1-(4-Aminobutyl)guanidine (original) (raw)
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Tetrahedron Letters, 2007
In this Letter, we describe the unexpected reaction pattern of N,N 0 N 00-tri-Boc-guanidine (TBG) with amines at room temperature and under reflux conditions affording N-substituted guanidines and amidinoureas, potentially important compounds with extensive applications in medicinal chemistry. This investigation shows that TBG is an excellent, readily available common starting material for the synthesis of various N-alkyl guanidines as well as N-alkyl-N 0-substituted amidinoureas by simply manipulating the reaction conditions.
Bioorganic & Medicinal Chemistry Letters, 2008
Transformation of aminoacridines into N-acridinyl-N 0 -alkylguanidines is described. The chosen procedure allows introduction of pendent substituents (exemplified by N,N-dimethylaminopropyl chain) into key acridinyl thioureas, thus opening the way to structural diversity. Spectroscopic study and pK a determination show that the presence of the strongly basic guanidine has a dramatic influence on the ionization of the acridine nucleus by lowering the pk a value down to 4.49.
Guanidine Motif in Biologically Active Peptides
Australian Journal of Chemistry, 2014
In the past decade, guanidines have attracted attention as valuable hydrogen bond-based catalysts while they have long been considered as organic superbases with a broad scope of synthetic applicability. Their easy modification has also expanded their capacity to form complexes with a wide range of metal salts as effective metal scavengers. All these attractive aspects have promoted a huge growth in the field of organic synthesis involving guanidines and examples of such reactions have been collected in numerous reviews and some books. Moreover, this structural motif is also present in a large number of natural products and biologically active compounds that exhibit appealing properties and play important roles in medicinal chemistry. In this highlight, we will only cover the synthesis and properties of biologically active guanidine-containing peptides reported in the past 3 years.
Synthesis and Evaluation of Antimicrobial Activity of Some Guanidine Derivatives
2020
A series of substituted piperazine guanidine derivatives were synthesized and evaluated for in vitro antimicrobial activity. The UV band with λmax around 216-218nm was present in all compounds, whereas typical IR peaks at 3600-3000 (N-H stretch), 2050-1500 (C=N strech), 1650-1500 (N-H bending), 13501150 (C-N strech) along with specific peaks for a proposed structures were noted in IR spectra gave confirmation of proposed structure. The cup plate agar diffusion method was used to evaluate the antibacterial activity of synthesized compounds. This classic method yields a quantitative result for the amount of antibacterial agent needed to inhibit the growth of specific bacterial strains. The minimum inhibitory concentration (MIC) determination was carried out to find out the minimum concentration of antimicrobial compound found to inhibit the growth of particular test microorganisms.
Preparation of Mono-Cbz Protected Guanidines
Organic Syntheses, 2015
A. Carbonylbenzyloxycyanamide (1). A one-necked 500-mL roundbottomed flask open to the atmosphere, equipped with a magnetic stirring bar (Note 1) is charged with cyanamide (50 weight % solution in H 2 O) (12.6 g, 11.7 mL, 0.15 mol) (Notes 2 and 3) and distilled water (100 mL). Sodium hydroxide pellets (6.16 g, 0.154 mol, 2.05 equiv) are then added in portions (~3 x 2 g) over a 15 min period. The mixture is then stirred for 30 min at room temperature and then cooled to 0 °C (Note 4). The flask is fitted with a 100 mL addition funnel and the addition funnel charged with O Cl
A novel facile solid-phase strategy for the synthesis of N, N', N?-substituted guanidines
Tetrahedron, 2002
AbstractÐA new facile solid-phase synthesis of N,N 0 ,N 00 -substituted guanidines from an immobilised amine component is described. The resin-bound amine was reacted with di-(2-pyridyl)thionocarbonate to generate the isothiocyanate which was treated with aryl/alkyl amines to yield the corresponding resin-bound thiourea. Desulfurisation of the thiourea was readily achieved by treatment with triphenylphosphine dichloride, and further reaction with aryl/alkyl amines followed by acidic cleavage with tri¯uoroacetic acid yielded N,N 0 ,N 00 -substituted guanidines of excellent purity and in good yield. q
N NMR and Ab Initio/IGLO/GIAO-MP2 Study of Mono-, Di-, Tri-, and Tetraprotonated Guanidine
Mono-and diprotonated guanidines were prepared in superacid solutions and studied by 1 H, 13 C, and 15 N NMR spectroscopy. The structures, energies, and NMR chemical shifts were also calculated by ab initio/IGLO/ GIAO-MP2 method. Excellent agreement were found between experimental and calculated 13 C and 15 N NMR chemical shifts. No persistent triprotonated guanidine was observed. Tri-and tetraprotonated guanidines were also studied by ab initio/IGLO/GIAO-MP2 method.