Synthesis and antihypertensive activity of 2,4-dioxoimidazolidin-1-yl and perhydro-2,4-dioxopyrimidin-1-yl ergoline derivatives

A new synthesis of 3-arylideneamino- and 3-alkylideneamino-substituted hydantoins

“…For example, derivatives of 1-aminohydantoin such as dantrolene, azimilide, and nitrofurantoin are used as important drugs (Figure 1). It is also known that some 3-aminohydantoin derivatives are formyl peptide receptor modulators [6] and TNF-α inhibitors [7], show anticonvulsant [8], antihypertensive [9], antibacterial [10], and fungicidal activities [11]. However, in contrast to 1-aminohydantoins, their 3-amino analogues are much less studied.…”

Efficient Solid-Phase Synthesis of Sulfahydantoins

“…Compounds with this structural motif found applications as agrochemicals , and therapeutics. , Sulfahydantoins are analogues of hydantoins and provide heterocyclic scaffolds with a great potential for the construction of bioactive compounds (Figure ). Indeed, sulfahydantoins have been shown recently to be serine protease inhibitors − and are investigated as antihypertensives, artificial sweeteners, and histamine H 2 receptor antagonists and for their affinity for MHC class II proteins 1 Retrosynthetic scheme and general structure of sulfahydantoins synthesized herein, illustrating the great diversity (R 1 −R 4 ) of pharmacophores that can be oriented by the heterocyclic scaffold. …”

“…5,6 Sulfahydantoins are analogues of hydantoins and provide heterocyclic scaffolds with a great potential for the construction of bioactive compounds (Figure 1). Indeed, sulfahydantoins have been shown recently to be serine protease inhibitors [7][8][9][10][11][12][13][14] and are investigated as antihypertensives, 15 artificial sweeteners, 16 and histamine H 2 receptor antagonists 17 and for their affinity for MHC class II proteins. 18 Despite their potential as druglike compounds, the solidphase synthesis of sulfahydantoins has only been explored scarcely and very recently.…”

Expedient Syntheses of Sulfonylhydantoins and Two Six-Membered Analogues

“…The first report of the 1,2,5-thiadiazolidin-3-one 1,1-dioxide moiety ('sulfonylhydantoin', 1) was in 1965 by the group of Ziegler. 1 Since then, this heterocycle has received a lot of attention amongst the synthetic and medicinal chemistry community particularly in relation to serine protease inhibitors, 2 crop protection agents, 3 antihypertensives, 4 artificial sweetners 5 and others. 6 More recently, they have been described as PTB-1b inhibitors which may have a role in controlling blood sugar in diabetes 7a and as anti-cancer compounds.…”

“…We hoped to react our amino esters with sulfamide (NH 2 SO 2 NH 2 ) in the presence of a base to effect a sulfamoylation and cyclisation in one pot. There is one literature example of this transformation being achieved directly without the use of base, 4 although the substrate scope was not examined. The amino esters were either commercially available or prepared by standard aminemonoalkylation of methyl bromoacetate or reductive amination with glycine methylester hydrochloride with the corresponding aldehyde according to the procedure of Groutas and co-workers.…”