Synthesis and Analgesic Activity of New Analogs of 1-[1-phenylcyclohexyl]piperidine with Modified Structures in its Tricyclic System
1-[1-Phenylcyclohexyl]piperidine (Phencyclidine, PCP) is a tricyclic compound with an aromatic ring that can create a negative charge area, a fundamental heterocyclic nitrogen ring that bears a local positive charge and a cycloalkyl ring that has a lipophilic character. This compound and its analogs are very potent and vastly abused psychotomimetic drugs that affect the central nervous system. Some analogs of PCP are prepared by replacements in substitution on this tricyclic structure for obtaining new ones with extra analgesic activities. New derivatives (II-IV) were synthesized with changing of substituting on aromatic, cyclohexyl, and amine moieties of PCP. In vivo evaluation of acute and chronic pain activities of the new compounds were carried out by applying tail immersion and formalin tests on mice. Then the results were compared with control and PCP groups at 10 mg/kg dosage. Obtained results suggested compounds II and IV showed better activity to decrease acute thermal and chemical pains, respectively, compared with other compounds (III) and PCP animal groups which may concern more nociception opioid receptor (NOP) antagonistic characterizes and a close affinity for NMDAantagonists in the family. It is concluded that compound II with three and compound IV with two changing moieties of PCP on phenyl, cyclohexyl, and amine rings were suitable candidates to reduce acute thermal and chronic chemical pains in Tail immersion and formalin tests, respectively..
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:57 |
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| Enthalten in: |
Pharmaceutical chemistry journal - 57(2023), 5 vom: Aug., Seite 656-662 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Shokrollahi, Maryam [VerfasserIn] |
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| Links: |
Volltext [lizenzpflichtig] |
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| Themen: |
Phencyclidine |
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| Anmerkungen: |
© Springer Science+Business Media, LLC, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. |
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| doi: |
10.1007/s11094-023-02934-w |
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| funding: |
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| Förderinstitution / Projekttitel: |
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SPR053163907 |
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| 520 | |a 1-[1-Phenylcyclohexyl]piperidine (Phencyclidine, PCP) is a tricyclic compound with an aromatic ring that can create a negative charge area, a fundamental heterocyclic nitrogen ring that bears a local positive charge and a cycloalkyl ring that has a lipophilic character. This compound and its analogs are very potent and vastly abused psychotomimetic drugs that affect the central nervous system. Some analogs of PCP are prepared by replacements in substitution on this tricyclic structure for obtaining new ones with extra analgesic activities. New derivatives (II-IV) were synthesized with changing of substituting on aromatic, cyclohexyl, and amine moieties of PCP. In vivo evaluation of acute and chronic pain activities of the new compounds were carried out by applying tail immersion and formalin tests on mice. Then the results were compared with control and PCP groups at 10 mg/kg dosage. Obtained results suggested compounds II and IV showed better activity to decrease acute thermal and chemical pains, respectively, compared with other compounds (III) and PCP animal groups which may concern more nociception opioid receptor (NOP) antagonistic characterizes and a close affinity for NMDAantagonists in the family. It is concluded that compound II with three and compound IV with two changing moieties of PCP on phenyl, cyclohexyl, and amine rings were suitable candidates to reduce acute thermal and chronic chemical pains in Tail immersion and formalin tests, respectively. | ||
| 650 | 4 | |a Phencyclidine |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Tricyclic structure compound |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Tail Immersion and formalin tests |7 (dpeaa)DE-He213 | |
| 700 | 1 | |a Sobhanian, Seyed Ali |4 aut | |
| 700 | 1 | |a Khalili, Mohsen |4 aut | |
| 700 | 1 | |a Ahmadi, Abbas |4 aut | |
| 700 | 1 | |a Barzin, Mahnaz |4 aut | |
| 700 | 1 | |a Pooladi, Mohsen |4 aut | |
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