5418-95-1

Basic information

• Product Name: 2-GUANIDINOBENZIMIDAZOLE
• Synonyms: AKOS BC-1905;2-GUANIDINOBENZIMIDAZOLE;OTAVA-BB BB0111070250;TOSLAB-BB TOS-BB-1283;TIMTEC-BB SBB003790;1h-benzimidazol-2-yl-guanidin;1-(benzimidazol-2-yl)guanidine;2-GUANIDINOBENZIMIDAZOLE 95%
• CAS NO: 5418-95-1
• Molecular Formula: C₈H₉N₅
• Molecular Weight: 175.19
• EINECS: 226-527-8
• Product Categories: BENZIMIDAZOLE;Benzimidazoles;Building Blocks;Heterocyclic Building Blocks;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 5418-95-1.mol

Chemical Properties

• Melting Point: 242-244 °C (dec.)(lit.)
• Boiling Point: 296.48°C (rough estimate)
• Flash Point: 233 °C
• Appearance: /
• Density: 1.2954 (rough estimate)
• Vapor Pressure: 1.05E-08mmHg at 25°C
• Refractive Index: 1.6900 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in DMSO (up to 50 mg/ml) or in Water (up to 4 mg/ml with warming)
• PKA: 13.67±0.30(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: 2-GUANIDINOBENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-GUANIDINOBENZIMIDAZOLE(5418-95-1)
• EPA Substance Registry System: 2-GUANIDINOBENZIMIDAZOLE(5418-95-1)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5418-95-1(Hazardous Substances Data)

Usage

Chemical Properties

BROWN-PURPLE FINE CRYSTALLINE POWDER

Uses

N-1H-Benzimidazol-2-ylguanidine is used as a reagent in the synthesis of novel fused pyrimidines and imidazoles as potential analgesics.

References

1) Hong?et al. (2015),?Interrogation of the intersubunit interface if the open Hv1 proton channel with a probe of allosteric coupling; Sci. Rep.,?5?14077 2) Hong?et al.?(2014),?Molecular determinants of Hv1 proton channel inhibition by guanidine derivatives; Proc. Natl. Acad. Sci. USA,?111?9971 3) Gianti?et al. (2016),?On the role of water density fluctuations in the inhibition of a proton channel; Proc. Natl. Acad. Sci. USA,?113?E8359 4) Pupo and Gonzalez (2014),?In pursuit of an inhibitory drug for the proton channel; Proc. Natl. Acad. Sci. USA,?111?9673

InChI:InChI=1/C8H9N5/c9-7(10)13-8-11-5-3-1-2-4-6(5)12-8/h1-4H,(H5,9,10,11,12,13)/p+1

Upstream product

• 39145-59-0 o-phenylenediamine hydrochloride 
• 127099-85-8 N-Cyanoguanidine 
• 95-54-5 1,2-diamino-benzene 
• 127099-85-8 dicyandiamide 

Downstream Products

• 78650-08-5 4-Thiophen-2-yl-3,4-dihydro-benzo[4,5]imidazo[1,2-a][1,3,5]triazin-2-ylamine 
• 55864-37-4 2-benzimidazolylcarbamonitrile 
• 24370-25-0 1-(1H-benzo[d]-imidazol-2-yl)urea 
• 52066-00-9 2-amino-4-oxo-3,4-dihydrobenzimidazo<1,2-a>-s-triazine 
• 923954-91-0 ethyl 6-(3-methylphenyl)-4-oxo-4,6-dihydro-1^(12)(13)H-pyrimido[2',1':4,5][1,3,5]triazino[1,2-a]benzimidazole-3-carboxylate 
• 923954-90-9 ethyl 6-(2-methylphenyl)-4-oxo-4,6-dihydro-1^(12)(13)H-pyrimido[2',1':4,5][1,3,5]triazino[1,2-a]benzimidazole-3-carboxylate 
• 923954-92-1 ethyl 6-(4-methylphenyl)-4-oxo-4,6-dihydro-1^(12)(13)H-pyrimido[2',1':4,5][1,3,5]triazino[1,2-a]benzimidazole-3-carboxylate 
• 26958-67-8 4-phenyl-3,4-dihydrobenzo[4,5]imidazo[1,2-a][1,3,5]triazin-2-amine 
• 406928-23-2 4-(4-methylphenyl)-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazole-2-amine 

Relevant articles and documents

Cobalt-catalyzed isocyanide insertion cyclization to dihydrobenzoimidazotriazins

We have developed an isocyanide insertion reaction for the synthesis of dihydrobenzo[4,5]imidazo[1,2-a][1,3,5]triazins and imidazol-quinoxaline-5-carboxamides utilizing cobalt catalyst. Cobalt-catalyzed system is inexpensive and more acceptable from industrial point of view.

