5805-59-4

Usage

Uses

Used in Pharmaceutical Research:
(1H-Benzimidazol-2-ylmethyl)-phenylamine is used as a building block in pharmaceutical research for its versatile reactivity and potential pharmacological properties. It aids in the development of new compounds and drugs with medical applications.
Used in Organic Synthesis:
In the field of organic synthesis, (1H-Benzimidazol-2-ylmethyl)-phenylamine is utilized as a key component for creating a variety of complex organic molecules, leveraging its unique structure and reactivity.
Used in Cancer Treatment Research:
(1H-Benzimidazol-2-ylmethyl)-phenylamine is studied for its potential as a therapeutic agent in cancer treatment, targeting various types of cancer through its interaction with biological systems.
Used in Neurological Disorder Treatment Research:
(1H-BENZOIMIDAZOL-2-YLMETHYL)-PHENYL-AMINE is also being investigated for its potential role in treating neurological disorders, capitalizing on its ability to modulate specific biological pathways and mechanisms.

InChI:InChI=1/C14H13N3/c1-2-6-11(7-3-1)15-10-14-16-12-8-4-5-9-13(12)17-14/h1-9,15H,10H2,(H,16,17)

Upstream product

• 103-01-5 N-Phenylglycine 
• 95-54-5 1,2-diamino-benzene 
• 4857-04-9 2-chloromethyl-1H-benzimidazole 
• 62-53-3 aniline 

Downstream Products

• 108-74-7 1,3,5-trimethyl-1,3,5-triazacyclohexane 
• 127855-52-1 6-Methyl-8-phenyl-6,7,8,9-tetrahydro-5H-4b,6,8,10-tetraaza-benzo[a]azulene 
• 108275-03-2 C₁₄H₁₂N₃O 
• 1335544-44-9 [PdCl₂((1H-benzimidazol-2-ylmethyl)-N-phenyl amine)]*H₂O 
• 1422736-44-4 [Ni((1H-benzimidazol-2-ylmethyl)-N-phenylamine)Cl₂(OH₂)₃] 
• 1422736-46-6 [Zn(?(1H-benzimidazol-2-ylmethyl)-N-phenylamine)(CH₃CO₂)₂] 

Relevant academic research and scientific papers

(Benzimidazolylmethyl)amine ZnII and CuII carboxylate complexes: Structural, mechanistic and kinetic studies of polymerisation reactions of ε-caprolactone

Compounds N-(1H-benzimidazol-2-ylmethyl)aniline (L1), N-(1H-benzimidazol-2- ylmethyl)-2-bromoaniline (L2), and N-(1H-benzimidazol-2-ylmethyl)-2- aminothiophenol (L3) react with ZnII and CuII carboxylates to form complexes [Zn2(L1)2(OBn)4] (1), [Zn2(L2)2(OBn)4] (2), [Zn2(L3) 2(OBn)4] (3), [Cu2(L2)2(OBn) 4] (4), [Zn(L1)2(OAc)2] (5), [Zn(L2) 2(OAc)2] (6) and [Cu2(L1)2(OAc) 4] (7). Structures of 2, 4 and 6 revealed that L1-L3 are monodentate, binding through the imidazolyl N-atom. The X-band EPR spectrum of 4 in the solid state is consistent with an antiferromagnetically-coupled (singlet) ground state and a low-lying EPR-active triplet excited state characterised by two main transitions. In dimethyl sulfoxide (DMSO) solution, a single resonance confirmed the retention of the dinuclear paddlewheel core. Complexes 1-7 formed active catalysts towards ring-opening polymerisation of ε-caprolactone. The polymerisation reactions follow first-order kinetics with respect to the monomer and occur through a coordination-insertion pathway. Copyright

Exploring electronic structure, and substituent effect of some biologically active benzimidazole derivatives: Experimental insights and DFT calculations

