<term>Antiviral Agents</term>
<term>Thiophenes</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="therapeutic use" xml:lang="en"><term>Anti-HIV Agents</term>
<term>Antineoplastic Agents</term>
<term>Thiophenes</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Cytomegalovirus</term>
<term>HIV-1</term>
<term>HIV-2</term>
<term>Simplexvirus</term>
</keywords>
<keywords scheme="MESH" qualifier="drug therapy" xml:lang="en"><term>Breast Neoplasms</term>
<term>Colonic Neoplasms</term>
<term>Leukemia</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Agents antiVIH</term>
<term>Antinéoplasiques</term>
<term>Antiviraux</term>
<term>Thiophènes</term>
</keywords>
<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Acides arènesulfoniques</term>
<term>Agents antiVIH</term>
<term>Antinéoplasiques</term>
<term>Antiviraux</term>
<term>Thiophènes</term>
</keywords>
<keywords scheme="MESH" qualifier="traitement médicamenteux" xml:lang="fr"><term>Leucémies</term>
<term>Tumeurs du côlon</term>
<term>Tumeurs du sein</term>
</keywords>
<keywords scheme="MESH" qualifier="usage thérapeutique" xml:lang="fr"><term>Agents antiVIH</term>
<term>Antinéoplasiques</term>
<term>Thiophènes</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Cells, Cultured</term>
<term>Humans</term>
<term>Inhibitory Concentration 50</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Cellules cultivées</term>
<term>Concentration inhibitrice 50</term>
<term>Cytomegalovirus</term>
<term>Humains</term>
<term>Relation structure activité</term>
<term>Simplexvirus</term>
<term>Synthèse chimique</term>
<term>Sulfone</term>
<term>Carboxamide</term>
<term>Hétérocycle soufre</term>
<term>Hétérocycle azote</term>
<term>Thiophène dérivé</term>
<term>Benzène dérivé</term>
<term>Antiviral</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term>
<term>VIH-2 (Virus de l'Immunodéficience Humaine de type 2)</term>
<term>Virus HIV1</term>
<term>Cytomegalovirus</term>
<term>Virus varicelle</term>
<term>In vitro</term>
<term>Acétamide(N-[3-([4-chlorobenzène]sulfonyl)-2-thiényl]-trifluoro)</term>
<term>Pyrrole(2-amino-3-[(4-chlorobenzène)sulfonyl]-4,5-diméthyl-1-[(1-naphtyl)méthyl])</term>
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</teiHeader>
<front><div type="abstract" xml:lang="en">Based on general SARs previously described for anti-HIV-I diarylsulfone derivatives, a series of 2-amino- and 2-carboxamido-3-arylsulfonylthiophenes has been prepared and evaluated as potential antiviral and antitumor agents. In cell culture, some of the 2-aminothiophenes exhibited moderate and selective activity against HIV-1, with 2-amino-3-(2-nitro-phenylsulfonyl)thiophene (7e) being most attractive (EC<sub>50</sub>
 = 3.8 μg/mL, CC<sub>50</sub>
 = > 100 μg/mL). In broad-spectrum antiviral assays, the 3-arylsulfonyl-2-(trifluoroacetamido)thiophenes (8c-g) and 2-acetamido-3-arylsulfonyl-5-nitrothiophenes (9f-g) proved considerably active (IC<sub>50</sub>
 = 0.1-10 μg/mL) against human cytomegalovirus (CMV) and/or varicella zoster virus (VZV). Based on the activity of the trifluoroacetamides, ring-modified furan, N-(substituted)pyrrole, phenyl, and 3,4-thiophene analogues were prepared, and these compounds were also active against CMV and/or VZV, with the notable exception of the 3,4-thiophene derivative. In contrast to other amines, the 2-aminopyrrole precursors (13a-d) also exhibited potent activity against CMV. Unfortunately, most of these compounds displayed significant cytotoxicity against human fibroblasts, the cells supporting CMV and VZV replication, and thus selectivity indices were low. The most notable exception to this was the naphthyl-substituted aminopyrrole 13d, which exhibited both potent (IC<sub>50</sub>
 = 0.3 3 μg/mL) and selective (CC<sub>50</sub>
 = > 50 μg/mL) activity against CMV. Finally, thiophene aryl amides 8i k displayed moderate in vitro activity against certain leukemia, breast, and colon cancer cell lines.</div>
</front>
</TEI>
<affiliations><list><country><li>Belgique</li>
<li>États-Unis</li>
</country>
<region><li>Caroline du Sud</li>
<li>Province du Brabant flamand</li>
</region>
<settlement><li>Columbia (Caroline du Sud)</li>
<li>Louvain</li>
</settlement>
<orgName><li>Katholieke Universiteit Leuven</li>
<li>Université de Caroline du Sud</li>
</orgName>
</list>
<tree><country name="États-Unis"><region name="Caroline du Sud"><name sortKey="Stephens, Chad E" sort="Stephens, Chad E" uniqKey="Stephens C" first="Chad E." last="Stephens">Chad E. Stephens</name>
</region>
<name sortKey="Felder, Takita M" sort="Felder, Takita M" uniqKey="Felder T" first="Takita M." last="Felder">Takita M. Felder</name>
<name sortKey="Sowell, J Walter Sr" sort="Sowell, J Walter Sr" uniqKey="Sowell J" first="J. Walter Sr" last="Sowell">J. Walter Sr Sowell</name>
</country>
<country name="Belgique"><region name="Province du Brabant flamand"><name sortKey="Andrei, Graciela" sort="Andrei, Graciela" uniqKey="Andrei G" first="Graciela" last="Andrei">Graciela Andrei</name>
</region>
<name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name>
<name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name>
<name sortKey="Snoeck, Robert" sort="Snoeck, Robert" uniqKey="Snoeck R" first="Robert" last="Snoeck">Robert Snoeck</name>
</country>
</tree>
</affiliations>
</record>

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Synthesis and antiviral/antitumor evaluation of 2-amino- and 2-carboxamido-3-arylsulfonylthiophenes and related compounds as a new class of diarylsulfones

Synthesis and antiviral/antitumor evaluation of 2-amino- and 2-carboxamido-3-arylsulfonylthiophenes and related compounds as a new class of diarylsulfones

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