5993-91-9

Usage

Uses

Used in Chemical Synthesis:
2-(AMINOMETHYL)BENZIMIDAZOLE DIHYDROis used as a synthetic intermediate for the preparation of various organic compounds. Its reactivity and functional groups make it a versatile building block in organic synthesis.
Used in Pharmaceutical Industry:
2-(AMINOMETHYL)BENZIMIDAZOLE DIHYDROis used as a key component in the synthesis of N-(benzimidazol-2-ylmethyl)iminodiacetic acid, which has potential applications in the development of pharmaceuticals and drug candidates. 2-(AMINOMETHYL)BENZIMIDAZOLE DIHYDRO-'s unique structure and properties may contribute to the discovery of new therapeutic agents with novel mechanisms of action.

InChI:InChI=1/C8H9N3/c9-5-8-10-6-3-1-2-4-7(6)11-8/h1-4H,5,9H2,(H,10,11)/p+1

Upstream product

• 30770-21-9 N-[(1H-benzo[d]imidazol-2-yl)methyl]acetamide 
• 95-54-5 1,2-diamino-benzene 
• 56-40-6 glycine 

Downstream Products

• 108784-84-5 N-benzimidazol-2-ylmethyl-N'-cyclohexyl-thiourea 
• 108784-86-7 1-(1H-Benzoimidazol-2-ylmethyl)-3-o-tolyl-thiourea 
• 77523-96-7 1-(1H-Benzoimidazol-2-ylmethyl)-3-m-tolyl-thiourea 
• 175530-26-4 Methyl (+/-)-7-[[[(2-benzimidazolyl)methyl]amino]carbonyl]-3-oxo-4-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate 
• 5805-57-2 2-Aminomethylbenzimidazole 
• 1046048-64-9 2-chloro-4-(2-chloro-4-methoxyphenoxy)-6-[(1H-benzoimidazol-2-ylmethyl)-amino]pyrimidine 
• 1046048-65-0 6-chloro-4-(2-chloro-4-methoxyphenoxy)-2-[(1H-benzoimidazol-2-ylmethyl)-amino]pyrimidine 
• 1046048-67-2 6-[(1H-benzoimidazol-2-ylmethyl)-amino]-4-(2-chloro-4-methoxyphenoxy)-2-(methylthio)pyrimidine 

Relevant academic research and scientific papers

Novel antiviral benzofuran-transition metal complexes

(5-(1H-benzo[d]imidazol-2-yl)-1H-pyrrol-3-yl)(6-hydroxy-4, 7-dimethoxybenzofuran-5-yl)methanone (4) and 3-(6-hydroxy-4,7- dimethoxybenzofuran-5-carbonyl)-6H-pyrimido[1,6-a]pyrimidine-6,8(7H)-dione (5) were synthesized by the reaction of 4,7-dimethoxy-5-oxo-5H-furo[3,2-g]chromene- 6-carbaldehyde (1) with (1H-benzo[d]imidazol-2-yl)methanamine dihydrochloride and 4-amino-2,6-dihydroxypyrimidine, respectively, via ROR in the presence of alcoholic KOH. The metal complexes 6-9 of compound 4; H2L1 with (CuCl2, FeCl3, ZnCl2, and LaCl 3) and the metal complexes 10-13 of compound 5; H2L 2 with (CuCl2, FeCl3, CoCl2 and LaCl3) were synthesized to form 1:1 or 1:2 (metal: ligand) complexes. The HIV inhibitory activity of all new compounds was tested. The EC50 values showed that, all of tested compounds were more potent than Atevirdine. Moreover, the benzoimidazolylpyrrole derivative 4 (EC50=9×10 6mM) had higher therapeutic index than the standard. The HIV-1 RT inhibitory activity showed that all of the tested compounds showed significant potency but none of them showed higher activity than Atevirdine. The HCV NS3-4A protease inhibitor activity of the tested compounds revealed that the complex formation had great positive effect on the bioactivity, where the Fe-complex 7 was the most potent compound with higher therapeutic index than VX-950, the standard. Also, the cytotoxicity of the synthesized compounds on hepatocyte cell line, showed that Cu-complex 10 was the most potent compound with potency nearly to that of the standard.

