102-02-3

Basic information

• Product Name: PHENYLBIGUANIDE
• Synonyms: phenyldiguanide;1-PHENYLBIGUANIDE;N-PHENYLIMINODICARBONIMIDIC-DIAMIDE;PHENYLBIGUANIDE;2-(N2-Phenylamidino)guanidine;1-phenyl-biguanid;n-phenyl-n’-guanylguanidine;p1426
• CAS NO: 102-02-3
• Molecular Formula: C₈H₁₁N₅
• Molecular Weight: 177.21
• EINECS: 202-998-5
• Product Categories: AgonistsOrganic Building Blocks;Guanidines;Neurotransmitters;Nitrogen Compounds;Serotonergics
• Mol File: 102-02-3.mol

Chemical Properties

• Melting Point: 135-142 °C(lit.)
• Boiling Point: 299.13°C (rough estimate)
• Flash Point: 188.7°C
• Appearance: /
• Density: 1.2512 (rough estimate)
• Vapor Pressure: 3.08E-06mmHg at 25°C
• Refractive Index: 1.6900 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: alcohol: freely soluble
• PKA: 10.76, 2.13(at 25℃)
• Merck: 14,7276
• CAS DataBase Reference: PHENYLBIGUANIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLBIGUANIDE(102-02-3)
• EPA Substance Registry System: PHENYLBIGUANIDE(102-02-3)

Safety Data

• WGK Germany: 3
• RTECS: DU2450000
• Hazardous Substances Data: 102-02-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
PHENYLBIGUANIDE is used as a 5-hydroxytryptamine receptor agonist for its ability to increase extracellular dopamine release in rat nucleus accumbens in vivo. This makes it a potential candidate for the development of treatments related to dopamine-related disorders.
Used in Chemical Synthesis:
PHENYLBIGUANIDE is used as a building block for the synthesis of heterocyclic compounds, which are important in various chemical and pharmaceutical applications. Its unique structure allows for the creation of a wide range of complex molecules with diverse properties and functions.

Purification Methods

Crystallise the biguanide from water or toluene. [Beilstein 12 H 370, 12 I 236, 12 III 807.]

InChI:InChI=1/C8H11N5/c9-7(10)13-8(11)12-6-4-2-1-3-5-6/h1-5H,(H6,9,10,11,12,13)

Upstream product

• 110-86-1 pyridine 
• 628-13-7 pyridine hydrochloride 
• 62-53-3 aniline 
• 127099-85-8 N-Cyanoguanidine 
• 15989-47-6 1-phenyl-3-guanylthiourea 
• 142-04-1 aniline hydrochloride 
• 4484-20-2 aniline benzenesulfonate 
• 103-72-0 phenyl isothiocyanate 
• 55-57-2 1-phenylbiguanide monohydrochloride 

Downstream Products

• 16018-52-3 N-(4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)-N'-phenylguanidine 
• 50427-04-8 1-(4-amino-6-anilino-[1,3,5]triazin-2-yl)-propan-2-one 
• 91719-85-6 4-Anilino-6-amino-s-triazin-2-propionsaeure 
• 64432-68-4 2-(4-amino-6-anilino-[1,3,5]triazin-2-yl)-ethanol 
• 64432-65-1 N-(phenylcarbamimidoyl-carbamimidoyl)-β-alanine 
• 537-17-7 W 1191-2 
• 7426-35-9 2-amino-4-anilino-6-methyl-1,3,5-triazine 
• 30359-95-6 2-Phenylamino-4-amino-6-n-propyl-s-triazin 
• 46917-61-7 6-(2-methoxy-ethyl)-N²-phenyl-[1,3,5]triazine-2,4-diyldiamine 
• 99845-72-4 (amino-anilino-[1,3,5]triazin-2-yl)-acetonitrile 
• 101080-83-5 4-amino-6-(phenylamino)-1,3,5-triazine-2-carboxylic acid 
• 93002-58-5 amino-anilino-[1,3,5]triazine-2-carboxylic acid ethyl ester 
• 99845-00-8 methyl 4-amino-6-(phenylamino)-1,3,5-triazine-2-carboxylate 
• 41282-85-3 N²,6-diphenyl-1,3,5-triazine-2,4-diamine 

