1984
DOI: 10.1021/jm00369a025
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(Imidazolylphenyl)formamidines. A structurally novel class of potent histamine H2 receptor antagonists

Abstract: Structure-activity considerations of N alpha-guanylhistamine, the first compound found with detectable H2-antagonist activity, led to the synthesis of a series of conformationally rigid guanylhistamine analogues, namely, (imidazolylphenyl)guanidines, imidazolylbenzamidines, and (imidazolylphenyl)formamidines. It was found that in the guanidine and benzamidine classes, the meta-substituted derivatives (3, 4, 7, and 8) possessed H2-antagonist activity, whereas in the class of formamidines, only the para-substitu… Show more

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Cited by 54 publications
(19 citation statements)
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“…The synthesis of a novel class of H 2-antagonists, the imidazolylphenyl formamidines, characterized by a semi-rigid conformational structure has been recently described [ 1 ]. We now report preliminary investigations on mifentidine, a representative compound of this class.…”
Section: Introductionmentioning
confidence: 97%
“…The synthesis of a novel class of H 2-antagonists, the imidazolylphenyl formamidines, characterized by a semi-rigid conformational structure has been recently described [ 1 ]. We now report preliminary investigations on mifentidine, a representative compound of this class.…”
Section: Introductionmentioning
confidence: 97%
“…Even after healing, the treatment with such compounds must be continued for a long time and perhaps for ever [9], Taking into account all these consider ations, the availability of H2-antagonist de void of untoward effects and long-acting (thus with a high degree of compliance) [19] would be desirable. In this connection, Donelti et al [8] reported quite recently a novel class of potent H2-antagonists: the imidazolylphenyl formamidines. Among the mem bers of this class, one compound marked DA 4577 and later labelled as mifentidine (N1-[4-(4-imida/.olyl)-phenyl]N2-isopropyl formamidine) exhibited high antagonist affinity at the H2-reccptor level.…”
mentioning
confidence: 99%
“…In our series with R=n-butyl, /-butyl, s-butyl and t-butyl (Table 1) the rank order of percentage E,E paralleled the rank order of tight antagonist binding. According to the model originally suggested [2,3] for the interaction of the mifentidine with the H2-receptor (Fig. 1), a bidentate hydrogen bonding between the neutral species of the antagonist and the H2-receptor is probably involved.…”
Section: Discussionmentioning
confidence: 90%