Synthesis of some heterocyclic derivatives of biguanide with antibacterial activity

Guanylated Diamines, Triamines, and Polyamines: Chemistry and Biological Properties

“…Compounds 301 are bisbiguanylated diamines whose diamino portion is represented by a heterocycle, namely, a substituted piperazine. Compounds were obtained from cyanides 300 through reaction with appropriate amines …”

“…Chlorhexidine is probably the oldest known drug with guanylated diamine structure possessing antibacterial activity. Chlorhexidine showed activity against several bacteria such as S. aureus (MIC = 3 μg mL –1 ), E. coli (MIC = 3 μg mL –1 ), and S. thypi (MIC = 1.5 μg mL –1 ). ,, Studies to evaluate the structure–activity relationships (SARs) on Chlorhexidine 297 and its derivatives were carried out, in particular to establish the optimum distance that should exist between the two guanidine groups and the most effective types of substituents on these ending groups (Figure ). The highest antibacterial activity was shown by derivatives with bisbiguanylated diamine structure, and in particular from those compounds where n = 5 , 6 , or 7 .…”

Synthesis and Characterization of Biguanide and Biguanidium Surfactants for Efficient and Recyclable Application in the Suzuki–Miyaura Reaction

“…Their antihyperglycemic properties have been extensively studied, and metformin hydrochloride became one of the most prescribed drugs for the treatment of type 2 diabetes patients . The antimalarial and antimicrobial properties of biguanides have also been reported, as a result of their membrane disruption activity . Recently, the capacity of biguanides to inhibit the proliferation of cancer cells has begun to be considered as a potential anticancer therapy, and even if their mechanism of action is still uncertain, the major limitation for their use is considered to be their inadequate ability to penetrate mitochondria in vivo .…”

“…X-ray Diffraction. Single crystals of each alkylbiguanide were obtained by slow evaporation of methanol (1, 2, and 4) or by crystallization at low temperature in a mixture of methanol and acetone (3). They all appeared as overlapping plates (twinned crystals), which made their analysis difficult.…”

An in Vivo Comparison of Chlorhexidine and Picloxydine Mouthrinses: A Possible Association Between Chemical Structure and Antiplaque Activity

“…It seems to have been established that the plaque inhibitory action of chlorhexidine is independent of its antibacterial activity 3 and perhaps related to the ability of chlorhexidine to bind to and be slowly released from acidic proteins in the mouth. 4 ' 5 In order to understand the role of the chemical structure of antibacterial substances in plaque inhibition, piclox ydine, a heterocyclic biguanide, 6 was investigated. In this experiment the in vivo antibacterial and antiplaque activity of picloxydine was compared with that of chlor hexidine.…”