The Preparation of Some Structurally Related Monoguanidines

Braun, Charles E.

doi:10.1021/ja01330a074

Cited by 29 publications

(8 citation statements)

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“…Several procedures for guanylation of amine salts with cyanamide in aqueous or alcoholic solution (2,4,5,6) were examined b u t all of these in our hands gave yields of alkylguanidines in the range 0-20%. T h e only method found t o be effective was a fusion technique due t o Sugino et al (16,17), by which procedure cyclohexylguanidine hydrochloride was obtained in 48% yield.…”

Section: Resultsmentioning

confidence: 99%

Guanidine Compounds. Ii. Preparation of Mono- And N,n-Di-Alkylguanidines

Bannard¹,

Casselman²,

Cockburn³

et al. 1958

Can. J. Chem.

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1-Guanyl-3,5-diniethylpyrazolc nitrate is superior to S-methylisothiourorlium sulphate as a reagent for preparation of simple salts of mono-and N,N-di-allcylg~~anitlines from cyclohesylaniine, tra~zs-2-anii11ocyclo1~~~a11o1, pyrrolidine, and piperidir~e. S-h'Icthylisothiouro~~iurn sulphate, however, gave a higher conversion in the case of tlimctIi>.lan~ine. Cyanamide is not as useful a guanylatilig agent as those n i c~~t i o~i e d above. The paper cliromatography of the nio~io-and N,N-di-alkylguanidines and the parent arni~rcs \\,as studied using four solvent systems. l NTRODUCTIONOf the ilumerous methods reported in the literature for preparation of mono-and N,N-di-alliylguanidines, those \vhich have been used most frecluently are the Erlenmeyer synthesis ( I ) , from amine salts and cyanamide (2, 3 , 1 , 5 , G ) , and the Rath1.e synthesis ( 7 ) , from amines and an all;ylisothiouronium or alkylisouronium salt (8, 9,10,11,12). Both methods, however, frequently lead to poor jrields of all

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Section: Resultsmentioning

confidence: 99%

Guanidine Compounds. Ii. Preparation of Mono- And N,n-Di-Alkylguanidines

Bannard¹,

Casselman²,

Cockburn³

et al. 1958

Can. J. Chem.

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“…The modified analogs phenylbiguanide 35 HCl, 38 2HCl, 40 hemisulfate, 41 hemisulfate, 42 hemisulfate, 43 HCl, and 45 nitrate 49 are known, and methods of preparation were employed from cited references. The arylguanidines 46 nitrate, 47 nitrate, 48 nitrate, 49 nitrate, 50 hemisulfate, 51 , 52 , 53 HCl, 54 HCl, 57 HCl, 58 HCl, 59 hemisulfate, and 61 61 were synthesized using the literature procedures. Compounds 2 , 4 , 8 , 9 , 12 , 13 , and 15 were commercially available (Aldrich Chemical Co.).…”

Section: Methodsmentioning

confidence: 99%

“…38 2HCl,47 40 hemisulfate,48 41 hemisulfate,48 42 hemisulfate,28 43 HCl,28 and 45 nitrate 49 are known, and methods of preparation were employed from cited references. The arylguanidines 46 nitrate,50 47 nitrate, 51 48 nitrate,52 49 nitrate,53 …”

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confidence: 99%

Structure−Activity Relationships for the Binding of Arylpiperazines and Arylbiguanides at 5-HT₃Serotonin Receptors

et al. 1996

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Arylpiperazines are nonselective agents that bind at 5-HT3 serotonin receptors with moderate to high affinity, whereas 1-phenylbiguanide is a low-affinity but more selective 5-HT3 agonist. In an attempt to enhance the affinity of the latter agent, and working with the assumption that similarities might exist between the binding of the two types of agents, we formulated structure-activity relationships for the binding of the arylpiperazines and then incorporated those substituents, leading to high affinity for the arylpiperazines, into 1-phenylbiguanide. A subsequent investigation examined the structure-activity relationships of the arylbiguanides and identified arylguanidines as a novel class of 5-HT3 ligands. Although curious similarities exist between the structure-activity relationships of the arylpiperazines, arylbiguanides, and arylguanidines, it cannot be concluded that all three series of compounds are binding in the same manner. Furthermore, upon investigating pairs of compounds in the three series, the arylpiperazines behaved as 5-HT3 antagonists (von Bezold-Jarisch assay) whereas the arylbiguanides and arylguanidines acted as 5-HT3 agonists.

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“…Dibenzyldimethylammonium chloride (DDA"") was prepared from benzyldimethylamine and benzyl chloride according to the procedure reported by Beard & Hauser (1961) and recrystallized from a mixture of ethyl alcohol and ethyl acetate. Hexylguanidine (HG) and octylguanidine (OG) were obtained by condensing hexyl-and octyl-amine with S-Methylisothiourea as indicated by Braun (1933).…”

Section: Chemicalsmentioning

confidence: 99%

Dissociation of H ⁺ extrusion from K⁺ uptake by means of lipophilic cations

Bellando

Trotta

Bonetti³

et al. 1979

Plant Cell & Environment

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Dissociation of active H+ extrusion (−ΔH+) from K+ uptake in pea and maize root segments was attempted by substituting K+ in the incubation medium with lipophilic cations assumed to enter the cell by passive, non‐specific, permeation through the lipid component of the plasmalemma. Among the compounds tested, tributylbenzylammonium significantly stimulated −ΔH+ in the absence of other monovalent cations in the medium. This effect was much more evident when the experiment was carried out in the presence of fusicoccin, which strongly stimulates proton extrusion and monovalent cation uptake, and hyperpolarizes the trans‐membrane electric potential in these materials. Also the lipophilic cations tetraphenylphosphonium, dimethyldibenzylammonium and hexylguanidine markedly stimulated FC‐promoted −ΔH+. Octylguanidine at a low concentration induced an early stimulation followed by a strong inhibition of −ΔH+. A complete lack of additivity was observed between the effects of lipophilic cations and that of K+ on H+ extrusion. Lipophilic cations severely inhibited K+ uptake. These data are interpreted as supporting the view of an electric, rather than a chemical, (namely, involving the same carrier system) nature of the coupling of active H+ extrusion with K+ influx.

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The Preparation of Some Structurally Related Monoguanidines

Cited by 29 publications

References 0 publications

Guanidine Compounds. Ii. Preparation of Mono- And N,n-Di-Alkylguanidines

Guanidine Compounds. Ii. Preparation of Mono- And N,n-Di-Alkylguanidines

Structure−Activity Relationships for the Binding of Arylpiperazines and Arylbiguanides at 5-HT₃Serotonin Receptors

Dissociation of H ⁺ extrusion from K⁺ uptake by means of lipophilic cations

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The Preparation of Some Structurally Related Monoguanidines

Cited by 29 publications

References 0 publications

Guanidine Compounds. Ii. Preparation of Mono- And N,n-Di-Alkylguanidines

Guanidine Compounds. Ii. Preparation of Mono- And N,n-Di-Alkylguanidines

Structure−Activity Relationships for the Binding of Arylpiperazines and Arylbiguanides at 5-HT3Serotonin Receptors

Dissociation of H + extrusion from K+ uptake by means of lipophilic cations

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Product

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Structure−Activity Relationships for the Binding of Arylpiperazines and Arylbiguanides at 5-HT₃Serotonin Receptors

Dissociation of H ⁺ extrusion from K⁺ uptake by means of lipophilic cations