Boosting the catalytic performance of zinc linked amino acid complex as an eco-friendly for synthesis of novel pyrimidines in aqueous medium

Zinc linked amino acid complex, Zn(l-proline)2, is considered as a green catalyst for the synthesis of novel series of pyrimidine derivatives 5a–q. The pyrimidines 5a–q were prepared via two pathways: the first is a one-pot reaction of guanidines 3a–c with aromatic aldehyde 1 and acetophenones 2; and the second one is the reaction of guanidines 3a–c with different chalcones 4a–j in aqueous medium. The simplicity of the operation, the short reaction time, and the high efficiency (97%) are the main advantages of this protocol. Furthermore, the green aspects of this synthetic protocol were further investigated by examining the reusability of Zn(l-proline)2 complex throughout five consecutive cycles without a significant loss of catalytic activity. This new procedure has presented remarkable advantages in terms of safety, simplicity, stability, mild conditions, a short reaction time, excellent yields, and high purities without using any organic solvents.

Design, synthesis, DFT studiesand anticancer activity of novel metal complexes containing 1,3,5-triazino[1,2-a]benzimidazole moiety using microwave as an approach for green chemistry

2-(2-amino-4,10-dihydrobenzo[4,5]imidazo[1,2-a][1,3,5]triazin-4-yl)phenol (ligand)and its related metal complexes of Mn (II), Co (II), Ni (II), Cu (II) and Zn (II)were prepared under microwave irradiation. The structures of prepared compounds were elucidated in terms of elemental analysis, FT-IR, UV-Vis, 1HNMR, 13CNMR, EPR spectra and mass spectra in addition to magnetic studies at room temperature and thermal properties. Elemental analysis results determined mole ratios between the ligand and metal 1:1 or 1:2. The microwave approach provides clean, shorter reaction times and enhancements in yields. Coats Redfern and Horowitz Metzger equation were used to study Thermal kinetic parameters of dehydration and decomposition of the complexes.The geometries of the ligand and its Mn (II), Co (II),Cu (II) and Zn (II) complexes were optimized using Gaussian 09 W; density functional theory (DFT) B3LYP method. Also, the cytotoxic activity of the ligand and its metal complexes were evaluated against liver cancer cells (HepG-2) and the Cu (II) complex exhibited the highest cytotoxic activity with promising IC50 value = 3.5μg/mlcompared to standard referencecisplatin.

Kinase and GPCR polypharmacological approach for the identification of efficient anticancer medicines

Discovery of an anticancer medicine using a single target protein has often been unsuccessful due to the complexity of pathogenic mechanisms as well as the presence of redundant signaling pathways. In this work, we attempted to find promising anticancer drug candidates by simultaneously targeting casein kinase 1 delta (CK1δ) and muscarinic acetylcholine receptor M3 (M3R). Through the structure-based virtual screening and de novo design with the modified potential function for protein-ligand binding, a series of benzo[4,5]imidazo[1,2-a][1,3,5]triazine-2-amine (BITA) derivatives were identified as CK1δ inhibitors and also as M3R antagonists. The biochemical potencies of these bifunctional molecules reached the nanomolar and low-micromolar levels with respect to CK1δ and M3R, respectively. A common interaction feature in the calculated CK1δ-inhibitor and M3R-antagonist complexes is that the BITA moiety is well-stabilized in the orthosteric site of M3R and the hinge region of CK1δ through the establishment of the three hydrogen bonds and the hydrophobic contacts in the vicinity. The computational and experimental results found in this work exemplify the efficiency of kinase and GPCR polypharmacology in developing anticancer medicines. This journal is

Synthesis and Anti-inflammatory Screening of Some Mono and Bis-Alkoxyphthalimide Linked Benzimidazole and their Quinazoline and Pyrimidine Derivatives

