cas 56-03-1, Biguanide | Articles data

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Regioselective synthesis of pyrimido[1,2-a][1,3,5]triazin-6-ones via reaction of 1-(6-oxo-1,6-dihydropyrimidin-2-yl)guanidines with triethylorthoacetate: Observation of an unexpected rearrangement
A novel thermal rearrangement, involving pyrimidine ring opening and subsequent ring closure leading to recyclization of the system, was identified in the reaction of (6-oxo-1,6-dihydropyrimidin-2-yl)guanidines 3 (where NR 1R2 = NH2, NH alkyl, NH aralkyl, NHCH 2Ph(R)) with triethyl orthoacetate, affording 4-substituted-2-methyl- 6H-pyrimido[1,2-a][1,3,5]triazin-6-ones 6 and their ring opened products. However, no such rearrangement was observed with (6-oxo-1,6-dihydropyrimidin-2- yl)guanidines 3 bearing a tertiary amino or anilino substituent (i.e. where NR1R2 = N(CH3)2, indoline, morpholino, NHAr). As expected, 2-substituted-4-methyl-6H-pyrimido[1,2-a][1,3,5] triazin-6-ones 4 were obtained as the final products. Experimental structural determination and theoretical studies were carried out to get an understanding of the observed thermal rearrangement. In addition, an attempt to obtain similar pyrimido[1,2-a][1,3,5]triazin-6-ones using N,N-dimethylacetamide dimethyl acetal (DMA-DMA) as one carbon inserting synthon had furnished triazine ring annulated product 14 bearing N,N-dimethyl enamino substituent at position 4 as a result of further reaction with a second molecule of DMA-DMA.
Sachdeva, Nikhil,Dolzhenko, Anton V.,Keung Chui, Wai
scheme or table
p. 4586 - 4596
(2012/07/28)

Inorganic salts of biguanide - Searching for new materials for second harmonic generation
Five inorganic salts of biguanide with carbonic, nitric, phosphoric and phosphorous acids were prepared and X-ray structural analysis has been performed for three novel compounds. Biguanidium(1+) phosphite trihydrate crystallizes in the triclinic space group P over(1, ?), a = 7.1470(1) ?, b = 9.6530(2) ?, c = 11.3140(2) ?, α = 70.094(1)°, β = 75.688(1)°, γ = 86.099(1)°, V = 713.71(2) ?3, Z = 2, R = 0.0350 for 3031 observed reflections. The crystal structure is based on a network of phosphite anions and water molecules. Biguanidium(1+) cations form pairs through two intermolecular hydrogen bonds of the N-H...N type and fill the network with anions and water molecules. Biguanidium(2+) phosphite monohydrate crystallizes in the triclinic space group P over(1, ?), a = 6.9690(2) ?, b = 7.3500(3) ?, c = 8.1730(3) ?, α = 82.518(2)°, β = 83.015(2)°, γ = 82.811(2)°, V = 409.44(3) ?3, Z = 2, R = 0.0308 for 1779 observed reflections. The structure is formed of a network of alternating biguanidium(2+) cations, phosphite anions and pairs of water molecules interconnected by a system of intermolecular hydrogen bonds. Biguanidium(2+) hydrogen phosphate monohydrate crystallizes in the triclinic space group P over(1, ?), a = 7.0630(2) ?, b = 7.8740(3) ?, c = 8.1120(3) ?, α = 102.706(2)°, β = 104.976(2)°, γ = 92.632(3)°, V = 422.61(3) ?3, Z = 2, R = 0.0337 for 1827 observed reflections. The crystal structure is formed by pairs of anions that are mutually connected in chains through two water molecules. These chains are interconnected by biguanidium(2+) cations to form a three-dimensional network. The FTIR and FT Raman spectra of all five compounds were recorded, calculated (HF, B3LYP and MP2 methods) and discussed. Quantitative measurements of second harmonic generation of powdered biguanidium(2+) nitrate and novel biguanidium(2+) carbonate monohydrate at 800 nm were performed and a relative efficiency (compared to KDP) of 87% and 20% was observed, respectively.
Matulková, Irena,Němec, Ivan,Císa?ová, Ivana,Němec, Petr,Mi?ka, Zdeněk
experimental part
p. 103 - 120
(2009/02/04)

