131851-89-3Relevant academic research and scientific papers
Synthesis and structural, conformational, biochemical, and pharmacological study of new compounds derived from tropane-3-spiro-4'(5')-imidazoline as potential 5-HT3 receptor antagonists
Whelan,Iriepa,Galvez,Orjales,Berisa,Labeaga,Garcia,Uceda,Sanz-Aparicio,Fonseca
, p. 101 - 106 (1995)
A series of tropane-3-spiro-4'(5')-imidazolines was synthesized and studied by 1H and 13C NMR spectroscopy, and the crystal structure of 2'- (1H-indol-3-yl)tropane-3-spiro-4'(5')-imidazoline hydrochloride 5(6)f was determined by X-ray diffraction. In CD3OD solution, compounds 5(6)a-f display the same preferred conformation. The pyrrolidine and piperidine rings adopt an envelope conformation flattened at N8 and a distorted chair conformation puckered at N8 and flattened at C3, respectively, with the N- substituent in the equatorial position with respect to the piperidine ring. This conformation is similar to that observed for compound 5(6)f in the solid state. From binding studies on the compounds synthesized, compound 5(6)d demonstrated the ability to efficiently displace the binding of [3H]GR65630 to bovine brain area postrema membranes to an extent comparable to MDL 72222. In the von Bezold-Jarisch reflex, compound 5(6)d was equipotent with metoclopramide. It is, therefore, likely that the imidazoline ring may provide a useful bioisosteric replacement for the carbonyl group in 5-HT3 antagonists.
Iminium Carbonic Acid Derivative Salts. XI [1]. Synthesis of N,S-Containing Heterobicycles from N-Protected 2-Methylthio-1,3-thiazinium and 2-Methylthiothiazolium Salts. Part 3. Reaction of N-Protected 2-Methylthio-1,3-thiazinium and 2-Methylthiothiazolium Salts with 3-Amino-2-cyano-3-arylacrylonitriles
Hanefeld, Wolfgang,Naeeni, Mahmoud,Schlitzer, Martin
, p. 1903 - 1907 (2007/10/03)
N-Boc-protected 2-methylthio-1,3-thiazinium 1 and 2-methylthiothiazolium iodides 2,3 obtained from the corresponding 3,4,5,6-tetrahydro-2H-1,3-thiazine-2-thiones and thiazolidine-2-thiones by the action of methyl iodide were reacted with 3-amino-2-cyano-3-arylacrylonitriles forming the cyclic isothioureas 5-7. The protection group was removed with trifluoroacetic acid whereupon the desired cyclisation to 3,4-dihydro-2H,6H-pyrimido[2,1-b][1,3]thiazines 8a-c, 8a′-c′ and thiazolo[3,2-b]pyrimidines 9a,b, 9a′,b′, 10a,b took place.
Synthesis of 2'-arylazabicyclo-3-spiro-4'(5')-imidazolines
Whelan,Iriepa,Galvez
, p. 832 - 836 (2007/10/02)
A method is described for the synthesis of a series of 2'-aryl-3-azabicyclospiro-4'(5')-imidazolines via the reaction of azabicyclic 1,2-diamines with aryl imidate salts. Competing reactions in the synthesis of the diamines such as the reduction of amino nitriles with LiAlH4 lead to some anomalous products. In the Pinner synthesis, unstable pyridine-type imidates were stabilized as their N-oxide derivatives.
Preparation of Triazolopyrimidines as Potential Antiasthma Agents
Medwid, Jeffrey B.,Paul, Rolf,Baker, Jannie S.,Brockman, John A.,Du, Mila T.,et al.
, p. 1230 - 1241 (2007/10/02)
With the use of the human basophil histamine release assay, 5-aryl-2-aminotriazolopyrimidines were found to be active as mediator release inhibitors.These compounds were prepared by reacting arylamidines with sodium ethyl formylacetate or with ethyl propiolate to give pyrimidinones.Treatment with phosphorus oxychloride gave a chloropyrimidine, which was converted to a hydrazinopyrimidine with hydrazine.Cyclization, using cyanogen bromide, gave the triazolopyrimidines, after a Dimroth rearrangement.Following a structure-activity evaluation, the5--2-amino (8-10), 5-(3-bromophenyl)-2-amino (8-13), 5--2-amino (8-11), and 5-(4-pyridinyl)-2-amino (6-7) compounds were found to have the best activity.They were chosen for further pharmacological and toxicological study.
