A practical guide to arylbiguanides — Synthesis and structural characterization

Abstract

Monohydrochloride salts of diverse 1-arylbiguanides and 1,5-diarylbiguanides were synthesized by the reaction of anilinium chlorides with dicyandiamide or sodium dicyanamide, and the biguanidinium chlorides were converted into the corresponding biguanides by deprotonation with methanolic NaOCH3. The resulting biguanides and their salts were fully characterized by spectroscopic methods, and the structures of representative compounds were determined by X-ray crystallography.Key words: biguanide, biguanidinium, synthesis, structure, hydrogen bonds, noncovalent interactions, supramolecular chemistry.

Responsiveness of parasite Cys His proteases to iron redox

“…Drugs that co-bind Fe 3+ and the protease substrate regions might enhance the natural inhibitory action of Fe 3+ . Antimalarial synergy between metalinteractive CysHis protease inhibitors and increased Fe 3+ under pro-oxidative agents merits further consideration for efficacy and safety (Jones and Ward 2002;Sweeney et al 2003;Lockwood 2004;Bharatam 2005;LeBel et al 2005).…”

The Brønsted-Lowry Reaction Revisited: Glass-Forming Properties of Salts of 1,5-Dimexylbiguanide

“…6 Most of these molecular glasses are polyaromatic, nonplanar, star-shaped compounds that can adopt several conformations and typically do not interact strongly with each other. 1a,3,4 However, we have identified a group of 4,6-bis(mexylamino)-1,3,5-triazines, 7 along with related 1,5-dimexylbiguanide 1, 8 which are capable of readily forming long-lived glassy phases despite the obvious presence of hydrogen-bonding groups. For these compounds, it has been shown that hydrogen bonding actually contributes to glass formation by generating supramolecular aggregates that pack poorly and interact weakly, and hydrogen bonding contributes to the stability of the glassy phase by providing a barrier toward molecular reorganization in the solid.…”

The Synthesis of 3,3'-dimethyl (p-guanidino) dicyclohexylmethane

“…Big guanidine substances have been recognized and applied has a long history [1][2][3], the synthesis method has multiple [4]. Big guanidine and its derivatives are mainly through the amine and dicyandiamide in the acidic conditions of the addition reaction [1,5].…”

“…Big guanidine and its derivatives are mainly through the amine and dicyandiamide in the acidic conditions of the addition reaction [1,5]. Canada Olivier LeBel and so on with aniline and dicyandiamide in acidic conditions, heating reaction, after cooling to obtain 1-phenyl guanidine hydrochloride, the product with tetrahydrofuran, n-hexane and acetone after the addition of methanol solution of sodium methoxide to obtain the purity of 95 % of the phenyl biguanide [6]. DMDC is an alicyclic amine type curing agent, with a saturated six-membered ring structure, at the same time with a space conformation, good flexibility and so on, but also has a similar structure with the aromatic amine-ring structure of the rigidity and strength.…”