1197-49-5

Upstream product

• 420-04-2 CYANAMID 
• 3287-99-8 benzylamine hydrochloride 
• 4023-02-3 1H-pyrazole-1-carboximidamide hydrochloride 
• 100-46-9 benzylamine 
• 145013-06-5 N,N′-bis(tert-butoxycarbonyl)-N′′-benzylguanidine 
• 538-28-3 S-benzylisothiourea hydrochloride 
• 107-13-1 acrylonitrile 
• 930-68-7 cyclohexenone 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 95134-66-0 O,O'-Dibenzyl--phosphonat, (N-Dibenzylphospho-N'-benzyl-guanidin) 
• 100185-40-8 2-Amino-1-benzyl-5,6-dihydro-4(1H)-pyrimidinon 
• 223687-87-4 N-(2,6-dichlorophenylacetyl)-N'-benzylguanidine 
• 103085-65-0 Benzyl-{4-phenyl-8-[1-phenyl-meth-(E)-ylidene]-5,6,7,8-tetrahydro-quinazolin-2-yl}-amine 
• 89242-69-3 N²-benzyl-4-methyl-6-phenyl-2-pyrimidineamine 
• 90198-12-2 N'-Benzyl-guanidido-(N)-phosphonat 
• 92871-00-6 O-Benzyl--phosphonat, (N-Monobenzyl-phospho-N'-benzyl-guanidin) 

Relevant academic research and scientific papers

New cellulose-supported reagent: A sustainable approach to guanidines

(Chemical Equation Presented) A new cellulose-supported reagent for the synthesis of guanidine in aqueous medium is reported starting from commercially available functionalized cellulose beads. Primary and secondary amines, anilines, and amino acids were transformed to the corresponding guanidines in high yields and under very mild conditions.

Guanidine cyclic diimides and their polymers

We report the formation and degradation of a unique guanidine cyclic diimide (GCDI) structure and GCDI-based polymers. The GCDI structure is readily formed under mild conditions. The X-ray crystal structure showed that the delocalized π-orbitals in the guanidine plane are significantly disrupted in the GCDI structure. Unlike amine-based imides, the GCDI structure readily degrades into the initial guanidine in protic solvents at ambient temperatures. Furthermore, poly(GCDI)s, a new category of polymers with the GCDI backbones, can be synthesized from guanidines and dianhydrides. Similar to the monomeric GCDIs, poly(GCDI)s are degraded in protic solvents unlike polyimides with high chemical stability.

A mild and inexpensive procedure for the synthesis of N, N′ -di-boc-protected guanidines

A novel and efficient synthetic procedure for converting a diverse set of amines to N,N′-di-Boc-protected guanidines is described. The methodology comprises the use of cyanuric chloride (TCT) as activating reagent for di-Boc-thiourea. The employ of inexpensive TCT instead of classical HgCl 2 eliminates the environmental hazard of heavy-metal waste without appreciable loss of yield or reactivity. This protocol provides an alternative route for the guanylation of amines from those currently employed. Georg Thieme Verlag Stuttgart - New York.

Amine-guanidine switch: A promising approach to improve DNA binding and antiproliferative activities

A series of polyaromatic guanidino derivatives was synthesized and evaluated for growth inhibitory properties in several human carcinoma cell lines. The properties of these guanidino compounds were compared to those of their corresponding synthetic amino precursors. The size of the polyaromatic ring system as well as the length of the tether attached to the ring had a direct impact on the observed antiproliferative profiles, compound 14 having the broadest spectrum of activity. As both series intercalate DNA, guanidine derivatives showed a remarkable affinity for DNA and the guanidinium group appeared to be essential, yet not sufficient for caspase-3/7 activation. Compound 14 also showed significant in vivo activity against breast cancer cell xenografts in NOG/SCID mice. These results suggest that the electronic nature of chain tethering an intercalator not only influences the DNA-binding process but also controls the antitumoral activity of the whole compound.

Total deprotection of N,N'-bis(tert-butoxycarbonyl)guanidines using SnCl4

The total deprotection of NdV'-bis-Boc guanidines using SnCl4 proceeds smoothly in ethyl acetate at room temperature and leads to the easily isolable corresponding guanidinium chlorides.

One-pot synthesis of N-alkyl substituted phosphoryl guanidines

This article describes an attractive and one-pot synthesis of the title compound by phosphorylation of just prepared N-substituted guanidines from cyanamide and the desired amine. The method allows a variety of N-substituents to hang on the final phosphoryl guanidine as a function of the wider availability of commercial simple amines.

Nucleophilic Substitution at the Guanidine Carbon Center via Guanidine Cyclic Diimide Activation

Despite the electron-deficient nature of the guanidine carbon centers, nucleophilic reactions at these sites have been underdeveloped because of the resonance stabilization of the guanidine group. We propose a guanidine C-N bond substitution strategy entailing the formation of guanidine cyclic diimide (GCDI) structures, which effectively destabilize the resonance structure of the guanidine group. In the presence of acid additives, the guanidine carbon center of GCDIs undergoes nucleophilic substitution reactions with various amines and alcohols.

2-Aminoquinazolines by Chan-Evans-Lam Coupling of Guanidines with (2-Formylphenyl)boronic Acids

A new method is presented for the synthesis of 2-aminoquinazolines, which is based on a Chan-Evans-Lam coupling of (2-formylphenyl)boronic acids with guanidines. Relatively mild conditions involving the use of inexpensive CuI as a catalyst and methanol as a solvent permit the application of the method to a wide range of substrates. Nonsubstituted, N-monosubstituted, and N,N-disubstituted guanidines can be used as reactants to give the corresponding 2-aminoquinazolines in moderate yields from readily available (2-formylphenyl)boronic acids.

Dimethoxyphenyl derivatives, preparation method and composition for anti-inflammatory and skin whitening comprising the same

The present invention relates to a dimethoxyphenyl derivatives, to a preparation method thereof, and to an anti-inflammatory and skin whitening composition comprising the same, wherein a compound represented by the chemical formula 1 according to the present invention has excellent solubility, is excellent in an effect of inhibiting the activity of NF-andkappa;B transcription factor, and thus may be useful for prevention, improvement or treatment of inflammatory diseases, and has an excellent inhibitory effect on melanin formation due to alpha-melanocyte stimulating hormone (andalpha;-MSH) inhibitory activity, thereby being useful as a cosmetic composition for preventing, improving or treating melanin pigment over-deposition disease and for whitening the skin.COPYRIGHT KIPO 2018

Using N-substituted-2-amino-4,6-dimethoxypyrimidines in the synthesis of aliphatic guanidines

Abstract The use of 2-chloro-4,6-dimethoxypyrimdine as a tool for the syntheses of substituted guanidines is presented. This method, that we had previously shown to be very useful for aromatic amines, introduces an atom economical, cost effective and environmentally safe method for the installation of the guanidine functionality in aliphatic primary and secondary amines.