Highly efficient synthesis and characterization of the GPR30-selective agonist G-1 and related tetrahydroquinoline analogs.
The GPR30 agonist probe G-1 and structural analogs were efficiently synthesized using multicomponent or stepwise Sc(III)-catalyzed aza-Diels-Alder cyclization. Optimization of solvent and reaction temperature provided enhanced endo-diastereoselectivity.
Burai
Ritwik
R
Department of Chemistry and Biochemistry MSC 3C, New Mexico State University, P.O. Box 30001, Las Cruces, New Mexico 88003, USA.
Ramesh
Chinnasamy
C
Shorty
Marvin
M
Curpan
Ramona
R
Bologa
Cristian
C
Sklar
Larry A
LA
Oprea
Tudor
T
Prossnitz
Eric R
ER
Arterburn
Jeffrey B
JB
D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D043562:Receptors, G-Protein-Coupled / Q000819:agonists*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C517943:1-(4-(6-bromobenzo(1,3)dioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta(c)quinolin-8-yl)ethanone; D003517:Cyclopentanes; D011804:Quinolines; D043562:Receptors, G-Protein-Coupled; C542964:1,2,3,4-tetrahydroquinoline
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