2211-57-6

Usage

Uses

Used in Medicinal Chemistry:
N'-Benzylguanidineacetate is used as a pharmaceutical candidate for its antitumor and antiviral properties, making it a promising compound for the development of new therapeutic agents.
Used in Organic Synthesis:
N'-Benzylguanidineacetate is used as a reagent in organic synthesis for the synthesis of various compounds, contributing to the creation of new chemical entities with potential applications in various industries.
Used as a Chelating Agent:
N'-Benzylguanidineacetate is used as a chelating agent in various chemical processes, where its ability to form complexes with metal ions can be utilized for specific applications.
Used as a Catalyst in Organic Reactions:
N'-Benzylguanidineacetate is used as a catalyst to enhance the rate of organic reactions, improving the efficiency and selectivity of chemical processes in research and development.

InChI:InChI=1/C8H11N3.H2O4S/c9-8(10)11-6-7-4-2-1-3-5-7;1-5(2,3)4/h1-5H,6H2,(H4,9,10,11);(H2,1,2,3,4)

Upstream product

• 17356-08-0 thiourea 
• 100-46-9 benzylamine 
• 674-81-7 nitrosoguanidine 
• 14527-26-5 2-methylisothiourea sulphate 
• 1000875-21-7 N,N''-bis(tert-butoxycarbonyl)-N-(3-trimethylstannylbenzyl)guanidine 
• 1415910-64-3 C₈H₁₁N₃*H₂O₃S 
• 4023-02-3 1H-pyrazole-1-carboximidamide hydrochloride 
• 19503-22-1 1H-benzotriazole-1-carboxamidine hydrochloride 
• 145013-06-5 N,N′-bis(tert-butoxycarbonyl)-N′′-benzylguanidine 
• 7732-18-5 water 
• 6630-99-5 1,2,3,4-thiatriazole-5-amine 
• 145013-06-5 C₁₈H₂₇N₃O₄ 
• 29427-58-5 O-methylisourea hemisulfate 
• 38184-47-3 3,5-dimethyl-1-pyrazolylformaminidium nitrate 

Downstream Products

• 104296-01-7 6-Amino-2-benzylamino-4-pyrimidon 
• 90434-94-9 N¹-Benzyl-N³-sulfamoyl-guanidin 
• 81547-04-8 N-Benzyl-N'-(3-nitro-quinolin-4-yl)-guanidine 
• 89242-69-3 N²-benzyl-4-methyl-6-phenyl-2-pyrimidineamine 
• 111971-07-4 2-benzylamino-3,4-dihydropyrimidin-4(3H)-one 
• 14252-56-3 2-amino-3-benzyl-5,5-diphenyl-3,5-dihydro-imidazol-4-one 
• 78451-64-6 2-benzylamino-5,5-diphenylimidazolin-4-one 
• 1197002-83-7 1,2-diacetyl-3-benzylguanidine 
• 88637-00-7 2-benzylamino-6-methylpyrimidin-4(3H)-one 
• 106270-42-2 N-benzyl-2-amino-4,6-dimethylpyrimidine 
• 1421333-37-0 N¹-benzyl-N²,N³-diisopropylguanidine 
• 1435840-49-5 N¹,N²,N⁶,N⁷-tetraisopropyl-N⁴-benzyltriguanide acetate 
• 1435840-98-4 4-benzylamino-1-isopropyl-6-isopropylamino-2-isopropylimino-1,2-dihydro-1,3,5-triazine acetate 
• 78822-77-2 N¹-cyano-N²,N³-diisopropylguanidine 

Relevant academic research and scientific papers

Large-scale synthesis of no-carrier-added [123I]mIBG, using two different stannylated precursors

The clinical advantages of no-carrier-added (n.c.a) radioiodinated meta-iodobenzylguanidine ([*I]mIBG) over its carrieradded (c.a.) analogue have previously been reported. A large-scale synthesis of n.c.a. [ 123I]mIBG was therefore investigated

Expression in yeast, new substrates, and construction of a first 3D model of human orphan cytochrome P450 2U1: Interpretation of substrate hydroxylation regioselectivity from docking studies

Abstract Background Cytochrome P450 2U1 (CYP2U1) has been identified from the human genome and is highly conserved in the living kingdom. In humans, it has been found to be predominantly expressed in the thymus and in the brain. CYP2U1 is considered as an orphan enzyme as few data are available on its physiological function(s) and active site topology. Its only substrates reported so far were unsaturated fatty acids such as arachidonic acid, and, much more recently, N-arachidonoylserotonin. Methods We expressed CYP2U1 in yeast Saccharomyces cerevisiae, built a 3D homology model of CYP2U1, screened a library of compounds known to be substrates of CYP2 family with metabolite detection by high performance liquid chromatography-mass spectrometry, and performed docking experiments to explain the observed regioselectivity of the reactions. Results We show that drug-related compounds, debrisoquine and terfenadine derivatives, subtrates of CYP2D6 and CYP2J2, are hydroxylated by recombinant CYP2U1 with regioselectivities different from those reported for CYP2D6 and 2J2. Docking experiments of those compounds and of arachidonic acid allow us to explain the regioselectivity of the hydroxylations on the basis of their interactions with key residues of CYP2U1 active site. Major conclusion Our results show for the first time that human orphan CYP2U1 can oxidize several exogenous molecules including drugs, and describe a first CYP2U1 3D model. General significance These results could have consequences for the metabolism of drugs particularly in the brain. The described 3D model should be useful to identify other substrates of CYP2U1 and help in understanding its physiologic roles.