Relevant articles and documents

Synthesis and in Vitro AMPK Activation of Cycloalkyl/Alkarylbiguanides with Robust in Vivo Antihyperglycemic Action

This work describes the design, synthesis in one step, and the in vitro, in vivo, and in silico antidiabetic evaluation of a series of ten alicyclic and aromatic (alkyl +aryl: alkaryl)biguanides, analogues of metformin and phenformin. The design was conceived using isosteric replacement, chain-ring transformation, and lower and higher homologation strategies. All compounds were obtained as crystals and their structure was confirmed on the basis of their spectral data (NMR and mass spectra), and their purity was ascertained by microanalysis. Compounds were in vitro evaluated as activators of AMP-Activated Protein Kinase (AMPK). The results indicated that compounds 4, 5, and 6 showed similar or even better effect compared to metformin. Docking analysis was performed with regulatory subunit γ of AMPK, showing several interactions with nucleotide binding pocket. The in vivo evaluation of compounds 4-6 at a single dose of 50 mg/kg was performed in a murine experimental model of diabetes. The results showed an important and robust decrease of plasmatic glucose levels (-40%). Compound 6 was selected for an oral glucose tolerance test, showing an antihyperglycemic effect similar to metformin. The in vivo results indicated that compounds 4-6 may be effective in treating experimental T2DM.

NOVEL CYCLIC GMP-AMP SYNTHASE (CGAS) INHIBITORS AND THEIR METHOD OF USE

Methods of treating diseases related to cGAS activation. Small molecule inhibitors of cGAS and pharmaceutical compositions and uses thereof in treating autoimmune diseases or inflammation.

Rethinking the old antiviral drug moroxydine: Discovery of novel analogues as anti-hepatitis C virus (HCV) agents

The discovery of a novel class of HCV inhibitors is described. The new amidinourea compounds were designed as isosteric analogues of the antiviral drug moroxydine. The two derivatives 11g and 11h showed excellent HCV inhibition activity and viability and proved to inhibit a step(s) of the RNA replication. The new compounds have been synthesized in only three synthetic steps from cheap building blocks and in high yields, thus turning to be promising drug candidates in the development of cheaper HCV treatments.

Novel compounds having treatment of immune diseases and use therof

The present invention relates to a novel compound capable of effectively treating and preventing immune disease and to a use thereof. The novel compound of the present invention suppresses the production of inflammatory cytokines and increases activities of regulatory T cells having immune regulatory ability. In addition, the compound of the present invention controls over an excessive immune response by inhibiting the production of autoantibodies and differentiation of osteoclasts, thereby being able to be used for treating immune diseases induced by regulatory anomalies of various immune response such as autoimmune disease, inflammatory diseases, and transplant rejection.(a) Cell toxicity effect control(MTT assay)(AA) Normal mouse cell(b) Autoantibody production immune reaction control(c) Inflammatory cytokine production control(d) Inflammatory gene expression controlCOPYRIGHT KIPO 2016

Optimised synthesis of diamino-triazinylmethyl benzoates as inhibitors of Rad6B ubiquitin conjugating enzyme

Recently, we have identified the first inhibitors of Rad6B, an E2 enzyme essential for post-replication DNA repair and a potential new drug target for the treatment of breast cancer. We report two newly optimised synthetic routes to our [4-amino-6-(phenylamino)-1,3,5-triazin-2-yl]methyl 4-nitrobenzoate target compounds TZ8 and TZ9 with general applicability for further structure-activity relationship studies around this pharmacophore. The key step involved the condensation/cyclisation between phenylbiguanide and either ethyl bromoacetate or dimethyloxalate in good yield.

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.

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.

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.

Substituted benzene derivatives useful as neuraminidase inhibitors

A compound of the Formula (I): STR1 or pharmaceutically-suitable salts or prodrug forms thereof, wherein: n is 0-1; m is 0; p is 0-1; R1 is --CO2 H; R2 is selected from the group consisting of H, --OH, and --NH2 ; R3 is H; R4 is --C(O)NHR8 ; R5 is --NHC(R6)NH2 R6 is selected from the group consisting of =NH, =NOH, =NCN, =O, and =S; and R8 is selected from the group consisting of C1 -C4 linear or branched alkyl substituted with 0-3 halogens on each carbon.

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.