Functionally Selective Dopamine D 2 /D 3 Receptor Agonists Comprising an Enyne Moiety (original) (raw)

2013, Journal of Medicinal Chemistry

Contents 1) 1 Hand 13 C-NMR Data of the Target Compounds……………………………. S2 2) HPLC Data of the Target Compounds…………………………………………. S8 3) Chiral Separation………………………………………………………………… S14 4) X-ray Crystal Structure Determination of 3,5-dinitrobenzamide (S)-7………. S15 5) Dose-Response Curves of the Target Compounds in the [ 35 S]GTPγS Assay… S26 6) Representative Dose-Response Curves of the Reference Compounds Ropinirole and Rotigotine in a [ 35 S]GTPγS Assay with D 2long Expressing Cells………………..… S29 7) Comparison of the Binding Affinities of Representative Compounds at the D 2long Receptor Stably Expressed in CHO Cells and Transiently Expressed in HEK 293 Cells as well as at Membranes from Porcine Striatum………………………………….. S30 8) Amino acid sequence alignment of DRD2, DRD3, 5HT1B and 5HT2B………. S31 S2 1) 1 Hand 13 C-NMR Data and HPLC Data of the Target Compounds (R)-N-{4-[(4-Ethynylcyclohex-3-enyl)propylamino]butyl}biphenyl-4-carboxamide ((R)-1) 1 H-NMR 1 H (600MHz, CD 3 OD) 13 C-NMR 13 C (360MHz, CD 3 OD) S3 (R)-N-{4-[(4-Ethynylcyclohex-3-enyl)propylamino]butyl}pyrazolo[1,5-a]pyridine-2carboxamide ((R)-2a). 1 H-NMR 1 H (600MHz, CDCl 3) 13 C-NMR 13 C (360MHz, CDCl 3) S4 (R)-N-{4-[(4-Ethynylcyclohex-3-enyl)propylamino]butyl}pyrazolo[1,5-a]pyridine-3carboxamide ((R)-2b) 1 H-NMR 1 H (360MHz, CDCl 3) 13 C-NMR 13 C (600MHz, CDCl 3) S5 (R)-4-[3-(1-Butyl-1H-1,2,3-triazol-4-yl)propoxy]-N-{4-[(6-ethynylcyclohex-3enyl)propylamino]-butyl}-3-methoxybenzamide ((R)-2c) 1 H-NMR 1 H (360MHz, CDCl 3) 13 C-NMR 13 C (360MHz, CDCl 3) S6 (R)-N-{4-[(4-Ethynylcyclohex-3-enyl)propylamino]butyl}benzo[b]thiophene-2carboxamide ((R)-2d). 1 H-NMR 1 H (600MHz, CDCl 3) 13 C-NMR 13 C (360MHz, CDCl 3)