New aromatic iminoimidazolidine derivatives as α 1 -adrenoceptor antagonists: a novel synthetic approach and pharmacological activity

Bisguanidine, Bis(2-aminoimidazoline), and Polyamine Derivatives as Potent and Selective Chemotherapeutic Agents against Trypanosoma brucei rhodesiense. Synthesis and in Vitro Evaluation

“…The diphenyl compounds (Table 5, entries 5-8 and 12-15) present α 1 -adrenergic antagonist activity in various tissues. 26,51 In particular, the blood pressure and heart rate responses of two compounds (29b and 31b)…”

“…Compounds 1a, 1b-1d, 2a, 2b, 2c, 2d, 3b, 3c, 3d, 4a-6a, 53 4b, 5b, 5d, 6b, 7, 8, 9, 11, 12, 13, 21, 22, 23, 24, 27a-33a, 27b-33b and 34 were prepared as previously reported. [26][27][28]53 N-{3-[(2-Guanidino-ethyl)-phenethyl-amino]-propyl}-guanidine (10). A solution of 9 (0.5mmol) and S-methylisothiouronium sulfate (148 mg, 0.53 mmol) in dry MeOH (7 mL) was heated for 12 h at reflux.…”

“…Hence, a rapid look at the structure of the polyamine, diguanidine and diamidine compounds reported as antiprotozoal agents in the literature put into evidence the potential as possible trypanocides of a series of bisguanidine and bis(2-aminoimidazoline) compounds previously synthesized in our laboratory for other purposes. [26][27][28] Moreover, some of the alkanediguanidine [1, 8-octanediguanidine (1b), 29 1,12-dodecanediguanidine (1d), 6,30,31 bis(guanidinopropyl)amine (6a) 32 trypanosomal agent in vivo. 15 Hence, in the search for new HAT chemotherapy, we decided to carry out an in vitro screening against the parasite T. brucei rhodesiense of a total of 62 compounds (Tables 1-5) taken from our in-house library and structurally related to the trypanocidal agents synthalin (1,10-decanediguanidine) and 4,4'-diguanidinodiphenylmethane (31b), and the polyamine N 1 -(3-amino-propyl)-propane-1,3-diamine respectively.…”

“…26,27,28 Synthesis of the 3-aza-1,6-hexanediamine derivatives (Scheme 1). Guanylation of 3-aza-1,6-hexanediamine with an excess of DCC in CH 3 CN afforded a mixture of the di-substituted dicyclohexylguanidine derivative 5c and the tri-substituted compound 17.…”

C-N bond forming reactions in the synthesis of substituted 2-aminoimidazole derivatives

“…[28][29][30][31] Other procedures involve the condensation of amines with dihydroimidazol-3-ium-2-sulfonate 32 or with protected imidazolidine-2-thione, though the last procedure requires the use of mercury (II) chloride. 9 As part of our program to develop new procedures for the synthesis of heterocyclic systems, [33][34][35] we investigated several carbon-nitrogen bond forming reactions directed to the synthesis of 2-aminoimidazole derivatives. The aim was to achieve the amination at the C-2 position of both imidazole and imidazolidine moieties, avoiding metalation with strong (and potentially nucleophilic) bases.…”