ChloroquineV1, PascalFrancis, Checkpoint, bibRecord, 000029

Synthesis and antimalarial activity of carbamate and amide derivatives of 4-anilinoquinoline

Identifieur interne : 000029 ( PascalFrancis/Checkpoint ); précédent : 000028; suivant : 000030

Synthesis and antimalarial activity of carbamate and amide derivatives of 4-anilinoquinoline

Auteurs : Sandrine Delarue-Cochin [France] ; Philippe Grellier [France] ; Louis Maes [Belgique] ; Elisabeth Mouray [France] ; Christian Sergheraert [France] ; Patricia Melnyk [France]

Source :

European journal of medicinal chemistry [ 0223-5234 ] ; 2008.

RBID : Pascal:08-0535287

Descripteurs français

Pascal (Inist)
- Synthèse chimique, Antipaludique, Relation structure activité, Carbamate organique, Carboxamide, Dérivé de l'aniline, Dérivé de la quinoléine, Plasmodium falciparum, Amodiaquine, Hétérocycle azote, Dérivé du benzène, Composé bicyclique, Cycle 6 chaînons, In vitro, In vivo, Chimiothérapie, Plasmodium berghei, Toxicité, Cytotoxicité, Composé aromatique, Voie orale, Paludisme, Souris, Antiparasitaire, Antiprotozoaire, Amine aromatique, Foetus, Poumon, Homme, Lignée cellulaire, Animal, Pipéridine-1-acétamide dérivé, Lignée MRC5.
Wicri :
- topic : Homme.

English descriptors

KwdEn :
- Amodiaquine, Aniline derivatives, Animal, Antimalarial, Antiprotozoal agent, Aromatic amine, Aromatic compound, Benzene derivatives, Bicyclic compound, Carboxamide, Cell line, Chemical synthesis, Chemotherapy, Cytotoxicity, Fetus, Human, In vitro, In vivo, Lung, Malaria, Mouse, Nitrogen heterocycle, Oral administration, Organic carbamate, Parasiticide, Plasmodium berghei, Plasmodium falciparum, Quinoline derivatives, Six membered ring, Structure activity relation, Toxicity.

Abstract

A series of 4-anilinoquinolines bearing an amino side chain linked to the aromatic ring with a carbamate or an amide bond were synthesized and evaluated for their antimalarial activity and their cytotoxicity upon MRC-5 cells. Among the 17 compounds, a majority was found to be active in the low nanomolar range against both chloroquine-sensitive and -resistant strains of Plasmodium falciparum in vitro with relative low cytotoxicity. Two compounds were then tested on mice infected by Plasmodium berghei and were found to exhibit reasonable in vivo activity.

Affiliations:

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Pascal:08-0535287

Le document en format XML

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<term>Aromatic amine</term>
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<front><div type="abstract" xml:lang="en">A series of 4-anilinoquinolines bearing an amino side chain linked to the aromatic ring with a carbamate or an amide bond were synthesized and evaluated for their antimalarial activity and their cytotoxicity upon MRC-5 cells. Among the 17 compounds, a majority was found to be active in the low nanomolar range against both chloroquine-sensitive and -resistant strains of Plasmodium falciparum in vitro with relative low cytotoxicity. Two compounds were then tested on mice infected by Plasmodium berghei and were found to exhibit reasonable in vivo activity.</div>
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</fC03>
<fC03 i1="07" i2="X" l="SPA"><s0>Quinolina derivado</s0>
<s2>FF</s2>
<s5>07</s5>
</fC03>
<fC03 i1="08" i2="X" l="FRE"><s0>Plasmodium falciparum</s0>
<s2>NS</s2>
<s5>09</s5>
</fC03>
<fC03 i1="08" i2="X" l="ENG"><s0>Plasmodium falciparum</s0>
<s2>NS</s2>
<s5>09</s5>
</fC03>
<fC03 i1="08" i2="X" l="SPA"><s0>Plasmodium falciparum</s0>
<s2>NS</s2>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="FRE"><s0>Amodiaquine</s0>
<s2>NK</s2>
<s2>FR</s2>
<s5>10</s5>
</fC03>
<fC03 i1="09" i2="X" l="ENG"><s0>Amodiaquine</s0>
<s2>NK</s2>
<s2>FR</s2>
<s5>10</s5>
</fC03>
<fC03 i1="09" i2="X" l="SPA"><s0>Amodiaquina</s0>
<s2>NK</s2>
<s2>FR</s2>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="FRE"><s0>Hétérocycle azote</s0>
<s5>11</s5>
</fC03>
<fC03 i1="10" i2="X" l="ENG"><s0>Nitrogen heterocycle</s0>
<s5>11</s5>
</fC03>
<fC03 i1="10" i2="X" l="SPA"><s0>Heterociclo nitrógeno</s0>
<s5>11</s5>
</fC03>
<fC03 i1="11" i2="X" l="FRE"><s0>Dérivé du benzène</s0>
<s5>12</s5>
</fC03>
<fC03 i1="11" i2="X" l="ENG"><s0>Benzene derivatives</s0>
<s5>12</s5>
</fC03>
<fC03 i1="11" i2="X" l="SPA"><s0>Benceno derivado</s0>
<s5>12</s5>
</fC03>
<fC03 i1="12" i2="X" l="FRE"><s0>Composé bicyclique</s0>
<s5>13</s5>
</fC03>
<fC03 i1="12" i2="X" l="ENG"><s0>Bicyclic compound</s0>
<s5>13</s5>
</fC03>
<fC03 i1="12" i2="X" l="SPA"><s0>Compuesto bicíclico</s0>
<s5>13</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE"><s0>Cycle 6 chaînons</s0>
<s5>14</s5>
</fC03>
<fC03 i1="13" i2="X" l="ENG"><s0>Six membered ring</s0>
<s5>14</s5>
</fC03>
<fC03 i1="13" i2="X" l="SPA"><s0>Ciclo 6 eslabones</s0>
<s5>14</s5>
</fC03>
<fC03 i1="14" i2="X" l="FRE"><s0>In vitro</s0>
<s5>15</s5>
</fC03>
<fC03 i1="14" i2="X" l="ENG"><s0>In vitro</s0>
<s5>15</s5>
</fC03>
<fC03 i1="14" i2="X" l="SPA"><s0>In vitro</s0>
<s5>15</s5>
</fC03>
<fC03 i1="15" i2="X" l="FRE"><s0>In vivo</s0>
<s5>16</s5>
</fC03>
<fC03 i1="15" i2="X" l="ENG"><s0>In vivo</s0>
<s5>16</s5>
</fC03>
<fC03 i1="15" i2="X" l="SPA"><s0>In vivo</s0>
<s5>16</s5>
</fC03>
<fC03 i1="16" i2="X" l="FRE"><s0>Chimiothérapie</s0>
<s5>17</s5>
</fC03>
<fC03 i1="16" i2="X" l="ENG"><s0>Chemotherapy</s0>
<s5>17</s5>
</fC03>
<fC03 i1="16" i2="X" l="SPA"><s0>Quimioterapia</s0>
<s5>17</s5>
</fC03>
<fC03 i1="17" i2="X" l="FRE"><s0>Plasmodium berghei</s0>
<s2>NS</s2>
<s5>19</s5>
</fC03>
<fC03 i1="17" i2="X" l="ENG"><s0>Plasmodium berghei</s0>
<s2>NS</s2>
<s5>19</s5>
</fC03>
<fC03 i1="17" i2="X" l="SPA"><s0>Plasmodium berghei</s0>
<s2>NS</s2>
<s5>19</s5>
</fC03>
<fC03 i1="18" i2="X" l="FRE"><s0>Toxicité</s0>
<s5>20</s5>
</fC03>
<fC03 i1="18" i2="X" l="ENG"><s0>Toxicity</s0>
<s5>20</s5>
</fC03>
