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Novel pyrrolocycloalkylpyrazole analogues as CB1 ligands
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| Zeitschriftentitel: | Chemical Biology & Drug Design |
|---|---|
| Personen und Körperschaften: | , , , , , , , , |
| In: | Chemical Biology & Drug Design, 91, 2018, 1, S. 181-193 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
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| Schlagwörter: |
| author_facet |
Asproni, Battistina Manca, Ilaria Pinna, Giansalvo Cichero, Elena Fossa, Paola Murineddu, Gabriele Lazzari, Paolo Loriga, Giovanni Pinna, Gérard A. Asproni, Battistina Manca, Ilaria Pinna, Giansalvo Cichero, Elena Fossa, Paola Murineddu, Gabriele Lazzari, Paolo Loriga, Giovanni Pinna, Gérard A. |
|---|---|
| author |
Asproni, Battistina Manca, Ilaria Pinna, Giansalvo Cichero, Elena Fossa, Paola Murineddu, Gabriele Lazzari, Paolo Loriga, Giovanni Pinna, Gérard A. |
| spellingShingle |
Asproni, Battistina Manca, Ilaria Pinna, Giansalvo Cichero, Elena Fossa, Paola Murineddu, Gabriele Lazzari, Paolo Loriga, Giovanni Pinna, Gérard A. Chemical Biology & Drug Design Novel pyrrolocycloalkylpyrazole analogues as CB1 ligands Molecular Medicine Biochemistry Drug Discovery Pharmacology Organic Chemistry |
| author_sort |
asproni, battistina |
| spelling |
Asproni, Battistina Manca, Ilaria Pinna, Giansalvo Cichero, Elena Fossa, Paola Murineddu, Gabriele Lazzari, Paolo Loriga, Giovanni Pinna, Gérard A. 1747-0277 1747-0285 Wiley Molecular Medicine Biochemistry Drug Discovery Pharmacology Organic Chemistry http://dx.doi.org/10.1111/cbdd.13069 <jats:p>Novel 1,4‐dihydropyrazolo[3,4‐<jats:italic>a</jats:italic>]pyrrolizine‐, 4,5‐dihydro‐1<jats:italic>H</jats:italic>‐pyrazolo[4,3‐<jats:italic>g</jats:italic>]indolizine‐ and 1,4,5,6‐tetrahydropyrazolo[3,4‐<jats:italic>c</jats:italic>]pyrrolo[1,2‐<jats:italic>a</jats:italic>]azepine‐3‐carboxamide‐based compounds were designed and synthesized for cannabinoid <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> and <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>2</jats:sub> receptor interactions. Any of the new synthesized compounds showed high affinity for <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>2</jats:sub> receptor with <jats:italic>K</jats:italic><jats:sub><jats:italic>i</jats:italic></jats:sub> values superior to 314 n<jats:sc>m</jats:sc>, whereas some of them showed moderate affinity for <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> receptor with <jats:italic>K</jats:italic><jats:sub><jats:italic>i</jats:italic></jats:sub> values inferior to 400 n<jats:sc>m</jats:sc>. 7‐Chloro‐1‐(2,4‐dichlorophenyl)<jats:italic>‐N‐</jats:italic>(homopiperidin‐1‐yl)‐4,5‐dihydro‐1<jats:italic>H</jats:italic>‐pyrazolo[4,3<jats:italic>‐g</jats:italic>]indolizine‐3‐carboxamide (<jats:bold>2j</jats:bold>) exhibited good affinity for <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> receptor (<jats:italic>K</jats:italic><jats:sub><jats:italic>i</jats:italic></jats:sub><jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> = 81 n<jats:sc>m</jats:sc>) and the highest <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>2</jats:sub>/<jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> selectively ratio (>12). Docking studies carried out on such compounds were performed using the <jats:styled-content style="fixed-case">hCB</jats:styled-content><jats:sub>1</jats:sub> X‐ray in complex with the close pyrazole analogue <jats:styled-content style="fixed-case">AM</jats:styled-content>6538 and disclosed specific pattern of interactions related to the tricyclic pyrrolopyrazole scaffolds as <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> ligands.</jats:p> Novel pyrrolocycloalkylpyrazole analogues as CB<sub>1</sub> ligands Chemical Biology & Drug Design |
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10.1111/cbdd.13069 |
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Online |
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Medizin Chemie und Pharmazie |
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ElectronicArticle |
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| imprint |
Wiley, 2018 |
| imprint_str_mv |
Wiley, 2018 |
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1747-0277 1747-0285 |
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English |
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asproni2018novelpyrrolocycloalkylpyrazoleanaloguesascb1ligands |
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2018 |
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Wiley |
