56108-07-7Relevant academic research and scientific papers
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.
Histamine analogues. 33rd communication: 2-phenylhistamines with high histamine H1-agonistic activity
Zingel, V.,Elz, S.,Schunack, W.
, p. 673 - 680 (2007/10/02)
2-Phenylhistamines with various substituents at the phenyl ring were synthesized and the influence of substitution in ortho, meta or para position on histamine H1-agonistic activity was investigated.Compounds with high activity occured in the meta phenyl series.Increased activity in the guinea-pig ileum assay was achieved by monosubstitution with halogen on the phenyl ring. 2-ethanamine (12) is the most potent highly selective H1-agonist known so far, showing 87percent relative potency compared with histamine and full efficacy at theH1-receptor.Relative activities of the 3-chloro analogue (11) and the 3-methyl analogue (13) are 81percent and 29percent, respectively.Histamine H2-activity could not be detected. 2-Phenylhistamines are available via reaction of the corresponding benzimidates with 2-oxo-4-phthalimido-1-butyl acetate (6) in liquid ammonia.