<fC03 i1="18" i2="X" l="SPA"><s0>Toxicidad</s0>
<s5>20</s5>
</fC03>
<fC03 i1="19" i2="X" l="FRE"><s0>Cytotoxicité</s0>
<s5>21</s5>
</fC03>
<fC03 i1="19" i2="X" l="ENG"><s0>Cytotoxicity</s0>
<s5>21</s5>
</fC03>
<fC03 i1="19" i2="X" l="SPA"><s0>Citotoxicidad</s0>
<s5>21</s5>
</fC03>
<fC03 i1="20" i2="X" l="FRE"><s0>Composé aromatique</s0>
<s5>22</s5>
</fC03>
<fC03 i1="20" i2="X" l="ENG"><s0>Aromatic compound</s0>
<s5>22</s5>
</fC03>
<fC03 i1="20" i2="X" l="SPA"><s0>Compuesto aromático</s0>
<s5>22</s5>
</fC03>
<fC03 i1="21" i2="X" l="FRE"><s0>Voie orale</s0>
<s5>23</s5>
</fC03>
<fC03 i1="21" i2="X" l="ENG"><s0>Oral administration</s0>
<s5>23</s5>
</fC03>
<fC03 i1="21" i2="X" l="SPA"><s0>Vía oral</s0>
<s5>23</s5>
</fC03>
<fC03 i1="22" i2="X" l="FRE"><s0>Paludisme</s0>
<s5>24</s5>
</fC03>
<fC03 i1="22" i2="X" l="ENG"><s0>Malaria</s0>
<s5>24</s5>
</fC03>
<fC03 i1="22" i2="X" l="SPA"><s0>Paludismo</s0>
<s5>24</s5>
</fC03>
<fC03 i1="23" i2="X" l="FRE"><s0>Souris</s0>
<s5>25</s5>
</fC03>
<fC03 i1="23" i2="X" l="ENG"><s0>Mouse</s0>
<s5>25</s5>
</fC03>
<fC03 i1="23" i2="X" l="SPA"><s0>Ratón</s0>
<s5>25</s5>
</fC03>
<fC03 i1="24" i2="X" l="FRE"><s0>Antiparasitaire</s0>
<s5>32</s5>
</fC03>
<fC03 i1="24" i2="X" l="ENG"><s0>Parasiticide</s0>
<s5>32</s5>
</fC03>
<fC03 i1="24" i2="X" l="SPA"><s0>Antiparasitario</s0>
<s5>32</s5>
</fC03>
<fC03 i1="25" i2="X" l="FRE"><s0>Antiprotozoaire</s0>
<s5>33</s5>
</fC03>
<fC03 i1="25" i2="X" l="ENG"><s0>Antiprotozoal agent</s0>
<s5>33</s5>
</fC03>
<fC03 i1="25" i2="X" l="SPA"><s0>Antiprotozoario</s0>
<s5>33</s5>
</fC03>
<fC03 i1="26" i2="X" l="FRE"><s0>Amine aromatique</s0>
<s5>34</s5>
</fC03>
<fC03 i1="26" i2="X" l="ENG"><s0>Aromatic amine</s0>
<s5>34</s5>
</fC03>
<fC03 i1="26" i2="X" l="SPA"><s0>Amina aromática</s0>
<s5>34</s5>
</fC03>
<fC03 i1="27" i2="X" l="FRE"><s0>Foetus</s0>
<s5>35</s5>
</fC03>
<fC03 i1="27" i2="X" l="ENG"><s0>Fetus</s0>
<s5>35</s5>
</fC03>
<fC03 i1="27" i2="X" l="SPA"><s0>Feto</s0>
<s5>35</s5>
</fC03>
<fC03 i1="28" i2="X" l="FRE"><s0>Poumon</s0>
<s5>36</s5>
</fC03>
<fC03 i1="28" i2="X" l="ENG"><s0>Lung</s0>
<s5>36</s5>
</fC03>
<fC03 i1="28" i2="X" l="SPA"><s0>Pulmón</s0>
<s5>36</s5>
</fC03>
<fC03 i1="29" i2="X" l="FRE"><s0>Homme</s0>
<s5>37</s5>
</fC03>
<fC03 i1="29" i2="X" l="ENG"><s0>Human</s0>
<s5>37</s5>
</fC03>
<fC03 i1="29" i2="X" l="SPA"><s0>Hombre</s0>
<s5>37</s5>
</fC03>
<fC03 i1="30" i2="X" l="FRE"><s0>Lignée cellulaire</s0>
<s5>38</s5>
</fC03>
<fC03 i1="30" i2="X" l="ENG"><s0>Cell line</s0>
<s5>38</s5>
</fC03>
<fC03 i1="30" i2="X" l="SPA"><s0>Línea celular</s0>
<s5>38</s5>
</fC03>
<fC03 i1="31" i2="X" l="FRE"><s0>Animal</s0>
<s5>39</s5>
</fC03>
<fC03 i1="31" i2="X" l="ENG"><s0>Animal</s0>
<s5>39</s5>
</fC03>
<fC03 i1="31" i2="X" l="SPA"><s0>Animal</s0>
<s5>39</s5>
</fC03>
<fC03 i1="32" i2="X" l="FRE"><s0>Pipéridine-1-acétamide dérivé</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>76</s5>
</fC03>
<fC03 i1="33" i2="X" l="FRE"><s0>Lignée MRC5</s0>
<s4>INC</s4>
<s5>77</s5>
</fC03>
<fC07 i1="01" i2="X" l="FRE"><s0>Chlore Composé organique</s0>
<s2>NC</s2>
<s2>FX</s2>
<s2>NA</s2>
<s5>08</s5>
</fC07>
<fC07 i1="01" i2="X" l="ENG"><s0>Chlorine Organic compounds</s0>
<s2>NC</s2>
<s2>FX</s2>
<s2>NA</s2>
<s5>08</s5>
</fC07>
<fC07 i1="01" i2="X" l="SPA"><s0>Cloro Compuesto orgánico</s0>
<s2>NC</s2>
<s2>FX</s2>
<s2>NA</s2>
<s5>08</s5>
</fC07>
