Chromenopyrazole, a Versatile Cannabinoid Scaffold with in Vivo Activity in a Model of Multiple Sclerosis

A combination of molecular modeling and structure activity relationship studies has been used to fine-tune CB2 selectivity in the chromenopyrazole ring, a versatile CB1/CB2 cannabinoid scaffold. Thus, a series of 36 new derivatives covering a wide range of structural diversity has been synthesized,...

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Veröffentlicht in:Journal of medicinal chemistry Jg. 59; H. 14; S. 6753 - 6771
Hauptverfasser: Morales, Paula, Gomez-Canas, Maria, Navarro, Gemma, Hurst, Dow P., Carrillo-Salinas, Francisco J., Lagartera, Laura, Pazos, Ruth, Goya, Pilar, Reggio, Patricia H., Guaza, Carmen, Franco, Rafael, Fernandez-Ruiz, Javier, Jagerovic, Nadine
Format: Journal Article
Sprache:Englisch
Veröffentlicht: WASHINGTON Amer Chemical Soc 28.07.2016
Schlagworte:
Chemistry, Medicinal
Dose-Response Relationship, Drug
HEK293 Cells
Humans
Life Sciences & Biomedicine
Models, Molecular
Molecular Structure
Multiple Sclerosis - drug therapy
Pharmacology & Pharmacy
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Pyrazoles - pharmacology
Receptor, Cannabinoid, CB1 - agonists
Receptor, Cannabinoid, CB2 - agonists
Science & Technology
Structure-Activity Relationship
TARGET
SELECTIVE LIGANDS
LIGAND-BINDING
THEILERS-VIRUS
PROTEIN-COUPLED RECEPTOR
CB2 RECEPTOR
DISEASE
ENDOCANNABINOID SYSTEM
EXPRESSION
AGONISTS
ISSN:0022-2623, 1520-4804, 1520-4804
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Abstract A combination of molecular modeling and structure activity relationship studies has been used to fine-tune CB2 selectivity in the chromenopyrazole ring, a versatile CB1/CB2 cannabinoid scaffold. Thus, a series of 36 new derivatives covering a wide range of structural diversity has been synthesized, and docking studies have been performed for some of them. Biological evaluation of the new compounds includes, among others, cannabinoid binding assays, functional studies, and surface plasmon resonance measurements. The most promising compound [43 (PM226)], a selective and potent CB2 agonist isoxazole derivative, was tested in the acute phase of Theiler's murine encephalomyelitis virus-induced demyelinating disease (TMEV-IDD), a well established animal model of primary progressive multiple sclerosis. Compound 43 dampened neuroinflammation by reducing microglial activation in the TMEV.
AbstractList A combination of molecular modeling and structure-activity relationship studies has been used to fine-tune CB2 selectivity in the chromenopyrazole ring, a versatile CB1/CB2 cannabinoid scaffold. Thus, a series of 36 new derivatives covering a wide range of structural diversity has been synthesized, and docking studies have been performed for some of them. Biological evaluation of the new compounds includes, among others, cannabinoid binding assays, functional studies, and surface plasmon resonance measurements. The most promising compound [43 (PM226)], a selective and potent CB2 agonist isoxazole derivative, was tested in the acute phase of Theiler's murine encephalomyelitis virus-induced demyelinating disease (TMEV-IDD), a well-established animal model of primary progressive multiple sclerosis. Compound 43 dampened neuroinflammation by reducing microglial activation in the TMEV.
A combination of molecular modeling and structure-activity relationship studies has been used to fine-tune CB2 selectivity in the chromenopyrazole ring, a versatile CB1/CB2 cannabinoid scaffold. Thus, a series of 36 new derivatives covering a wide range of structural diversity has been synthesized, and docking studies have been performed for some of them. Biological evaluation of the new compounds includes, among others, cannabinoid binding assays, functional studies, and surface plasmon resonance measurements. The most promising compound [43 (PM226)], a selective and potent CB2 agonist isoxazole derivative, was tested in the acute phase of Theiler's murine encephalomyelitis virus-induced demyelinating disease (TMEV-IDD), a well-established animal model of primary progressive multiple sclerosis. Compound 43 dampened neuroinflammation by reducing microglial activation in the TMEV.A combination of molecular modeling and structure-activity relationship studies has been used to fine-tune CB2 selectivity in the chromenopyrazole ring, a versatile CB1/CB2 cannabinoid scaffold. Thus, a series of 36 new derivatives covering a wide range of structural diversity has been synthesized, and docking studies have been performed for some of them. Biological evaluation of the new compounds includes, among others, cannabinoid binding assays, functional studies, and surface plasmon resonance measurements. The most promising compound [43 (PM226)], a selective and potent CB2 agonist isoxazole derivative, was tested in the acute phase of Theiler's murine encephalomyelitis virus-induced demyelinating disease (TMEV-IDD), a well-established animal model of primary progressive multiple sclerosis. Compound 43 dampened neuroinflammation by reducing microglial activation in the TMEV.
Author Jagerovic, Nadine
Navarro, Gemma
Lagartera, Laura
Guaza, Carmen
Reggio, Patricia H.
Pazos, Ruth
Fernandez-Ruiz, Javier
Carrillo-Salinas, Francisco J.
Morales, Paula
Hurst, Dow P.
Gomez-Canas, Maria
Goya, Pilar
Franco, Rafael
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  orcidid: 0000-0003-2549-4919
  surname: Franco
  fullname: Franco, Rafael
  organization: Univ Barcelona, Fac Biol, Dept Bioquim & Biol Mol, E-08028 Barcelona, Spain
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  givenname: Javier
  surname: Fernandez-Ruiz
  fullname: Fernandez-Ruiz, Javier
  organization: Univ Complutense Madrid, Inst Univ Invest Neuroquim, Dept Bioquim & Biol Mol, Fac Med, E-28040 Madrid, Spain
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  givenname: Nadine
  orcidid: 0000-0003-2642-6969
  surname: Jagerovic
  fullname: Jagerovic, Nadine
  email: nadine@iqm.csic.es
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/27309150$$D View this record in MEDLINE/PubMed
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Issue 14
Keywords TARGET
SELECTIVE LIGANDS
LIGAND-BINDING
THEILERS-VIRUS
PROTEIN-COUPLED RECEPTOR
CB2 RECEPTOR
DISEASE
ENDOCANNABINOID SYSTEM
EXPRESSION
AGONISTS
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Snippet A combination of molecular modeling and structure activity relationship studies has been used to fine-tune CB2 selectivity in the chromenopyrazole ring, a...
A combination of molecular modeling and structure-activity relationship studies has been used to fine-tune CB2 selectivity in the chromenopyrazole ring, a...
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webofscience
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StartPage 6753
SubjectTerms Chemistry, Medicinal
Dose-Response Relationship, Drug
HEK293 Cells
Humans
Life Sciences & Biomedicine
Models, Molecular
Molecular Structure
Multiple Sclerosis - drug therapy
Pharmacology & Pharmacy
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Pyrazoles - pharmacology
Receptor, Cannabinoid, CB1 - agonists
Receptor, Cannabinoid, CB2 - agonists
Science & Technology
Structure-Activity Relationship
Title Chromenopyrazole, a Versatile Cannabinoid Scaffold with in Vivo Activity in a Model of Multiple Sclerosis
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https://www.ncbi.nlm.nih.gov/pubmed/27309150
https://www.proquest.com/docview/1807897328
Volume 59
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