1. Synthesis and Neuropeptide Y Y1 Receptor Antagonistic Activity ofN,N-Disubstituted ω-Guanidino- and ω-Aminoalkanoic Acid Amides
2. The first highly potent and selective non-peptide neuropeptide Y Y1 receptor antagonist: BIBP3226
3. NPY Y1 antagonists: structure–activity relationships of arginine derivatives and hybrid compounds with arpromidine-like partial structures
4. (R)-Nα-Diphenylacetyl-N-[(RS)-1-(4-hydroxyphenyl)-ethyl] argininamide (10): (R)-Nα-Diphenylacetyl-NG-nitro-N-[(RS)-1-(4-hydroxyphenyl)ethyl]argininamide (0.26 g, 0.49 mmol) was dissolved in 60% acetic acid and hydrogenated at room temperature in an autoclave (5 bar, H2/Pd-C 10%). The catalyst was filtered off, washed with 60% acetic acid and the filtrate was evaporated in vacuo. The crude product was purified chromatographically on silica gel with CHCl3:MeOH (1:1) as eluent. Yield: 0.20 g (0.37 mmol; 62%) hygroscopic yellow solid; C28H32N5O3·CH3CO2H (547.65); mp 76–80°C (CHCl3:MeOH); [α]d25=+9.4±2° (c=0.16 g/100 ml; MeOH); IR (KBr): ν 3408 br (OH, NH), 3061w, 3013w (Ar-H), 2958w, 2883w (CH), 1652s (CO); 1H NMR (300 MHz, DMSO-d6): δ 1.27 (d, J=6.7Hz, 3H, CH3), 1.39−71 (m, 4H, CH2CH2CH2), 3.00−17 (m, 2H, CH2CH2CH2), 4.29–4.31 (m, 1H, CH), 4.76–4.81 (m, 1H, CHCH3), 5.11 and 5.13 (2s, 0.6/0.4H, Ph2CH), 6.04 (br, 3H, NH), 6.66 (d, J=8.3 Hz, 2H, Ar-OH), 7.03 (d, J=8.3Hz, 2H, Ar-OH), 7.21–7.30 (m, 10H, Ph), 7.99–8.29 (br, 1H, OH), 8.31–8.37 (m, 1H, NHCH), 8.40–8.46 (m, 1H, NHCH), 8.61–8.68 (m, 1H, NHCH2), 9.32 (br, 1H, NH); +FAB–MS m/z (relative intensity): 975 (>1, [2M+H]+), 488 (100, [M+H]+), 167 (62, [Ph2CH]+).
5. New 2-Aryliminomidazolidines. II. Synthesis and Antihypertensive Activity of 2-(Biphenylimino)imidiazolidines.