A series of (1H-benzimidazol-2-ylmethyl)-N-(4-phenyl)amine derivatives incorporating different electron-donating and withdrawing groups (X = 4[sbnd]OCH3 (1), 4[sbnd]CH3 (2), H (3), 4[sbnd]Cl (4), and 4[sbnd]Br (5)) on the para-position of the phenyl substituent was prepared, characterized and screened for their potential antimicrobial activity against some microbes. The substituent effect on the spectroscopic data (vibrational modes and NMR resonances) is well established by fitting with the Hammett constant. The unsubstituted derivative 4 exhibited comparable activity (MIC = 0.26 μM) to the standard tetracycline (MIC = 0.18 μM) against Staphylococcus aureus. Introduction of a substituent to the phenyl ring led to diminishing of the antibacterial activity. The substituent effect on the electron structure of 1–5 was investigated by TDDFT calculations. The acid dissociation constants of the ionizable NH group correlate well with Kubota's σ? parameter (R2 = 0.9196). The solvatochromism behavior of 1–5, in solvents of different polarity and hydrogen-bond tendency, was investigated by linear solvation–energy relationship equation analysis. Correlation between various quantum chemical descriptors, and antibacterial activity was carried out to verify a structural activity relation for this series of benzimidazole derivatives.

Light-activated cytotoxicity of dicarbonyl Ru(ii) complexes with a benzimidazole coligand towards breast cancer

Reaction between [RuCl2(CO)2]n and 1H-benzimidazol-2-ylmethyl-(N-phenyl)amine ligands (LR) functionalized with various electron-donating and electron-withdrawing substituents on the phenyl ring (R = H, 4-CH3, 4-Cl, 4-COOCH3, and 3-COOCH3) afforded the dark-stable photoactivatable carbon monoxide prodrugs of the general formula [RuCl2(CO)2LR]. Release of the CO molecules from the Ru(ii) compounds was examined by monitoring the electronic and IR spectra upon illumination at 365 nm. A noticeable decrease in the intensities of the two characteristic ν(CO) modes for Ru(CO)II2 species, and the growth of two new bands for the mono-carbonyl species and free CO, were the main features of the photolysis profiles. The cytotoxicity of the complexes towards breast cancer (MCF-7) cells was assessed with and without illumination at 365 nm. All the complexes except that with a 4-COOCH3 group (IC50 = 45.08 ± 3.5 μM) are nontoxic under dark conditions. Upon illumination, all the compounds acquired cytotoxicity in the following order: H > 4-COOCH3 > 4-CH3 > 4-Cl > 3-COOCH3. Investigation of the cytotoxicity of the CO-depleted fragments showed that the light-induced cytotoxicity can be attributed to the liberated CO and CO-depleted metal fragments, including the liberated benzimidazole ligands.

Benzimidazole derivative, benzothiophene derivative as well as preparation method and application of benzoimidazole derivative and benzothiophene derivative

The invention provides a benzimidazole derivative and a benzothiophene derivative. The benzimidazole derivative and the benzothiophene derivative respectively have structures shown in a formula (I) and a formula (IV). Experimental results show that the benzimidazole derivative and the benzothiophene derivative provided by the invention have good anti-tumor activity and can be used for preparing related tumor disease treatment medicines.

Cooperative Mn(i)-complex catalyzed transfer hydrogenation of ketones and imines

The synthesis and reactivity of Mn(i) complexes bearing bifunctional ligands comprising both the amine N-H and benzimidazole fragments are reported. Among the various ligands, the N-((1H-benzimidazol-2-yl)methyl)aniline ligand containing Mn(i) complex presented higher reactivity in the transfer hydrogenation (TH) of ketones in 2-propanol. Experimentally, it was established that both the benzimidazole and amine N-H proton played a vital role in the enhancement of the catalytic activity. Utilizing this system a wide range of aldehydes and ketones were reduced efficiently. Notably, the TH of several imines, as well as chemoselective reduction of unsaturated ketones, was achieved in the presence of this catalyst. DFT calculations were carried out to understand the plausible reaction mechanism which disclosed that the transfer hydrogenation reaction followed a concerted outer-sphere mechanism.