3-deoxyglucosone and skin
The invention relates to a method of removing 3-deoxyglucosone and other alpha-dicarbonyl sugars from skin. The invention further relates to methods of inhibiting production and function of 3-deoxyglucosone and other alpha-dicarbonyl sugars in skin. The invention also relates to methods of treating 3-deoxyglucosone and other alpha-dicarbonyl sugars associated diseases and disorders of skin.
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(2008/06/13)

Synergistic biocide composition
A biocide composition is provided as an addition to substances that can be infected by harmful microorganisms, in which the biocide composition has at least two active biocidal substances, one of which is 2-methylisothiazolin-3-one. The composition is characterized in that it contains 1,2-benzisothiazolin-3-one, compositions containing 5-chloro-2-methylisothiazolin-3-one being excluded. In comparison with its individual components, the composition of the invention has a synergistic biocidal activity.
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(2008/06/13)

Biguanides and derivatives thereof as inhibitors of advanced glycosylation of a target protein
The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises an agent capable of inhibiting the formation of advanced glycosylation endproducts of target proteins by reacting with the carbonyl moiety of the early glycosylation product of such target proteins formed by their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.
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(2008/06/13)

Preparation and Properties of Substituted 1,6-Dihydro-1,3,5-triazin-2,4-diamines, 1',5',6',7'-Tetrahydrospiro-2'(3'H)-imines and 6-Phenyl-2,4-pyrimidindiamine
Guanidine reacts with cyclohexanone, cycloheptanone, acetone and 3-pentanone, resp., in a molar ratio 2:1 to give the 1,3,5-triazaspiroundeca- and dodeca-1,3-dien-2,4-diamines 3a and 3b resp. and the 6,6-dimethyl- resp. diethyl-1,6-dihydro-1,3,5-triazin-2,4-diamines 3d and 3e resp.On the contrary, action of guanidine on cyclpentanone yields not 3c, but the 1',5',6',7'-tetrahydrospiro-2'(3'H)-imines 2c, 5c and 6c resp., which are 1:2- and 1:3-condensates.Phenylacetone is transformed by guanidine (1:2) to give 6-phenyl-2,4-pyrimidindiamine (8f).The structure of the compounds cited is proved by NMR-, IR-, and (partially) mass spectra.The different courses of the formation of 3a, b, d, e, 2c, 5c and 6c resp. and 8f are also discussed.The structural formulae of some additional bases, which were synthesized from guanidine and cyclopentanone, 3-pentanone and phenylacetone resp. could not be established. - Keywords: Guanidine, reactions with ketones; Ketones, reactions with guanidine; 2,4-Pyrimidindiamine, 6-phenyl; Spiro-2'(3'H)-imine, 1',5',6',7'-tetrahydro; 1,3,5-Triazaspiroundeca- and dodeca-1,3-dien-2,4-diamine; 1,3,5-Triazine-2,4-diamines, 1,6-dihydro-6,6-dialkyl, and salts
Wendelin, Winfried,Zmoelnig, Ilse,Schramm, Hans-Wolfgang
p. 1189 - 1202
(2007/10/02)

Method of making 1-(alkoxyphenyl)-5-(phenyl)biguanide compounds which are useful as agricultural fungicides
The present invention provides an improved method of making 1-(alkoxyphenyl)-5-(phenyl)biguanide compounds which are useful as agricultural fungicides, having the formula: STR1 where R is alkyl, linear of branched, having from 1-14 carbon atoms; and acid addition salts thereof. The method comprises the steps of (a) alkylating a nitrophenol with a suitable alkyl halide in a reaction solvent to form an alkoxynitrobenzene intermediate, (b) reducing the nitro group of the itermediate in situ by catalytic hydrogenation to form an alkoxyaniline, and (c) condensing the alkoxyaniline with phenyldicyandiamide to form the desired biguanide as the acid addition salt. The invention also includes a novel isolation and purification procedure for obtaining purified biguanide acid addition salts and purified free biguanide base.
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(2008/06/13)