Characterization of biguanides by15N NMR spectroscopy

Clement, Bernd; Girreser, Ulrich

doi:10.1002/(sici)1097-458x(199909)37:9<662::aid-mrc518>3.0.co;2-d

Cited by 15 publications

(9 citation statements)

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“…For uses of biguanide complexes in medicine, see: Sirtori & Pasik (1994); Clement & Girreser (1999); Thompson et al (1999); Ross et al (2004); Woo et al (1999); Watkins et al (1987); Morain et al (1994); Marchi et al (1999); Shapiro et al (1959a,b). The salts of biguanidium (1+) or (2+) cations have been tested for non-linear optical properties, see: Matulková et al (2008Matulková et al ( , 2010; ; ; Pinkerton et al (1978).…”

Section: Related Literaturementioning

confidence: 99%

“…The wide area of application of biguanides involves the field of medical research (Sirtori & Pasik, 1994;Clement & Girreser, 1999), especially in the treatment of diabetes mellitus (N,N-dimethylbiguanide and N-phenylethylbiguanide) (Thompson et al, 1999;Ross et al, 2004;Woo et al, 1999). Biguanide derivatives are also used in the synthesis of antimalarial drugs (N-butylbiguanide) (Watkins et al, 1987), and in therapeutic treatment of pain, anxiety, memory disorders (Morain et al, 1994) and hypoglycaemic activity (Marchi et al, 1999;Sirtori & Pasik, 1994;Shapiro et al, 1959aShapiro et al, , 1959b.…”

Section: S1 Commentmentioning

confidence: 99%

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Bis(2-phenylbiguanidium) adipate tetrahydrate

2010

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Section: Related Literaturementioning

confidence: 99%

Section: S1 Commentmentioning

confidence: 99%

Bis(2-phenylbiguanidium) adipate tetrahydrate

2010

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“…Biguanides forms stable complexes, see: Marchi et al (1999); Ray (1961); Anderson et al (1995) and also have applications in medicine, see: Sirtori & Pasik (1994); Clement & Girreser (1999); Thompson et al (1999); Ross et al (2004); Woo et al (1999); Watkins et al (1987); Morain et al (1994); Shapiro et al (1959a,b). Ionic crystal structures containing biguanide cations are formed by relatively strong hydrogen bonds, see: ; ; Pinkerton et al (1978); Matulková et al (2008Matulková et al ( , 2010.…”

Section: Related Literaturementioning

confidence: 99%

“…Another application of biguanides lies in the field of medicine (Sirtori & Pasik, 1994;Clement & Girreser, 1999). N-dimethylbiguanide and N-phenylethylbiguanide are used for the treatment of diabetes mellitus (Thompson et al, 1999;Ross et al, 2004;Woo et al, 1999), therapeutic treatment of pain, anxiety, memory disorders (Morain et al, 1994).…”

Section: S1 Commentmentioning

confidence: 99%

2-Phenylbiguanidinium hydrogen succinate methanol monosolvate

2010

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In the crystal of the title compound, C8H12N5 +·C4H5O4 −·CH3OH, the hydrogen succinate anions form infinite [010] chains via short, almost symmetrical, O⋯H⋯O hydrogen bonds. The 2-phenylbiguanidium cations interconnect these chains into layers lying parallel to the bc plane by way of N—H⋯O links. These planes only weakly interact in the direction of the a axis via C—H⋯π contacts between offset phenyl rings, leaving as much as 17% of the unit-cell volume accessible for the solvent. However, the methanol solvent molecules could not be resolved due to extensive disorder and their assumed presence was removed from the overall scattering by the PLATON SQUEEZE procedure.

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“…In very acidic aqueous solutions (pH < 2), biguanide residues are diprotonated. On the basis of tautomeric structure of biguanide,16 the positive charges are predicted to be distributed between all the nitrogen and carbon atoms in the biguanide moiety. Solvent attack on an electron‐deficient carbon would lead to a tetrahedral intermediate with potential leaving groups including PCA and ammonia, giving rise to PBG–AU or PBG–APU, respectively.…”

Section: Resultsmentioning

confidence: 99%