60006-46-4Relevant academic research and scientific papers
Ph3P/I2-mediated synthesis of N,N′,N″-substituted guanidines and 2-iminoimidazolin-4-ones from aryl isothiocyanates
Wangngae, Sirilak,Pattarawarapan, Mookda,Phakhodee, Wong
, p. 10331 - 10340 (2018/05/31)
A convenient one-pot procedure for the synthesis of acyclic and cyclic guanidines mediated by the Ph3P/I2 system is described. Sequential condensation of aryl isothiocyanates with amines followed by dehydrosulfurization and guanylation could lead to both symmetric and unsymmetric N,N′,N″-substituted derivatives. Through a tandem guanylation-cyclization, a series of 2-iminoimidazolin-4-ones could also be prepared in good yields from the reaction of aryl isothiocyanates with amino acid methyl esters.
Lac sulfur on alumina-triethanolamine - An effective reagent for the synthesis of substituted guanidines
Ramadas, Krishnamurthy
, p. 5161 - 5162 (2007/10/03)
A direct synthesis of substituted guanidines is reported from their thiourea analogues. The strategy adopted is a concise approach to the synthesis of the title compounds.
Synthesis and diuretic activity of alkyl- and arylguanidine analogs of N,N'-dicyclohexyl-4-morpholinecarboxamidine in rats and dogs
Perricone,Humphrey,Skaletzky,Graham,Zandt,Zins
, p. 3693 - 3700 (2007/10/02)
Random screening identified N,N'-dicyclohexyl-4-morpholinecarboxamidine (U-18177, 1) as an orally effective nonkaliuretic diuretic in rats. The diuretic profile of 1 and its 1-adamantyl analog (U-37883A, 4) was confirmed orally in dogs, where they were less potent than standard diuretics but showed furosemide-like natriuresis at ≥100 μmol/kg. However, acute 1 at 61 and 90 μmol/kg iv resulted in lethal cardiac toxicity in dogs. Many analogs of 1 exhibited qualitatively similar diuretic profiles, but none was sufficiently safe to warrant development. Compound 1 also reversed minoxidil's vasodilation in dogs, which led to vascular interaction studies suggesting that analog 4 may block ATP-sensitive K channels. This K channel- blocking mechanism may contribute to the diuretic activity of the series. This is the first report broadly characterizing the diuretic activity of 1 and representative guanidine analogs in rats and dogs and its toxicity and minoxidil-blocking effects in dogs.