PREVENTION AND TREATMENT OF HUMAN METABOLIC SYNDROME INCLUDING TYPE 2 DIABETES, STEATOHEPITITIS AND RELATED CONDITIONS USING NON-ABSORBABLE, ORALLY ADMINISTERED COMPOUNDS

Compounds and oral pharmaceutical compositions which neutralize microbially-produced electrophilic carbonyl species, comprising: a non-absorbable compound containing one or more nitrogen nucleophiles having a first pKa between 5 and 10, and a molecular weight less than 800, wherein said non-absorbable compound reacts locally in the gastrointestinal tract and combines with microbially-produced electrophilic carbonyl species by C-N bond formation, thereby protecting gastrointestinal peptide hormones containing arginine or lysine residues, and also preventing diffusion of said electrophilic species into systemic circulation where they may cause damage to proteins, DNA or RNA that adversely affects health; and a pharmaceutically acceptable carrier or excipient

Synthesis and applications in Henry reactions of novel chiral thiazoline tridentate ligands

Several novel chiral tridentate ligands containing thiazoline were efficiently synthesized from commercially available l=cysteine in high yield. These ligands were subsequently applied to the asymmetric Henry reaction of nitromethane and various aldehydes. It was found that the structures of the thiazoline ligands had a significant influence on the enantioselectivity. It was shown that the optimal catalyst for this reaction was a ligand complexed with CuCl, which was formed from chiral thiazoline with chiral aminoalcohol. At -20°C, with 10 mol% of this ligand, a product with (S)-configuration was isolated in 93% yield and 98% enantiomeric excess.

Synthesis, characterization, and cytotoxic activity on MCF-7 cell line of some novel metal complexes with substituted benzimidazole ligands

A series of novel metal complexes with the Schiff base ligands 4-((((1H-benzo[d]imidazol-2-yl)methyl)imino)methyl) benzene-1,3-diol, H 3L1, and (((1H-benzo[d]imidazol-2-yl)methyl) thio)propanenitrile, HL2, have been synthesized and identified by elemental and spectral (UV-vis, IR, 1H NMR, mass) analyses, molar conductivities, as well asmagnetic moment measurements technique. The ligands behave either as neutral tridentate or bidentate ligand. The antitumor activity of the new compounds was tested against breast cancer cell line MCF-7. Ag and Cu complexes 2, 8 and 9 showed a remarkable smaller value of IC50 than that of the Tamoxifen, the standard. This would provide a new potential antitumor drug that deserves more attention. Copyright Taylor & Francis Group, LLC 2013.

Design, synthesis, and biological evaluation of new 4-thiazolidinone derivatives substituted with benzimidazole ring as potential chemotherapeutic agents

In search of novel antiviral and anticancer agents with promising pharmacotoxicological profile, a study was initiated to synthesize new 2-thioxo-4-thiazolidinones as well as 2-phenylimino-4-thiazolidinones substituted with benzimidazole ring system. The compounds were screened primarily for their antiviral as well as anticancer activities. The synthesis of some novel 5-substituted thiazolidinones was also described. None of the tested compounds showed inhibitory activity against Hepatitis C virus replication. Two 2-phenylimino-4-thiazolidinone derivatives (9a and 10) exhibited significant antiproliferative activity against human colon carcinoma cell line HCT 116 and human hepatocellular carcinoma HEPG2 cell line, respectively. Results also indicated that six thiazolidinone derivatives (5a, 5d, 5e, 5f, 5h, and 9d) showed moderate antiproliferative activity against human breast adenocarcinoma cell line MCF7 in comparison to the standard drug Doxorubicin. Moreover, a docked pose of the most potent three cytotoxic compounds 5a, 5h, and 9d against MCF7 was obtained bound to Human N-acetyl transferase1 NAT1 binding pocket by molecular operating environment module.