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ai |
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ai |
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Chemical Biology & Drug Design |
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49 |
| title |
Novel pyrrolocycloalkylpyrazole analogues as CB1 ligands |
| title_unstemmed |
Novel pyrrolocycloalkylpyrazole analogues as CB1 ligands |
| title_full |
Novel pyrrolocycloalkylpyrazole analogues as CB1 ligands |
| title_fullStr |
Novel pyrrolocycloalkylpyrazole analogues as CB1 ligands |
| title_full_unstemmed |
Novel pyrrolocycloalkylpyrazole analogues as CB1 ligands |
| title_short |
Novel pyrrolocycloalkylpyrazole analogues as CB1 ligands |
| title_sort |
novel pyrrolocycloalkylpyrazole analogues as cb<sub>1</sub> ligands |
| topic |
Molecular Medicine Biochemistry Drug Discovery Pharmacology Organic Chemistry |
| url |
http://dx.doi.org/10.1111/cbdd.13069 |
| publishDate |
2018 |
| physical |
181-193 |
| description |
<jats:p>Novel 1,4‐dihydropyrazolo[3,4‐<jats:italic>a</jats:italic>]pyrrolizine‐, 4,5‐dihydro‐1<jats:italic>H</jats:italic>‐pyrazolo[4,3‐<jats:italic>g</jats:italic>]indolizine‐ and 1,4,5,6‐tetrahydropyrazolo[3,4‐<jats:italic>c</jats:italic>]pyrrolo[1,2‐<jats:italic>a</jats:italic>]azepine‐3‐carboxamide‐based compounds were designed and synthesized for cannabinoid <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> and <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>2</jats:sub> receptor interactions. Any of the new synthesized compounds showed high affinity for <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>2</jats:sub> receptor with <jats:italic>K</jats:italic><jats:sub><jats:italic>i</jats:italic></jats:sub> values superior to 314 n<jats:sc>m</jats:sc>, whereas some of them showed moderate affinity for <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> receptor with <jats:italic>K</jats:italic><jats:sub><jats:italic>i</jats:italic></jats:sub> values inferior to 400 n<jats:sc>m</jats:sc>. 7‐Chloro‐1‐(2,4‐dichlorophenyl)<jats:italic>‐N‐</jats:italic>(homopiperidin‐1‐yl)‐4,5‐dihydro‐1<jats:italic>H</jats:italic>‐pyrazolo[4,3<jats:italic>‐g</jats:italic>]indolizine‐3‐carboxamide (<jats:bold>2j</jats:bold>) exhibited good affinity for <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> receptor (<jats:italic>K</jats:italic><jats:sub><jats:italic>i</jats:italic></jats:sub><jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> = 81 n<jats:sc>m</jats:sc>) and the highest <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>2</jats:sub>/<jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> selectively ratio (>12). Docking studies carried out on such compounds were performed using the <jats:styled-content style="fixed-case">hCB</jats:styled-content><jats:sub>1</jats:sub> X‐ray in complex with the close pyrazole analogue <jats:styled-content style="fixed-case">AM</jats:styled-content>6538 and disclosed specific pattern of interactions related to the tricyclic pyrrolopyrazole scaffolds as <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> ligands.</jats:p> |
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| author | Asproni, Battistina, Manca, Ilaria, Pinna, Giansalvo, Cichero, Elena, Fossa, Paola, Murineddu, Gabriele, Lazzari, Paolo, Loriga, Giovanni, Pinna, Gérard A. |
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| description | <jats:p>Novel 1,4‐dihydropyrazolo[3,4‐<jats:italic>a</jats:italic>]pyrrolizine‐, 4,5‐dihydro‐1<jats:italic>H</jats:italic>‐pyrazolo[4,3‐<jats:italic>g</jats:italic>]indolizine‐ and 1,4,5,6‐tetrahydropyrazolo[3,4‐<jats:italic>c</jats:italic>]pyrrolo[1,2‐<jats:italic>a</jats:italic>]azepine‐3‐carboxamide‐based compounds were designed and synthesized for cannabinoid <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> and <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>2</jats:sub> receptor interactions. Any of the new synthesized compounds showed high affinity for <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>2</jats:sub> receptor with <jats:italic>K</jats:italic><jats:sub><jats:italic>i</jats:italic></jats:sub> values superior to 314 n<jats:sc>m</jats:sc>, whereas some of them showed moderate affinity for <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> receptor with <jats:italic>K</jats:italic><jats:sub><jats:italic>i</jats:italic></jats:sub> values inferior to 400 n<jats:sc>m</jats:sc>. 