74418-11-4Relevant articles and documents
Structure-affinity relationships of a unique nicotinic ligand: N1-dimethyl-N4-phenylpiperazinium iodide (DMPP)
Romanelli,Manetti,Scapecchi,Borea,Dei,Bartolini,Ghelardini,Gualtieri,Guandalini,Varani
, p. 3946 - 3955 (2007/10/03)
DMPP is a well-known nicotinic agonist that does not fit any proposed pharmacophore for nicotinic binding and represents a unique ligand among the hundreds of nicotinic agonists studied in the past decades. A systematic modulation of the chemical structure of DMPP, aimed to establish its structure-affinity relationships, is reported. The research has allowed to identify molecules such as 11c, 13c, 14c, and 28c, with affinities for α4β2 receptors in the low nanomolar range, some 2 orders of magnitude lower than the lead compound. The agonistic properties of the most interesting compounds have been assessed by measuring their analgesic activity on mice (hot-plate test). Another result of the research was the identification of DMPP analogues, such as 3a (Ki = 90 nM) and 14b (Ki = 180 nM), that maintain affinity for the central nicotinic receptor when the ammonium function is changed into an aminic one and are therefore possible leads for drug development in neurodegenerative diseases.
Formation of phenylpiperazines by a novel alumina supported bis-alkylation
Mishani, Eyal,Dence, Carmen S.,McCarthy, Timothy J.,Welch, Michael J.
, p. 319 - 322 (2007/10/02)
The phenylpiperazine ring which could not be obtained by reacting aniline derivatives with bis(2-bromoethyl)-N-(ethoxycarbonyl)amine (1a) in a wide spectrum of solvents and temperatures was synthesized rapidly on solid support in high yield. By this approach the potent serotonin agonist TFMPP (2) was synthesized in 40 min. in 80% yield. The time scale of this reaction and the simplicity of the work-up match the requirements for short lived neurological radiopharmaceutical production.