In the present study, synthesis of some nonsymmetrical 2-(1H-benzimidazol-2-ylamino)-7,7-dimethyl-7,8-dihydroquinazolin-5(6H)-one (3) and substituted-(1H-benzo[d]imidazol-2-yl)amino-pyrimidine derivatives (4a, 4b, 4c and 5a, 5b) is described as a three-component reaction of 2-guanidinobenzimidazole (2) with triethyl orthoformate and different reactive methylene compounds. Subsequent condensation of compounds 3, 4a, 4b, 4c, and 5a, 5b with bromoethoxyphthalimide (1) gave final compounds 6, 7a, 7b, 7c, and 8a, 8b. Synthesized final compounds have been screened for their in-vivo anti-inflammatory activity against carrageenan-induced paw edema in albino rats. Diclofenac was used as standard anti-inflammatory agents. Some of the compounds exhibited significant anti-inflammatory activity, as compared to standard drug. Structures of synthesized compounds have been confirmed on the basis of chemical tests and spectral studies.

ORGANIC COMPOUNDS

The invention provides novel compounds, composition comprising said compounds and methods for inhibiting CK1 as well as methods of treating CK1 related disorders such as Alzheimer's disease comprising administering a therapeutically effective amount of a CK1 inhibitor to a patient in need thereof.

ORGANIC COMPOUNDS

The invention provides novel compounds, composition comprising said compounds and methods for inhibiting CK1 as well as methods of treating CK1 related disorders such as Alzheimer's disease comprising administering a therapeutically effective amount of a CK1 inhibitor to a patient in need thereof.

Synthesis of novel fused pyrimidines and imidazoles as potential analgesics from 2-amino-4-substituted-striazino[1,2-a]-benzimidazoles

The synthesis of novel fused pyrimidines and imidazole derivatives from 2-amino-s-triazino[1,2-a]benzimidazoles 2a-e and 3a-c was successfully carried out by a ring annelation reaction in a very good yield. Compound 3c was screened for analgesic activity against acetic acid irritation and has shown protection equal to the reference drug (diclofenac sodium). The acute toxicity study revealed that compound 3c is safe up to 300 mg/kg and there is no sign and symptoms of toxicity and mortality for 72 hours.

Synthesis of 2-amino-s-triazino[1,2-a]benzimidazoles as potential antifolates from 2-guanidino- and 2-guanidino-5-methylbenzimidazoles

The syntheses of 2-amino-s-triazino[1,2-a]benzimidazoles from 2-guanidinobenzimidazoles were successfully carried out by a ring annelation reaction. The regiochemistry of the ring closure of 5-methyl-2- guanidinobenzimidazole with diethyl azodicarboxylate, aldehydes, acetone, diethyl ethoxymethylene-malonate and orthoesters, leading to the formation of s-triazine ring was studied. High regioselectivity was not observed in any of these reactions. However, the synthesis of s-triazino[1,2-a]benzimidazole system was found to be more regioselective than its 3,4-dihydro analogue. NOESY experiment indicated that the compound, 2-amino-4,4-dimethyl-3,4-dihydro-s- triazino[1,2-a]benzimidazole existed predominantly as the 3,4-dihydro tautomer in dimethyl sulfoxide. It was found to inhibit bovine dihydrofolate reductase with IC50 10.9 μM.

Microwave-assisted synthesis of s-triazino[2,1-b][1,3]benzoxazoles, s-triazino[2,1-b][1,3]benzothiazoles, and s-triazino[1,2-a]benzimidazoles

2-Amino-4-oxo-derivatives of s-triazino[2,1e][1,3]benzoxazoles, s-triazino[2,1,b][1,3]benzothiazoles, and s-triazino[1,2-a]benzimidazoles were synthesized by carbonylation of 2-benz-oxazolylguanidines, 2- benzothiazolylguanidines, and 2-benzimidazolylguanidines with phenyl isocyanate under microwave irradiation (180°C, 15 minutes). Using phenyl isothiocyanate instead of phenyl isocyanate under the same conditions led to the successful ring closure via thiocarbonylation of 2-benzoxazolylguanidines. However, the formation of 2-imino-4-phenylimino-s-triazino[2,1-b][1,3]benzothiazoles from 2-benzothiazolylguanidines was observed instead under microwave irradiation conditions. Georg Thieme Verlag Stuttgart.