title: Syntheses of tetrahydrothiophenes and tetrahydrofurans and studies of their derivatives as melanocortin-4 receptor ligands.
abstract: Piperazinebenzylamine derivatives from trans-4-(4-chlorophenyl)tetrahydrothiophene-3-carboxylic acid 6 and its S-oxide 7 and sulfone 8, and the tetrahydrofuran 9 and its two regioisomers 11 and 13 were synthesized and studied for their binding affinities at the human melanocortin-4 receptor. These five-membered ring constrained compounds possessed similar or lower potency compared to the acyclic analogs.
authors: Department of Medicinal Chemistry, Neurocrine Biosciences, Inc., 12790 El Camino Real, San Diego, CA 92130, USA.
authors: Joe A
authors: JA
authors: Tran
authors: Caroline W
authors: CW
authors: Chen
authors: Fabio C
authors: FC
authors: Tucci
authors: Wanlong
authors: W
authors: Jiang
authors: Beth A
authors: BA
authors: Fleck
authors: Chen
authors: C
authors: Chen
mesh_terms: D020650:Combinatorial Chemistry Techniques; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D008024:Ligands; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D044105:Receptor, Melanocortin, Type 4 / Q000187:drug effects*; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D005663:Furans; D008024:Ligands; C470072:MC4R protein, human; D010879:Piperazines; D044105:Receptor, Melanocortin, Type 4; D013876:Thiophenes