Synthesis and pharmacological evaluation of aryl/heteroaryl piperazinyl alkyl benzotriazoles as ligands for some serotonin and dopamine receptor subtypes

Alkylation of 1,3-bis(benzotriazol-1-yl)propan-2-one with α-iodo ketones

“…Yield 1.25 g (50%), dark red powder, mp 99-102°C. 1 12,16,23,24-Tetraaza-1,5-diazoniapentacyclo-[14.6.1.1 5,12 .0 6,11 .0 17,22 ]tetracosa-1(23),5(24),6(11),7,-9,17(22),18,20-octaene-3,14-dione polyiodide (V). Compound I, 0.37 g (1.27 mmol), was added in portions under argon to 1.06 g (3.42 mmol) of molten 1,3-diiodopropan-2-one (IV), and the mixture was stirred for 6 h at 80°C (until initial ketone IV disappeared).…”

“…Yield 0.75 g (69%), dark red powder, mp 124-126°C. 1 The IR spectra were recorded in KBr on a Bruker Vertex 70 spectrometer. The 1 H and 13 C NMR spectra were measured on a Bruker DPX-400 instrument at 400.13 and 100.61 MHz, respectively, using DMSO-d 6 or acetone-d 6 as solvent and tetramethylsilane as internal reference.…”

α1- andα2-Adrenoreceptor Antagonist Profiles of 1- and 2-[ω-(4-Arylpiperazin-1-yl)alkyl]-1,2,3-benzotriazoles

“…For a more-precise structure ± activity relationship, six additional compounds (22 ± 27), bearing only one or no MeO group on the benzotriazole ring, were also included in this study. The latter compounds, with the exception of 24, have been described before [14] [23].…”

“…Therefore, the w-bromoalkyl derivatives 33 and 34 were prepared by reacting 28 with an excess of the suitable oligomethylene dibromide in the presence of KF/Al 2 O 3 prepared according to Texier ± Boullet et al [30] (Method B). This procedure has been used before by Mokrosz et al [23] and by us [14] for the preparation of 1-and 2-(4-bromobutyl)benzotriazole. The 1-and 2-substituted isomers were separated as usual.…”

“…The unknown compound 24 was synthesized according to Method B, but starting from 1-(5-bromopentyl)-1H-1,2,3-benzotriazole. Compound 27 was already prepared by us [14].…”