Molecular docking guided structure based design of symmetrical N,N′-disubstituted urea/thiourea as HIV-1 gp120-CD4 binding inhibitors

Induced fit molecular docking studies were performed on BMS-806 derivatives reported as small molecule inhibitors of HIV-1 gp120-CD4 binding. Comprehensive study of protein-ligand interactions guided in identification and design of novel symmetrical N,N′-disubstituted urea and thiourea as HIV-1 gp120-CD4 binding inhibitors. These molecules were synthesized in aqueous medium using microwave irradiation. Synthesized molecules were screened for their inhibitory ability by HIV-1 gp120-CD4 capture enzyme-linked immunosorbent assay (ELISA). Designed compounds were found to inhibit HIV-1 gp120-CD4 binding in micromolar (0.013-0.247 μM) concentrations.

Synthesis of potent antitumor and antiviral benzofuran derivatives

A new series of potent antitumor and antiviral benzofuran derivatives was synthesized by the reaction of the furochromone-6-carboxaldehydes 1 and 2 with different heterocyclic amines to yield the benzofuran-5-carbonyl derivatives 4-11. The synthesized compounds 1, 3-11 were tested against twelve different human cancer cell lines and all of the compounds were more potent than the comparative standards. The HIV inhibitory activity of the tested compounds 1, 3-11 showed that they have higher potency than Atevirdine. Moreover, compound 6 was significantly potent with wider therapeutic index. The HIV-1 RT inhibitory activity showed that compounds 10, 11, 3 and 4 were notably potent but with lower therapeutic index than Atevirdine. The HCV NS3-4A protease inhibitor activity of the tested compounds revealed that they have weaker potency and less therapeutic index than VX-950, although compounds 1, 4, 9 and 6, respectively exhibited significant activity.

ANTIMICROBIAL COMPOSITIONS AND METHODS OF USE

The present invention is directed to compounds of formula I, pharmaceutical compositions comprising the compounds, and methods for making and using the inventive compounds.

Benzimidazole, benzoxazole and benzothiazole derivatives as 5HT 2B receptor ligands. Synthesis and preliminary pharmacological evaluation

2-Phenethylbenzimidazole, 2-phenethylbenzoxazole and 2- phenethylbenzothiazole derivatives were synthesized to explore the structural features of the serotonin 5-HT2B receptor antagonists. Those molecules were designed to recognize the 5-HT2B receptor and to discriminate it from the 5-HT2A and 5-HT2c subtypes. All compounds were characterized by binding affinity determination for 5-HT 2A and 5-HT2c subtypes and antagonistic activity for 5-HT2B receptor in rat stomach fundus. None of the new compounds showed affinity for 5-HT2A and 5-HT2c subtypes, but some of them displayed antagonistic activity in rat stomach fundus at micromolar concentrations. Birkhaeuser Boston 2005.

Six-co-ordinated vanadium-(IV) and -(V) complexes of benzimidazole and pyridyl containing ligands

A new series of vanadium-(IV) and -(V) complexes with ligands containing functionalities including hydroxyethyl, carboxylate, amine, pyridyl and benzimidazole have been prepared. The crystal structures of three complexes have been determined. All the vanadium atoms are six-co-ordinate even though previous complexes of the diethanolamine type have contained five-co-ordinate vanadium. The V-N (amine) bonds of the benzimidazole complexes are significantly longer than those of pyridyl complexes. An empirical relationship between pKa value of the protonated ligand and the V-N (amine) bond length (trans to an oxo group) of the corresponding vanadium-(IV), -(V) and -(IV/V) complexes was observed. Spectroscopic studies (NMR, ESR and UV/VIS) showed that the complexes remain intact in aqueous solution. In general, the hydroxyethyl substituted vanadium complexes are less stable than corresponding acetate substituted ones and the benzimidazole complexes are less stable than corresponding pyridyl complexes. The combined knowledge concerning the properties of all these complexes provides an excellent platform to design new vanadium complexes pertinent to biological applications.