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Syntheses and evaluation of pyridazine and pyrimidine containing bioisosteres of (+/-)-pyrido[3.4-b]homotropane and pyrido-[3.4-b]tropane as novel nAChR ligands.
In comparison to PHT, well known to exhibit affinity for agonist binding sites in rat brain approximately equivalent to that of (+)-anatoxin-a, replacement of the pyridine by the bioisosteric pyridazine resulted in 30-fold lower affinity at the (alpha4)2(beta2)3 subtype.
3D QSAR analyses-guided rational design of novel ligands for the (alpha4)2(beta2)3 nicotinic acetylcholine receptor.
Three-dimensional quantitative structure-activity relationship methods and physicochemical determinants of binding, such as steric and electrostatic and, for the first time, hydrophobic, hydrogen bond donor, and hydrogen bond acceptor properties, were mapped back onto the molecular structures of a set of nAChR modulators.
Synthesis and nicotinic binding studies on enantiopure diazine analogues of the novel (2-chloro-5-pyridyl)-9-azabicyclo[4.2.1]non-2-ene UB-165.
The pyrimidine-containing bioisostere 8 turned out to be the most active diazine analogue, which interacts potently (K(i) = 0.14 nM) with the (alpha4)(2)(beta2)(3) subtype and differentiates significantly among the nAChR subtypes investigated.
A new and efficient synthetic route to enantiopure (+)-anatoxin-a from (−)-cocaine hydrochloride
Abstract The potent nAChR agonist (+)-anatoxin-a was efficiently synthesized in enantiomerically pure form starting from a readily available confiscated grade (−)-cocaine hydrochloride. The
Synthesis and evaluation of diazine containing bioisosteres of (-)-ferruginine as ligands for nicotinic acetylcholine receptors.
The bioisosteric replacement of the acetyl moiety as structural part of the lead compound 3 with the pyridazine, pyrimidine and pyrazine nucleus resulted in ligands with high to moderate affinity for the central alpha4beta2 and remarkably low affinity forThe alpha7* nAChR subtypes.
Weak interionic interactions in 2-bromoimidazolium derivatives
Abstract The 2-bromoimidazolium bromide [ImBr]Br (5, Im=2,3-dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene) is prepared from Im (4) and bromine. From 4 and CBr4, the adduct [ImBr]Br · CBr4
3D QSAR Analyses-Guided Rational Design of Novel Ligands for the (α4)2(β2)3 Nicotinic Acetylcholine Receptor
Three-dimensional quantitative structure−activity relationship methods, the comparative molecular field analysis (CoMFA) and the comparative molecular similarity indices analysis (CoMSIA), were
Synthese, Struktur und Eigenschaften der Komplexe [(H2O)Cl4Os≡N‐IrCl(C5Me5)(AsPh3)], [(Ph3Sb)Cl4Os≡N‐IrCl(C5Me5)(SbPh3)], [(Ph3Sb)2Cl3Os≡N‐IrCl(COD)] und [{(Me2PhP)2(CO)Cl2Re≡N}2ReNCl2(PMe2Ph)]
Synthesis, Crystal Structure, and Properties of the Complexes [(H2O)Cl4Os≡N-IrCl(C5Me5)(AsPh3)], [(Ph3Sb)Cl4Os≡N-IrCl(C5Me5)(SbPh3)], [(Ph3Sb)2Cl3Os≡N-IrCl(COD)] and
Synthesis and nicotinic binding studies on enantiopure pinnamine variants with an 8-azabicyclo[3.2.1]octane moiety.
Despite obvious structural similarities with the potent alkaloids pinnamine (5) and (-)-ferruginine (4) the pyranotropanes 6a and 6c exhibited distinctly lower nAChR affinities.