7‐Chloro‐1‐(2,4‐dichlorophenyl)<jats:italic>‐N‐</jats:italic>(homopiperidin‐1‐yl)‐4,5‐dihydro‐1<jats:italic>H</jats:italic>‐pyrazolo[4,3<jats:italic>‐g</jats:italic>]indolizine‐3‐carboxamide (<jats:bold>2j</jats:bold>) exhibited good affinity for <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> receptor (<jats:italic>K</jats:italic><jats:sub><jats:italic>i</jats:italic></jats:sub><jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> = 81 n<jats:sc>m</jats:sc>) and the highest <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>2</jats:sub>/<jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> selectively ratio (>12). Docking studies carried out on such compounds were performed using the <jats:styled-content style="fixed-case">hCB</jats:styled-content><jats:sub>1</jats:sub> X‐ray in complex with the close pyrazole analogue <jats:styled-content style="fixed-case">AM</jats:styled-content>6538 and disclosed specific pattern of interactions related to the tricyclic pyrrolopyrazole scaffolds as <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> ligands.</jats:p> |
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| spelling | Asproni, Battistina Manca, Ilaria Pinna, Giansalvo Cichero, Elena Fossa, Paola Murineddu, Gabriele Lazzari, Paolo Loriga, Giovanni Pinna, Gérard A. 1747-0277 1747-0285 Wiley Molecular Medicine Biochemistry Drug Discovery Pharmacology Organic Chemistry http://dx.doi.org/10.1111/cbdd.13069 <jats:p>Novel 1,4‐dihydropyrazolo[3,4‐<jats:italic>a</jats:italic>]pyrrolizine‐, 4,5‐dihydro‐1<jats:italic>H</jats:italic>‐pyrazolo[4,3‐<jats:italic>g</jats:italic>]indolizine‐ and 1,4,5,6‐tetrahydropyrazolo[3,4‐<jats:italic>c</jats:italic>]pyrrolo[1,2‐<jats:italic>a</jats:italic>]azepine‐3‐carboxamide‐based compounds were designed and synthesized for cannabinoid <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> and <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>2</jats:sub> receptor interactions. Any of the new synthesized compounds showed high affinity for <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>2</jats:sub> receptor with <jats:italic>K</jats:italic><jats:sub><jats:italic>i</jats:italic></jats:sub> values superior to 314 n<jats:sc>m</jats:sc>, whereas some of them showed moderate affinity for <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> receptor with <jats:italic>K</jats:italic><jats:sub><jats:italic>i</jats:italic></jats:sub> values inferior to 400 n<jats:sc>m</jats:sc>. 7‐Chloro‐1‐(2,4‐dichlorophenyl)<jats:italic>‐N‐</jats:italic>(homopiperidin‐1‐yl)‐4,5‐dihydro‐1<jats:italic>H</jats:italic>‐pyrazolo[4,3<jats:italic>‐g</jats:italic>]indolizine‐3‐carboxamide (<jats:bold>2j</jats:bold>) exhibited good affinity for <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> receptor (<jats:italic>K</jats:italic><jats:sub><jats:italic>i</jats:italic></jats:sub><jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> = 81 n<jats:sc>m</jats:sc>) and the highest <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>2</jats:sub>/<jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> selectively ratio (>12). Docking studies carried out on such compounds were performed using the <jats:styled-content style="fixed-case">hCB</jats:styled-content><jats:sub>1</jats:sub> X‐ray in complex with the close pyrazole analogue <jats:styled-content style="fixed-case">AM</jats:styled-content>6538 and disclosed specific pattern of interactions related to the tricyclic pyrrolopyrazole scaffolds as <jats:styled-content style="fixed-case">CB</jats:styled-content><jats:sub>1</jats:sub> ligands.</jats:p> Novel pyrrolocycloalkylpyrazole analogues as CB<sub>1</sub> ligands Chemical Biology & Drug Design |
| spellingShingle | Asproni, Battistina, Manca, Ilaria, Pinna, Giansalvo, Cichero, Elena, Fossa, Paola, Murineddu, Gabriele, Lazzari, Paolo, Loriga, Giovanni, Pinna, Gérard A., Chemical Biology & Drug Design, Novel pyrrolocycloalkylpyrazole analogues as CB1 ligands, Molecular Medicine, Biochemistry, Drug Discovery, Pharmacology, Organic Chemistry |
| title | Novel pyrrolocycloalkylpyrazole analogues as CB1 ligands |
| title_full | Novel pyrrolocycloalkylpyrazole analogues as CB1 ligands |
| title_fullStr | Novel pyrrolocycloalkylpyrazole analogues as CB1 ligands |
| title_full_unstemmed | Novel pyrrolocycloalkylpyrazole analogues as CB1 ligands |
| title_short | Novel pyrrolocycloalkylpyrazole analogues as CB1 ligands |
| title_sort | novel pyrrolocycloalkylpyrazole analogues as cb<sub>1</sub> ligands |
| title_unstemmed | Novel pyrrolocycloalkylpyrazole analogues as CB1 ligands |
| topic | Molecular Medicine, Biochemistry, Drug Discovery, Pharmacology, Organic Chemistry |
| url | http://dx.doi.org/10.1111/cbdd.13069 |