<fC07 i1="02" i2="X" l="FRE"><s0>Apicomplexa</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="02" i2="X" l="ENG"><s0>Apicomplexa</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="02" i2="X" l="SPA"><s0>Apicomplexa</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="03" i2="X" l="FRE"><s0>Protozoa</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="03" i2="X" l="ENG"><s0>Protozoa</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="03" i2="X" l="SPA"><s0>Protozoa</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="04" i2="X" l="FRE"><s0>Traitement</s0>
</fC07>
<fC07 i1="04" i2="X" l="ENG"><s0>Treatment</s0>
</fC07>
<fC07 i1="04" i2="X" l="SPA"><s0>Tratamiento</s0>
</fC07>
<fC07 i1="05" i2="X" l="FRE"><s0>Protozoose</s0>
</fC07>
<fC07 i1="05" i2="X" l="ENG"><s0>Protozoal disease</s0>
</fC07>
<fC07 i1="05" i2="X" l="SPA"><s0>Protozoosis</s0>
</fC07>
<fC07 i1="06" i2="X" l="FRE"><s0>Parasitose</s0>
</fC07>
<fC07 i1="06" i2="X" l="ENG"><s0>Parasitosis</s0>
</fC07>
<fC07 i1="06" i2="X" l="SPA"><s0>Parasitosis</s0>
</fC07>
<fC07 i1="07" i2="X" l="FRE"><s0>Infection</s0>
</fC07>
<fC07 i1="07" i2="X" l="ENG"><s0>Infection</s0>
</fC07>
<fC07 i1="07" i2="X" l="SPA"><s0>Infección</s0>
</fC07>
<fC07 i1="08" i2="X" l="FRE"><s0>Rodentia</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="08" i2="X" l="ENG"><s0>Rodentia</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="08" i2="X" l="SPA"><s0>Rodentia</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="09" i2="X" l="FRE"><s0>Mammalia</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="09" i2="X" l="ENG"><s0>Mammalia</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="09" i2="X" l="SPA"><s0>Mammalia</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="10" i2="X" l="FRE"><s0>Vertebrata</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="10" i2="X" l="ENG"><s0>Vertebrata</s0>
<s2>NS</s2>
</fC07>
<fC07 i1="10" i2="X" l="SPA"><s0>Vertebrata</s0>
<s2>NS</s2>
</fC07>
<fN21><s1>350</s1>
</fN21>
</pA>
</standard>
</inist>
<affiliations><list><country><li>Belgique</li>
<li>France</li>
</country>
<region><li>Hauts-de-France</li>
<li>Nord-Pas-de-Calais</li>
<li>Île-de-France</li>
</region>
<settlement><li>Lille</li>
<li>Paris</li>
</settlement>
</list>
<tree><country name="France"><region name="Hauts-de-France"><name sortKey="Delarue Cochin, Sandrine" sort="Delarue Cochin, Sandrine" uniqKey="Delarue Cochin S" first="Sandrine" last="Delarue-Cochin">Sandrine Delarue-Cochin</name>
</region>
<name sortKey="Grellier, Philippe" sort="Grellier, Philippe" uniqKey="Grellier P" first="Philippe" last="Grellier">Philippe Grellier</name>
<name sortKey="Melnyk, Patricia" sort="Melnyk, Patricia" uniqKey="Melnyk P" first="Patricia" last="Melnyk">Patricia Melnyk</name>
<name sortKey="Melnyk, Patricia" sort="Melnyk, Patricia" uniqKey="Melnyk P" first="Patricia" last="Melnyk">Patricia Melnyk</name>
<name sortKey="Mouray, Elisabeth" sort="Mouray, Elisabeth" uniqKey="Mouray E" first="Elisabeth" last="Mouray">Elisabeth Mouray</name>
<name sortKey="Sergheraert, Christian" sort="Sergheraert, Christian" uniqKey="Sergheraert C" first="Christian" last="Sergheraert">Christian Sergheraert</name>
</country>
<country name="Belgique"><noRegion><name sortKey="Maes, Louis" sort="Maes, Louis" uniqKey="Maes L" first="Louis" last="Maes">Louis Maes</name>
</noRegion>
</country>
</tree>
</affiliations>
</record>

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Serveur d'exploration Chloroquine

Synthesis and antimalarial activity of carbamate and amide derivatives of 4-anilinoquinoline

Synthesis and antimalarial activity of carbamate and amide derivatives of 4-anilinoquinoline

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