Production of new amilorides as potent inhibitors of mitochondrial respiratory complex I

Amilorides, well-known inhibitors of Na+/H+ antiporters, have also shown to inhibit bacterial and mitochondrial NADH-quinone oxidoreductase (complex I). Since the membrane subunits ND2, ND4, and ND5 of bovine mitochondrial complex I

Ligustrazine derivatives. Part 6: Design, synthesis and evaluation of novel ligustrazinyl acylguanidine derivatives as potential cardiovascular agents

A series of novel Ligustrazinyl acylguanidines was designed, synthesized and evaluated for their protective effect on injured vascular endothelial cell (ECV-304). The preliminary results demonstrated that some compounds possessed more potent activities than that of Ligustrazine in stimulating replication of the injured endothelial cell. Among the active compounds, compounds 8b, 8f and 8l displayed remarkable antioxidative activity with low EC50 values of 0.097, 0.059 and 0.094 mM, respectively. Structure-activity relationships were briefly discussed.

CURABLE COMPOSITION

The present invention has its object to provide a curable composition which comprises a guanidine compound as a non-organotin type catalyst, is less discolored, has good surface curability, depth curability, strength rise and adhesiveness, and can retain the curability even after storage; the above object can be achieved by a curable composition which comprises: (A) an organic polymer containing a silyl group capable of crosslinking under siloxane bond formation, the silyl group being a group represented by the general formula (1): -SiX 3 (1) (wherein X represents a hydroxyl group or a hydrolyzable group and the three X groups may be mutually the same or different), (B) a guanidine compound (B-1) as a silanol condensation catalyst, and (C) a plasticizer, wherein the content of the component (B-1) is not lower than 0.1 part by weight but lower than 8 parts by weight per 100 parts by weight of the component (A), and a non-phthalate ester plasticizer accounts for 80 to 100% by weight of the (C) component plasticizer.

Discovery and initial optimization of 5,5′-disubstituted aminohydantoins as potent β-secretase (BACE1) inhibitors

8,8-Diphenyl-2,3,4,8-tetrahydroimidazo[1,5-a]pyrimidin-6-amine (1) was identified through HTS, as a weak (micromolar) inhibitor of BACE1. X-Ray crystallographic studies indicate the 2-aminoimidazole ring forms key H-bonding interactions with Asp32 and Asp228 in the catalytic site of BACE1. Lead optimization using structure-based focused libraries led to the identification of low nanomolar BACE1 inhibitors such as 20b with substituents which extend from the S1 to the S3 pocket.

One-pot two-step solvent-free rapid and clean synthesis of 2-(substituted amino)pyrimidines by microwave irradiation

abs A series of diversely 2-(substituted amino)pyrimidines (along with ring substitution) has been synthesized under solvent- and catalyst-free microwave conditions from substituted guanidines and β-diketones. The substituted guanidines are synthesized from (S)-methylisothiourea sulfate and different amines (various alkyl, aryl, or heterocyclic and also chiral amines) under microwave irradiation. These two-step reactions are performed in one-pot without isolating any intermediate. This protocol has been successfully applied for the synthesis of bisaminopyrimidines and 2-substituted aminopyrimidines containing chiral moiety where chirality remains undisturbed.

Amidination of amines under microwave conditions using recyclable polymer-bound 1H-pyrazole-1-carboxamidine

A convenient one-step transformation of primary and secondary amines into the corresponding unprotected guanidines using 4-benzyl-3,5-dimethyl-1H- pyrazole-1-carboxamidine and its polymer-bound variant is described. The scopes and limitations of the method, the microwave-assistance of amidination as well as a recycling protocol are examined. Georg Thieme Verlag Stuttgart.

Solvent-free synthesis of azole carboximidamides

A one-pot procedure is described for the preparation of azole carboximidamides 2, 3 and guanidinylation of amines with 3. The X-ray crystal structure of 3b, has been determined. A one-pot procedure is described for the preparation of 1H-pyrazole-carboximidamides 2, 1H-benzotriazole-carboximidamides 3 and guanidinylation of amines with 3. The X-ray crystal structure of N,N-dimethyl-1H-benzotriazole-1-carboximidamide 3b, has been determined.

A novel, facile methodology for the synthesis of N,N′-bis(tert-butoxycarbonyl)-protected guanidines using polymer-supported carbodiimide

A novel methodology for the synthesis of guanidines from amines has been developed using polymer assisted synthesis, potentially allowing the preparation of series of compounds in a high throughput manner. The methodology comprises the use of polymer-supported carbodiimide as the activating agent for N,N′-bis(tert-butoxycarbonyl) thiourea with polymer-supported trisamine as a scavenger, followed by deprotection with trifluoroacetic acid. For the first time, polymer-supported carbodiimide has been utilized as an activating agent to synthesize guanidines.