Novel tertiary sulfonamide derivatives containing benzimidazole moiety as potent anti-gastric cancer agents: Design, synthesis and SAR studies

With the expectation to find out new anti-gastric cancer agents with high efficacy and selectivity, a series of novel tertiary sulfonamide derivatives were synthesized and the anti-cancer activity was studied in three selected cancer cell lines (MGC-803, PC-3, MCF-7) in vitro. Some of the synthesized compounds could significantly inhibit the proliferation of these tested cancer cells and were more potent than the positive control (5-Fu). The structure-activity relationship of tertiary sulfonamide derivatives was explored in this report. Among the tested compounds, compound 13g containing benzimidazole moiety showed the best anti-proliferation activities against MGC-803 cells (IC50 = 1.02 μM), HGC-27 cells (IC50 = 1.61 μM), SGC-7901 (IC50 = 2.30 μM) cells as well as the good selectivity between the cancer and normal cells. Cellular mechanism studies elucidated compound 13g inhibited the colony formation of gastric cancer cell lines. Meanwhile, compound 13g arrested cell cycle at G2/M phase and induced cell apoptosis. Mechanistically, compound 13g markedly decreased p-Akt and p-c-Raf expression, which revealed that compound 13g targeted gastric cancer cell lines via interfering with AKT/mTOR and RAS/Raf/MEK/ERK pathways. All the findings suggest that compound 13g might be a valuable lead compound for the anti-gastric cancer agents.

Wavelength-Dependent Control of the CO Release Kinetics of Manganese(I) Tricarbonyl PhotoCORMs with Benzimidazole Coligands

A series of photoactivatable CO-releasing molecules (PhotoCORMs) was prepared from manganese pentacarbonyl bromide and 1H-benzimidazol-2-ylmethyl-(N-phenyl)amine ligands (L) bearing different electron-donating and electron-withdrawing groups R = H, 4-CHs

(Benzimidazolylmethyl)amine ZnII and CuII Carboxylate Complexes: Structural, Mechanistic and Kinetic Studies of Polymerisation Reactions of ε-Caprolactone

Compounds N-(1H-benzimidazol-2-ylmethyl)aniline (L1), N-(1H-benzimidazol-2-ylmethyl)-2-bromoaniline (L2), and N-(1H-benzimidazol-2-ylmethyl)-2-aminothiophenol (L3) react with ZnII and CuII carboxylates to form complexes [Zn2/su

Synthesis of aniline substituted benzimidazole derivatives

2-Chloromethyl benzimidazole can be synthesized by the reaction of o-phenylene diamine with chloroacetic acid. This on reaction with substituted anilines in presence of ethanolic KOH gives corresponding benzimidazole derivatives. The synthesized compounds were characterized by IR, 1H NMR and mass spectral data.

Structural and in vitro cytotoxicity studies on 1H-benzimidazol-2-ylmethyl- N-phenyl amine and its Pd(II) and Pt(II) complexes

[MLCl2]·zH2O (L = (1H-benzimidazol-2-ylmethyl) -N-phenyl amine; M = Pd, z = 0; M = Pt, z = 1) and [PdL(OH2) 2]·2X·zH2O (X = Br, I, NO3, z = 0; X = SCN, z = 1) complexes were synthesized as potential anticancer compounds and characterized by elemental analysis, spectral and thermal methods. FT-IR and 1H NMR studies revealed that the benzimidazole L is coordinated to the metal ions via the pyridine-type nitrogen (Npy) of the benzimidazole ring and secondary amino group (NHsec). Quantum mechanical calculations of energies, geometries, vibrational wavenumbers, and 1H NMR of the benzimidazole L and its complexes were carried out by density functional theory using B3LYP functional combined with 6-31G(d) and LANL2DZ basis sets. Natural bond orbitals (NBOs) and frontier molecular orbitals were performed at B3LYP/LANL2DZ level of theory. The synthesized ligand, in comparison to its metal complexes was screened for its antibacterial activity. The benzimidazole L is more toxic against the bacterium Staphylococcus aureus (MIC = 58 μg/mL) than the standard tetracycline (MIC = 82 μg/mL). The complexes showed cytotoxicity against breast cancer, Colon Carcinoma, and human heptacellular Carcinoma cells. The platinum complex (6) displays cytotoxicity (IC50 = 12.4 μM) against breast cancer compared with that reported for cis-platin 9.91 μM.